Showing Compound Card for Behenic acid (CDB006178)

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Record Information
Version1.0
Created at2020-03-18 23:22:41 UTC
Updated at2020-12-07 19:06:59 UTC
CannabisDB IDCDB006178
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBehenic acid
DescriptionBehenic acid, also known as docosanoate, C22:0 or 1-docosanoic acid, 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. Behenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. In appearance, it consists of white to cream color crystals or powder with a melting point of 80 °C and boiling point of 306 °C. It is a major component of Ben oil (or behen oil), which is extracted from the seeds of the Ben-oil tree (Moringa oleifera). Behenic acid is also found in canola oil and peanut oil. As a dietary oil, behenic acid is poorly absorbed. In spite of its low bioavailability compared with oleic acid, behenic acid is a cholesterol-raising (LDL) saturated fatty acid in humans and is therefore not a suitable substitute for palmitic acid in manufactured triacylglycerols (PMID: 11124748 ). Behenic acid is often used to give hair conditioners and moisturizers their smoothing properties. It is also used in lubricating oils, and as a solvent evaporation retarder in paint removers. Behenic acid amide is used as an anti-foaming agent in detergents, floor polishes and dripless candles. Behenic acid is also a constituent of cannabis plant and cannabis smoke. It is volatilized during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Docosanoic acidChEBI
BehensaeureChEBI
CH3-[CH2]20-COOHChEBI
Docosanic acidChEBI
DocosanoateChEBI
DocosansaeureChEBI
Docosoic acidChEBI
DokosansaeureChEBI
N-Docosanoic acidChEBI
1-DocosanoateGenerator
DocosanateGenerator
Docosanoic acidGenerator
DocosoateGenerator
N-DocosanoateGenerator
BehenateGenerator
FA(22:0)HMDB
Behenic acidHMDB
Chemical FormulaC22H44O2
Average Molecular Weight340.58
Monoisotopic Molecular Weight340.3341
IUPAC Namedocosanoic acid
Traditional Namebehenic acid
CAS Registry Number112-85-6
SMILES
CCCCCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C22H44O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H,23,24)
InChI KeyUKMSUNONTOPOIO-UHFFFAOYSA-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
  • 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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point81 °CNot Available
Boiling Point306 °CWikipedia
Water Solubility1.6e-05 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.19ALOGPS
logP8.92ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity104.69 m³·mol⁻¹ChemAxon
Polarizability47.25 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)splash10-0596-9422000000-4799a4c5794b597920502014-09-20View Spectrum
GC-MSBehenic acid, non-derivatized, GC-MS Spectrumsplash10-0159-0900000000-3bbb6d3ae586b9b33415Spectrum
GC-MSBehenic acid, 1 TMS, GC-MS Spectrumsplash10-0159-2900000000-348efcfc8f1d67f7b5b2Spectrum
GC-MSBehenic acid, non-derivatized, GC-MS Spectrumsplash10-0596-9100000000-eb78c2ccaf4cc9882ed1Spectrum
GC-MSBehenic acid, non-derivatized, GC-MS Spectrumsplash10-0159-0900000000-3bbb6d3ae586b9b33415Spectrum
GC-MSBehenic acid, non-derivatized, GC-MS Spectrumsplash10-0159-2900000000-348efcfc8f1d67f7b5b2Spectrum
GC-MSBehenic acid, non-derivatized, GC-MS Spectrumsplash10-0159-1900000000-118efeed433fc3141bc9Spectrum
Predicted GC-MSBehenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-7690000000-97da3fdb0e98064049b6Spectrum
Predicted GC-MSBehenic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00g1-9551000000-fd9768208a1797291a14Spectrum
Predicted GC-MSBehenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBehenic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0006-0109000000-bda321e754dd42fb8bb82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0a4j-5900000000-809bb3193f37942db9092012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0a4i-7900000000-22ebd8fe304be08b915e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0596-9100000000-eb78c2ccaf4cc9882ed12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-000i-0900000000-d09512035285f332d56c2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0900000000-d09512035285f332d56c2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-000i-0900000000-d09512035285f332d56c2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0009000000-3a6826d318c7e16341202017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-000i-0009000000-3a6826d318c7e16341202017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-000i-0009000000-b29cc64ce52ea552b8d12017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0009000000-9f560a0c6bac7043337f2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-000i-0009000000-3cdf1b17a2391c889f5b2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0009000000-3a6826d318c7e16341202017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-000i-0009000000-183662ae4ac2ef63046e2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0009000000-b29cc64ce52ea552b8d12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0009000000-9f560a0c6bac7043337f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0009000000-3cdf1b17a2391c889f5b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0009000000-183662ae4ac2ef63046e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-59e981660d097942b2b82021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0019000000-7a5055e53e55c3579d342015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ed-2494000000-d58d52e3d2392ca040472015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-6980000000-36eb30e33ef7e33830d62015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-2e1668571d77736f2b5e2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-007a-1039000000-9420d9704691f31b35dd2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9130000000-68de74e83f8a8e6cadba2015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, 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 IDHMDB0000944
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005830
KNApSAcK IDC00001211
Chemspider ID7923
KEGG Compound IDC08281
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBehenic acid
METLIN ID260
PubChem Compound8215
PDB IDNot Available
ChEBI ID28941
References
General References
  1. Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4. doi: 10.1093/ajcn/73.1.41. [PubMed:11124748 ]