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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-10-09 21:01:13 UTC
HMDB IDHMDB0000944
Secondary Accession Numbers
  • HMDB00944
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 . Behenic acid has been identified in the human placenta (PMID: 32033212 ).
Structure
Data?1582752166
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
Behenic acidHMDB
FA(22:0)HMDB
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 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:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility3.0e-05 g/LALOGPS
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-0900000000-3bbb6d3ae586b9b33415Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-2900000000-348efcfc8f1d67f7b5b2Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0596-9100000000-eb78c2ccaf4cc9882ed1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0900000000-3bbb6d3ae586b9b33415Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2900000000-348efcfc8f1d67f7b5b2Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-1900000000-118efeed433fc3141bc9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7690000000-97da3fdb0e98064049b6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00g1-9551000000-fd9768208a1797291a14Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0006-0109000000-bda321e754dd42fb8bb8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0a4j-5900000000-809bb3193f37942db909Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0a4i-7900000000-22ebd8fe304be08b915eSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0596-9100000000-eb78c2ccaf4cc9882ed1Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-000i-0900000000-d09512035285f332d56cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0900000000-d09512035285f332d56cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-000i-0900000000-d09512035285f332d56cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0009000000-3a6826d318c7e1634120Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-000i-0009000000-3a6826d318c7e1634120Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-000i-0009000000-b29cc64ce52ea552b8d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0009000000-9f560a0c6bac7043337fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-000i-0009000000-3cdf1b17a2391c889f5bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0009000000-3a6826d318c7e1634120Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-000i-0009000000-183662ae4ac2ef63046eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0009000000-b29cc64ce52ea552b8d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0009000000-9f560a0c6bac7043337fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0009000000-3cdf1b17a2391c889f5bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0009000000-183662ae4ac2ef63046eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0019000000-7a5055e53e55c3579d34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ed-2494000000-d58d52e3d2392ca04047Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-6980000000-36eb30e33ef7e33830d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-2e1668571d77736f2b5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-007a-1039000000-9420d9704691f31b35ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9130000000-68de74e83f8a8e6cadbaSpectrum
MSMass Spectrum (Electron Ionization)splash10-0596-9422000000-4799a4c5794b59792050Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.160 +/- 0.007 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.012 +/- 0.262 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified31.681 +/- 20.935 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified23.277 +/- 0.913 umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified61.661 +/- 2.281 umol/mmol creatinineAdolescent (13-18 years old)Both
Obese
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Obesity
  1. Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDDOCOSAC
MarkerDB IDMDB00000288
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. 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. [PubMed:11522057 ]
  2. 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. [PubMed:14552672 ]
  3. 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. [PubMed:16207972 ]
  4. 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. [PubMed:10725154 ]
  5. 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. [PubMed:11124748 ]
  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. [PubMed:15299241 ]
  7. 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 ]