Vaccenic acid (CED0004641)

Record Information
Version1.0
Creation Date2016-05-25 22:03:25 UTC
Update Date2026-05-14 18:10:32 UTC
Accession NumberCHEM024978
Identification
Common NameVaccenic acid
ClassSmall Molecule
Description
Vaccenic acid is an organic compound with the formula C18H34O2 and an average molecular weight of 282.46 g/mol. Vaccenic acid belongs to the fatty acids and conjugates, a subclass of fatty acyls within the organic compounds. This compound is found in or released from three recorded sources: antennas (electrical & electronic equipment), indoor air (air, dust & atmospheric transport), and the preparation of vinegar (food, food processing & cookware). The recorded route of exposure is inhalation. Regarding its biological activity, vaccenic acid acts as an inhibitor of the protein target peroxisome proliferator-activated receptor delta (PPARD).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
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 Molecular Mass282.461 g/mol
Monoisotopic Mass282.256 g/mol
CAS Registry Number506-17-2
IUPAC Name(11E)-octadec-11-enoic acid
Traditional Nametrans-vaccenic acid
SMILESCCCCCC\C=C/CCCCCCCCCC(O)=O
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9740000000-12d0456cbe2e20785a59Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00g0-9541000000-161e2d96dfa373186655Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0090000000-dee621bf09f57d88e5edNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-9340000000-654e2ea72d5477e26606Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aou-9000000000-413d3363f22e7baf1df7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0090000000-58579e8fd3d4191bcfadNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0090000000-c103acdc552ec63933b3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-65d62db890dca1a5d687Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0090000000-da9002214663921b23eeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-0090000000-1f781254725896ac3b8dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0079-5590000000-f37f297862ce49aba569Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-9830000000-9d6de2e63255b7b0f435Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0090000000-431aee5e7f472babb97bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001r-1090000000-0721ddce5ca61545b4ddNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9230000000-504045e17f7775e10a62Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0090000000-8b8562cadde7e7a8ba4fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01q9-1090000000-827ccf4b0fb321cd543dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9220000000-9024da2ccb79132d937aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-4290000000-ef21daa5591bbeb17f87Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-067j-9310000000-8cc733ca58b618258ca0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aou-9000000000-60e1d3c5c8de0e9f209cNot AvailableView Spectrum
MSMS Spectrumsplash10-0apl-9200000000-f39f178414756ab6ad8aNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6482.0Log mg/kg[3600:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
19Indoor airAir, dust & atmospheric transportNot Available
506AntennasElectrical & Electronic EquipmentNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)0.0778492
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)0.0778492
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)0.0778492
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)0.155698
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)0.389246
Fatty acid-binding protein, adipocyte structureClick to view 3D structureFatty acid-binding protein, adipocyteP15090HumansPredicted (SEA)0.0778492
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)2.64687
Free fatty acid receptor 4 structureClick to view 3D structureFree fatty acid receptor 4Q5NUL3HumansPredicted (SEA)0.0778492
Free fatty acid receptor 1 structureClick to view 3D structureFree fatty acid receptor 1O14842HumansPredicted (SEA)0.233548
Click to view 3D structureCannabinoid receptor 1P20272Rattus norvegicusPredicted (SEA)3.65891
G-protein coupled receptor 84 structureClick to view 3D structureG-protein coupled receptor 84Q9NQS5HumansPredicted (SEA)0.467095
Click to view 3D structureHistone deacetylase 11Q96DB2HumansPredicted (SEA)1.94623
Click to view 3D structureOxoeicosanoid receptor 1Q8TDS5HumansPredicted (SEA)0.233548
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)6.92858
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)7.39568
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansPredicted (SEA)3.19182
Click to view 3D structureEsteraseA3QR02Chilo suppressalisPredicted (SEA)0.467095
Click to view 3D structureFatty-acid amide hydrolase 1P97612Rattus norvegicusPredicted (SEA)7.47353
Click to view 3D structureCannabinoid receptor 2P47936Mus musculusPredicted (SEA)5.68299
Click to view 3D structureLysophosphatidic acid receptor 4Q8BLG2Mus musculusPredicted (SEA)1.32344
Fatty acid-binding protein 5 structureClick to view 3D structureFatty acid-binding protein 5Q01469HumansPredicted (SEA)0.0778492
Fatty acid-binding protein, heart structureClick to view 3D structureFatty acid-binding protein, heartP05413HumansPredicted (SEA)0.467095
Click to view 3D structureLysophosphatidic acid receptor 3Q9UBY5HumansPredicted (SEA)1.55698
Click to view 3D structureCannabinoid receptor 2Q9QZN9Rattus norvegicusPredicted (SEA)1.94623
Click to view 3D structureCannabinoid receptor 1P47746Mus musculusPredicted (SEA)4.20386
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0003231
FooDB IDFDB002952
Phenol Explorer IDNot Available
KNApSAcK IDC00052543
BiGG ID2217962
BioCyc IDNot Available
METLIN ID3407
PDB IDNot Available
Wikipedia LinkVaccenic acid
Chemspider ID4444571
ChEBI ID28727
PubChem Compound ID5281127
Kegg Compound IDC08367
YMDB IDNot Available
ECMDB IDECMDB21443
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15465769
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18275620
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19923390
4. 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.
5. Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.
6. Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.
7. Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026.
8. van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.
9. 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.
10. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.