CITRAL

CAS NO: 5392-40-5

Synonyms:
Sitral; ;Citral;5392-40-5;trans-Citral;3,7-dimethylocta-2,6-dienal;geranialdehyde;(E)-Citral;Citral a;(2E)-3,7-dimethylocta-2,6-dienal;Lemsyn GB;alpha-Citral;(E)-Geranial;3,7-Dimethyl-2,6-octadienal;Geranaldehyde;Genanial;beta-Geranial;Citral alpha;Citral (natural);(E)-Neral;2,6-Octadienal, 3,7-dimethyl-, (E)-;CITRAL NATURAL;Caswell No. 221B;citral-b;FEMA Number 2303;Lemarome n;NCI-C56348;(E)-3,7-Dimethylocta-2,6-dienal;trans-3,7-Dimethyl-2,6-octadienal;UNII-758ZMW724E;FEMA No. 2303;CCRIS 1043;HSDB 993;CITRAL SINTETICO;2,6-Octadienal, 3,7-dimethyl-, (2E)-;2,6-Dimethyloctadien-2,6-al-8;3,7-Dimethyl-1,2,6-octadienal;cis-3,7-Dimethyl-2,6-octadienal;NSC 6170;3,7-Dimethyl-trans-2,6-octadienal;EINECS 205-476-5;EINECS 226-394-6;(E)-3,7-Dimethyl-2,6-octadienal;141-27-5;EPA Pesticide Chemical Code 040510;BRN 1721871;BRN 1721873;cis/trans-3,7-Dimethyl-2,6-octadienal;AI3-01011;AI3-28519;CHEBI:16980;Citral, mixture of cis and trans; NSC6170; WTEVQBCEXWBHNA-JXMROGBWSA-N; ST50308094; Citral, analytical standard; lemonal; 147060-73-9; Z-Citral; CHEBI:23316; Natural Citral; (Z)-3,7-Dimethyl-2,6-octadienal;MFCD00006997;cis,trans-Citral;(2Z)-3,7-Dimethyl-2,6-octadienal;.alpha.-Citral;3,6-octadienal;cis/trans Citral;;3,2,6-octadienal;Citral, cis + trans; AC1LCVGF;Citral, 95%;AC1Q1NUZ;AC1Q6POW;Citral Ex Litsea(Citral ); litsea cubeba oil terpeneless; SCHEMBL23073 ;3-01-00-03053 ;4-01-00-03569 ;GTPL6327; CHEMBL1080997; STOCK1N-24160; 3,7- dimethylocta-2,6-dienal; InChI=1/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7; MolPort-001-783-112;MolPort-003-909-614;WLN: VH1UY1&3Y1&U1;758ZMW724E;NSC-6170;ZINC1529208;BBL011666;SBB060834;STK802499;ZINC01529208;AKOS000119519;Citral, natural, >=96%, FCC, FG;EBD2204555; LMPR0102010003 ;LS41486 ;RP21648; RTR-037028; (2E)-3,7-dimethyl-octa-2,6-dienal;Citral, Vetec(TM) reagent grade, 94%;NCGC00091550-01;NCGC00091550-02;NCGC00091550-03;NCGC00091550-04;AJ-26578;AK116645;AN-21095;AN-23205;CJ-05166;CJ-23866;LP073605;LS-97778;OR011136;OR264090;(2E)-3,7-dimethyl-2,6-octadien-1-al;KB-234385; TL8003535; TR-037028;FT-0623954;FT-0623981; ST24028249; C01499;C15604; Citral, mixture of cis and trans, >=96%, FG;A829835 ;Q-200867;S14-1149;F0001-1403;UNII-T7EU0O9VPP component WTEVQBCEXWBHNA-JXMROGBWSA-N ;2,6-Octadienal,3,7-dimethyl-, reaction products with Et alc.; 1392408-16-0; 250599-19-0; 37350-34-8; 433282-33-8; 8022-94-4; 96680-15-8; geranialdehyde; citral; sitral; Citrale; Sitrale

Citral

Citral
Skeletal formula of geranial
Geranial
Ball-and-stick model of the geranial molecule
Skeletal formula of neral
Neral
Ball-and-stick model of the neral molecule
Names
IUPAC name
3,7-dimethylocta-2,6-dienal
Other names
citral
geranialdehyde
Identifiers
CAS Number    
5392-40-5 check
3D model (JSmol)    
Interactive image
Interactive image
3DMet    
B00306
ChEBI    
CHEBI:16980 check
ChEMBL    
ChEMBL1080997 check
ChemSpider    
553578 check
ECHA InfoCard    100.023.994 Edit this at Wikidata
EC Number    
226-394-6
IUPHAR/BPS    
6327
KEGG    
C01499 check
PubChem CID    
638011
RTECS number    
RG5075000
UNII    
T7EU0O9VPP check
UN number    2810
CompTox Dashboard (EPA)    
DTXSID6024836 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula    C10H16O
Molar mass    152.24 g/mol
Appearance    Pale yellow liquid
Odor    Lemon like
Density    0.893 g/cm3
Boiling point    229 °C (444 °F; 502 K)
Vapor pressure    0.22 mmHg (20 °C)
Magnetic susceptibility (χ)    −98.9×10−6 cm3/mol
Hazards
GHS pictograms    GHS07: Harmful
GHS Signal word    Warning
GHS hazard statements    H315, H317
GHS precautionary statements    P261, P264, P272, P280, P302+352, P321, P332+313, P333+313, P362, P363, P501
NFPA 704 (fire diamond)    
NFPA 704 four-colored diamond
100
Flash point    91 °C (196 °F; 364 K)
Related compounds
Related alkenals    
Citronellal
Methacrolein
trans-2-Methyl-2-butenal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Citral, or 3,7-dimethyl-2,6-octadienal or lemonal, is either a pair, or a mixture of terpenoids with the molecular formula C10H16O. The two compounds are geometric isomers. The E-isomer is known as geranial or citral A. The Z-isomer is known as neral or citral B.

Occurrence
Citral is present in the oils of several plants, including lemon myrtle (90–98%), Litsea citrata (90%), Litsea cubeba (70–85%), lemongrass (65–85%), lemon tea-tree (70–80%), Ocimum gratissimum (66.5%), Lindera citriodora (about 65%), Calypranthes parriculata (about 62%), petitgrain (36%), lemon verbena (30–35%), lemon ironbark (26%), lemon balm (11%), lime (6–9%), lemon (2–5%), and orange.[2][3][4]

Uses
Citral has a strong lemon (citrus) odor and is used as an aroma compound in perfumery. (Nerol, another perfumery compound, has a less intense but sweeter lemon odor.) In addition, Citral is used as a flavor and for fortifying lemon oil. It also has strong antimicrobial qualities,[5] and pheromonal effects in acari and insects.[6][7]

Citral is used in the synthesis of vitamin A, lycopene, ionone, and methylionone, to mask the smell of smoke.

Health and safety information
Two studies showed 1–1.7% of people to be allergic to citral, with allergies frequently reported.[citation needed] Citral on its own is strongly sensitizing to allergies; the International Fragrance Association recommends that citral only be used in association with substances that prevent a sensitizing effect.[citation needed] Citral has been extensively tested, with no known genotoxicity or carcinogenic effect.

EC Number: 226-394-6

Chemical and Physical Properties of Citral

Property Name    
Molecular Weight:    152.237 g/mol
Hydrogen Bond Donor Count:    0
Hydrogen Bond Acceptor Count:    1
Rotatable Bond Count:    4
Complexity:    171
Topological Polar Surface Area:    17.1 A^2
Monoisotopic Mass:    152.12 g/mol
Exact Mass:    152.12 g/mol
XLogP3-AA:    3
Compound Is Canonicalized:    true
Formal Charge:    0
Heavy Atom Count:    11
Defined Atom Stereocenter Count:    0
Undefined Atom Stereocenter Count:    0
Defined Bond Stereocenter Count:    1
Undefined Bond Stereocenter Count:    0
Isotope Atom Count:    0
Covalently-Bonded Unit Count:    1

Experimental Properties of Citral

Physical Description of Citral

Citral is a clear yellow colored liquid with a lemon-like odor. Less dense than water and insoluble in water. Toxic by ingestion. Used to make other chemicals.

Color of Citral
Mobile pale yellow liquid

Odor of Citral
Strong lemon odor

Citral (C10H16O), also called 3,7-dimethyl-2,6-octadienal, a pale yellow liquid, with a strong lemon odour, that occurs in the essential oils of plants. It is insoluble in water but soluble in ethanol (ethyl alcohol), diethyl ether, and mineral oil. It is used in perfumes and flavourings and in the manufacture of other chemicals. Chemically, citral is a mixture of two aldehydes that have the same molecular formula but different structures.

 Citral appears as a clear yellow colored liquid with a lemon-like odor. Less dense than water and insoluble in water. Toxic by ingestion. Used to make other chemicals.

Geranial is a monoterpenoid that is (2E,6E)-octa-2,6-dienal substituted by methyl groups at positions 3 and 7. It has a role as a plant metabolite and a volatile oil component. It is an enal, a monoterpenoid and a polyprenal.

Molecular Weight of Citral    152.23 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
XLogP3-AA of Citral    3    Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Hydrogen Bond Donor Count of Citral    0    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Hydrogen Bond Acceptor Count of Citral    1    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Rotatable Bond Count of Citral    4    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Exact Mass of Citral    152.120115 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Monoisotopic Mass of Citral    152.120115 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Topological Polar Surface Area of Citral 17.1 Ų    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Heavy Atom Count of Citral    11    Computed by PubChem
Formal Charge of Citral    0    Computed by PubChem
Complexity of Citral    171    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Isotope Atom Count of Citral    0    Computed by PubChem
Defined Atom Stereocenter Count of Citral    0    Computed by PubChem
Undefined Atom Stereocenter Count of Citral    0    Computed by PubChem
Defined Bond Stereocenter Count of Citral    1    Computed by PubChem
Undefined Bond Stereocenter Count of Citral    0    Computed by PubChem
Covalently-Bonded Unit Count of Citral    1    Computed by PubChem
Compound  of Citral Is Canonicalized    Yes

Citral appears as a clear yellow colored liquid with a lemon-like odor. Less dense than water and insoluble in water. Toxic by ingestion. Used to make other chemicals.

Citral (C10H16O), also called 3,7-dimethyl-2,6-octadienal, a pale yellow liquid, with a strong lemon odour, that occurs in the essential oils of plants. It is insoluble in water but soluble in ethanol (ethyl alcohol), diethyl ether, and mineral oil. It is used in perfumes and flavourings and in the manufacture of other chemicals. Chemically, citral is a mixture of two aldehydes that have the same molecular formula but different structures.

Lemongrass oil contains 70–80 percent citral, which may be isolated by distillation. Other natural sources include the oils of verbena and citronella. Citral can be synthesized from myrcene. Ionone and methylionone, made from citral, are used in perfumery; ionone is also converted into synthetic vitamin A.