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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:38:40 UTC
NP-MRD IDNP0000869
Secondary Accession NumbersNone
Natural Product Identification
Common NameElaidic acid
DescriptionElaidic acid is the major trans fat found in hydrogenated vegetable oils and occurs in small amounts in caprine and bovine milk (very roughly 0.1 % Of the fatty acids) [1] and some meats. It is the trans isomer of oleic acid. The name of the elaidinization reaction comes from elaidic acid. Elaidic acid increases CETP activity, which in turn raises VLDL and lowers HDL cholesterol. (Wiki).
Structure
Thumb
Synonyms
ValueSource
(9E)-Octadecenoic acidChEBI
(e)-Oleic acidChEBI
9-OCTADECENOIC ACIDChEBI
9-trans-Octadecenoic acidChEBI
Acide elaidiqueChEBI
D9-trans-Octadecenoic acidChEBI
ElaidinsaureChEBI
ElaidinsaeureChEBI
trans-9-Octadecenoic acidChEBI
trans-D9-Octadecenoic acidChEBI
trans-Delta(9)-Octadecenoic acidChEBI
trans-Elaidic acidChEBI
trans-Oleic acidChEBI
(9E)-OctadecenoateGenerator
(e)-OleateGenerator
9-OCTADECENOateGenerator
9-trans-OctadecenoateGenerator
D9-trans-OctadecenoateGenerator
trans-9-OctadecenoateGenerator
trans-D9-OctadecenoateGenerator
trans-delta(9)-OctadecenoateGenerator
trans-Δ(9)-octadecenoateGenerator
trans-Δ(9)-octadecenoic acidGenerator
trans-ElaidateGenerator
trans-OleateGenerator
ElaidateGenerator
FA(18:1(9E))HMDB
9-ElaidateHMDB
18:1 N-9HMDB
C18:1 N-9HMDB
Octadec-9-enoic acidHMDB
Octadec-9-enoateHMDB
9,10-OctadecenoateHMDB
9,10-Octadecenoic acidHMDB
Acid, 9-octadecenoicHMDB
9 Octadecenoic acidHMDB
(9E)-9-Octadecenoic acidHMDB
(e)-9-Octadecenoic acidHMDB
9-trans-Oleic acidHMDB
Elaidinic acidHMDB
delta9-trans-Octadecenoic acidHMDB
trans-delta9-Octadecenoic acidHMDB
trans-Δ9-octadecenoic acidHMDB
Δ9-trans-octadecenoic acidHMDB
Elaidic acidKEGG
Chemical FormulaC18H34O2
Average Mass282.4614 Da
Monoisotopic Mass282.25588 Da
IUPAC Name(9E)-octadec-9-enoic acid
Traditional Nameelaidic acid
CAS Registry Number112-79-8
SMILES
[H]\C(CCCCCCCC)=C(\[H])CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+
InChI KeyZQPPMHVWECSIRJ-MDZDMXLPSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agrimonia pilosaLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arnica montanaLOTUS Database
Bidens pilosaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Boswellia papyriferaLOTUS Database
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Consolida regalisLOTUS Database
Cynomorium songaricumLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Foeniculum vulgareLOTUS Database
Gallus gallusFooDB
Gryllotalpa orientalisLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Lilium longiflorumLOTUS Database
Macrococculus pomiferusLOTUS Database
Mangifera indicaLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Musa paradisiacaLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Panax ginsengKNApSAcK Database
Peperomia bracteataLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Portulaca oleraceaLOTUS Database
Punica granatumFooDB
Salmonella entericaLOTUS Database
Solanum tuberosumKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Serum)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain 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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point42 - 44 °CNot Available
Boiling Point360.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.012 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.78Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
logP7.68ALOGPS
logP6.78ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity87.4 m³·mol⁻¹ChemAxon
Polarizability37.64 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000573
DrugBank IDDB04224
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021621
KNApSAcK IDC00052377
Chemspider ID553123
KEGG Compound IDC01712
BioCyc IDNot Available
BiGG ID38213
Wikipedia LinkElaidic_acid
METLIN ID3406
PubChem Compound637517
PDB IDNot Available
ChEBI ID27997
Good Scents IDrw1242511
References
General References
  1. Andrei G, Snoeck R, Neyts J, Sandvold ML, Myhren F, De Clercq E: Antiviral activity of ganciclovir elaidic acid ester against herpesviruses. Antiviral Res. 2000 Mar;45(3):157-67. [PubMed:10771080 ]
  2. Stachowska E, Dolegowska B, Chlubek D, Wesolowska T, Ciechanowski K, Gutowski P, Szumilowicz H, Turowski R: Dietary trans fatty acids and composition of human atheromatous plaques. Eur J Nutr. 2004 Oct;43(5):313-8. Epub 2004 Jan 27. [PubMed:15309454 ]
  3. Roe M, Pinchen H, Church S, Elahi S, Walker M, Farron-Wilson M, Buttriss J, Finglas P: Trans fatty acids in a range of UK processed foods. Food Chem. 2013 Oct 1;140(3):427-31. doi: 10.1016/j.foodchem.2012.08.067. Epub 2012 Sep 6. [PubMed:23601386 ]
  4. Akmar ZD, Norhaizan ME, Azimah R, Azrina A, Chan YM: The trans fatty acids content of selected foods in Malaysia. Malays J Nutr. 2013 Apr;19(1):87-98. [PubMed:24800387 ]