52761-34-9

Usage

Uses

Used in Pharmaceutical Industry:
Cis-9,10-dihydroxy-8-nonenoic acid is used as a pharmaceutical agent for its potential health benefits. It has been found to have anti-inflammatory, antifungal, and antibacterial properties, making it a promising candidate for the development of new drugs and treatments.
Used in Cosmetic Industry:
Cis-9,10-dihydroxy-8-nonenoic acid is used as an ingredient in cosmetic products for its moisturizing and skin conditioning properties. Its ability to penetrate the skin and provide hydration makes it a valuable component in skincare formulations.
Used in Food Industry:
Cis-9,10-dihydroxy-8-nonenoic acid is used as a food additive for its potential health benefits. It has been found to have antioxidant properties, which can help protect the body from oxidative stress and support overall health.
Used in Research:
Cis-9,10-dihydroxy-8-nonenoic acid is used as a research compound for studying its chemical properties and potential applications in various fields. Its unique structure and properties make it an interesting subject for scientific investigation.

InChI:InChI=1/C18H30O3/c1-2-3-4-5-7-10-13-16-21-17-14-11-8-6-9-12-15-18(19)20/h7,10,13-14,16-17H,2-6,8-9,11-12,15H2,1H3,(H,19,20)/b10-7-,16-13+,17-14+

Upstream product

• 60-33-3 linoleic acid 
• 5502-91-0 9(S)-hydroperoxyoctadeca-10Z,12E-dienoic acid 

Downstream Products

• 52077-21-1 (8E,1'E,3'Z)-9-(1',3'-nonadienyloxy)-8-nonenoic acid methyl ester 
• 39692-46-1 Methyl Colneleate (8Z isomer) 

Relevant academic research and scientific papers

The CYP74B and CYP74D divinyl ether synthases possess a side hydroperoxide lyase and epoxyalcohol synthase activities that are enhanced by the site-directed mutagenesis

The CYP74 family of cytochromes P450 includes four enzymes of fatty acid hydroperoxide metabolism: allene oxide synthase (AOS), hydroperoxide lyase (HPL), divinyl ether synthase (DES), and epoxyalcohol synthase (EAS). The present work is concerned with catalytic specificities of three recombinant DESs, namely, the 9-DES (LeDES, CYP74D1) of tomato (Solanum lycopersicum), 9-DES (NtDES, CYP74D3) of tobacco (Nicotiana tabacum), and 13-DES (LuDES, CYP74B16) of flax (Linum usitatissimum), as well as their alterations upon the site-directed mutagenesis. Both LeDES and NtDES converted 9-hydroperoxides of linoleic and α?linolenic acids to divinyl ethers colneleic and colnelenic acids (respectively) with only minorities of HPL and EAS products. In contrast, LeDES and NtDES showed low efficiency towards the linoleate 13-hydroperoxide, affording only the low yield of epoxyalcohols. LuDES exhibited mainly the DES activity towards α?linolenate 13-hydroperoxide (preferred substrate), and HPL activity towards linoleate 13-hydroperoxide, respectively. In contrast, LuDES converted 9-hydroperoxides primarily to the epoxyalcohols. The F291V and A287G mutations within the I-helix groove region (SRS-4) of LuDES resulted in the loss of DES activity and the acquirement of the epoxyalcohol synthase activity. Thus, the studied enzymes exhibited the versatility of catalysis and its qualitative alterations upon the site-directed mutagenesis.

Detection of divinyl ether synthase in Lily-of-the-Valley (Convallaria majalis) roots

Incubations of linoleic acid with cell-free preparations from Lily-of-the-Valley (Convallaria majalis L., Ruscaceae) roots revealed the presence of 13-lipoxygenase and divinyl ether synthase (DES) activities. Exogenous linoleic acid was metabolized predominantly into (9Z,11E,1′E)-12-(1′-hexenyloxy)-9,11-dodecadienoic (etheroleic) acid. Its identification was confirmed by the data of ultraviolet spectroscopy, mass spectra, 1H NMR, COSY, catalytic hydrogenation. The isomeric divinyl ether (8E,1′E,3′Z)-12-(1′,3′-nonadienyloxy)-8-nonenoic (colneleic) acid was detected as a minor product. Incubations with linoleic acid hydroperoxides revealed that 13-hydroperoxide was a preferential substrate, while the 9-hydroperoxide was utilized with lesser efficiency.