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Merck

L2378

Sigma-Aldrich

γ-Linolensäure

≥99%, liquid

Synonym(e):

cis,cis,cis-6,9,12-Octadecatriensäure

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About This Item

Empirische Formel (Hill-System):
C18H30O2
CAS-Nummer:
Molekulargewicht:
278.43
Beilstein:
1712253
MDL-Nummer:
UNSPSC-Code:
12352211
PubChem Substanz-ID:
NACRES:
NA.25

Biologische Quelle

plant oil (borage)

Qualitätsniveau

Assay

≥99%

Form

liquid

Funktionelle Gruppe

carboxylic acid

Lipid-Typ

omega FAs

Versandbedingung

ambient

Lagertemp.

−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-

InChIKey

VZCCETWTMQHEPK-QNEBEIHSSA-N

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Anwendung

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. Wirkung

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.

Piktogramme

Exclamation mark

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 3

Flammpunkt (°F)

230.0 °F - closed cup

Flammpunkt (°C)

110 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


Analysenzertifikate (COA)

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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
V A Ziboh et al.
The American journal of clinical nutrition, 71(1 Suppl), 361S-366S (2000-01-05)
In the skin epidermis, the metabolism of polyunsaturated fatty acids (PUFAs) is highly active. Dietary deficiency of linoleic acid (LA), the major 18-carbon n-6 PUFA in normal epidermis, results in a characteristic scaly skin disorder and excessive epidermal water loss.
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
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

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