PRODUCTS

DIENOIC ACID

Low dienoic acid content of the tissues of rats has been produced in two ways: (a) withdrawal of essential fatty acid from the diet, and (b) exclusion of pyridoxine or thiamine from the diet or severe restriction of food (caloric deficiency).

By the first method dienoic acid content of the tissues fell to lower levels, and typical symptoms of the deficiency were produced. By the second procedure, the fall was more rapid in the acute vitamin deficiencies but no symptoms characteristic of linoleic acid deficiency occurred. A similar but less rapid course was followed in caloric restriction.

CAS No.: 626-99-3
EC No.: 210-976-1

Synonyms:
DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; 2,4-Pentadienoic acid; 626-99-3; Penta-2,4-dienoic acid; (E)-penta-2,4-dienoic acid; TRANS-2,4-PENTADIENOIC ACID; (2E)-2,4-Pentadienoic acid; 21651-12-7; 1,3-Butadiene-1-carboxylic acid; (2E)-penta-2,4-dienoic acid; (E)-2,4-Pentadienoic acid; beta-vinyl acrylic acid; C5:2n-1,3; 2,4-Pentadienoic acid, 97%, stabilized; pentadienoic acid; 1-Carboxybutadiene; EINECS 210-976-1; bet.-Vinylacrylic acid; AI3-28013; .beta.-Vinylacrylic acid; penta-2,4-dienoic acids; butadiene-1-carboxylic acid; CHEBI:35964; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; CHEBI:37331; 1,3-butadiene-1-carboxylic acids; but-1,3-diene-1-carboxylic acid; .alpha.,.gamma.-Pentadienoic acid; but-1,3-diene-1-carboxylic acids; BCP21342; ZINC1747122; LMFA01030099; MFCD00014017; NSC 16628; AKOS015919372; BP-21439; 2,4-Pentadienoic acid, >=97.0% (T); AB0052353; Z4964; M-8665; 4H-THIENO[3,2-C]CHROMENE-2-CARBOXYLICACID; W-200033; Q27117106; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; (9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid; (9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoate; 13(S)-HPODE; 13S-Hydroperoxy-9Z,11E-octadecadienoic acid; (2E)-Penta-2,4-dienoic acid; (2E)-2,4-Pentadienoic acid [ACD/IUPAC Name]; (2E)-2,4-Pentadiensäure [German] [ACD/IUPAC Name]; (E)-penta-2,4-dienoic acid; 1,3-Butadiene-1-carboxylic acid; 1739248; 2,4-Pentadienoic acid [ACD/IUPAC Name]; 2,4-Pentadienoic acid, (2E)- [ACD/Index Name]; 210-976-1 [EINECS], 626-99-3 [RN]; Acide (2E)-2,4-pentadiénoïque [French] [ACD/IUPAC Name]; MFCD00014017 [MDL number]; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; Penta-2,4-dienoic acid; TRANS-2,4-PENTADIENOIC ACID; "(2E)-PENTA-2,4-DIENOIC ACID"; "(E)-2,4-PENTADIENOIC ACID"; "2,4-PENTADIENOIC ACID"; "PENTA-2,4-DIENOIC ACID"; (2E)-2,4-PentadienoicAcid; (E)-1,3-Butadiene-1-carboxylic acid; (E)-2,4-Pentadienoic acid; (Z)-Penta-2,4-dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; ?-Vinylacrylic acid; [626-99-3]; 1,3-Butadiene-1-carboxylic acid| 1-Carboxybutadiene| NSC 16628| ß; Vinylacrylic acid; 1,3-Butadiene-1-carboxylicacid; 1-[2-(2-Hydroxyethoxy)Ethyl]Piperidine; 1720083 [Beilstein]; 1-Carboxybutadiene; 2,4-pentadienoic acid, 97%, stabilized; 2,4-Pentadienoic acid,(2E)-; 21651-12-7 [RN]; 6378-88-7 [RN]; Butadiene-1-carboxylic acid; MFCD19159875; NSC 16628; penta-2,4-dienoic acid; penta-???2,???4-???dienoic acid; pentadienoic acid; trans-1-Carboxybutadiene; TRANS-2,4-PENTADIENOIC ACID, STABILIZED WITH 1% HYDROQUINONE; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; α,γ-Pentadienoic acid; β-vinyl acrylic acid; β-Vinylacrylic acid; 5-Phenylpenta-2,4-dienoic acid; 1552-94-9; (2E,4E)-5-phenylpenta-2,4-dienoic acid; 5-Phenyl-2,4-pentadienoic acid; JUAREZIC ACID; 2,4-Pentadienoic acid, 5-phenyl-; cinnamylideneacetic acid; 28010-12-0; 2,4-Pentadienoicacid, 5-phenyl-, (2E,4E)-; (E,E)-cinnamylideneacetic acid; MFCD00014018; (2E,4E)-5-phenyl-2,4-pentadienoic acid; beta-Styrylacrylic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; cinnamylidene acetic acid; 38446-98-9; NSC 1778; EINECS 216-298-2; NSC 63972; 5-PHENYLPENTA-2,4-DIENOICACID; NSC 109408; Spectrum5_000481; Penta-2,4-dienoic acid, 5-phenyl-, (E,E)-; BSPBio_002523; SPECTRUM203008; 4-PHENYL-1,3-BUTADIENE-1-CARBOXYLIC ACID; CHEMBL1095566; 5-Phenylpenta-2,4-diecoic acid; NSC1778; CHEBI:108600; 5-Phenyl-penta-2,4-dienoic acid; 185152-35-6; 5-phenyl-penta-2e,4e-dienoic acid; HY-N7129; NSC-1778; NSC50789; ZINC1577023; CCG-40050; NSC-50789; s3978; STL570453; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; 2,4-Pentadienoic acid, 5-phenyl-,; 5-phenylpenta-(2e,4e)-dienoic acid; AKOS000304438; SDCCGMLS-0066886.P001; NCGC00095798-01; NCGC00095798-02; AS-19080; (2Z,4E)-5-Phenyl-2,4-pentadienoic acid; (2E,4E)-5-phenyl-penta-2,4-dienoic acid; CS-0030694; P2422; ST50827552, X4370; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; SR-05000002408; J-009185; J-507259; J-515930; SR-05000002408-1; BRD-K12345912-001-02-3; BRD-K12345912-001-03-1; 2,4-Pentadienoic acid, 5-phenyl- (VAN) (8CI)(9CI); DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; 2,4-Pentadienoic acid; 626-99-3; Penta-2,4-dienoic acid; (E)-penta-2,4-dienoic acid; TRANS-2,4-PENTADIENOIC ACID; (2E)-2,4-Pentadienoic acid; 21651-12-7; 1,3-Butadiene-1-carboxylic acid; (2E)-penta-2,4-dienoic acid; (E)-2,4-Pentadienoic acid; beta-vinyl acrylic acid; C5:2n-1,3; 2,4-Pentadienoic acid, 97%, stabilized; pentadienoic acid; 1-Carboxybutadiene; EINECS 210-976-1; bet.-Vinylacrylic acid; AI3-28013; .beta.-Vinylacrylic acid; penta-2,4-dienoic acids; butadiene-1-carboxylic acid; CHEBI:35964; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; CHEBI:37331; 1,3-butadiene-1-carboxylic acids; but-1,3-diene-1-carboxylic acid; .alpha.,.gamma.-Pentadienoic acid; but-1,3-diene-1-carboxylic acids; BCP21342; ZINC1747122; LMFA01030099; MFCD00014017; NSC 16628; AKOS015919372; BP-21439; 2,4-Pentadienoic acid, >=97.0% (T); AB0052353; Z4964; M-8665; 4H-THIENO[3,2-C]CHROMENE-2-CARBOXYLICACID; W-200033; Q27117106; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; (9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid; (9Z,11E)-(13S)-13-Hydroperoxyoctadeca-9,11-dienoate; 13(S)-HPODE; 13S-Hydroperoxy-9Z,11E-octadecadienoic acid; (2E)-Penta-2,4-dienoic acid; (2E)-2,4-Pentadienoic acid [ACD/IUPAC Name]; (2E)-2,4-Pentadiensäure [German] [ACD/IUPAC Name]; (E)-penta-2,4-dienoic acid; 1,3-Butadiene-1-carboxylic acid; 1739248; 2,4-Pentadienoic acid [ACD/IUPAC Name]; 2,4-Pentadienoic acid, (2E)- [ACD/Index Name]; 210-976-1 [EINECS], 626-99-3 [RN]; Acide (2E)-2,4-pentadiénoïque [French] [ACD/IUPAC Name]; MFCD00014017 [MDL number]; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; Penta-2,4-dienoic acid; TRANS-2,4-PENTADIENOIC ACID; "(2E)-PENTA-2,4-DIENOIC ACID"; "(E)-2,4-PENTADIENOIC ACID"; "2,4-PENTADIENOIC ACID"; "PENTA-2,4-DIENOIC ACID"; (2E)-2,4-PentadienoicAcid; (E)-1,3-Butadiene-1-carboxylic acid; (E)-2,4-Pentadienoic acid; (Z)-Penta-2,4-dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; ?-Vinylacrylic acid; [626-99-3]; 1,3-Butadiene-1-carboxylic acid| 1-Carboxybutadiene| NSC 16628| ß; Vinylacrylic acid; 1,3-Butadiene-1-carboxylicacid; 1-[2-(2-Hydroxyethoxy)Ethyl]Piperidine; 1720083 [Beilstein]; 1-Carboxybutadiene; 2,4-pentadienoic acid, 97%, stabilized; 2,4-Pentadienoic acid,(2E)-; 21651-12-7 [RN]; 6378-88-7 [RN]; Butadiene-1-carboxylic acid; MFCD19159875; NSC 16628; penta-2,4-dienoic acid; penta-???2,???4-???dienoic acid; pentadienoic acid; trans-1-Carboxybutadiene; TRANS-2,4-PENTADIENOIC ACID, STABILIZED WITH 1% HYDROQUINONE; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; α,γ-Pentadienoic acid; β-vinyl acrylic acid; β-Vinylacrylic acid; 5-Phenylpenta-2,4-dienoic acid; 1552-94-9; (2E,4E)-5-phenylpenta-2,4-dienoic acid; 5-Phenyl-2,4-pentadienoic acid; JUAREZIC ACID; 2,4-Pentadienoic acid, 5-phenyl-; cinnamylideneacetic acid; 28010-12-0; 2,4-Pentadienoicacid, 5-phenyl-, (2E,4E)-; (E,E)-cinnamylideneacetic acid; MFCD00014018; (2E,4E)-5-phenyl-2,4-pentadienoic acid; beta-Styrylacrylic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; cinnamylidene acetic acid; 38446-98-9; NSC 1778; EINECS 216-298-2; NSC 63972; 5-PHENYLPENTA-2,4-DIENOICACID; NSC 109408; Spectrum5_000481; Penta-2,4-dienoic acid, 5-phenyl-, (E,E)-; BSPBio_002523; SPECTRUM203008; 4-PHENYL-1,3-BUTADIENE-1-CARBOXYLIC ACID; CHEMBL1095566; 5-Phenylpenta-2,4-diecoic acid; NSC1778; CHEBI:108600; 5-Phenyl-penta-2,4-dienoic acid; 185152-35-6; 5-phenyl-penta-2e,4e-dienoic acid; HY-N7129; NSC-1778; NSC50789; ZINC1577023; CCG-40050; NSC-50789; s3978; STL570453; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; 2,4-Pentadienoic acid, 5-phenyl-,; 5-phenylpenta-(2e,4e)-dienoic acid; AKOS000304438; SDCCGMLS-0066886.P001; NCGC00095798-01; NCGC00095798-02; AS-19080; (2Z,4E)-5-Phenyl-2,4-pentadienoic acid; (2E,4E)-5-phenyl-penta-2,4-dienoic acid; CS-0030694; P2422; ST50827552, X4370; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid; SR-05000002408; J-009185; J-507259; J-515930; SR-05000002408-1; BRD-K12345912-001-02-3; BRD-K12345912-001-03-1; 2,4-Pentadienoic acid, 5-phenyl- (VAN) (8CI)(9CI); DIENOIC ACID; DİENOİK ASİT; dienoik asit; Dienoic acid

DIENOIC ACID

Abstract
Low dienoic acid content of the tissues of rats has been produced in two ways: (a) withdrawal of essential fatty acid from the diet, and (b) exclusion of pyridoxine or thiamine from the diet or severe restriction of food (caloric deficiency).

Since no essential difference in dienoic acid content of the tissues of rats was found under these several dietary conditions, it was concluded that pyridoxine under the conditions of these experiments does not exert a special supplementary action in the production or conservation of polyenoic fatty acids.

Decadienoic acid
Decadienoic acid is any mono-carboxylic acid with an unbranched chain of ten carbon atoms, connected by seven single bonds and two double bonds. That is, any compound with formula HO(O=)C–(CH

2. A salt or ester of such an acid is called a decadienoate.

These compounds are unsaturated fatty acids, although they are rarely found in natural lipids (fats, waxes, phospholipids, etc.).

Isomers
Positional isomerism
The various decadienoic acid isomers can be distinguished by the positions of their double bonds along the chain. A double bond is said to be at position k if it connects carbons k and k+1 of the chain, counting from 1 at the carboxyl end. The positions are x+2 and x+y+4 for the first type (21 possibilities), and r+2 and r+3 for the second type (7 possibilities). The systematic name of the acid is formed by prefixing the positions of the double bonds to "decadienoic" or inserting them before the "dienoic" suffix. as in "4,7-decadienoic" or "dec-4,7-dienoic" for HO(O=)C–(–CH

Geometric isomerism
Decadienoic acids with the two double bonds in the same positions can be further distinguished by the geometry of the adjacent single bonds.

Each double bond that is adjacent to two single C–C bonds can be in two cis-trans conformations, namely with those two single bonds on the same side (cis or Z) or opposite sides (trans or E) of the double bond's plane.

If the two double bonds overlap forming an allene core C=C=C surrounded by two single C–C bonds, the chain fragments C–C=C=C and C=C=C–C will lie on perpendicular planes. Then, instead of cis-trans isomers, there will be two axial isomers distinguished by the handedness of the C–C=C=C–C "screw". They are denoted by the letters R and S.

Double bonds at the very end of the chain (–C=CH
2 or -C=C=CH
2) will not cause geometric isomerism, because the two hydrogen atoms in the final carbon are symmetrically placed relative to the bond's plane. However, geometric isomerism may still occur at that position in derivative compounds where one or both terminal hydrogens are replaced by different groups.

Geometric isomerism raises the number of decadienoic acids with separate double bonds from 21 to 72, and of those with an allene core from 6 to 11.

Examples
Docadienoic acids that have received some attention include:

trans-2-cis-4-decadienoic acid, (2E,4Z) deca-2,4-dienoic acid (CAS 30361-33-2, Nikkaji J88.660B). It is about 8% of the fatty acids (per mole) of stillingia oil. The methyl ester is a flavoring agent (FEMA The propyl ester (CAS 3025-32-9, Nikkaji J309.441C, FDA D07SW1IHHP) is present in some extracts.
deca-(2E,4Z)-dienoic acid (CAS 544-48-9) The propyl ester (CAS 28316-62-3, FDA 2EEE2O3TE8) is a flavoring agent. The butyl ester (CAS 28369-24-6) is a flavor/fragrance agent. The ethyl ester (CAS 3025-30-7, Beilstein 1724176) is source of aroma of Bartlett pears; also present in fresh apple, Vitis sp., quince and Strychnos madagascariensis
deca-(2Z,4E)-dienoic acid (CAS 68676-77-7, Nikkaji J703.053C).
deca-(2Z,4Z)-dienoic acid. Propyl ester (CAS ??)
deca-4,8-dienoic acid (CAS 13159-49-4) Unspecified isomers present in some flavor extracts

Abstract
We analyzed the antimicrobial potential of a novel furan fatty acid, 7,10-epoxyoctadeca-7,9-dienoic acid (7,10-EODA) against methicillin-resistant and -sensitive S. aureus (MRSA and MSSA). The anti-staphylococcal activity of 7,10-EODA and its consequences on cell physiology was determined by disc diffusion, broth microdilution, and flow cytometry. Anti-virulence activity of 7,10-EODA was evaluated by bioassays. 7,10-EODA was anti-staphylococcal with minimum inhibitory concentration (MIC) range of 125-250 mg/L. 7,10-EODA exhibited a dose response and inhibited MRSA 01ST001 by 90.5% and ATCC 29213 (MSSA) by 85.3% at 125 mg/L. MIC of 7,10-EODA permeabilized >95 % of MRSA 01ST001 cells to small molecules. Sublethal dose of 7,10-EODA was non-toxic but markedly reduced the hemolytic, coagulase, and autolytic activities of MRSA and MSSA at 15.6 mg/L. The results provide a lead for the utilization of natural furan fatty acids as novel anti-MRSA agents.

2. A salt or ester of such an acid is called a decadienoate.

These compounds are unsaturated fatty acids, although they are rarely found in natural lipids (fats, waxes, phospholipids, etc.).

Geometric isomerism
Decadienoic acids with the two double bonds in the same positions can be further distinguished by the geometry of the adjacent single bonds.

Geometric isomerism raises the number of decadienoic acids with separate double bonds from 21 to 72, and of those with an allene core from 6 to 11.

Examples
Docadienoic acids that have received some attention include: