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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:32:00 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. 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. 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
FA(22:0)HMDB
Behenic acidHMDB
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point81 °CNot Available
Boiling Point391.00 to 392.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.6e-05 mg/mLNot Available
LogP9.910The Good Scents Company Information System
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M-H]-MetCCS_train_neg191.1830932474
AllCCS[M-H]-Not Available191.18http://allccs.zhulab.cn/database/detail?ID=AllCCS00000229
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.0e-05 g/LALOGPS
logP10(9.19) g/LALOGPS
logP10(8.92) g/LChemAxon
logS10(-7) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+192.04731661259
DarkChem[M-H]-192.33431661259
AllCCS[M+H]+202.64532859911
AllCCS[M-H]-192.66232859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Behenic acid,1TMS,#1CCCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C2639.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Behenic acid,1TBDMS,#1CCCCCCCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2894.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Behenic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-0900000000-3bbb6d3ae586b9b334152014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Behenic acid GC-MS (1 TMS)splash10-0159-2900000000-348efcfc8f1d67f7b5b22014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Behenic acid EI-B (Non-derivatized)splash10-0596-9100000000-eb78c2ccaf4cc9882ed12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Behenic acid GC-EI-TOF (Non-derivatized)splash10-0159-0900000000-3bbb6d3ae586b9b334152017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Behenic acid GC-MS (Non-derivatized)splash10-0159-2900000000-348efcfc8f1d67f7b5b22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Behenic acid GC-EI-TOF (Non-derivatized)splash10-0159-1900000000-118efeed433fc3141bc92017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Behenic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7690000000-97da3fdb0e98064049b62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Behenic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00g1-9551000000-fd9768208a1797291a142017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Behenic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0596-9422000000-4799a4c5794b597920502014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-0006-0109000000-bda321e754dd42fb8bb82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0a4j-5900000000-809bb3193f37942db9092012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-0a4i-7900000000-22ebd8fe304be08b915e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid EI-B (HITACHI M-80B) , Positive-QTOFsplash10-0596-9100000000-eb78c2ccaf4cc9882ed12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid ESI-TOF 40V, Negative-QTOFsplash10-000i-0900000000-d09512035285f332d56c2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid ESI-TOF 10V, Negative-QTOFsplash10-000i-0900000000-d09512035285f332d56c2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid ESI-TOF 30V, Negative-QTOFsplash10-000i-0900000000-d09512035285f332d56c2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid ESI-TOF , Negative-QTOFsplash10-000i-0009000000-3a6826d318c7e16341202017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid ESI-TOF 20V, Negative-QTOFsplash10-000i-0009000000-3a6826d318c7e16341202017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid ESI-TOF 40V, Negative-QTOFsplash10-000i-0009000000-b29cc64ce52ea552b8d12017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid ESI-TOF 10V, Negative-QTOFsplash10-000i-0009000000-9f560a0c6bac7043337f2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid ESI-TOF 30V, Negative-QTOFsplash10-000i-0009000000-3cdf1b17a2391c889f5b2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid ESI-TOF , Negative-QTOFsplash10-000i-0009000000-3a6826d318c7e16341202017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid ESI-TOF 20V, Negative-QTOFsplash10-000i-0009000000-183662ae4ac2ef63046e2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid LC-ESI-TOF , negative-QTOFsplash10-000i-0009000000-b29cc64ce52ea552b8d12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid LC-ESI-TOF , negative-QTOFsplash10-000i-0009000000-9f560a0c6bac7043337f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid LC-ESI-TOF , negative-QTOFsplash10-000i-0009000000-3cdf1b17a2391c889f5b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid LC-ESI-TOF , negative-QTOFsplash10-000i-0009000000-183662ae4ac2ef63046e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Behenic acid 10V, Positive-QTOFsplash10-000i-0009000000-59e981660d097942b2b82021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Behenic acid 10V, Positive-QTOFsplash10-00di-0019000000-7a5055e53e55c3579d342015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Behenic acid 20V, Positive-QTOFsplash10-00ed-2494000000-d58d52e3d2392ca040472015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Behenic acid 40V, Positive-QTOFsplash10-0536-6980000000-36eb30e33ef7e33830d62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Behenic acid 10V, Negative-QTOFsplash10-000i-0019000000-2e1668571d77736f2b5e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Behenic acid 20V, Negative-QTOFsplash10-007a-1039000000-9420d9704691f31b35dd2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Behenic acid 40V, Negative-QTOFsplash10-052f-9130000000-68de74e83f8a8e6cadba2015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
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
Good Scents IDrw1242111
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [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 ]