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Record Information
Version1.0
Created at2006-05-22 14:17:35 UTC
Updated at2021-08-19 20:22:29 UTC
NP-MRD IDNP0000021
Secondary Accession NumbersNone
Natural Product Identification
Common NameErucic acid
DescriptionErucic acid is a 22-carbon, monounsaturated omega-9 fatty acid found mainly in the Brassica family of plants such as canola, rapeseed, wallflower seed, mustard seed as well as Brussels spouts and broccoli. Some Brassica cultivars can have up to 40 to 50 percent of their oil recovered as erucic acid. Erucic acid is also known as cis-13-docosenoic acid. The trans isomer is known as brassidic acid. Erucic acid occurs in nature only along with bitter-tasting compounds. Erucic acid has many of the same uses as mineral oils but with the advantage that it is more readily bio-degradable. Its high tolerance to temperature makes it suitable for transmission oil. Erucic acid’s ability to polymerize and dry means it can be - and is - used as a binder for oil paints. Increased levels of eicosenoic acid (20:Ln9) and erucic acid (22:1N9) have been found in the red blood cell membranes of autistic subjects with developmental regression (PMID: 16581239 ). Erucic acid is broken down long-chain acyl-coenzyme A (CoA) dehydrogenase, which is produced in the liver. This enzyme breaks this long chain fatty acid into shorter-chain fatty acids. Human infants have relatively low amounts of this enzyme and because of this, babies should not be given foods high in erucic acid. Food-grade rapeseed oil (also known as canola oil) is regulated to a maximum of 2% erucic acid by weight in the US and 5% in the EU, with special regulations for infant food. Canola was bred from rapeseed cultivars of B. Napus and B. Rapa at the University of Manitoba, Canada. Canola oil is derived from a variety of rapeseed that is low in erucic acid.
Structure
Thumb
Synonyms
ValueSource
(13Z)-13-Docosenoic acidChEBI
(13Z)-Docosenoic acidChEBI
(Z)-13-Docosenoic acidChEBI
(Z)-Docos-13-enoic acidChEBI
13-cis-Docosenoic acidChEBI
22:1Omega9ChEBI
C22:1N-9ChEBI
cis-13-Docosenoic acidChEBI
cis-Delta(13)-Docosenoic acidChEBI
cis-Eruic acidChEBI
Docos-13C-enoic acidChEBI
ErucasaeureChEBI
(13Z)-13-DocosenoateGenerator
(13Z)-DocosenoateGenerator
(Z)-13-DocosenoateGenerator
(Z)-Docos-13-enoateGenerator
13-cis-DocosenoateGenerator
cis-13-DocosenoateGenerator
cis-delta(13)-DocosenoateGenerator
cis-Δ(13)-docosenoateGenerator
cis-Δ(13)-docosenoic acidGenerator
cis-EruateGenerator
Docos-13C-enoateGenerator
ErucateGenerator
13-Docosenoic acidHMDB
Erucic acid, (Z)-isomerHMDB
13-DocosenoateHMDB
13-Docosenoic acid (acd/name 4.0)HMDB
cis-Erucic acidHMDB
delta 13-cis-DocosenoateHMDB
delta 13-cis-Docosenoic acidHMDB
Delta.13-cis-docosenoateHMDB
Delta.13-cis-docosenoic acidHMDB
Prifrac 2990HMDB
(Z)-Erucic acidHMDB
13(Z)-Docosenoic acidHMDB
FA(22:1(13Z))HMDB
FA(22:1n9)HMDB
cis-13-Erucic acidHMDB
delta13-cis-Docosenoic acidHMDB
Δ13-cis-docosenoic acidHMDB
Erucic acidHMDB
Chemical FormulaC22H42O2
Average Mass338.5677 Da
Monoisotopic Mass338.31848 Da
IUPAC Name(13Z)-docos-13-enoic acid
Traditional Nameerucic acid
CAS Registry Number112-86-7
SMILES
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H,23,24)/b10-9-
InChI KeyDPUOLQHDNGRHBS-KTKRTIGZSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)Varshavi.d262021-08-14View 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
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskei
AnguilliformesFooDB
Annona cherimolaFooDB
Annona muricata
Annona reticulata
Annona squamosa
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 heterophyllus
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
Borago officinalisFooDB
Bos taurusFooDB
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
Byrsonima crassifolia
Cajanus cajan
Calophyllum calabaKNApSAcK Database
Calophyllum inophyllumKNApSAcK Database
Canarium ovatum
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosa
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
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
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 longa
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
Durio zibethinus
Dysphania ambrosioides
ElaeisFooDB
Eleocharis dulcis
Elettaria cardamomum
Empetrum nigrum
EngraulidaeFooDB
Eragrostis tef
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Esox luciusFooDB
EucheumaFooDB
Eugenia javanica
Eugenia uniflora
Eutrema japonicum
Fagopyrum esculentumFooDB
Fagopyrum tataricum
Fagus
Feijoa sellowiana
Ficus caricaFooDB
Flammulina velutipes
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
GadiformesFooDB
GadusFooDB
Gallus gallusFooDB
Garcinia mangostana
GastropodaFooDB
Gaylussacia baccata
Ginkgo biloba
Glycine maxFooDB
GossypiumFooDB
Grifola frondosa
Hedysarum alpinum
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffa
Hippoglossus hippoglossusFooDB
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
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 albusFooDB
Luzuriaga parvifloraKNApSAcK Database
Macadamia
Macadamia tetraphylla
Malpighia emarginata
MalusFooDB
Malus pumilaFooDB
Mammea americana
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapota
Maranta arundinacea
Matricaria recutita
Matteuccia struthiopteris
Medicago sativaFooDB
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
Morchellaceae
Morella rubra
Moringa oleifera
Morus
Morus nigra
Musa acuminata
Musa x paradisiacaFooDB
Myrica
Myristica fragransFooDB
MytilidaeFooDB
Nelumbo
Nelumbo nuciferaFooDB
Nephelium lappaceum
NephropidaeFooDB
Nephrops norvegicusFooDB
Nuphar lutea
Ocimum basilicum
Octopus vulgarisFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
Oncorhynchus mykissFooDB
OpuntiaFooDB
Opuntia cochenillifera
Opuntia macrorhiza
Origanum majorana
Origanum onites
Origanum vulgare
Origanum X majoricum
Oryza rufipogon
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
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 sapota
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 tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifolia
Quercus
RanidaeFooDB
Raphanus sativusFooDB
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
Sebastes alutusFooDB
Sebastes viviparusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosa
SiluriformesFooDB
Sinapis albaFooDB
Sisymbrium
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiforme
Solanum lycopersicum var. lycopersicum
Solanum melongenaFooDB
Solanum quitoense
Solanum tuberosumFooDB
Sorbus aucuparia
Sorghum bicolor
Spinacia oleraceaFooDB
Squalus acanthiasFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticum
Syzygium cumini
Syzygium jambos
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioides
Thelesperma
ThunnusFooDB
Thymus pulegioides
Thymus vulgaris
Tilia cordata
Tilia L.
Tragopogon porrifolius
Trigonella foenum-graecum
Trisopterus esmarkiiFooDB
TriticumFooDB
Triticum aestivum
Triticum durumFooDB
Triticum spelta
Triticum turanicum
Tropaeolum majusKNApSAcK Database
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. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalis
Vitis labrusca
Vitis rotundifolia
Vitis vinifera L.FooDB
Xanthosoma sagittifolium
Zea mays L.FooDB
Zingiber officinaleFooDB
Zizania
Zizania aquatica
Ziziphus zizyphus
Chemical Taxonomy
Description Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very 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 Point33.5 °CNot Available
Boiling Point386.15 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility9.5e-05 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP9.459 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility2.3e-05 g/LALOGPS
logP8.97ALOGPS
logP8.56ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity105.81 m³·mol⁻¹ChemAxon
Polarizability45.6 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002068
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004287
KNApSAcK IDC00001217
Chemspider ID4444561
KEGG Compound IDC08316
BioCyc IDCPD-14292
BiGG IDNot Available
Wikipedia LinkErucic_acid
METLIN ID6470
PubChem Compound5281116
PDB IDNot Available
ChEBI ID28792
Good Scents IDrw1242821
References
General References
  1. Rizzo WB, Leshner RT, Odone A, Dammann AL, Craft DA, Jensen ME, Jennings SS, Davis S, Jaitly R, Sgro JA: Dietary erucic acid therapy for X-linked adrenoleukodystrophy. Neurology. 1989 Nov;39(11):1415-22. [PubMed:2682348 ]
  2. Bu B, Ashwood P, Harvey D, King IB, Water JV, Jin LW: Fatty acid compositions of red blood cell phospholipids in children with autism. Prostaglandins Leukot Essent Fatty Acids. 2006 Apr;74(4):215-21. [PubMed:16581239 ]
  3. 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. [PubMed:32033212 ]
  4. Charlton KM, Corner AH, Davey K, Kramer JK, Mahadevan S, Sauer FD: Cardiac lesions in rats fed rapeseed oils. Can J Comp Med. 1975 Jul;39(3):261-9. [PubMed:1170010 ]
  5. Crowther MA, Barr RD, Kelton J, Whelan D, Greenwald M: Profound thrombocytopenia complicating dietary erucic acid therapy for adrenoleukodystrophy. Am J Hematol. 1995 Feb;48(2):132-3. doi: 10.1002/ajh.2830480217. [PubMed:7847331 ]