ContaminantDB: Behenic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-09-05 17:13:00 UTC

Update Date

2026-04-16 22:15:32 UTC

Accession Number

CHEM003565

Identification

Common Name

Behenic acid

Class

Small Molecule

Description

Behenic 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.

Contaminant Sources

Cosmetic Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HPV EPA Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Food Toxin
Household Toxin
Metabolite
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Docosanoic acid	ChEBI
Behensaeure	ChEBI
CH3-[CH2]20-COOH	ChEBI
Docosanic acid	ChEBI
Docosanoate	ChEBI
Docosansaeure	ChEBI
Docosoic acid	ChEBI
Dokosansaeure	ChEBI
N-Docosanoic acid	ChEBI
1-Docosanoate	Generator
Docosanate	Generator
Docosanoic acid	Generator
Docosoate	Generator
N-Docosanoate	Generator
Behenate	Generator
FA(22:0)	HMDB
Behenic acid	HMDB

Chemical Formula

C₂₂H₄₄O₂

Average Molecular Mass

340.584 g/mol

Monoisotopic Mass

340.334 g/mol

CAS Registry Number

112-85-6

IUPAC Name

docosanoic acid

Traditional Name

behenic acid

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 Key

UKMSUNONTOPOIO-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very 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 Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:28941 )
straight-chain saturated fatty acid (CHEBI:28941 )
Straight chain fatty acids (C08281 )
Saturated fatty acids (C08281 )
Straight chain fatty acids (LMFA01010022 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	81 °C
Boiling Point	306°C
Solubility	1.6e-05 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	3.0e-05 g/L	ALOGPS
logP	9.19	ALOGPS
logP	8.92	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	104.69 m³·mol⁻¹	ChemAxon
Polarizability	47.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0159-0900000000-3bbb6d3ae586b9b33415	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0159-2900000000-348efcfc8f1d67f7b5b2	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0596-9100000000-eb78c2ccaf4cc9882ed1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0900000000-3bbb6d3ae586b9b33415	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-2900000000-348efcfc8f1d67f7b5b2	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-1900000000-118efeed433fc3141bc9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7690000000-97da3fdb0e98064049b6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00g1-9551000000-fd9768208a1797291a14	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0006-0109000000-bda321e754dd42fb8bb8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0a4j-5900000000-809bb3193f37942db909	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0a4i-7900000000-22ebd8fe304be08b915e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0596-9100000000-eb78c2ccaf4cc9882ed1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-000i-0900000000-d09512035285f332d56c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0900000000-d09512035285f332d56c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-000i-0900000000-d09512035285f332d56c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0009000000-3a6826d318c7e1634120	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-000i-0009000000-3a6826d318c7e1634120	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-000i-0009000000-b29cc64ce52ea552b8d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0009000000-9f560a0c6bac7043337f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-000i-0009000000-3cdf1b17a2391c889f5b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0009000000-3a6826d318c7e1634120	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-000i-0009000000-183662ae4ac2ef63046e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0009000000-b29cc64ce52ea552b8d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0009000000-9f560a0c6bac7043337f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0009000000-3cdf1b17a2391c889f5b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0009000000-183662ae4ac2ef63046e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-59e981660d097942b2b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0019000000-7a5055e53e55c3579d34	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ed-2494000000-d58d52e3d2392ca04047	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0536-6980000000-36eb30e33ef7e33830d6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0019000000-2e1668571d77736f2b5e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-007a-1039000000-9420d9704691f31b35dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9130000000-68de74e83f8a8e6cadba	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0596-9422000000-4799a4c5794b59792050	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000944

FooDB ID

FDB005830

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001211

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

260

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Lu, 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.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11124748

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12357383

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15716582

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20565070

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=32601219

6. Lu, 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.

7. 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.

8. 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.

9. 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.

10. 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.

11. 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.

12. 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.

13. 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.

Behenic acid (CHEM003565)

Structure for CHEM003565: Behenic acid