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(Z,Z)-9,12-Octadecadienoic acid (FDB012760)

Record Information
Version1.0
Creation date2010-04-08 22:10:21 UTC
Update date2019-11-26 03:07:33 UTC
Primary IDFDB012760
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(Z,Z)-9,12-Octadecadienoic acid
DescriptionConstituent of most vegetable oils and animal fats. The Fe salt is the major component of metallic drier compositions used to line food cans Linoleic acid is one of two essential fatty acids that humans and other animals must ingest for good health, because the body requires them for various biological processes, but cannot synthesize them from other food components. (Z,Z)-9,12-Octadecadienoic acid is found in many foods, some of which are green bean, cloves, kumquat, and pecan nut.
CAS Number60-33-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP7.06ALOGPS
logP6.42ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity88.52 m³·mol⁻¹ChemAxon
Polarizability35.41 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H32O2
IUPAC name(9E,12Z)-octadeca-9,12-dienoic acid
InChI IdentifierInChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9+
InChI KeyOYHQOLUKZRVURQ-IXWMQOLASA-N
Isomeric SMILES[H]\C(CCCCC)=C(/[H])C\C([H])=C(/[H])CCCCCCCC(O)=O
Average Molecular Weight280.4455
Monoisotopic Molecular Weight280.240230268
Classification
Description Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 77.09%; H 11.50%; O 11.41%DFC
Melting PointMp -5°DFC
Boiling PointBp0.02 129°DFC
Experimental Water SolubilityNot Available
Experimental logP7.05SANGSTER (1993)
Experimental pKa4.77
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd254 0.9DFC
Refractive Indexn20D 1.4697DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(Z,Z)-9,12-Octadecadienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0007-8950000000-f63c2f7a4fb796f5b2d7Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-8bdf8d54a29f734942422018-04-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0239-4590000000-fc68aa6b94e2557137752018-04-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rf-9830000000-8617b3536d6af2a7f35f2018-04-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f1e9e4b543f7d4f48bf82018-04-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0090000000-665523c6142ff4e39c962018-04-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-dca36a25ad7519d500c32018-04-06View Spectrum
NMRNot Available
ChemSpider ID4444105
ChEMBL IDCHEMBL267476
KEGG Compound IDC01595
Pubchem Compound ID5280450
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00673
CRC / DFC (Dictionary of Food Compounds) IDHDX10-F:HKR32-G
EAFUS ID2056
Dr. Duke IDLINOLEIC-ACID|OCTADECA-9,12-DIENOIC-ACID
BIGG ID37956
KNApSAcK IDNot Available
HET IDEIC
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1045901
SuperScent IDNot Available
Wikipedia IDLinoleic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
5alpha-reductase inhibitor50781 An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone.DUKE
anti acne50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti alopecic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti anaphylactic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti androgenic35497 A compound which inhibits or antagonises the biosynthesis or actions of androgens.DUKE
anti arteriosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti arthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti coronary52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti eczemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti fibrinolyticDUKE
anti granularDUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukotriene-D435222 A substance that diminishes the rate of a chemical reaction.DUKE
anti menorrhagic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti monosodium-glutamateDUKE
anti prostatiticDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
comedolyticDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hypocholesterolemicDUKE
immunomodulator50846 Biologically active substance whose activity affects or plays a role in the functioning of the immune system.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
metastaticDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
propecicDUKE
Enzymes
NameGene NameUniProt ID
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
Cytochrome P450 2D6CYP2D6Q6NWU0
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Cytosolic acyl coenzyme A thioester hydrolaseACOT7O00154
Acyl-coenzyme A thioesterase 2, mitochondrialACOT2P49753
Acyl-coenzyme A thioesterase 4ACOT4Q8N9L9
Acyl-coenzyme A thioesterase 8ACOT8O14734
Acyl-coenzyme A thioesterase 1ACOT1Q86TX2
Pathways
NameSMPDB LinkKEGG Link
Alpha Linolenic Acid and Linoleic Acid MetabolismSMP00018 map00592
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
faint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).