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Merck
CN

L2378

γ-Linolenic acid

≥99%, liquid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C18H30O2
CAS Number:
506-26-3
Molecular Weight:
278.43
UNSPSC Code:
12352211
NACRES:
NA.25
PubChem Substance ID:
24896312
MDL number:
MFCD00065718
Beilstein/REAXYS Number:
1712253

Key Documents

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Product Name

γ-Linolenic acid, ≥99%, liquid

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-

SMILES string

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

InChI key

VZCCETWTMQHEPK-QNEBEIHSSA-N

biological source

plant oil (borage)

assay

≥99%

form

liquid

functional group

carboxylic acid

lipid type

omega FAs

shipped in

ambient

storage temp.

−20°C

Quality Level

100

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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
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX1176
MKCW1265
MKCV3583
MKCV1440
MKCV4689

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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
Inmaculada Tasset-Cuevas et al.
PloS one, 8(2), e56986-e56986 (2013-03-06)
Borage (Borago officinalis L.) seed oil has been used as a treatment for various degenerative diseases. Many useful properties of this oil are attributed to its high gamma linolenic acid content (GLA, 18:3 ω-6). The purpose of this study was
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
P Darcet et al.
Annales de la nutrition et de l'alimentation, 34(2), 277-290 (1980-01-01)
33 healthy men, 72 years old on average, ingested during five week: 2,4 g of Oenothera Biennis oil rich in PUFA. Before and after ingestion, platelet aggregation was measured according to the Born's photometric method, which divided the original group
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