*** Welcome to piglix ***

Gamma-linolenic acid

γ-Linolenic acid
GLAnumbering.png
Gamma linolenic acid spacefill.png
Gamma linolenic acid.png
Names
IUPAC name
all-cis-6,9,12-octadecatrienoic acid
Other names
Gamma-linolenic acid, gamolenic acid, GLA
Identifiers
506-26-3 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:28661 YesY
ChEMBL ChEMBL464982 YesY
ChemSpider 4444436 YesY
ECHA InfoCard 100.107.263
4710
PubChem 5280933
UNII 78YC2MAX4O YesY
Properties
C18H30O2
Molar mass 278.44 g·mol−1
Appearance Colorless oil
Pharmacology
D11AX02 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Gamma-linolenic acid or GLA (γ-Linolenic acid), (INN and USAN gamolenic acid) is a fatty acid found primarily in vegetable oils. When acting on GLA, 5-lipoxygenase produces no leukotrienes and the conversion by the enzyme of arachidonic acid to leukotrienes is inhibited.

GLA is categorized as an n−6 (also called ω−6 or omega-6) fatty acid, meaning that the first double bond on the methyl end (designated with n or ω) is the sixth bond. In physiological literature, GLA is designated as 18:3 (n−6). GLA is a carboxylic acid with an 18-carbon chain and three cis double bonds. It is an isomer of α-linolenic acid, which is a polyunsaturated n−3 (omega-3) fatty acid, found in rapeseed canola oil, soy beans, walnuts, flax seed (linseed oil), perilla, chia, and hemp seed.

GLA was first isolated from the seed oil of evening primrose. This herbal plant was grown by Native Americans to treat swelling in the body. In the 17th century, it was introduced to Europe and became a popular folk remedy, earning the name king's cure-all. in 1919, Heiduschka and Lüft extracted the oil from evening primrose seeds and described an unusual linolenic acid, which they name γ-. Later, the exact chemical structure was characterized by Riley.


...
Wikipedia

...