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L6503

Sigma-Aldrich

Methyl γ-linolenate

≥99% (GC)

Synonym(s):

γ-Linolenic acid methyl ester, ω-6 Linolenic acid methyl ester, 6,9,12-Octadecatrienoic acid methyl ester, Fame 18:3n-6, Methyl (Z,Z,Z)-6,9,12-octadecatrienoate

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About This Item

Linear Formula:
CH3(CH2)3(CH2CH=CH)3(CH2)4CO2CH3
CAS Number:
16326-32-2
Molecular Weight:
292.46
MDL number:
MFCD00010455
UNSPSC Code:
12352211
PubChem Substance ID:
24896437
NACRES:
NA.25

biological source

plant seeds (Borage)

assay

≥99% (GC)

form

liquid

refractive index

n20/D 1.476 (lit.)

bp

162 °C/0.5 mmHg (lit.)

functional group

ester

lipid type

omega FAs

shipped in

ambient

storage temp.

−20°C

SMILES string

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

InChI

1S/C19H32O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h7-8,10-11,13-14H,3-6,9,12,15-18H2,1-2H3/b8-7-,11-10-,14-13-

InChI key

JFRWATCOFCPIBM-JPFHKJGASA-N

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Application


  • Isolation of methyl gamma linolenate from Spirulina platensis using flash chromatography and its apoptosis inducing effect.: This study explores the extraction and potential anticancer effects of methyl gamma-linolenate from Spirulina platensis by using it as a standard for identification, suggesting its use in developing natural anticancer compounds (Jubie et al., 2015).

Biochem/physiol Actions

Methyl γ-linolenate (C18:6,9,12) differs from methyl α-linolenate (C18:9,12,15) in the positions of the double bonds. Methyl γ-linolenate may be used in nutritional studies regarding weight regain and as a possible tumor suppression agent.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

143.6 °F - closed cup

flash_point_c

62.0 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certificates of Analysis (COA)

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Michael M Meguid et al.
Nutrition (Burbank, Los Angeles County, Calif.), 24(9), 832-842 (2008-08-30)
Roux-en-Y gastric bypass (RYGB) produces rapid and dramatic weight loss in very heavy obese patients. Up to 20% cannot sustain their weight loss beyond 2 to 3 y after surgery. To identify putative etiologic factors producing post-RYGB weight regain, a
Marie A Schirmer et al.
The Journal of nutrition, 137(6), 1430-1435 (2007-05-22)
The purpose of this study was to determine whether gamma-linolenate (GLA) supplementation would suppress weight regain following major weight loss. Fifty formerly obese humans were randomized into a double-blind study and given either 890 mg/d of GLA (5 g/d borage
Hung Pham et al.
Prostaglandins, leukotrienes, and essential fatty acids, 74(4), 271-282 (2006-03-29)
Prostate cancer poses considerable threat to the aging male population as it has become a leading cause of cancer death to this group. Due to the complexity of this age-related disease, the mechanism(s) and factors resulting in prostate cancer remain
Jim-Wen Liu et al.
Journal of agricultural and food chemistry, 52(12), 3960-3966 (2004-06-10)
Dietary supplementation of a high-gamma-linolenic acid canola oil (HGCO) containing approximately 36% (w/w) of gamma-linolenic acid (GLA, 18:3n-6) from the seeds of a genetically transformed canola strain, was assessed for its long-term biological effects. Growing Sprague-Dawley rats (n = 30)
S Jubie et al.
BMC complementary and alternative medicine, 15, 263-263 (2015-08-05)
Isolation of methyl gamma linolenate from Spirulina platensis using flash chromatography and its apoptosis inducing effect against human lung carcinoma A- 549 cell lines. Gamma linolenic acid is an important omega-6 polyunsaturated fatty acid (PUFA) of medicinal interest was isolated
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