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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
2D NMR[1H, 13C]-HSQC 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
Abelmoschus esculentusFooDB
Abramis bramaFooDB
AcipenseridaeFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
Agave
Allium ampeloprasum
Allium ascalonicum
Allium cepa
Allium cepa L.FooDB
Allium fistulosum
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosum
Aloysia triphylla
Amaranthus
Amelanchier alnifolia
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
Anas platyrhynchos
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskei
AnguilliformesFooDB
Annona cherimolaFooDB
Annona muricata
Annona reticulata
Annona squamosa
Anser anser
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulce
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arachis hypogaeaFooDB
Arctium lappa
Armoracia rusticanaFooDB
Artemisia dracunculus
Artemisia vulgaris
Artocarpus altilis
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
AstacideaFooDB
Attalea speciosa
Auricularia auricula-judae
Auricularia polytricha
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella alba
Belone beloneFooDB
Benincasa hispida
Bertholletia excelsaFooDB
Beta vulgaris
Beta vulgaris ssp. ciclaFooDB
Bison bison
Borago officinalis
Bos taurusFooDB
Bos taurus X Bison bison
BrachyuraFooDB
Brassica alboglabra
Brassica juncea
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitata
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridis
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensis
Brassica rapa var. rapaFooDB
Brassica ruvo
Brosimum alicastrum
Bubalus bubalis
Byrsonima crassifolia
Cajanus cajan
Canarium ovatum
Cantharellus cibariusFooDB
Capparis spinosa
Capra aegagrus hircus
Capsicum annuumFooDB
Capsicum annuum L.
Capsicum annuum var. annuum
Capsicum chinense
Capsicum pubescens
Carica papaya L.FooDB
CarideaFooDB
Carissa macrocarpa
Carthamus tinctoriusFooDB
Carum carvi
Carya
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenata
Castanea mollissima
Castanea sativa
Ceratonia siliqua
Cervidae
Cervus canadensis
Chamaemelum nobile
Chamerion angustifolium
Chenopodium album
Chenopodium quinoa
Chrysanthemum coronarium
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticum
Cinnamomum verum
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifolia
Citrus limonFooDB
Citrus maxima
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
ClupeinaeFooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculenta
Columba
ColumbidaeFooDB
Corchorus olitorius
CoregonusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellana
Crateva religiosa
Crocus sativus
Cucumis meloFooDB
Cucumis metuliferus
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschata
Cuminum cyminum
Curcuma longaFooDB
CyclopteridaeFooDB
Cydonia oblongaFooDB
Cymbopogon citratus
Cynara cardunculus
Cynara scolymusFooDB
Daucus carota
Daucus carota ssp. sativusFooDB
Dimocarpus longan
DioscoreaFooDB
Dioscorea pentaphylla
DiospyrosFooDB
Diospyros kaki
Diospyros virginiana
Dromaius novaehollandiae
Durio zibethinus
Dysphania ambrosioides
ElaeisFooDB
Eleocharis dulcis
Elettaria cardamomum
Empetrum nigrum
EngraulidaeFooDB
Equus caballus
Eragrostis tef
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. Sativa
Esox luciusFooDB
EucheumaFooDB
Eugenia javanica
Eugenia uniflora
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricum
Fagus
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipes
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
GadiformesFooDB
GadusFooDB
Gadus macrocephalusFooDB
Gallus gallusFooDB
Garcinia mangostana
GastropodaFooDB
Gaylussacia baccata
Ginkgo biloba
Glycine maxFooDB
GossypiumFooDB
Grifola frondosa
Hedysarum alpinum
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffa
HippoglossusFooDB
Hippoglossus hippoglossusFooDB
Hippoglossus stenolepisFooDB
Hippophae rhamnoides
Hordeum vulgareFooDB
Hyssopus officinalis L.
Illicium verum
Ipomoea aquatica
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifolia
Juglans cinerea
Juglans nigra L.FooDB
Juglans regia
Lablab purpureus
Lactobacillus plantarumFirmicutes
Lactuca sativaFooDB
Lagenaria siceraria
Lagopus mutaFooDB
Lathyrus sativus
Laurus nobilis L.
Lens culinarisFooDB
Lentinus edodes
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinale
Limanda limandaFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lota lotaFooDB
Luffa aegyptiaca
Lupinus
Lupinus albus
Macadamia
Macadamia tetraphylla
Malpighia emarginata
MalusFooDB
Malus pumilaFooDB
Mammea americana
Mangifera indicaKNApSAcK Database
Manihot esculentaFooDB
Manilkara zapota
Maranta arundinacea
Matricaria recutita
Matteuccia struthiopteris
Medicago sativaFooDB
Melanitta fusca
Melanogrammus aeglefinusFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.
Mentha
Mentha aquatica
Mentha arvensis
Mentha spicata
Mentha x piperita
Merlangius merlangusFooDB
Mespilus germanica
Metroxylon sagu
Micromesistius poutassouFooDB
Microstomus kittFooDB
Molva molvaFooDB
Momordica charantia
MorchellaceaeFooDB
Morella rubra
Moringa oleifera
Morus
Morus nigra
Musa acuminata
Musa x paradisiacaFooDB
Myrica
Myristica fragransFooDB
MytilidaeFooDB
Nelumbo
Nelumbo nucifera
Nephelium lappaceum
NephropidaeFooDB
Nephrops norvegicusFooDB
Numida meleagris
Nuphar lutea
Ocimum basilicum
Octopus vulgarisFooDB
Odocoileus
Oenothera biennis
Olea europaeaFooDB
Oncorhynchus gorbuschaFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
OpuntiaFooDB
Opuntia cochenillifera
Opuntia macrorhiza
Origanum majorana
Origanum onites
Origanum vulgareFooDB
Origanum X majoricumFooDB
Oryctolagus
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosus
Panax ginseng
Pangium edule
Panicum miliaceumFooDB
PapaverFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentum
PerciformesFooDB
Perideridia oregana
Persea americanaFooDB
Petasites japonicus
Petroselinum crispumFooDB
Phaseolus coccineus
Phaseolus lunatus
Phaseolus vulgarisFooDB
Phasianidae
Phasianus colchicus
Phoenix dactyliferaFooDB
Photinia melanocarpa
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculata
Phytolacca americana
Pimenta dioica
Pimpinella anisum
PinusFooDB
Pinus edulis
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
PleuronectidaeFooDB
PleuronectiformesFooDB
Pleurotus ostreatusFooDB
PollachiusFooDB
Polygonum alpinum
Portulaca oleracea
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus avium
Prunus avium L.FooDB
Prunus cerasus
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persica
Prunus tomentosa
Prunus virginiana
Psidium cattleianum
Psidium guajavaFooDB
Psophocarpus tetragonolobus
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifolia
Quercus
RanidaeFooDB
Raphanus sativus
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativus
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Ribes aureum
Ribes glandulosum
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticus
Rubus chamaemorus
Rubus idaeus
Rubus occidentalis
Rubus spectabilis
Rumex
Rumex acetosaFooDB
Rumex articus
Saccharina japonicaFooDB
Sagittaria latifolia
Salix pulchra
SalmonidaeFooDB
SalvelinusFooDB
Salvelinus namaycushFooDB
Salvia elegans
Salvia hispanica
Salvia officinalis
Salvia rosmarinus
Sambucus nigra
Sambucus nigra L.FooDB
Sander luciopercaFooDB
Satureja hortensis L.
Satureja montana
ScombridaeFooDB
Scophthalmus maximusFooDB
Scorzonera hispanicaFooDB
SebastesFooDB
Sebastes alutusFooDB
Sebastes viviparusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosa
SiluriformesFooDB
Sinapis alba
Sisymbrium
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiforme
Solanum lycopersicum var. lycopersicum
Solanum melongenaFooDB
Solanum quitoense
Solanum tuberosumFooDB
SoleidaeFooDB
Sorbus aucuparia
Sorghum bicolor
Spinacia oleraceaFooDB
Squalus acanthiasFooDB
Struthio camelus
Sus scrofa
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cumini
Syzygium jambos
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioides
Thelesperma
ThunnusFooDB
Thunnus albacaresFooDB
Thymus pulegioides
Thymus vulgaris
Tilia cordata
Tilia L.
Tragopogon porrifolius
Trigonella foenum-graecum
Trisopterus esmarkiiFooDB
TriticumFooDB
Triticum aestivum
Triticum durumFooDB
Triticum spelta
Triticum turanicum
Typha angustifolia
VacciniumFooDB
Vaccinium angustifolium
Vaccinium angustifolium X Vaccinium corymbosum
Vaccinium arboreum
Vaccinium corymbosum
Vaccinium deliciosum
Vaccinium elliottii
Vaccinium macrocarpon
Vaccinium myrtilloides
Vaccinium myrtillusFooDB
Vaccinium ovalifolium
Vaccinium ovatum
Vaccinium oxycoccos
Vaccinium parvifolium
Vaccinium reticulatum
Vaccinium stamineum
Vaccinium uliginosum
Vaccinium vitis-idaeaFooDB
Valerianella locusta
Vanilla
Verbena officinalis
Viburnum edule
Vicia faba
Vigna aconitifolia
Vigna angularisFooDB
Vigna mungo
Vigna radiataFooDB
Vigna umbellata
Vigna unguiculata
Vigna unguiculata ssp. cylindrica
Vigna unguiculata ssp. unguiculata
Vigna unguiculata var. sesquipedalis
VitisFooDB
Vitis aestivalis
Vitis labrusca
Vitis rotundifolia
Vitis vinifera L.
Xanthosoma sagittifolium
Xiphias gladiusFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
Zizania
Zizania aquatica
Ziziphus zizyphus
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 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
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 ]