7-hydroxycoumarinyl-γ-Linolenate

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7-hydroxycoumarinyl-γ-Linolenate

7-hydroxycoumarinyl-γ-Linolenate | 161180-12-7

Catalog Number A18-0019
Category Fluorescent Enzyme Substrates
Molecular Formula C27H34O4
Molecular Weight 422.6
Catalog Number Size Price Quantity
A18-0019 -- $--

Product Introduction

7-hydroxycoumarinyl-γ-Linolenate is a PLA2 fluorogenic substrate used in the assays with phospholipid and Ca2+.

Chemical Information

Synonyms Umbelliferyl-γ-Linolenate; 6Z,9Z,12Z-octadecatrienoic acid, 2-oxo-2H-1-benzopyran-7-yl ester; (2-Oxochromen-7-yl) octadeca-6,9,12-trienoate
Purity ≥98%
Canonical SMILES CCCCCC=CCC=CCC=CCCCCC(=O)OC1=CC2=C(C=C1)C=CC(=O)O2
InChI InChI=1S/C27H34O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-26(28)30-24-20-18-23-19-21-27(29)31-25(23)22-24/h6-7,9-10,12-13,18-22H,2-5,8,11,14-17H2,1H3/b7-6-,10-9-,13-12-
InChI Key LPIXSKJJCANUQD-QNEBEIHSSA-N
Appearance A solution in ethanol
  • Product Specification
  • Application
Storage Store at -20°C

7-Hydroxycoumarinyl-γ-Linolenate is a compound derived from the combination of 7-hydroxycoumarin and γ-Linolenic acid (GLA). 7-Hydroxycoumarin, also known as umbelliferone, is a natural product from the coumarin family, characterized by its yellowish-white crystalline powder form, moderate solubility in hot water, and high solubility in ethanol. Notably, it absorbs ultraviolet light strongly, which contributes to its use in sunscreens and fluorescence indicators. On the other hand, γ-Linolenic acid is an omega-6 fatty acid found in seed oils. It is primarily obtained from sources like evening primrose oil and borage seed oil. GLA is crucial as it contributes to the formation of physiologically significant molecules such as dihomo-γ-linolenic acid, a precursor to various anti-inflammatory agents. These two components, when combined, form 7-Hydroxycoumarinyl-γ-Linolenate, offering potential applications in medicinal and industrial domains.

The first significant application of 7-Hydroxycoumarinyl-γ-Linolenate is in the cosmetic industry, particularly in sunscreens. Umbelliferone, due to its ability to absorb ultraviolet light strongly across multiple wavelengths, is utilized to protect the skin from harmful UV rays. By integrating GLA, the compound might enhance the skin’s resilience against inflammation caused by UV exposure, thereby offering dual benefits of sun protection and skin soothing. This makes 7-Hydroxycoumarinyl-γ-Linolenate a valuable addition to advanced sunscreen formulations.

Another critical application of this compound lies in the field of anti-inflammatory treatments. GLA is well-documented for its anti-inflammatory properties, resulting from its conversion into dihomo-γ-linolenic acid, which further metabolizes into anti-inflammatory eicosanoids. When 7-Hydroxycoumarinyl is attached, it may potentially enhance these effects, aiming to amplify the compound’s efficacy in treating inflammatory conditions. Consequently, this makes it a compound of interest in developing new anti-inflammatory pharmaceuticals, particularly for skin and joint inflammation treatments.

In the realm of dermatology, 7-Hydroxycoumarinyl-γ-Linolenate shows promise as a therapeutic agent for eczema. Although traditional evening primrose oil containing GLA had its marketing authorization withdrawn for eczema treatment, the coupling with 7-Hydroxycoumarin might offer a renewed approach. By combining the soothing and anti-inflammatory properties, this compound may help alleviate symptoms of eczema, providing alternative solutions for patients seeking relief from skin ailments not adequately addressed by conventional medications.

Furthermore, this compound could be explored as a fluorescence indicator. Umbelliferone’s ability to fluoresce under UV light, coupled with GLA’s biochemical properties, may open avenues for its use in tracing biological processes involving fatty acid metabolism. This dual-functionality allows researchers to utilize it in experimental setups aimed at understanding metabolic pathways and cellular interactions influenced by fatty acids. Thus, its application in research laboratories as a bio-indicator stands as a compelling proposition.

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