NP 30

CAS No.: 127087-87-0/ 9016-45-9/26027-38-3
EC No.: 500-024-6

Synonyms:
NP 30; np 30; NONİYONİK; NONYLPHENOL 30; NONİLFENOL 30; Nonilfenol 30 ; Nonilfenol 30  etoksile; Nonilfenol 30  etoksile; Nonilfenol 30 etoksile; Nonilfenol 30  etoksile; np 30; polioksietilen; Nonylphenol 30 ethoxylate-30; Nonilfenol 30  EO; ; Nonilfenol 30  EO; Polyoxyethylene Alkylphenyl Ether; arkopal; polyoxyethylene; Nonilfenol 30  30; Nonylphenol 30 with 30 ethoxylate; Nonylphenol 30 ethoxylate- 30; Polyoxyethylene Alkylphenyl Ether; Nonilfenol 30 -30; Nonilfenol 30 ; Nonilfenol 30 /30; Nonilfenol 3030; nonil fenol 30; Nonilfenol 30 etoksilat; polioksietilen alkilfenil eter; polioksietilen; poli oksietilen; poli oksi etilen; polioksi etilen; Nonilfenol 30 ;  Nonilfenol 30 ;  Nonilfenol 30  etoksile;  Nonylphenol 30 ethoxylate;  Cas No : 127087-87-0;  Nonilfenol 30  EO; Polyoxyethylene Alkylphenyl Ether;  arkopal; polyoxyethylene; Nonilfenol 30  30;  Nonylphenol 30 with 30 ethoxylate;  Nonylphenol 30 ethoxylate- 30; Polyoxyethylene Alkylphenyl Ether ;nonifenol; non i fenol; noni fenol; noniphenol; non i phenol; noni phenol; nonylfenol; nony fenol; nonyl fenol; Nonylphenol 30; nonyl Phenol; nonil phenol; nonifenol30 ; non i fenol30; noni fenol30; noniphenol30; non i phenol30; noni phenol30; nonylfenol30; nony fenol30; nonilfenol30; nonyl fenol30;  nonifenol 30; Nonylphenol 3030; nonyl Phenol30; nonil phenol30; nonifenol-30 ; non i fenol-30; noni fenol-30; noniphenol-30; non i phenol-30; noni phenol-30; nonylfenol-30; nony fenol-30; nonyl fenol-30; Nonylphenol 30-30; nonyl Phenol-30; nonil phenol-30; Nonilfenol 30; non il fenol; nonil fenol; nonilphenol; non il phenol; nonil phenol; nonylfenol; nony fenol; nonyl fenol; Nonilfenol 30; ETHOXYLATE; nonilfenol30eo; noniylfenol30; nonylphenol30; nonilfenol30eo; nonilfenol30eo; nonyl phenol 30; nonyl phenol 30; nonil phenol 30; nonil fenol30; nonilphenol30; 30nonilfenol; 30eononilfenol; nonilfenol30; nonifenol30; noni fenol 30; noni phenol 30; noni phenol-30; noni fenol30-; noniyl phenol; noniyl phenol 30; nonilfenol; nonilfenol30; nonil fenol 30 ; nonlfenol30; nonilfenol30; nonilfenol 30; nonyl fenol 30; nonylphenol30; nonyl phenol 30; noniyil fenol 30; noniyil fenol 30 eo; noniyil fenol 30; noniyil phenol 30; noniyil penol 30; nonilpenol 30; nonilpenol30; nonilpenol 30; nonilphenol30; nonilphenol 30; nonilphenol-30; nonil fenol-30; np-30 nonil fenol; np-30 nonyl phenol 30; nonil fenol 30 np-30; nonil fenol-30 np30; nonilfenol30; nonilfenol-30; nonilfenaol-30 np 30;  nonil fenol 30 eo; nonil phenol 30; nonilphenol;  POE nonil Fenil Eter; Etoksile Nonilfenol 30; Polioksietilen nonilfenil eter; nonilfenil eter;  polietilen glikol;  noniyonik; makrogol nonilfenil eter;  Polietilen Mono (nonilfenil) eter Glikoller; polioksi etilen; polioxyetilen; poli-oksietilen; polioksi-etilen; polioksi; etilen; akropal; AKROPAL; Nonylphenol 30 ethoxylate-30; Nonylphenol 30 Ethoxylate 30; Nonylphenol 30 ethoxylate 30; Nonylphenol 30 Ethoxylate; Nonylphenol 30 30 Ethoxylate; polyoxyethylene alkyl phenyl ether; alkyl phenyl polyoxyethylene ether;anti-was agent OP-1021; KONION Nonilfenol 30 -2; KONION Nonilfenol 30 -3; KONION Nonilfenol 30 -4; KONION Nonilfenol 30 -5; KONION Nonilfenol 30 -6; KONION Nonilfenol 30 -8; KONION Nonilfenol 30 -8.5; KONION Nonilfenol 30 -9; KONION Nonilfenol 30 -10; KONION Nonilfenol 30 -12; KONION Nonilfenol 30 -14; KONION Nonilfenol 30 -40F; KONION OP-10; KONION OP-40F; 20427-84-3;  2-[2-(4 nonylphenoxy)ethoxy]ethanol; 2-(2-(4-Nonylphenoxy)ethoxy)ethanol; 2-[2-(4-Nonylphenoxy)ethoxy]ethanol; 238635_ALDRICH; 238651_ALDRICH; 238678_ALDRICH;  26027-38-3;  9016-45-9;  9062-77-5;   A 730; A 730 (surfactant);  Adekatol Nonilfenol 30 ; Adekatol Nonilfenol 30  1000;  Adekatol Nonilfenol 30  1100; Adekatol Nonilfenol 30  638;  Adekatol Nonilfenol 30  650;  Adekatol Nonilfenol 30  660;  Adekatol Nonilfenol 30  675; Adekatol Nonilfenol 30  683; Adekatol Nonilfenol 30  686;  Adekatol Nonilfenol 30  690;  Adekatol Nonilfenol 30  700;   Adekatol Nonilfenol 30  710;  Adekatol Nonilfenol 30  720; Adekatol Nonilfenol 30  760; Adekatol Nonilfenol 30  900;  Afilan CVH;  Agral;  Agral 600; Agral 90; Agral LN;  Agral Plus;  Agral R;  Akyporox Nonilfenol 30  105;  Akyporox Nonilfenol 30  95;  Alcosist PN; Alfenol; Alfenol 10;   Alfenol 18;  Alfenol 22;  Alfenol 28;  Alfenol 710;  Alfenol 8;  Alfenol N 8;  Alkasurf Nonilfenol 30 ;  Alkasurf Nonilfenol 30  11; Alkasurf Nonilfenol 30  15;  Alkasurf Nonilfenol 30  8;  alpha-(Nonylphenyl)-omega-hydroxypoly(oxy-1; 2-ethanediyl); alpha-(Nonylphenyl)-omega-hydroxypolyoxyethylene;  Antarox 897;  Antarox CO; Antarox CO 430;  Antarox CO 530;   Antarox CO 630;  Antarox CO 730; Antarox CO 850;  Arkopal N-090;  C19H32O3;  Carsonon N-9;  Caswell No. 605; Chemax Nonilfenol 30  series;  Conco NI-90;  DIETHYLENE GLYCOL P-NONYLPHENYL ETHER;  Dowfax 9N20;  EINECS 243-816-4; Emulgen – 913; EPA Pesticide Chemical Code 079005;  Ethanol;  2-(2-(4-nonylphenoxy)ethoxy)-;  Ethanol;  2-[2-(4-nonylphenoxy)ethoxy]-; Ethoxylated Nonylphenol 30;  Glycols; polyethylene;  mono(nonylphenyl) ether;  Glycols; polyethylene;  monononylphenyl ether;   Glycols; polyethylene mono(nonylphenyl) ether (nonionic); HSDB 6825;  Igepal CO-210;  Igepal CO-630;  Igepal CO-720; Igepal CO-890;  Lissapol NX;  LS-118796; LS-15337;  NCGC00164410-01; Neutronyx 600;  Nonoxinolum [INN-Latin]; Nonoxynol-3; Nonoxynol-30; Nonoxynol-4;  Nonoxynol-44;  Nonyl phenol; ethoxylated;  Nonylphenol 30;  polyoxyethylene ether;  Nonylphenoxypolyethoxyethanol; Nonilfenol 30;   (Nonylphenoxy)polyethylene oxide;  Nonylphenoxypoly(ethyleneoxy)ethanol;  branched;  Nonyl phenyl polyethylene glycol;   Nonyl phenyl polyethylene glycol ether;  omega-Hydroxy-alpha-(nonylphenyl)poly(oxy-1; 2-ethanediyl); PEG-13 Nonyl phenyl ether;   PEG-15 Nonyl phenyl ether;  PEG-30 Nonyl phenyl ether;  PEG-3 Nonyl phenyl ether;  PEG-44 Nonyl phenyl ether; PEG-4 Nonyl phenyl ether;  Nonilfenol 30; PEG-9 Nonyl phenyl ether; Polyethylene glycol (13) nonyl phenyl ether; Polyethylene glycol (15) nonyl phenyl ether;  Polyethylene glycol 200 nonyl phenyl ether; Polyethylene glycol (30) nonyl phenyl ether; Polyethylene glycol (3) nonyl phenyl ether;  Polyethylene glycol (44) nonyl phenyl ether; Polyethylene glycol 450 nonyl phenyl ether; POLYETHYLENE GLYCOL NONYLPHENYL ETHER; Poly(oxy-1; 2-ethanediyl); alpha-(nonylphenyl)-omega-hydroxy-; Polyoxyethylene(10)nonylphenyl ether; Polyoxyethylene(12) nonylphenyl ether; Nonilfenol 30; branched;  Polyoxyethylene (13) nonyl phenyl ether; Polyoxyethylene (15) nonyl phenyl ether;  Polyoxyethylene(2) nonylphenyl ether;  branched; Polyoxyethylene (30) nonyl phenyl ether; Nonilfenol 30; Polyoxyethylene(30) nonylphenyl ether;  Polyoxyethylene (3) nonyl phenyl ether;  Polyoxyethylene(40) nonylphenyl ether;  branched; Polyoxyethylene (44) nonyl phenyl ether; Polyoxyethylene (4) nonyl phenyl ether; Polyoxyethylene (9) nonyl phenyl ether; Polyoxyethylene Nonylphenol 30;  Prevocel #12; Protachem 630; Rewopol HV-9; Synperonic NX; Tergetol Nonilfenol 30 ; Tergitol Nonilfenol 30 -10; Tergitol Nonilfenol 30 -14;  Tergitol Nonilfenol 30 -27;  Tergitol Nonilfenol 30 -33 (nonionic); Tergitol Nonilfenol 30 -35 (nonionic); Tergitol Nonilfenol 30 -40 (nonionic);  Tergitol Nonilfenol 30 X; Tergitol TP-9 (nonionic);  Triton N-100;  Trycol Nonilfenol 30 -1; ; 4-Nonylphenol 30; p-Nonylphenol 30; 4-n-Nonylphenol 30; Phenol;  4-nonyl-; 104-40-5; Nonilfenol 30; para-Nonylphenol 30; p-n-Nonylphenol 30 Phenol;  nonyl-; Phenol;  p-nonyl-; 4-nonyl phenol; Nonylphenol 30 (mixed); Phenol;  nonyl derivs. para Nonyl phenol; p -n -Nonylphenol 30; CCRIS 1251; HSDB 5359; EINECS 203-199-4; BRN 2047450; Nonylphenol 30 ethoxylate; Cas No : 127087-87-0; Nonilfenol 30  EO; Polyoxyethylene Alkylphenyl Ether; arkopal; polyoxyethylene; Nonilfenol 30;  Nonilfenol 30  30; Nonylphenol 30 with 30 ethoxylate; Nonylphenol 30 ethoxylate- 30; Polyoxyethylene Alkylphenyl Ether; Nonilfenol 30 -30; Nonilfenol 30 ; Nonilfenol 30 /30; Nonilfenol 3030; nonil fenol 30; Nonilfenol 30 etoksilat; polioksietilen alkilfenil eter; polioksietilen; poli oksietilen; poli oksi etilen; polioksi etilen; Nonilfenol 30  30;  Nonilfenol 30 ;  Nonilfenol 30  etoksile;  Nonylphenol 30 ethoxylate;  Cas No : 127087-87-0;  Nonilfenol 30  EO; Polyoxyethylene Alkylphenyl Ether;  arkopal; polyoxyethylene; Nonilfenol 30  30;  Nonylphenol 30 with 30 ethoxylate;  Nonylphenol 30 ethoxylate- 30; Polyoxyethylene Alkylphenyl Ether ;nonifenol; non i fenol; noni fenol; noniphenol; non i phenol; noni phenol; nonylfenol; nony fenol; nonyl fenol; Nonylphenol 30; nonyl Phenol; nonil phenol; nonifenol30 ; non i fenol30; noni fenol30; noniphenol30; non i phenol30; noni phenol30; nonylfenol30; nony fenol30; nonyl fenol30; Nonylphenol 3030; nonyl Phenol30; nonil phenol30; nonifenol-30 ; non i fenol-30; noni fenol-30; noniphenol-30; non i phenol-30; noni phenol-30; nonylfenol-30; nony fenol-30; nonyl fenol-30; Nonylphenol 30-30; nonyl Phenol-30; nonil phenol-30; Nonilfenol 30; non il fenol; nonil fenol; nonilphenol; non il phenol; nonil phenol; nonylfenol; nony fenol; nonyl fenol; Les nonylphénols; nonylphénols Les Nonylphenol 30s; nonylphénols; CHEBI:34440 IGFHQQFPSIBGKE-UHFFFAOYSA-N; MFCD00002396; SBB059316; DSSTox_CID_1857; DSSTox_RID_79098; DSSTox_GSID_33836 68081-86-7; 4-Nonilfenol 30 ; CAS-104-40-5; C9-Alkylated phenol; (C9)Alkylated phenol; Nonilfenol 30;  UNII-I03GBV4WEL; p-nonyl phenol Para-nonyl phenol; 4-Nonyl-Phenol; 4-n-Nonyl phenol; EINECS 268-359-8; Spectrum_001973; SpecPlus_000624; AC1Q2VYR Spectrum2_001832; Spectrum3_000872; Spectrum4_000712; Spectrum5_002066; 4-n-Nonylphenol 30;  85%; 4-n-Nonylphenol 30;  98% I03GBV4WEL; 1-(4-Hydroxyphenyl)nonane; AC1L1C5R; 30; Nonilfenol 30  etoksile; Nonylphenol 30 ethoxylate; Cas No : 127087-87-0; Nonilfenol 30  EO; Polyoxyethylene Alkylphenyl Ether; arkopal; polyoxyethylene; Nonilfenol 30  30; Nonylphenol 30 with 30 ethoxylate; Nonylphenol 30 ethoxylate- 30; Polyoxyethylene Alkylphenyl Ether; Nonilfenol 30 -30; Nonilfenol 30 ; Nonilfenol 30 /30; Nonilfenol 3030; nonil fenol 30; Nonilfenol 30 etoksilat; polioksietilen alkilfenil eter; polioksietilen; poli oksietilen; poli oksi etilen; polioksi etilen; Nonilfenol 30  30;  Nonilfenol 30 ;  Nonilfenol 30  etoksile;  Nonylphenol 30 ethoxylate;  Cas No : 127087-87-0;  Nonilfenol 30  EO; Polyoxyethylene Alkylphenyl Ether;  arkopal; polyoxyethylene; Nonilfenol 30  30;  Nonylphenol 30 with 30 ethoxylate;  Nonylphenol 30 ethoxylate- 30; Polyoxyethylene Alkylphenyl Ether ;nonifenol; non i fenol; noni fenol; noniphenol; non i phenol; noni phenol; nonylfenol; nony fenol; nonyl fenol; Nonylphenol 30; nonyl Phenol; nonil phenol; nonifenol30 ; non i fenol30; noni fenol30; noniphenol30; non i phenol30; noni phenol30; nonylfenol30; nony fenol30; nonilfenol30; nonyl fenol30;  nonifenol 30; Nonylphenol 3030; nonyl Phenol30; nonil phenol30; nonifenol-30 ; non i fenol-30; noni fenol-30; noniphenol-30; non i phenol-30; noni phenol-30; nonylfenol-30; nony fenol-30; nonyl fenol-30; Nonylphenol 30-30; nonyl Phenol-30; nonil phenol-30; Nonilfenol 30; non il fenol; nonil fenol; nonilphenol; non il phenol; nonil phenol; nonylfenol; nony fenol; nonyl fenol; Les nonylphénols; nonylphénols Les Nonylphenol 30s; nonylphénols; AC1Q7A7Y; BIDD:PXR0002; Nonylphenol 30 ethoxylate; Cas No : 127087-87-0; Nonilfenol 30  EO; Polyoxyethylene Alkylphenyl Ether; arkopal; polyoxyethylene; Nonilfenol 30  30; Nonylphenol 30 with 30 ethoxylate; Nonylphenol 30 ethoxylate- 30; Polyoxyethylene Alkylphenyl Ether; Nonilfenol 30 -30; Nonilfenol 30 ; Nonilfenol 30 /30; Nonilfenol 3030; nonil fenol 30; Nonilfenol 30 etoksilat; polioksietilen alkilfenil eter; polioksietilen; poli oksietilen; poli oksi etilen; polioksi etilen; Nonilfenol 30  30;  Nonilfenol 30 ;  Nonilfenol 30  etoksile; Nonylphenol 30 ethoxylate;  Cas No : 127087-87-0;  Nonilfenol 30  EO;  ;  Polyoxyethylene Alkylphenyl Ether;  arkopal; polyoxyethylene; Nonilfenol 30  30; Nonylphenol 30 with 30 ethoxylate; Nonylphenol 30 ethoxylate- 30; Polyoxyethylene Alkylphenyl Ether ;nonifenol; non i fenol; noni fenol; noniphenol; non i phenol; noni phenol; nonylfenol; nony fenol; nonyl fenol; Nonylphenol 30; nonyl Phenol; nonil phenol; nonifenol30 ; non i fenol30; noni fenol30; noniphenol30; non i phenol30; noni phenol30; nonylfenol30; nony fenol30; nonyl fenol30; Nonylphenol 3030; nonyl Phenol30; nonil phenol30; nonifenol-30 ; non i fenol-30; noni fenol-30; noniphenol-30; non i phenol-30; noni phenol-30; nonylfenol-30; nony fenol-30; nonyl fenol-30; Nonylphenol 30-30; nonyl Phenol-30; nonil phenol-30; Nonilfenol 30; non il fenol; nonil fenol; nonilphenol; non il phenol; nonil phenol; nonylfenol; nony fenol; nonyl fenol; Les nonylphénols; nonylphénols Les Nonylphenol 30s; nonylphénols; CCG-39613; LMPK15010001; LS-375; STL453644; AKOS015888197; MCULE-5930378829 RTR-000982; TRA0078987; NCGC00090918-01; NCGC00090918-02; NCGC00090918-03; NCGC00090918-05; NCGC00090918-06 NCGC00090918-07; NCGC00090918-08; 30; Nonilfenol 30  etoksile; Nonylphenol 30 ethoxylate; Cas No : 127087-87-0; Nonilfenol 30  EO; Polyoxyethylene Alkylphenyl Ether; arkopal; polyoxyethylene; Nonilfenol 30  30; Nonylphenol 30 with 30 ethoxylate; Nonylphenol 30 ethoxylate- 30; Polyoxyethylene Alkylphenyl Ether; Nonilfenol 30 -30; Nonilfenol 30 ; Nonilfenol 30 /30; Nonilfenol 3030; nonil fenol 30; Nonilfenol 30 etoksilat; polioksietilen alkilfenil eter; polioksietilen; poli oksietilen; poli oksi etilen; polioksi etilen; Nonilfenol 30  30;  Nonilfenol 30 ;  Nonilfenol 30  etoksile;  Nonylphenol 30 ethoxylate;  Cas No : 127087-87-0;  Nonilfenol 30  EO;  ;  Polyoxyethylene Alkylphenyl Ether;  arkopal; polyoxyethylene; Nonilfenol 30  30;  Nonylphenol 30 with 30 ethoxylate;  Nonylphenol 30 ethoxylate- 30; Polyoxyethylene Alkylphenyl Ether ;nonifenol; non i fenol; noni fenol; noniphenol; non i phenol; noni phenol; nonylfenol; nony fenol; nonyl fenol; Nonylphenol 30; nonyl Phenol; nonil phenol; nonifenol30 ; non i fenol30; noni fenol30; noniphenol30; non i phenol30; noni phenol30; nonylfenol30; nony fenol30; nonyl fenol30; Nonylphenol 3030; nonyl Phenol30; nonil phenol30; nonifenol-30 ; non i fenol-30; noni fenol-30; noniphenol-30; non i phenol-30; noni phenol-30; nonylfenol-30; nony fenol-30; nonyl fenol-30; Nonylphenol 30-30; nonyl Phenol-30; nonil phenol-30; Nonilfenol 30; non il fenol; nonil fenol; nonilphenol; non il phenol; nonil phenol; nonylfenol; nony fenol; nonyl fenol; Les nonylphénols; nonylphénols Les Nonylphenol 30s; nonylphénols;  NCGC00257420-01; NCGC00258793-01; AN-24676; CC-20192; LP002789 P-NONYLPHENOL 30 (ENDOCRINE DISRUPTER); KB-193654; TL8000182; TR-000982; FT-0619310; ST50827096 C14550; 4-Nonylphenol 30;  PESTANAL(R);  analytical standard; C-33468; J-001167; I01-10138; I14-50858 4-Nonylphenol 30;  certified reference material;  TraceCERT(R); 4-Nonylphenol 30 (mixture of compounds with branched sidechain); 29832-11-9; polioksi etilen; polioxyetilen; poli oksi etilen; nonilphenol 30; nonylfenol 30; Nonilfenol 30 ; Nonilfenol 30 etoksilat; Nonilfenol 30etoksilat; Nonilfenol 3030etoksilat; Np 30; Np-30; Nonilfenol 30 ; 30; Nonilfenol 30  30; DETERGENT BIOGRAD FL-70 TERGITOL(TM) TMN-6; TERGITOL(TM) TMN-10; TERGITOL TMN-6; TERGITOL TMN; TERGITOL(TM) 15-S-9 TERGITOL(TM) 15-S-7; TERGITOL(TM) 15-S-5;127087-87-0 BioChemical DETERGENT BIOGRAD FL-70 TERGITOL(TM); TMN-6 TERGITOL(TM) TMN-10; TERGITOL TMN-6; TERGITOL TMN; TERGITOL(TM) 15-S-9; TERGITOL(TM) 15-S-7; TERGITOL(TM) 15-S-5; TERGITOL(TM) 15-S-40;TERGITOL(TM) 15-S-30; TERGITOL(TM) 15-S-3; TERGITOL(R) TMN 6; TERGITOL(R) TMN 3; TERGITOL(R) 15-S-5; TERGITOL(R) TMN 10; TERGITOL TYPE 15-S-9; TERGITOL TYPE 15-S-7; TERGITOL TYPE 15-S-5; TERGITOL TYPE 15-S-30; TERGITOL TYPE 15-S-12; TERGITOL TYPE Nonilfenol 30 -7; TERGITOL TYPE Nonilfenol 30 -10; TERGITOL TYPE Nonilfenol 30 -9; POLYETHYLENE GLYCOL TRIMETHYLNONYL ETHER;  Detergents Non-Ionic 2-ethanediyl); alpha-(4-nonylphenyl)-omega-hydroxy-poly(oxy-branched 2-ethanediyl) poly(oxy-alpha-(4-nonylphenyl)-omega-hydroxy-poly(oxy-branched alpha-(4-nonylphenyl)-omega-hydroxypoly(oxy-1; 2-ethanediyl)- branched tergitolnp-4surfactant TERGITOL TYPE Nonilfenol 30 -4; Polyethylene glycol mono(branched p-nonylphenyl) ether; 4-Nonylphenol 30 branched ethoxylated; Tergitol Tergitol(R) Nonilfenol 30 -4;  Surfactant Tergitol(R) Nonilfenol 30 -40;  Surfactant Tergitol(R) Nonilfenol 30 -7;  Surfactant Tergitol(R) Nonilfenol 30 -9;  Surfactant Tergitol 4-Nonylphenol 30 branched ethoxylated Tergitol[R]4-Nonylphenol 30 branched ethoxylated -(4-NONYLPHENYL)-OMEGA-HYDROXYPOLY-(OXY-1; 2-ETHANEDIYL)-BRANCHED Poly(oxy-1; 2-ethanediyl); a-(4-nonylphenyl)-w-hydroxy-;  branched; Polyethylene glycol nonylphenyl ether;alpha-(Nonylphenyl)-omega-hydroxypoly(oxy-1; 2-ethanediyl); Poly(oxy; 1; 2-ethanediyl) alpha-(4-nonylphenyl)-omega-hydroxy- branched; 4-NONYLPHENOL 30 POLYETHYLENE GLYCOL ETHER BRANCHED; 4-Nonylphenol 30;  branched;  ethoxylated BRANCHED NONYLPHENOL 30 POLYETHYLENE GLYCOL ETHER; Nonylphenol 30 and its ethoxylates Poly(oxy-1; 2-ethanediyl);  -(4-nonylphenyl)--hydroxy-branched; Poly(oxy-1; 2-ethanediyl);  -(4-nonylphenyl)-?-hydroxy-;  branched Poly(oxy-1; 2-ethanediyl);  -(4-nonylphenyl)-?-hydroxy-;  branched; POLY(OXY-1; 2-ETHANEDIYL);  ?-?-HYDROXY-; BRANCHED -(4-Nonylphenyl)-?-hydroxypoly(oxy-1; 2-ethanediyl);  branched; -(4-Nonylphenyl)-?-hydroxypoly(oxyethane-1; 2-diyl) ramifie; 4-Nonylphenol 30;  branched;  ethoxylated; Poly(oxy; 1; 2-ethanediyl) alpha-(4-nonylphenyl)-omega-hydroxy- branched 4-Nonylphenol 30 branched ethoxylated; Nonilfenol 30 E; Nonilfenol 30  30; Nonilfenol 30 ; Nonilfenol 30  etoksile; Nonylphenol 30 ethoxylate; Cas No : 127087-87-0; Nonilfenol 30  EO; Polyoxyethylene Alkylphenyl Ether; arkopal; polyoxyethylene; Nonilfenol 30  30; Nonylphenol 30 with 30 ethoxylate; Nonylphenol 30 ethoxylate- 30; Polyoxyethylene Alkylphenyl Ether; Nonilfenol 30 -30; Nonilfenol 30 ; Nonilfenol 30 /30; Nonilfenol 3030; nonil fenol 30; Nonilfenol 30 etoksilat; polioksietilen alkilfenil eter; polioksietilen; poli oksietilen; poli oksi etilen; polioksi etilen; Nonilfenol 30  30;  Nonilfenol 30 ;  Nonilfenol 30  etoksile;  Nonylphenol 30 ethoxylate;  Cas No : 127087-87-0;  Nonilfenol 30  EO;  ;  Polyoxyethylene Alkylphenyl Ether;  arkopal; polyoxyethylene; Nonilfenol 30  30;  Nonylphenol 30 with 30 ethoxylate;  Nonylphenol 30 ethoxylate- 30; Polyoxyethylene Alkylphenyl Ether ;nonifenol; non i fenol; noni fenol; noniphenol; non i phenol; noni phenol; nonylfenol; nony fenol; nonyl fenol; Nonylphenol 30; nonyl Phenol; nonil phenol; nonifenol30 ; non i fenol30; noni fenol30; noniphenol30; non i phenol30; noni phenol30; nonylfenol30; nony fenol30; nonyl fenol30; Nonylphenol 3030; nonyl Phenol30; nonil phenol30; nonifenol-30 ; non i fenol-30; noni fenol-30; noniphenol-30; non i phenol-30; noni phenol-30; nonylfenol-30; nony fenol-30; nonyl fenol-30; Nonylphenol 30-30; nonyl Phenol-30; nonil phenol-30; Nonilfenol 30; non il fenol; nonil fenol; nonilphenol; non il phenol; nonil phenol; nonylfenol; nony fenol; nonyl fenol; Les nonylphénols; nonylphénols Les Nonylphenol 30s; nonylphénols;

NP 30

NP 30
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NP 30
NP 30es V.svg
Names
IUPAC name
4-(2,4-dimethylheptan-3-yl)phenol
Other names
Phenol, nonyl-
Identifiers
CAS Number    
25154-52-3 (general class) check
104-40-5 (4-n-Nonyl phenol) check
84852-15-3 (branched 4-Nonyl phenols) check
11066-49-2 (isoNP 30s) ☒
3D model (JSmol)    
Interactive image
ChEMBL    
ChEMBL153062 ☒
ChemSpider    
60628 check
PubChem CID    
67296
UNII    
79F6A2ILP5 (general class) check
I03GBV4WEL (4-n-Nonyl phenol) check
JRW3Q994VG (branched 4-Nonyl phenols) check
InChI[show]
SMILES[show]
Properties
Chemical formula    C15H24O
Molar mass    220.35 g/mol
Appearance    Light yellow viscous liquid with phenolic smell [1]
Density    0.953
Melting point    −8 to 2 °C (18 to 36 °F; 265 to 275 K)
Boiling point    293 to 297 °C (559 to 567 °F; 566 to 570 K)
Solubility in water    6 mg/L (pH 7)
Hazards
Main hazards    low level endrocrine disruptor
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒ verify (what is check☒ ?)
Infobox references
NP 30s are a family of closely related organic compounds composed of phenol bearing a 9 carbon-tail. NP 30s can come in numerous structures, all of which may be considered alkylphenols. They are used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers.[2] These compounds are also precursors to the commercially important non-ionic surfactants alkylphenol ethoxylates and NP 30 ethoxylates, which are used in detergents, paints, pesticides, personal care products, and plastics. NP 30 has attracted attention due to its prevalence in the environment and its potential role as an endocrine disruptor and xenoestrogen, due to its ability to act with estrogen-like activity.[3] The estrogenicity and biodegradation heavily depends on the branching of the nonyl sidechain.[4][5][6] NP 30 has been found to act as an agonist of the GPER (GPR30).[7]

Contents
1    Structure and basic properties
2    Production
3    Applications
4    Prevalence in the environment
4.1    Environmental hazards
5    Human health hazards
5.1    Effects in pregnant women
5.2    Effects on metabolism
5.3    Cancer
5.4    Human exposure and breakdown
5.4.1    Exposure
5.4.2    Breakdown
6    Analytics
7    Regulation
8    References
Structure and basic properties
NP 30s fall into the general chemical category of alkylphenols.[8] The structure of NPs may vary. The nonyl group can be attached to the phenol ring at various locations, usually the 4- and, to lesser extent, the 2-positions, and can be either branched or linear. A branched NP 30, 4-NP 30, is the most widely produced and marketed NP 30.[9] The mixture of NP 30 isomers is a pale yellow liquid, although the pure compounds are colorless. The NP 30s are moderately soluble in water [9] but soluble in alcohol.

NP 30 arises from the environmental degradation of NP 30 ethoxylates, which are the metabolites of commercial detergents called alkylphenol ethoxylates. NPEs are a clear to light orange color liquid. NP 30 ethoxylates are nonionic in water, which means that they have no charge. Because of this property they are used as detergents, cleaners, emulsifiers, and a variety of other applications. They are amphipathic, meaning they have both hydrophilic and hydrophobic properties, which allows them to surround non-polar substances like oil and grease, isolating them from water.[2]

Production
NP 30 can be produced industrially, naturally, and by the environmental degradation of alkylphenol ethoxylates. Industrially, NP 30s are produced by the acid-catalyzed alkylation of phenol with a mixture of nonenes. This synthesis leads to a very complex mixture with diverse NP 30s.[10][11][12] Theoretically there are 211 constitutional isomers and this number rise to 550 isomers if we take the enantiomers into account.[4] To make NPEs, manufacturers treat NP with ethylene oxide under basic conditions.[9] Since its discovery in 1940, NP 30 production has increased exponentially, and between 100 and 500 million pounds of NP 30 are produced globally every year,[9][13] meeting the definition of High Production Volume Chemicals.

NP 30s are also produced naturally in the environment. One organism, the velvet worm, produces NP 30 as a component of its defensive slime. The NP 30 coats the ejection channel of the slime, stopping it from sticking to the organism when it is secreted. It also prolongs the drying process long enough for the slime to reach its target.[14]

Another surfactant called nonoxynol, which was once used as intravaginal spermicide and condom lubricant, was found to metabolize into free NP 30 when administered to lab animals.[8]

Applications
NP 30 is used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers.[2] It can also be used to produce tris(4-nonyl-phenyl) phosphite (TNPP), which is an antioxidant used to protect polymers, such as rubber, Vinyl polymers, polyolefins, and polystyrenics in addition to being a stabilizer in plastic food packaging. Barium and calcium salts of NP 30 are also used as heat stabilizers for polyvinyl chloride (PVC).[15] NP 30 is also often used an intermediate in the manufacture of the non-ionic surfactants NP 30 ethoxylates, which are used in detergents, paints, pesticides, personal care products, and plastics. NP 30 and NP 30 ethoxylates are only used as components of household detergents outside of Europe.[2] Nonyl Phenol, is used in many epoxy formulations mainly in North America.

Prevalence in the environment
NP 30 persists in aquatic environments and is moderately bioaccumulative. It is not readily biodegradable, and it can take months or longer to degrade in surface waters, soils, and sediments. Nonbiological degradation is negligible.[3] NP 30 is partially removed during municipal wastewater treatment due to sorption to suspended solids and biotransformation.[16][17] Many products that contain NP 30 have "down-the-drain" applications, such as laundry and dish soap, so the contaminants are frequently introduced into the water supply. In sewage treatment plants, NP 30 ethoxylate degrades into NP 30, which is found in river water and sediments as well as soil and groundwater.[18] NP 30 photodegrades in sunlight, but its half-life in sediment is estimated to be more than 60 years. Although the concentration of NP 30 in the environment is decreasing, it is still found at concentrations of 4.1 μg/L in river waters and 1 mg/kg in sediments.[2]

A major concern is that contaminated sewage sludge is frequently recycled onto agricultural land. The degradation of NP 30 in soil depends on oxygen availability and other components in the soil. Mobility of NP 30 in soil is low.[2]

Bioaccumulation is significant in water-dwelling organisms and birds, and NP 30 has been found in internal organs of certain animals at concentrations of 10 to 1,000 times greater than the surrounding environment.[3] Due to this bioaccumulation and persistence of NP 30, it has been suggested that NP 30 could be transported over long distances and have a global reach that stretches far from the site of contamination.[19]

NP 30 is not persistent in air, as it is rapidly degraded by hydroxyl radicals.[3]

Environmental hazards
NP 30 is considered to be an endocrine disruptor due to its ability to mimic estrogen and in turn disrupt the natural balance of hormones in affected organisms.[4][5][6][20][21] The effect is weak because NP 30s are not very close structural mimics of estradiol, but the levels of NP 30 can be sufficiently high to compensate.

Structure of the hormone estradiol and one of the NP 30s.
The effects of NP 30 in the environment are most applicable to aquatic species. NP 30 can cause endocrine disruption in fish by interacting with estrogen receptors and androgen receptors. Studies report that NP 30 competitively displaces estrogen from its receptor site in rainbow trout.[22] It has much less affinity for the estrogen receptor than estrogen in trout (5 x 10−5 relative binding affinity compared to estradiol) making it 100,000 times less potent than estradiol.[22][23] NP 30 causes the feminization of aquatic organisms, decreases male fertility, and decreases survival in young fish.[2] Studies show that male fish exposed to NP 30 have lower testicular weight.[22] NP 30 can disrupt steroidogenesis in the liver. One function of endogenous estrogen in fish is to stimulate the liver to make vitellogenin, which is a phospholipoprotein.[22] Vitellogenin is released by the maturing female and sequestered by developing oocytes to produce the egg yolk.[22] Males do not normally produce vitellogenin, but when exposed to NP 30 they produce similar levels of vitellogenin to females.[22] The concentration needed to induce vitellogenin production in fish is 10 ug/L for NP in water.[22] NP 30 can also interfere with the level of FSH (follicle-stimulating hormone) being released from the pituitary gland. Concentrations of NP that inhibit reproductive development and function in fish also damages kidneys, decreases body weight, and induces stressed behavior.[24]

Human health hazards
Alkylphenols like NP 30 and bisphenol A have estrogenic effects in the body. They are known as xenoestrogens.[25] Estrogenic substances and other endocrine disruptors are compounds that have hormone-like effects in both wildlife and humans. Xenoestrogens usually function by binding to estrogen receptors and acting competitively against natural estrogens. NP 30 has been shown to mimic the natural hormone 17β-estradiol, and it competes with the endogeous hormone for binding with the estrogen receptors ERα and ERβ.[2] NP 30 was discovered to have hormone-like effects by accident because it contaminated other experiments in laboratories that were studying natural estrogens that were using polystyrene tubes.[8]

Effects in pregnant women
Subcutaneous injections of NP 30 in late pregnancy causes the expression of certain placental and uterine proteins, namely CaBP-9k, which suggest it can be transferred through the placenta to the fetus. It has also been shown to have a higher potency on the first trimester placenta than the endogenous estrogen 17β-estradiol. In addition, early prenatal exposure to low doses of NP 30 cause an increase in apoptosis (programmed cell death) in placental cells. These “low doses” ranged from 10−13-10−9 M, which is lower than what is generally found in the environment.[26]

NP 30 has also been shown to affect cytokine signaling molecule secretions in the human placenta. In vitro cell cultures of human placenta during the first trimester were treated with NP 30, which increase the secretion of cytokines including interferon gamma, interleukin 4, and interleukin 10, and reduced the secretion of tumor necrosis factor alpha. This unbalanced cytokine profile at this part of pregnancy has been documented to result in implantation failure, pregnancy loss, and other complications.[26]

Effects on metabolism
NP 30 has been shown to act as an obesity enhancing chemical or obesogen, though it has paradoxically been shown to have anti-obesity properties.[27] Growing embryos and newborns are particularly vulnerable when exposed to NP 30 because low-doses can disrupt sensitive processes that occur during these important developmental periods.[28] Prenatal and perinatal exposure to NP 30 has been linked with developmental abnormalities in adipose tissue and therefore in metabolic hormone synthesis and release (Merrill 2011). Specifically, by acting as an estrogen mimic, NP 30 has generally been shown to interfere with hypothalamic appetite control.[27] The hypothalamus responds to the hormone leptin, which signals the feeling of fullness after eating, and NP 30 has been shown to both increase and decrease eating behavior by interfering with leptin signaling in the midbrain.[27] NP 30 has been shown mimic the action of leptin on neuropeptide Y and anorectic POMC neurons, which has an anti-obesity effect by decreasing eating behavior. This was seen when estrogen or estrogen mimics were injected into the ventromedial hypothalamus.[29] On the other hand, NP 30 has been shown to increase food intake and have obesity enhancing properties by lowering the expression of these anorexigenic neurons in the brain.[30] Additionally, NP 30 affects the expression of ghrelin: an enzyme produced by the stomach that stimulates appetite.[31] Ghrelin expression is positively regulated by estrogen signaling in the stomach, and it is also important in guiding the differentiation of stem cells into adipocytes (fat cells). Thus, acting as an estrogen mimic, prenatal and perinatal exposure to NP 30 has been shown to increase appetite and encourage the body to store fat later in life.[32] Finally, long-term exposure to NP 30 has been shown to affect insulin signaling in the liver of adult male rats.[33]

Cancer
NP 30 exposure has also been associated with breast cancer.[2] It has been shown to promote the proliferation of breast cancer cells, due to its agonistic activity on ERα (estrogen receptor α) in estrogen-dependent and estrogen-independent breast cancer cells. Some argue that NP 30's suggested estrogenic effect coupled with its widespread human exposure could potentially influence hormone-dependent breast cancer disease.[34]

Human exposure and breakdown
Exposure
Diet seems the most significant source of exposure of NP 30 to humans. For example, food samples were found with concentrations ranging from 0.1 to 19.4 µg/kg in a diet survey in Germany and a daily intake for an adult were calculated to be 7.5 µg/day.[35] Another study calculated a daily intake for the more exposed group of infants in the range of 0.23-0.65 µg/ kg bodyweight/ day.[36] In Taiwan, NP 30 concentrations in food ranged from 5.8 to 235.8 µg/kg. Seafood in particular was found to have a high concentration of NP 30.[37]

One study conducted in Italian women showed that NP 30 was one of the highest contaminants at a concentration of 32 ng/mL in breast milk when compared to other alkyl phenols, such as octylphenol, NP 30 monoethoxylate, and two octylphenol ethoxylates. The study also found a positive correlation between fish consumption and the concentration of NP 30 in breast milk.[37] This is a large problem because breast milk is the main source of nourishment for newborns, who are in early stages of development where hormones are very influential. Elevated levels of endocrine disruptors in breast milk have been associated with negative effects on neurological development, growth, and memory function.

Drinking water does not represent a significant source of exposure in comparison to other sources such as food packing materials, cleaning products, and various skin care products. Concentrations of NP 30 in treated drinking water varied from 85 ng/L in Spain to 15 ng/L in Germany.[2]

Microgram amounts of NP 30 have also been found in the saliva of patients with dental sealants.[34]

Breakdown
When humans orally ingest NP 30, it is rapidly absorbed in the gastrointestinal tract. The metabolic pathways involved in its degradation are thought to involve glucuronide and sulfate conjugation, and the metabolites are then concentrated in fat. There is inconsistent data on bioaccumulation in humans, but NP 30 has been shown to bioaccumulate in water-dwelling animals and birds. NP 30 is excreted in feces and in urine.[3]

Analytics
Since NP 30s are ubiquitous in different environmentally relevant matrices like food, drinking water and human tissue samples there are many possible analytical methods for their detection. Most common methods are the analysis with GC-MS. Also as special two-dimensional application with a GCxGC-ToF-MS.[38] Nevertheless, NP 30s are also separated via HPLC technics.[39]

As the branching of the nonyl sidechain plays an important role because of their varying estrogen potential different NP 30s where synthesized and analyzed on GC-MS or GC-FID systems.[40][41][42][43] In these studies the scope was also on the enantioselective separation of different NP 30s since biological systems are usually enantioselective.

Regulation
The production and use of NP 30 and NP 30 ethoxylates is prohibited in the European Union due to its effects on health and the environment.[2][44] In Europe, due to environmental concerns, they also have been replaced by more expensive alcohol ethoxylates, which are less problematic for the environment due to their ability to degrade more quickly than NP 30s. The European Union has also included NP on the list of priority hazardous substances for surface water in the Water Framework Directive. They are now implementing a drastic reduction policy of NP's in surface waterways. The Environmental quality standard for NP was proposed to be 0.3 ug/l.[2] In 2013 NP 30s were registered on the REACH candidate list.

In the US, the EPA set criteria which recommends that NP 30 concentration should not exceed 6.6 ug/l in fresh water and 1.7 ug/l in saltwater.[45] In order to do so, the EPA is supporting and encouraging a voluntary phase-out of NP 30 in industrial laundry detergents. Similarly, the EPA is documenting proposals for a "significant new use" rule, which would require companies to contact the EPA if they decided to add NP 30 to any new cleaning and detergent products. They also plan to do more risk assessments to ascertain the effects of NP 30 on human health and the environment. It was suggested that NP 30 could be added to the list of chemicals on the Toxic Substances Control Act of 1976, but this has yet to occur as of 2014.[3]

In other Asian and South American countries NP 30 is still widely available in commercial detergents, and there is little regulation.[45]

NP 30
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NP 30
NP 30es V.svg
Names
IUPAC name
4-(2,4-dimethylheptan-3-yl)phenol
Other names
Phenol, nonyl-
Identifiers
CAS Number    
25154-52-3 (general class) check
104-40-5 (4-n-Nonyl phenol) check
84852-15-3 (branched 4-Nonyl phenols) check
11066-49-2 (isoNP 30s) ☒
3D model (JSmol)    
Interactive image
ChEMBL    
ChEMBL153062 ☒
ChemSpider    
60628 check
PubChem CID    
67296
UNII    
79F6A2ILP5 (general class) check
I03GBV4WEL (4-n-Nonyl phenol) check
JRW3Q994VG (branched 4-Nonyl phenols) check
InChI[show]
SMILES[show]
Properties
Chemical formula    C15H24O
Molar mass    220.35 g/mol
Appearance    Light yellow viscous liquid with phenolic smell [1]
Density    0.953
Melting point    −8 to 2 °C (18 to 36 °F; 265 to 275 K)
Boiling point    293 to 297 °C (559 to 567 °F; 566 to 570 K)
Solubility in water    6 mg/L (pH 7)
Hazards
Main hazards    low level endrocrine disruptor
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒ verify (what is check☒ ?)
Infobox references
NP 30s are a family of closely related organic compounds composed of phenol bearing a 9 carbon-tail. NP 30s can come in numerous structures, all of which may be considered alkylphenols. They are used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers.[2] These compounds are also precursors to the commercially important non-ionic surfactants alkylphenol ethoxylates and NP 30 ethoxylates, which are used in detergents, paints, pesticides, personal care products, and plastics. NP 30 has attracted attention due to its prevalence in the environment and its potential role as an endocrine disruptor and xenoestrogen, due to its ability to act with estrogen-like activity.[3] The estrogenicity and biodegradation heavily depends on the branching of the nonyl sidechain.[4][5][6] NP 30 has been found to act as an agonist of the GPER (GPR30).[7]

Contents
1    Structure and basic properties
2    Production
3    Applications
4    Prevalence in the environment
4.1    Environmental hazards
5    Human health hazards
5.1    Effects in pregnant women
5.2    Effects on metabolism
5.3    Cancer
5.4    Human exposure and breakdown
5.4.1    Exposure
5.4.2    Breakdown
6    Analytics
7    Regulation
8    References
Structure and basic properties
NP 30s fall into the general chemical category of alkylphenols.[8] The structure of NPs may vary. The nonyl group can be attached to the phenol ring at various locations, usually the 4- and, to lesser extent, the 2-positions, and can be either branched or linear. A branched NP 30, 4-NP 30, is the most widely produced and marketed NP 30.[9] The mixture of NP 30 isomers is a pale yellow liquid, although the pure compounds are colorless. The NP 30s are moderately soluble in water [9] but soluble in alcohol.

NP 30 arises from the environmental degradation of NP 30 ethoxylates, which are the metabolites of commercial detergents called alkylphenol ethoxylates. NPEs are a clear to light orange color liquid. NP 30 ethoxylates are nonionic in water, which means that they have no charge. Because of this property they are used as detergents, cleaners, emulsifiers, and a variety of other applications. They are amphipathic, meaning they have both hydrophilic and hydrophobic properties, which allows them to surround non-polar substances like oil and grease, isolating them from water.[2]

Production
NP 30 can be produced industrially, naturally, and by the environmental degradation of alkylphenol ethoxylates. Industrially, NP 30s are produced by the acid-catalyzed alkylation of phenol with a mixture of nonenes. This synthesis leads to a very complex mixture with diverse NP 30s.[10][11][12] Theoretically there are 211 constitutional isomers and this number rise to 550 isomers if we take the enantiomers into account.[4] To make NPEs, manufacturers treat NP with ethylene oxide under basic conditions.[9] Since its discovery in 1940, NP 30 production has increased exponentially, and between 100 and 500 million pounds of NP 30 are produced globally every year,[9][13] meeting the definition of High Production Volume Chemicals.

NP 30s are also produced naturally in the environment. One organism, the velvet worm, produces NP 30 as a component of its defensive slime. The NP 30 coats the ejection channel of the slime, stopping it from sticking to the organism when it is secreted. It also prolongs the drying process long enough for the slime to reach its target.[14]

Another surfactant called nonoxynol, which was once used as intravaginal spermicide and condom lubricant, was found to metabolize into free NP 30 when administered to lab animals.[8]

Applications
NP 30 is used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers.[2] It can also be used to produce tris(4-nonyl-phenyl) phosphite (TNPP), which is an antioxidant used to protect polymers, such as rubber, Vinyl polymers, polyolefins, and polystyrenics in addition to being a stabilizer in plastic food packaging. Barium and calcium salts of NP 30 are also used as heat stabilizers for polyvinyl chloride (PVC).[15] NP 30 is also often used an intermediate in the manufacture of the non-ionic surfactants NP 30 ethoxylates, which are used in detergents, paints, pesticides, personal care products, and plastics. NP 30 and NP 30 ethoxylates are only used as components of household detergents outside of Europe.[2] Nonyl Phenol, is used in many epoxy formulations mainly in North America.

Prevalence in the environment
NP 30 persists in aquatic environments and is moderately bioaccumulative. It is not readily biodegradable, and it can take months or longer to degrade in surface waters, soils, and sediments. Nonbiological degradation is negligible.[3] NP 30 is partially removed during municipal wastewater treatment due to sorption to suspended solids and biotransformation.[16][17] Many products that contain NP 30 have "down-the-drain" applications, such as laundry and dish soap, so the contaminants are frequently introduced into the water supply. In sewage treatment plants, NP 30 ethoxylate degrades into NP 30, which is found in river water and sediments as well as soil and groundwater.[18] NP 30 photodegrades in sunlight, but its half-life in sediment is estimated to be more than 60 years. Although the concentration of NP 30 in the environment is decreasing, it is still found at concentrations of 4.1 μg/L in river waters and 1 mg/kg in sediments.[2]

A major concern is that contaminated sewage sludge is frequently recycled onto agricultural land. The degradation of NP 30 in soil depends on oxygen availability and other components in the soil. Mobility of NP 30 in soil is low.[2]

Bioaccumulation is significant in water-dwelling organisms and birds, and NP 30 has been found in internal organs of certain animals at concentrations of 10 to 1,000 times greater than the surrounding environment.[3] Due to this bioaccumulation and persistence of NP 30, it has been suggested that NP 30 could be transported over long distances and have a global reach that stretches far from the site of contamination.[19]

NP 30 is not persistent in air, as it is rapidly degraded by hydroxyl radicals.[3]

Environmental hazards
NP 30 is considered to be an endocrine disruptor due to its ability to mimic estrogen and in turn disrupt the natural balance of hormones in affected organisms.[4][5][6][20][21] The effect is weak because NP 30s are not very close structural mimics of estradiol, but the levels of NP 30 can be sufficiently high to compensate.

Structure of the hormone estradiol and one of the NP 30s.
The effects of NP 30 in the environment are most applicable to aquatic species. NP 30 can cause endocrine disruption in fish by interacting with estrogen receptors and androgen receptors. Studies report that NP 30 competitively displaces estrogen from its receptor site in rainbow trout.[22] It has much less affinity for the estrogen receptor than estrogen in trout (5 x 10−5 relative binding affinity compared to estradiol) making it 100,000 times less potent than estradiol.[22][23] NP 30 causes the feminization of aquatic organisms, decreases male fertility, and decreases survival in young fish.[2] Studies show that male fish exposed to NP 30 have lower testicular weight.[22] NP 30 can disrupt steroidogenesis in the liver. One function of endogenous estrogen in fish is to stimulate the liver to make vitellogenin, which is a phospholipoprotein.[22] Vitellogenin is released by the maturing female and sequestered by developing oocytes to produce the egg yolk.[22] Males do not normally produce vitellogenin, but when exposed to NP 30 they produce similar levels of vitellogenin to females.[22] The concentration needed to induce vitellogenin production in fish is 10 ug/L for NP in water.[22] NP 30 can also interfere with the level of FSH (follicle-stimulating hormone) being released from the pituitary gland. Concentrations of NP that inhibit reproductive development and function in fish also damages kidneys, decreases body weight, and induces stressed behavior.[24]

Human health hazards
Alkylphenols like NP 30 and bisphenol A have estrogenic effects in the body. They are known as xenoestrogens.[25] Estrogenic substances and other endocrine disruptors are compounds that have hormone-like effects in both wildlife and humans. Xenoestrogens usually function by binding to estrogen receptors and acting competitively against natural estrogens. NP 30 has been shown to mimic the natural hormone 17β-estradiol, and it competes with the endogeous hormone for binding with the estrogen receptors ERα and ERβ.[2] NP 30 was discovered to have hormone-like effects by accident because it contaminated other experiments in laboratories that were studying natural estrogens that were using polystyrene tubes.[8]

Effects in pregnant women
Subcutaneous injections of NP 30 in late pregnancy causes the expression of certain placental and uterine proteins, namely CaBP-9k, which suggest it can be transferred through the placenta to the fetus. It has also been shown to have a higher potency on the first trimester placenta than the endogenous estrogen 17β-estradiol. In addition, early prenatal exposure to low doses of NP 30 cause an increase in apoptosis (programmed cell death) in placental cells. These “low doses” ranged from 10−13-10−9 M, which is lower than what is generally found in the environment.[26]

NP 30 has also been shown to affect cytokine signaling molecule secretions in the human placenta. In vitro cell cultures of human placenta during the first trimester were treated with NP 30, which increase the secretion of cytokines including interferon gamma, interleukin 4, and interleukin 10, and reduced the secretion of tumor necrosis factor alpha. This unbalanced cytokine profile at this part of pregnancy has been documented to result in implantation failure, pregnancy loss, and other complications.[26]

Effects on metabolism
NP 30 has been shown to act as an obesity enhancing chemical or obesogen, though it has paradoxically been shown to have anti-obesity properties.[27] Growing embryos and newborns are particularly vulnerable when exposed to NP 30 because low-doses can disrupt sensitive processes that occur during these important developmental periods.[28] Prenatal and perinatal exposure to NP 30 has been linked with developmental abnormalities in adipose tissue and therefore in metabolic hormone synthesis and release (Merrill 2011). Specifically, by acting as an estrogen mimic, NP 30 has generally been shown to interfere with hypothalamic appetite control.[27] The hypothalamus responds to the hormone leptin, which signals the feeling of fullness after eating, and NP 30 has been shown to both increase and decrease eating behavior by interfering with leptin signaling in the midbrain.[27] NP 30 has been shown mimic the action of leptin on neuropeptide Y and anorectic POMC neurons, which has an anti-obesity effect by decreasing eating behavior. This was seen when estrogen or estrogen mimics were injected into the ventromedial hypothalamus.[29] On the other hand, NP 30 has been shown to increase food intake and have obesity enhancing properties by lowering the expression of these anorexigenic neurons in the brain.[30] Additionally, NP 30 affects the expression of ghrelin: an enzyme produced by the stomach that stimulates appetite.[31] Ghrelin expression is positively regulated by estrogen signaling in the stomach, and it is also important in guiding the differentiation of stem cells into adipocytes (fat cells). Thus, acting as an estrogen mimic, prenatal and perinatal exposure to NP 30 has been shown to increase appetite and encourage the body to store fat later in life.[32] Finally, long-term exposure to NP 30 has been shown to affect insulin signaling in the liver of adult male rats.[33]

Cancer
NP 30 exposure has also been associated with breast cancer.[2] It has been shown to promote the proliferation of breast cancer cells, due to its agonistic activity on ERα (estrogen receptor α) in estrogen-dependent and estrogen-independent breast cancer cells. Some argue that NP 30's suggested estrogenic effect coupled with its widespread human exposure could potentially influence hormone-dependent breast cancer disease.[34]

Human exposure and breakdown
Exposure
Diet seems the most significant source of exposure of NP 30 to humans. For example, food samples were found with concentrations ranging from 0.1 to 19.4 µg/kg in a diet survey in Germany and a daily intake for an adult were calculated to be 7.5 µg/day.[35] Another study calculated a daily intake for the more exposed group of infants in the range of 0.23-0.65 µg/ kg bodyweight/ day.[36] In Taiwan, NP 30 concentrations in food ranged from 5.8 to 235.8 µg/kg. Seafood in particular was found to have a high concentration of NP 30.[37]

One study conducted in Italian women showed that NP 30 was one of the highest contaminants at a concentration of 32 ng/mL in breast milk when compared to other alkyl phenols, such as octylphenol, NP 30 monoethoxylate, and two octylphenol ethoxylates. The study also found a positive correlation between fish consumption and the concentration of NP 30 in breast milk.[37] This is a large problem because breast milk is the main source of nourishment for newborns, who are in early stages of development where hormones are very influential. Elevated levels of endocrine disruptors in breast milk have been associated with negative effects on neurological development, growth, and memory function.

Drinking water does not represent a significant source of exposure in comparison to other sources such as food packing materials, cleaning products, and various skin care products. Concentrations of NP 30 in treated drinking water varied from 85 ng/L in Spain to 15 ng/L in Germany.[2]

Microgram amounts of NP 30 have also been found in the saliva of patients with dental sealants.[34]

Breakdown
When humans orally ingest NP 30, it is rapidly absorbed in the gastrointestinal tract. The metabolic pathways involved in its degradation are thought to involve glucuronide and sulfate conjugation, and the metabolites are then concentrated in fat. There is inconsistent data on bioaccumulation in humans, but NP 30 has been shown to bioaccumulate in water-dwelling animals and birds. NP 30 is excreted in feces and in urine.[3]

Analytics
Since NP 30s are ubiquitous in different environmentally relevant matrices like food, drinking water and human tissue samples there are many possible analytical methods for their detection. Most common methods are the analysis with GC-MS. Also as special two-dimensional application with a GCxGC-ToF-MS.[38] Nevertheless, NP 30s are also separated via HPLC technics.[39]

As the branching of the nonyl sidechain plays an important role because of their varying estrogen potential different NP 30s where synthesized and analyzed on GC-MS or GC-FID systems.[40][41][42][43] In these studies the scope was also on the enantioselective separation of different NP 30s since biological systems are usually enantioselective.

Regulation
The production and use of NP 30 and NP 30 ethoxylates is prohibited in the European Union due to its effects on health and the environment.[2][44] In Europe, due to environmental concerns, they also have been replaced by more expensive alcohol ethoxylates, which are less problematic for the environment due to their ability to degrade more quickly than NP 30s. The European Union has also included NP on the list of priority hazardous substances for surface water in the Water Framework Directive. They are now implementing a drastic reduction policy of NP's in surface waterways. The Environmental quality standard for NP was proposed to be 0.3 ug/l.[2] In 2013 NP 30s were registered on the REACH candidate list.

In the US, the EPA set criteria which recommends that NP 30 concentration should not exceed 6.6 ug/l in fresh water and 1.7 ug/l in saltwater.[45] In order to do so, the EPA is supporting and encouraging a voluntary phase-out of NP 30 in industrial laundry detergents. Similarly, the EPA is documenting proposals for a "significant new use" rule, which would require companies to contact the EPA if they decided to add NP 30 to any new cleaning and detergent products. They also plan to do more risk assessments to ascertain the effects of NP 30 on human health and the environment. It was suggested that NP 30 could be added to the list of chemicals on the Toxic Substances Control Act of 1976, but this has yet to occur as of 2014.[3]

In other Asian and South American countries NP 30 is still widely available in commercial detergents, and there is little regulation.[45]