16326-32-2 Usage
Uses
Used in Analytical Standards:
GAMMA-LINOLENIC ACID METHYL ESTER is used as an analytical standard for the determination of aldehydes such as pentanal and hexanal via peroxidation, further analyzed by gas chromatography technique.
Used in Quantification of Analytes:
GAMMA-LINOLENIC ACID METHYL ESTER is used as an analytical reference standard for the quantification of the analyte in serum lipid extract and Arthrospira (Spirulina) platensis using the gas-chromatography technique.
Used in Pharmaceutical Industry:
GAMMA-LINOLENIC ACID METHYL ESTER is used as a pharmaceutical candidate for the development of GLA-containing diets and dietary supplements, targeting various health benefits related to the essential nutrient GLA.
Used in Research and Development:
GAMMA-LINOLENIC ACID METHYL ESTER is used as a research compound to study its properties and potential applications in various fields, including its role as a weak LTB4 receptor antagonist and its inhibition of LTB4-induced bronchoconstriction in in vivo models.
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.
in vitro
γ-linolenic acid methyl ester is an esterified version of the free acid which is less water soluble but more amenable for the formulation of gla-containing diets and dietary supplements. gla was identified as an ω-6 fatty acid which could be elongated to arachidonic acid for endogenous eicosanoid synthesis. gla was found to be a weak leukotriene b4 (ltb4) receptor antagonist, which was able to inhibit [3h]-ltb4 binding to porcine neutrophil membranes with a ki of 1 μm [1].
in vivo
in an in-vivo model of ltb4-induced bronchoconstriction, ricinelaidic acid andγ-linolenic acid methyl ester at a 1 mg/kg i.v. dose could result in 46% and 53% inhibition, respectively, indicating that essential fatty acids are ltb4 receptor antagonists, which may account in part for their reported anti-inflammatory activities [1].
references
[1] yagaloff, k. a.,franco, l.,simko, b., et al. essential fatty acids are antagonists of the leukotriene b4 receptor. prostaglandins, leukotrienes and essential fatty acids 52, 293-297 (1995).
Check Digit Verification of cas no
The CAS Registry Mumber 16326-32-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,3,2 and 6 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 16326-32:
(7*1)+(6*6)+(5*3)+(4*2)+(3*6)+(2*3)+(1*2)=92
92 % 10 = 2
So 16326-32-2 is a valid CAS Registry Number.
InChI:InChI=1/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-
16326-32-2Relevant academic research and scientific papers
DIRECT METHOD AND REAGENT KITS FOR FATTY ACID ESTER SYNTHESIS
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Page/Page column 18; 21-22; 29, (2008/12/07)
Provided are efficient, cost-effective and water tolerant methods (e.g., single-vial methods) for preparing fatty acid esters from organic matter, comprising: obtaining organic matter comprising at least one fat substituent, contacting the organic matter in a reaction mixture with a basic solution under conditions suitable to provide for hydrolytic release of monomeric fatty acids from the at least one fat substituent to provide a base-treated reaction mixture, and esterifying the monomeric fatty acids of the base-treated reaction mixture by acidification of the reaction mixture and treating in the presence of an organic alcohol to provide fatty acid esters. The methods optionally further comprise, prior to esterifying, neutralizing the base-treated reaction mixture to provide for neutralized fatty acids, separating the neutralized fatty acids from the neutralized reaction mixture, and dissolving the separated fatty acids in the esterification reaction mixture. Also provided are related methods and kits for fat analysis.
Insecticidal compounds against mosquito larvae from Oscillatoria agardhii strain 27
Harada, Ken-Ichi,Suomalainen, Mette,Uchida, Hideaki,Masui, Hiroaki,Ohmura, Kuniyo,Kiviranta, Jari,Niku-Paavola, Marja-Leena,Ikemoto, Takaya
, p. 114 - 119 (2007/10/03)
It was found that Oscillatoria agardhii strain 27 produced compounds toxic against mosquito larvae (Aedes albopictus), therefore, these compounds were extracted and separated for insecticide development. Structural characterization of the toxic fraction by 1H-NMR and GC-MS showed that these compounds are not the neurotoxins or hepatotoxins conventionally produced by Oscillatoria, but it contained a mixture of unsaturated fatty acids, oleic, linoleic, and γ-linolenic acids, as well as saturated fatty acids, myristic, palmitic, and stearic acids. In a bioassay developed for these hydrophobic compounds using mosquito larvae, authentic unsaturated fatty acids were shown to be toxic, whereas saturated ones were active. The results suggested that it might be possible to use unsaturated fatty acids as environmentally safe and effective insecticides without the side effects of the chemically synthesized insecticides. (C) 2000 by John Wiley and Sons, Inc.
A large scale and concise synthesis of γ-linolenic acid from 4- chlorobut-2-yn-1-ol
Durand, Sandrine,Parrain, Jean-Luc,Santelli, Maurice
, p. 1015 - 1018 (2007/10/03)
A large scale and concise synthesis of γ-linolenic acid is described. The key step of the synthesis involves a copper salt mediated cross-coupling of two different alkynes and chlorobutynol.
