Behenic acid

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
112-85-6 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:28941 YesY
ChEMBL ChEMBL1173474 YesY
ChemSpider 7923 YesY
ECHA InfoCard 100.003.646
EC Number 204-010-8
KEGG C08281 YesY
PubChem 8215
UNII H390488X0A YesY
Properties
C22H44O2
Molar mass 340.59 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
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored 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

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.

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

References

  1. ↑ "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. 2001. doi:10.1351/pac200173040685.
  2. ↑ http://www.numericana.com/answer/culture.htm
  3. 1 2 USDA Scientists Find Treasure in Peanut Skins.
  4. ↑ Caterm, Nilo B 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, pp41-44..
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