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Record Information
Version1.0
Created at2006-05-22 15:12:43 UTC
Updated at2021-06-29 00:47:42 UTC
NP-MRD IDNP0000040
Secondary Accession NumbersNone
Natural Product Identification
Common NameVaccenic acid
DescriptionVaccenic acid is a naturally occurring trans fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. Trans fat in human milk may depend on trans fat content in food. Its IUPAC name is (11E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 Trans-11. The name was derived from the Latin vacca (cow). Vaccenic acid 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. Vaccenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Thumb
Synonyms
ValueSource
(11E)-Octadecenoic acidChEBI
(e)-11-Octadecenoic acidChEBI
11(e)-Vaccenic acidChEBI
18:1 trans-11ChEBI
C18:1 trans-11ChEBI
Octadec-11(e)-enoic acidChEBI
trans-11-Octadecenoic acidChEBI
trans-11-OctadecensaeureChEBI
trans-Octadec-11-enoic acidChEBI
TVAChEBI
(11E)-OctadecenoateGenerator
(e)-11-OctadecenoateGenerator
11(e)-VaccenateGenerator
Octadec-11(e)-enoateGenerator
trans-11-OctadecenoateGenerator
trans-Octadec-11-enoateGenerator
VaccenateGenerator
(e)-Octadec-11-enoateHMDB
11-Octadecenoic acid, (e)-isomerHMDB
11-Octadecenoic acidHMDB
trans-Vaccenic acidHMDB
FA(18:1(11Z))HMDB
FA(18:1n7)HMDB
Vaccenic acidChEBI
Chemical FormulaC18H34O2
Average Mass282.4680 Da
Monoisotopic Mass282.25588 Da
IUPAC Name(11E)-octadec-11-enoic acid
Traditional Nametrans-vaccenic acid
CAS Registry Number693-72-1
SMILES
CCCCCC\C=C\CCCCCCCCCC(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/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+
InChI KeyUWHZIFQPPBDJPM-BQYQJAHWSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)V.dorna832021-08-15View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Varshavi.d262021-09-06View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Varshavi.d262021-09-06View Spectrum
Species
Species of Origin
Species NameSourceReference
Mangifera indicaKNApSAcK 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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point44 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
logP7.67ALOGPS
logP6.78ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity87.4 m³·mol⁻¹ChemAxon
Polarizability37.62 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0003231
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002952
KNApSAcK IDC00052543
Chemspider ID4444571
KEGG Compound IDC08367
BioCyc IDNot Available
BiGG ID2217962
Wikipedia LinkVaccenic acid
METLIN ID3407
PubChem Compound5281127
PDB IDNot Available
ChEBI ID28727
Good Scents IDNot Available
References
General References
  1. Schatowitz B, Gercken G: Simultaneous determination of C2-C22 non-esterified fatty acids and other metabolically relevant carboxylic acids in biological material by gas chromatography of their benzyl esters. J Chromatogr. 1988 Mar 18;425(2):257-68. [PubMed:3372640 ]
  2. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  3. Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C: The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats. J Nutr. 2004 Oct;134(10):2698-704. doi: 10.1093/jn/134.10.2698. [PubMed:15465769 ]
  4. Reynolds CM, Loscher CE, Moloney AP, Roche HM: Cis-9, trans-11-conjugated linoleic acid but not its precursor trans-vaccenic acid attenuate inflammatory markers in the human colonic epithelial cell line Caco-2. Br J Nutr. 2008 Jul;100(1):13-7. doi: 10.1017/S0007114508894329. [PubMed:18275620 ]
  5. Bassett CM, Edel AL, Patenaude AF, McCullough RS, Blackwood DP, Chouinard PY, Paquin P, Lamarche B, Pierce GN: Dietary vaccenic acid has antiatherogenic effects in LDLr-/- mice. J Nutr. 2010 Jan;140(1):18-24. doi: 10.3945/jn.109.105163. Epub 2009 Nov 18. [PubMed:19923390 ]