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Vaccenic acid (PC000763)

Record Information
Version1.0
Creation date2015-10-09 22:32:33 UTC
Update date2017-01-19 02:36:35 UTC
FoodComEx IDPC000763
FoodDB RecordFDB002952
Chemical Information
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
(11E)-Octadecenoatebiospider
(11E)-Octadecenoic acidbiospider
(11Z)-OctadecenoateHMDB
(11Z)-Octadecenoic acidHMDB
(E)-11-Octadecenoic acidmanual
(E)-Octadec-11-enoatebiospider
(E)-Octadec-11-enoic acidbiospider
(Z)-11-OctadecenoateGenerator
(Z)-Octadec-11-enoateGenerator
11-OctadecenoateHMDB
11-Octadecenoic acidHMDB
11-Octadecenoic acid, (E)-biospider
11E-Octadecenoatebiospider
11E-Octadecenoic acidbiospider
11t-Octadececonoic acidmanual
11Z-OctadecenoateHMDB
18:1 trans-11manual
AsclepateGenerator
C18:1n-7manual
cis-11-OctadecenoateGenerator
cis-Octadec-11-enoateGenerator
cis-Octadec-11-enoic acidChEBI
trans-11-Octadecenoatebiospider
trans-11-Octadecenoic acidbiospider
trans-11-OctadecensaeureChEBI
trans-18:1n-7manual
Vaccenatebiospider
Vaccenic aciddb_source
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
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointMp 43.5-44.1°DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 200 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Not Available