Sapienic acid is a fatty acid

Fatty acid

In chemistry, especially biochemistry, a fatty acid is a carboxylic acid with a long unbranched aliphatic tail , which is either saturated or unsaturated. Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28. Fatty acids are usually derived from...

 that is a major component of human sebum. Among hair-bearing animals, sapienic acid is unique to humans (thus sapien is the root of its name). The equivalent fatty acid in mouse sebum is palmitoleic acid

Palmitoleic acid

Palmitoleic acid, or -9-hexadecenoic acid, is an omega-7 monounsaturated fatty acid with the formula CH35CH=CH7COOH that is a common constituent of the glycerides of human adipose tissue. It is present in all tissues, but generally found in higher concentrations in the liver...

. Sapienic acid has been implicated in the development of acne

Acne

Acne is a general term used for acneiform eruptions. It is usually used as a synonym for acne vulgaris, but may also refer to:*Acne aestivalis*Acne conglobata*Acne cosmetica*Acne fulminans*Acne keloidalis nuchae*Acne mechanica...

, and it may have potent antibacterial activity.

Delta 6 desaturation

Desaturase

A fatty acid desaturase is an enzyme that removes two hydrogen atoms from a fatty acid, creating a carbon/carbon double bond. These desaturases are classified as...

 of palmitic acid

Palmitic acid

Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is one of the most common saturated fatty acids found in animals and plants. Its molecular formula is CH314CO2H. As its name indicates, it is a major component of the oil from palm trees . Palmitate is a term for the salts and esters of...

 leads to the biosynthesis of sapienic acid. In other tissues linoleic acid

Linoleic acid

Linoleic acid is an unsaturated n-6 fatty acid. It is a colorless liquid at room temperature. In physiological literature, it has a lipid number of 18:2...

 is the target for delta 6 desaturase, but linoleic acid is degraded in sebaceous cell

Sebaceous gland

The sebaceous glands are microscopic glands in the skin that secrete an oily/waxy matter, called sebum, to lubricate and waterproof the skin and hair of mammals...

s, allowing the enzyme to desaturate palmitic to sapienic acid. A two-carbon extension product of sapienic acid, sebaleic acid, is also present in sebum.

External links

• Waxes, The Lipid Library