Gamma-linolenic acid

γ-Linolenic acid

Names

IUPAC name

all-cis-6,9,12-octadecatrienoic acid

Other names

Gamma-linolenic acid, gamolenic acid, GLA

Identifiers

CAS Number

506-26-3^Y

3D model (Jmol)

CHEBI:28661^Y

ChEMBL464982^Y

4444436^Y

78YC2MAX4O^Y

InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-^Y

Key: VZCCETWTMQHEPK-QNEBEIHSSA-N^Y
InChI=1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-

Key: VZCCETWTMQHEPK-QNEBEIHSBP

SMILES

O=C(O)CCCC\C=C/C\C=C/C\C=C/CCCCC

Properties

Chemical formula

C₁₈H₃₀O₂

Molar mass

278.44 g·mol⁻¹

Appearance

Colorless oil

Pharmacology

ATC code

D11AX02 (WHO)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

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.

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