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Merck

L2378

Sigma-Aldrich

γ-Linolenic acid

≥99%, liquid

Sinónimos:

gamma-Linolenic acid, cis,cis,cis-6,9,12-Octadecatrienoic acid

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About This Item

Fórmula empírica (notación de Hill):
C18H30O2
Número de CAS:
Peso molecular:
278.43
Beilstein/REAXYS Number:
1712253
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.25

biological source

plant oil (borage)

Quality Level

assay

≥99%

form

liquid

functional group

carboxylic acid

lipid type

omega FAs

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.

Biochem/physiol Actions

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 .
Gamma-linolenate (C18:6,9,12) differs from α-linolenate (C18:9,12,15) in the positions of the double bonds.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


Certificados de análisis (COA)

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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
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)
P E Kankaanpää et al.
FEMS microbiology letters, 194(2), 149-153 (2001-02-13)
The establishment of the intestinal microflora, and probiotic bacteria, may control the inflammatory conditions in the gut. As polyunsaturated fatty acids (PUFA) possess antimicrobial activities, they may deter the action of probiotics. We assessed whether free linoleic, gamma-linolenic, arachidonic, alpha-linolenic
Y Y Fan et al.
The Journal of nutrition, 128(9), 1411-1414 (1998-09-10)
Considerable debate remains regarding the distinct biological activities of individual polyunsaturated fatty acids (PUFA). One of the most interesting yet controversial dietary approaches has been the possible prophylactic role of dietary gamma-linolenic acid (GLA) in treating various chronic disease states.
Gamma linolenic acid--occurrence and physical and chemical properties.
F D Gunstone
Progress in lipid research, 31(2), 145-161 (1992-01-01)

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