MilliporeSigma
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L2378

Sigma-Aldrich

γ-Linolenic acid

≥99%, liquid

Synonym(s):
gamma-Linolenic acid, cis,cis,cis-6,9,12-Octadecatrienoic acid
Empirical Formula (Hill Notation):
C18H30O2
CAS Number:
Molecular Weight:
278.43
Beilstein:
1712253
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

biological source

plant oil (borage)

assay

≥99%

form

liquid

functional group

carboxylic acid

shipped in

ambient

storage temp.

−20°C

SMILES string

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

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-

InChI key

VZCCETWTMQHEPK-QNEBEIHSSA-N

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Application

γ-linolenic acid has been used as an analytical standard in gas chromatography. It may be used in nutritional studies regarding weight regain and as a possible tumor suppression agent. γ-linolenic acid is used in studies on the mechanisms and prevention of oxidation/peroxidation of unsaturated fatty acids.

Packaging

10, 100, 500 mg in ampule
1 g in ampule

Biochem/physiol Actions

Gamma-linolenate (C18:6,9,12) differs from α-linolenate (C18:9,12,15) in the positions of the double bonds.
γ-Linolenic acid , a polyunsaturated fatty acid, exerts anti-inflammatory effect by decreasing both interleukin (IL) 6 and IL-8 production in the human enterocyte-like cell line Caco-2 and humandendritic cells in vitro .

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More Documents

Quotes and Ordering

Julianne Lindemann et al.
Current medical research and opinion, 25(12), 2865-2875 (2009-10-09)
Asthma can have a negative impact on quality of life although this is not well correlated with objective evaluations of pulmonary function. A medical food, EFF1009, containing the fatty acids gamma-linolenic acid (GLA) and eicosapentaenoic acid (EPA) decreases leukotriene B(4)
J Hindo et al.
Radiation research, 153(2), 201-207 (2000-01-12)
Peroxidation of unconjugated polyunsaturated fatty acids such as linolenic acid proceeds through a free radical chain mechanism and is accompanied by the formation of conjugated dienes such as hydroperoxides. In an investigation of radiation-induced oxidation of aqueous linolenate, we have
Nutritional and medical importance of gamma-linolenic acid.
D F Horrobin
Progress in lipid research, 31(2), 163-194 (1992-01-01)
P Kankaanpää et al.
Allergy, 56(7), 633-638 (2001-06-26)
The increased consumption of n-6 polyunsaturated fatty acids (PUFA) has been shown to coincide with the increased prevalence of atopic diseases. We aimed to investigate whether maternal diet and atopic status influence the PUFA composition of breast milk and the
R J Levy et al.
Clinical pharmacology and therapeutics, 25(5 Pt 1), 562-570 (1979-05-01)
The urinary excretion of gamma-carboxyglutamic acid (Gla), the amino acid involved in the vitamin K-dependent calcium binding of prothrombin and clotting factors VII, IX, and X, was studied in warfarin-anticoagulated patients. An isotope dilution procedure was developed for the measurement

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