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γ-Linolenic acid

analytical standard

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Synonym(s):
cis,cis,cis-6,9,12-Octadecatrienoic acid
Empirical Formula (Hill Notation):
C18H30O2
CAS Number:
506-26-3
Molecular Weight:
278.43
Beilstein:
1712253
MDL number:
MFCD00065718
PubChem Substance ID:
329759717
NACRES:
NA.24

biological source

synthetic

Quality Level

100

grade

analytical standard

Assay

≥98.5% (GC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

food and beverages

format

neat

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

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

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 .

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

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

Certificates of Analysis (COA)

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Elizabeth C Leigh-Firbank et al.
The British journal of nutrition, 87(5), 435-445 (2002-05-16)
Fish-oil supplementation can reduce circulating triacylglycerol (TG) levels and cardiovascular risk. This study aimed to assess independent associations between changes in platelet eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) and fasting and postprandial (PP) lipoprotein concentrations and LDL oxidation status
Fengyun Qin et al.
Journal of agricultural and food chemistry, 60(9), 2200-2204 (2012-02-14)
γ-Linolenic acid (GLA) has been used as a general nutraceutical for pharmacologic applications, particularly in the treatment of skin conditions such as eczema. Four transgenic soybean lines that produce GLA at high yields (4.21% of total fatty acids, up to
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.
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.
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
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