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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:35 UTC
HMDB IDHMDB00944
Secondary Accession NumbersNone
Metabolite Identification
Common NameBehenic acid
DescriptionBehenic acid, also docosanoic acid, is a normal carboxylic acid, a fatty acid with formula C21H43COOH. -- Wikipedia; It is an important constituent of the behen oil extracted from the seeds of the Ben-oil tree, and it is so named from the Persian month Bahman when the roots of this tree were harvested. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
1-Docosanoic acidChEBI
BehensaeureChEBI
CH3-[CH2]20-COOHChEBI
Docosanic acidChEBI
DocosanoateChEBI
Docosanoic acidChEBI
DocosansaeureChEBI
Docosoic acidChEBI
DokosansaeureChEBI
HeneicosansaeureChEBI
N-Docosanoic acidChEBI
1-DocosanoateGenerator
BehenateGenerator
DocosanateGenerator
DocosoateGenerator
N-DocosanoateGenerator
b 95HMDB
Edenor C 22-85RHMDB
EXL 5HMDB
Glycon b 70HMDB
Hydrofol 2022-55HMDB
Hydrofol acid 560HMDB
Prifac 2987HMDB
Chemical FormulaC22H44O2
Average Molecular Weight340.5836
Monoisotopic Molecular Weight340.334130652
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 KeyInChIKey=UKMSUNONTOPOIO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point81 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.6e-05 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.04e-05 mg/mLALOGPS
logP9.19ALOGPS
logP8.92ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity104.69 m3·mol-1ChemAxon
Polarizability47.25 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0159-0900000000-3bbb6d3ae586b9b33415View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-2900000000-348efcfc8f1d67f7b5b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0006-0109000000-bda321e754dd42fb8bb8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0a4j-5900000000-809bb3193f37942db909View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0a4i-7900000000-22ebd8fe304be08b915eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0596-9100000000-eb78c2ccaf4cc9882ed1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0019000000-7a5055e53e55c3579d34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ed-2494000000-d58d52e3d2392ca04047View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-6980000000-36eb30e33ef7e33830d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-2e1668571d77736f2b5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-007a-1039000000-9420d9704691f31b35ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9130000000-68de74e83f8a8e6cadbaView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0596-9422000000-4799a4c5794b59792050View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Feces
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.160 +/- 0.007 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.012 +/- 0.262 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021815
KNApSAcK IDC00001211
Chemspider ID7923
KEGG Compound IDC08281
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBehenic acid
NuGOwiki LinkHMDB00944
Metagene LinkHMDB00944
METLIN ID260
PubChem Compound8215
PDB IDNot Available
ChEBI ID28941
References
Synthesis ReferenceLu, Jianmin; Li, He; Yang, Yiping; Du, Baoshan. Preparation of behenic acid from erucic acid by hydrogenation at ordinary pressure. Zhongguo Youzhi (1997), 22(5), 57-58.
Material Safety Data Sheet (MSDS)Download (PDF)
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. [11124748 ]
  2. Paik MJ, Kim KR, Yoon HR, Kim HJ: Diagnostic patterns of very-long-chain fatty acids in plasma of patients with X-linked adrenoleukodystrophy. J Chromatogr B Biomed Sci Appl. 2001 Aug 25;760(1):149-57. [11522057 ]
  3. Neuhouser ML, Patterson RE, King IB, Horner NK, Lampe JW: Selected nutritional biomarkers predict diet quality. Public Health Nutr. 2003 Oct;6(7):703-9. [14552672 ]
  4. Mosquera MM, de Ory F, Gallardo V, Cuenca L, Morales M, Sanchez-Yedra W, Cabezas T, Hernandez JM, Echevarria JE: Evaluation of diagnostic markers for measles virus infection in the context of an outbreak in Spain. J Clin Microbiol. 2005 Oct;43(10):5117-21. [16207972 ]
  5. Grosso NR, Nepote V, Guzman CA: Chemical composition of some wild peanut species (Arachis L.) seeds. J Agric Food Chem. 2000 Mar;48(3):806-9. [10725154 ]
  6. Peerapattana J, Otsuka K, Otsuka M: Time-controlled pulse-drug release from dry-coated wax matrix tablets for colon drug delivery. Biomed Mater Eng. 2004;14(3):293-301. [15299241 ]