Behenic acid

Behenic acid (also docosanoic acid) is a carboxylic acid, the saturated fatty acid with formula C₂₁H₄₃COOH. 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.

Behenic acid

Names
IUPAC name Docosanoic acid
Other names Behenic acid, Docosanoic acid; 1-Docosanoic acid; n-Docosanoic acid, n-Docosanoate, Glycon B-70, Hydrofol Acid 560, Hydrofol 2022-55, Hystrene 5522, Hystrene 9022, Prifrac 2989, C22:0 (Lipid numbers)
Identifiers
CAS Number	112-85-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28941
ChEMBL	ChEMBL1173474
ChemSpider	7923
ECHA InfoCard	100.003.646
EC Number	204-010-8
KEGG	C08281
PubChem CID	8215
UNII	H390488X0A
CompTox Dashboard (EPA)	DTXSID3026930
InChI 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) Key: UKMSUNONTOPOIO-UHFFFAOYSA-N InChI=1/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) Key: UKMSUNONTOPOIO-UHFFFAOYAN
SMILES O=C(O)CCCCCCCCCCCCCCCCCCCCC
Properties
Chemical formula	C22H44O2
Molar mass	340.592 g·mol^−1
Appearance	White to yellowish crystals or powder
Melting point	80.0 °C (176.0 °F; 353.1 K)[1]
Boiling point	306 °C (583 °F; 579 K)
Hazards
NFPA 704 (fire diamond)	1 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Behenic acid comes from the ben oil tree, Moringa oleifera

Sources

At 9%, it is a major component of Ben oil (or behen oil), which is extracted from the seeds of the Ben-oil tree (Moringa oleifera). It is so named from the Persian month Bahman, when the roots of this tree were harvested.[2]

Behenic acid is also present in some other oils and oil-bearing plants, including rapeseed (canola) and peanut oil and skins. It is estimated that one ton of peanut skins contains 13 pounds (5.9 kg) of behenic acid.[3]

Properties

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 saturated fatty acid in humans.[4]

Uses

Commercially, behenic acid is often used to give hair conditioners and moisturizers their smoothing properties.[3] It is also used in lubricating oils, and as a solvent evaporation retarder in paint removers. Its amide is used as an anti-foaming agent in detergents, floor polishes and dripless candles. Reduction of behenic acid yields behenyl alcohol.

Pracaxi oil (from the seeds of Pentaclethra macroloba) is a natural product with one of the highest concentrations of behenic acid, and is used in hair conditioners.

See also

• Behenyl alcohol
• Glyceryl behenate
• Silver behenate

References

1. Beare-Rogers, J. L.; Dieffenbacher, A.; Holm, J. V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi:10.1351/pac200173040685. S2CID 84492006.
2. http://www.numericana.com/answer/culture.htm
3. USDA Scientists Find Treasure in Peanut Skins Archived 2006-03-23 at the Wayback Machine.
4. Nilo B Cater and Margo A Denke, January 2001, Behenic acid is a cholesterol-raising saturated fatty acid in humans. American Journal of Clinical Nutrition, v 73, No. 1, pp 41-44..