Showing Compound Behnic acid (FDB005830)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:52 UTC

Update date

2020-09-17 15:42:30 UTC

Primary ID

FDB005830

Secondary Accession Numbers

FDB021815

Chemical Information

FooDB Name

Behnic acid

Description

Behenic acid, also known as docosanoate, C22:0 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 is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. In appearance, it consists of white to cream color crystals or powder with a melting point of 80 ¬∞C and boiling point of 306 ¬∞C. It is a major component of Ben oil (or behen oil), which is extracted from the seeds of the Ben-oil tree (Moringa oleifera). Behenic acid is also found in canola oil and peanut oil. As a dietary oil, behenic acid is poorly absorbed. In spite of its low bioavailability compared with oleic acid, behenic acid is a cholesterol-raising (LDL) saturated fatty acid in humans and is therefore not a suitable substitute for palmitic acid in manufactured triacylglycerols (PMID: 11124748). Behenic acid is often used to give hair conditioners and moisturizers their smoothing properties. It is also used in lubricating oils, and as a solvent evaporation retarder in paint removers. Behenic acid amide is used as an anti-foaming agent in detergents, floor polishes and dripless candles.

CAS Number

112-85-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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

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	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C22H44O2

IUPAC name

docosanoic acid

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

Isomeric SMILES

CCCCCCCCCCCCCCCCCCCCCC(O)=O

Average Molecular Weight

340.5836

Monoisotopic Molecular Weight

340.334130652

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0596-9422000000-4799a4c5794b59792050	2014-09-20	View Spectrum
GC-MS	Behnic acid, non-derivatized, GC-MS Spectrum	splash10-0159-0900000000-3bbb6d3ae586b9b33415	Spectrum
GC-MS	Behnic acid, 1 TMS, GC-MS Spectrum	splash10-0159-2900000000-348efcfc8f1d67f7b5b2	Spectrum
GC-MS	Behnic acid, non-derivatized, GC-MS Spectrum	splash10-0596-9100000000-eb78c2ccaf4cc9882ed1	Spectrum
GC-MS	Behnic acid, non-derivatized, GC-MS Spectrum	splash10-0159-0900000000-3bbb6d3ae586b9b33415	Spectrum
GC-MS	Behnic acid, non-derivatized, GC-MS Spectrum	splash10-0159-2900000000-348efcfc8f1d67f7b5b2	Spectrum
GC-MS	Behnic acid, non-derivatized, GC-MS Spectrum	splash10-0159-1900000000-118efeed433fc3141bc9	Spectrum
Predicted GC-MS	Behnic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-7690000000-97da3fdb0e98064049b6	Spectrum
Predicted GC-MS	Behnic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00g1-9551000000-fd9768208a1797291a14	Spectrum
Predicted GC-MS	Behnic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Behnic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0006-0109000000-bda321e754dd42fb8bb8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0a4j-5900000000-809bb3193f37942db909	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0a4i-7900000000-22ebd8fe304be08b915e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0596-9100000000-eb78c2ccaf4cc9882ed1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-000i-0900000000-d09512035285f332d56c	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0900000000-d09512035285f332d56c	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-000i-0900000000-d09512035285f332d56c	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0009000000-3a6826d318c7e1634120	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-000i-0009000000-3a6826d318c7e1634120	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-000i-0009000000-b29cc64ce52ea552b8d1	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0009000000-9f560a0c6bac7043337f	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-000i-0009000000-3cdf1b17a2391c889f5b	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0009000000-3a6826d318c7e1634120	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-000i-0009000000-183662ae4ac2ef63046e	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0009000000-b29cc64ce52ea552b8d1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0009000000-9f560a0c6bac7043337f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0009000000-3cdf1b17a2391c889f5b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-000i-0009000000-183662ae4ac2ef63046e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-59e981660d097942b2b8	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0019000000-7a5055e53e55c3579d34	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ed-2494000000-d58d52e3d2392ca04047	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0536-6980000000-36eb30e33ef7e33830d6	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0019000000-2e1668571d77736f2b5e	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-007a-1039000000-9420d9704691f31b35dd	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9130000000-68de74e83f8a8e6cadba	2015-04-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

BEHNIC ACID

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Showing Compound Behnic acid (FDB005830)

Structure for FDB005830 (Behnic acid)