Behenic acid

Behenic acid
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 Y
PubChem 8215
ChemSpider 7923 Y
UNII H390488X0A Y
EC number 204-010-8
KEGG C08281 Y
ChEBI CHEBI:28941 Y
ChEMBL CHEMBL1173474 Y
Jmol-3D images Image 1
Properties
Molecular formula C22H44O2
Molar mass 340.58 g mol−1
Appearance White to yellowish crystals or powder
Melting point

80.0 °C[1]
Boiling point

306 °C
Hazards
NFPA 704
1
1
0
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Behenic acid (also docosanoic acid) is a normal 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.

Contents

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] Also used in lubricating oils, as solvent evaporation retarder in paint removers. Amide as anti-foam in the manufacturing of detergents, in 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. http://iupac.org/publications/pac/73/4/0685/. 
  2. ^ http://www.numericana.com/answer/culture.htm
  3. ^ a b 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..
Saturated
VFA: Acetic (C2) · Propionic (C3) · Butyric (C4) · Valeric (C5) · Caproic (C6) · Enanthic (C7) · Caprylic (C8) · Pelargonic (C9) · Capric (C10) · Undecylic (C11) · Lauric (C12) · Tridecylic (C13) · Myristic (C14) · Pentadecanoic (C15) · Palmitic (C16) · Margaric (C17) · Stearic (C18) · Nonadecylic (C19) · Arachidic (C20) · Heneicosylic (C21) · Behenic (C22) · Tricosylic (C23) · Lignoceric (C24) · Pentacosylic (C25) · Cerotic (C26) · Heptacosylic (C27) · Montanic (C28) · Nonacosylic (C29) · Melissic (C30) · Hentriacontylic (C31) · Lacceroic (C32) · Psyllic (C33) · Geddic (C34) · Ceroplastic (C35) · Hexatriacontylic (C36)
n−3 Unsaturated
n−6 Unsaturated
n−9 Unsaturated
biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i