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Showing Compound Vaccenic acid (FDB002952)

Record Information
Version1.0
Creation date2010-04-08 22:05:35 UTC
Update date2020-09-17 15:33:14 UTC
Primary IDFDB002952
Secondary Accession Numbers
  • FDB012766
Chemical Information
FooDB NameVaccenic acid
DescriptionCis-Vaccenic acid, (11Z)-11-octadecenoic acid, 18:1 cis-11, also known as vaccenate or asclepic acid, is an isomer of vaccenic acid. It 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. Cis-Vaccenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Cis-Vaccenic acid, an omega-7 fatty acid, is a naturally occurring trans fatty acid found in Sea Buckthorn (Hippophae rhamnoides) oil. Vaccenic acid was first discovered in 1928 in animal fats and butter. Mammals convert it into rumenic acid, a conjugated linoleic acid. In a study of chemically induced mammary carcinogenesis in rats, vaccenic acid, when converted to cis-9, trans-11 conjugated linoleic acid (CLA) by delta 9-desaturase, had anticarcinogenic properties (PMID: 15465769).
CAS Number693-72-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(Z)-11-Octadecenoic acidChEBI
(Z)-Octadec-11-enoic acidChEBI
Asclepic acidChEBI
cis-Octadec-11-enoic acidChEBI
VACCENIC ACIDChEBI
(Z)-11-OctadecenoateGenerator
(Z)-Octadec-11-enoateGenerator
AsclepateGenerator
cis-Octadec-11-enoateGenerator
VACCENateGenerator
cis-11-OctadecenoateGenerator
cis-11-Octadecenoic acidChEBI
(11Z)-OctadecenoateHMDB
(11Z)-Octadecenoic acidHMDB
11-OctadecenoateHMDB
11-Octadecenoic acidHMDB
11Z-OctadecenoateHMDB
11Z-Octadecenoic acidHMDB
cis-VaccenateGenerator
(11E)-Octadecenoatebiospider
(11E)-Octadecenoic acidbiospider
(E)-11-Octadecenoic acidmanual
(E)-Octadec-11-enoatebiospider
(E)-Octadec-11-enoic acidbiospider
11-Octadecenoic acid, (E)-biospider
11E-Octadecenoatebiospider
11E-Octadecenoic acidbiospider
11t-Octadececonoic acidmanual
18:1 trans-11manual
C18:1n-7manual
trans-11-Octadecenoatebiospider
trans-11-Octadecenoic acidbiospider
trans-11-OctadecensaeureChEBI
trans-18:1n-7manual
Vaccenatebiospider
Vaccenic aciddb_source
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
Polarizability37.1 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H34O2
IUPAC name(11Z)-octadec-11-enoic acid
InChI IdentifierInChI=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-FPLPWBNLSA-N
Isomeric SMILESCCCCCC\C=C/CCCCCCCCCC(O)=O
Average Molecular Weight282.4614
Monoisotopic Molecular Weight282.255880332
Classification
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
Ontology
Foods
  • Dairy products

    • Meats:

    Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 76.54%; H 12.13%; O 11.33%DFC
    Melting PointMp 43.5-44.1°DFC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    Charge-1
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-0apl-9200000000-f39f178414756ab6ad8a2015-03-01View Spectrum
    Predicted GC-MSVaccenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9740000000-12d0456cbe2e20785a59Spectrum
    Predicted GC-MSVaccenic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00g0-9541000000-161e2d96dfa373186655Spectrum
    Predicted GC-MSVaccenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSVaccenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0090000000-dee621bf09f57d88e5ed2012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9340000000-654e2ea72d5477e266062012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aou-9000000000-413d3363f22e7baf1df72012-07-25View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-0090000000-58579e8fd3d4191bcfad2020-07-21View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-001i-0090000000-c103acdc552ec63933b32020-07-21View Spectrum
    MS/MSLC-MS/MS Spectrum - n/a 19V, negativesplash10-03di-0090000000-65d62db890dca1a5d6872020-07-21View Spectrum
    MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0090000000-da9002214663921b23ee2021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0090000000-1f781254725896ac3b8d2017-07-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-5590000000-f37f297862ce49aba5692017-07-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9830000000-9d6de2e63255b7b0f4352017-07-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-431aee5e7f472babb97b2017-07-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-1090000000-0721ddce5ca61545b4dd2017-07-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-504045e17f7775e10a622017-07-26View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-8b8562cadde7e7a8ba4f2021-09-23View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-1090000000-827ccf4b0fb321cd543d2021-09-23View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9220000000-9024da2ccb79132d937a2021-09-23View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-4290000000-ef21daa5591bbeb17f872021-09-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067j-9310000000-8cc733ca58b618258ca02021-09-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9000000000-60e1d3c5c8de0e9f209c2021-09-25View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
    ChemSpider ID4445888
    ChEMBL IDNot Available
    KEGG Compound IDC08367
    Pubchem Compound ID5282761
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDDB04801
    HMDB IDHMDB03231
    CRC / DFC (Dictionary of Food Compounds) IDGMW04-B:CPM62-W
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG ID2217962
    KNApSAcK IDC00001240
    HET IDVCA
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    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.