Milk Composition Database: Showing metabocard for Behenic acid (BMDB0000944)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:38:57 UTC

Update Date

2020-06-04 21:07:38 UTC

MCDB ID

BMDB0000944

Secondary Accession Numbers

BMDB00944

Metabolite Identification

Common Name

Behenic acid

Description

Behenic acid, also known as docosanoate 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 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Behenic acid is a potentially toxic compound.

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 Weight

340.5836

Monoisotopic Molecular Weight

340.334130652

IUPAC Name

docosanoic acid

Traditional Name

behenic acid

CAS Registry Number

112-85-6

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 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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	81 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.6e-05 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Deposition Date	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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0159-2900000000-348efcfc8f1d67f7b5b2	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0596-9100000000-eb78c2ccaf4cc9882ed1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0900000000-3bbb6d3ae586b9b33415	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-2900000000-348efcfc8f1d67f7b5b2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-1900000000-118efeed433fc3141bc9	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7690000000-97da3fdb0e98064049b6	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00g1-9551000000-fd9768208a1797291a14	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0006-0109000000-bda321e754dd42fb8bb8	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0a4j-5900000000-809bb3193f37942db909	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0a4i-7900000000-22ebd8fe304be08b915e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0596-9100000000-eb78c2ccaf4cc9882ed1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-000i-0900000000-d09512035285f332d56c	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0900000000-d09512035285f332d56c	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-000i-0900000000-d09512035285f332d56c	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0009000000-3a6826d318c7e1634120	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-000i-0009000000-3a6826d318c7e1634120	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-000i-0009000000-b29cc64ce52ea552b8d1	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0009000000-9f560a0c6bac7043337f	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-000i-0009000000-3cdf1b17a2391c889f5b	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0009000000-3a6826d318c7e1634120	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-000i-0009000000-183662ae4ac2ef63046e	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0009000000-b29cc64ce52ea552b8d1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0009000000-9f560a0c6bac7043337f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0009000000-3cdf1b17a2391c889f5b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0009000000-183662ae4ac2ef63046e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-59e981660d097942b2b8	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0019000000-7a5055e53e55c3579d34	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ed-2494000000-d58d52e3d2392ca04047	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0536-6980000000-36eb30e33ef7e33830d6	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0019000000-2e1668571d77736f2b5e	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-007a-1039000000-9420d9704691f31b35dd	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9130000000-68de74e83f8a8e6cadba	2015-04-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0596-9422000000-4799a4c5794b59792050	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 11913692	details
Detected and Quantified	293 uM	Total fatty acid	M.J. Abarghuei, Y...	details

External Links

HMDB ID

HMDB0000944

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Behenic acid

METLIN ID

260

PubChem Compound

8215

PDB ID

Not Available

ChEBI ID

28941

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
Tang C, Zhang K, Zhan T, Zhao Q, Zhang J: Metabolic Characterization of Dairy Cows Treated with Gossypol by Blood Biochemistry and Body Fluid Untargeted Metabolome Analyses. J Agric Food Chem. 2017 Oct 25;65(42):9369-9378. doi: 10.1021/acs.jafc.7b03544. Epub 2017 Oct 17. [PubMed:28965405 ]
Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]
M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri (2014). M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021. Livestock Science.

Showing metabocard for Behenic acid (BMDB0000944)

Structure for BMDB0000944 (Behenic acid)