Showing Compound Card for Erucic acid (CDB005266)

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Record Information
Version1.0
Created at2020-04-17 19:25:58 UTC
Updated at2021-01-04 18:59:21 UTC
CannabisDB IDCDB005266
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameErucic acid
DescriptionErucic acid, also known as cis-eruic acid or cis-13-docosenoic acid is a monounsaturated omega-9 fatty acid. The trans isomer is known as brassidic acid. It is a 22-carbon-long fatty acid that 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. Erucic acid is a very hydrophobic molecule and is practically insoluble in water. Erucic acid is found mainly in the Brassica family of plants such as canola, rapeseed, wallflower seed, mustard seed as well as Brussels sprouts and broccoli. Some Brassica cultivars can have up to 40 to 50 percent of their oil recovered as erucic acid. Rapeseed oil has 20-54% erucic acid while mustard oil has 42%. Erucic acid occurs in nature only along with bitter-tasting compounds. For food purposes a 'low-erucic acid rapeseed' (LEAR) has been developed which is known as canola. Canola, which was developed in Canada, contains fats derived from oleic acid instead of erucic acid. Food-grade rapeseed oil (also known as canola oil) is regulated to a maximum of 2% erucic acid by weight in the USA and 5% in the EU. Erucic acid has many of the same uses as mineral oils but with the advantage that it is more readily biodegradable. Its high tolerance to temperature makes it suitable for transmission oil. Its limited ability to polymerize means it can be - and is - used as a binder for oil paints. Like other fatty acids, it can be converted into surfactants or lubricants, and can be used as a precursor to biodiesel fuel. 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. Erucic acid is one of many acidic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Molecular Weight338.57
Monoisotopic Molecular Weight338.3185
IUPAC Name(13Z)-docos-13-enoic acid
Traditional Nameerucic acid
CAS Registry Number112-86-7
SMILES
CCCCCCCC\C=C/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
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point33.5 °CNot Available
Boiling Point381.5 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a5c-9300000000-53ce9b6b1bd7db6018662015-03-01View Spectrum
GC-MSErucic acid, 1 TMS, GC-MS Spectrumsplash10-00nb-6900000000-5e6160a7a5341d6f55deSpectrum
GC-MSErucic acid, non-derivatized, GC-MS Spectrumsplash10-00nb-6900000000-5e6160a7a5341d6f55deSpectrum
Predicted GC-MSErucic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9670000000-abb8d10b97d3c63c8480Spectrum
Predicted GC-MSErucic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fmv-9452000000-be430773e3b82d00352dSpectrum
Predicted GC-MSErucic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSErucic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-0009000000-c637d7d9283da6dae58c2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-05ur-9100000000-4dfe9f552da0b8ea6e7c2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0159-9000000000-867fce64ced7de3a289e2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 23V, negativesplash10-014i-0009000000-a67df2342edb038f06472020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000i-0019000000-0026b53b7b328f5e51542020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00dr-1119000000-fa6979100366edcb28922020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-0fki-5829000000-ff16fd0e5a988fe38fa42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 20V, positivesplash10-0apj-9200000000-27116cd4b609b88b40052020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 27V, positivesplash10-0api-9100000000-0f82260b5b86e3b06b2a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-0aor-9000000000-0a3061b18adfe4ddad072020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-00di-0129000000-fa49cfc1738521b925d32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-000i-0290000000-b4f9a52c100defbf8a392020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-014i-0090000000-02a20bc6ce898cb3824c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-07l5-0950000000-0ca01024ab3b5ad027ec2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-0udi-0319000000-7b31f345d0546a6c25ab2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-00di-2209000000-d03f3b30c822ce8c5e262020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-00di-9608000000-2fc5f27c0bd54f0c003a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-059t-9502000000-8f68c9dbb8e1467805f72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-05nb-9300000000-0701894bd7e9b3d37f402020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0019000000-c06b5c8f2b9044af1c342017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00g3-5695000000-55896e489497235f6a672017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9880000000-69f41c34dca989e6c8102017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-cfb3c7afc93ecf28f3da2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-1039000000-c2dd9360fea23806c3132017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9131000000-393859815e6c1359d6df2017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
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
References
General References
  1. 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. doi: 10.1016/j.plefa.2006.02.001. [PubMed:16581239 ]