92693-03-3

Basic information

• Product Name: 17(S)-HDoHE
• Synonyms: 17(S)-HDoHE;SWTYBBUBEPPYCX-YTQNUIGOSA-N;17(S)-HDHA
• CAS NO: 92693-03-3
• Molecular Formula: C13H9F2N3OS
• Molecular Weight: 293.2918664
• Mol File: 92693-03-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 17(S)-HDoHE(CAS DataBase Reference)
• NIST Chemistry Reference: 17(S)-HDoHE(92693-03-3)
• EPA Substance Registry System: 17(S)-HDoHE(92693-03-3)

Safety Data

• Hazardous Substances Data: 92693-03-3(Hazardous Substances Data)

Usage

General Description

17(S)-HDoHE is a metabolite of the omega-3 fatty acid docosahexaenoic acid (DHA) that has been found to have anti-inflammatory and neuroprotective effects. It is a potent inhibitor of the 5-lipoxygenase pathway, which plays a key role in mediating inflammation, and has been implicated in the pathogenesis of various neurodegenerative diseases. 17(S)-HDoHE has also been shown to promote cell survival and reduce oxidative stress in neuronal cells, highlighting its potential therapeutic value in the treatment of conditions such as Alzheimer's disease and Parkinson's disease. Additionally, research has shown that 17(S)-HDoHE levels are altered in various disease states, suggesting that it may serve as a biomarker for certain conditions and potentially open up new avenues for diagnostic and therapeutic intervention. Overall, 17(S)-HDoHE represents a promising compound for the development of novel therapeutics for inflammatory and neurodegenerative disorders.

Upstream product

• 6217-54-5 docosahexaenoic acid 
• 123673-33-6 17(S)-hydroperoxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid 

Downstream Products

• 1233715-28-0 17-oxo-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid 
• 90780-52-2 (±)-(4Z,7Z,10Z,13Z,15E,19Z)-17-hydroxydocosa-4,7,10,13,15,19-hexaenoic acid 

Relevant articles and documents

First total synthesis of the anti-inflammatory and pro-resolving lipid mediator 16(R),17(S)-diHDHA

The first total synthesis of the anti-inflammatory and pro-resolving lipid mediator 16(R),17(S)-diHDHA, derived from docosahexaenoic acid (DHA), and its 16-epimer have been achieved. Two synthetic approaches are described for the synthesis of 16(R),17(S)-diHDHA. The first strategy started from DHA and used an enzymatic reaction, a vanadium catalyzed allylic epoxidation and a base-promoted epoxide isomerization. The second approach utilized a chiral pool strategy starting from 2-deoxy-D-ribose to establish the chiral centers; Wittig reactions, mild acetonide cleavage and ester hydrolysis were the key steps in the synthesis.

Production of hydroxy unsaturated fatty acids using crude lipoxygenase obtained from infected rice plants

In order to explore the oxidation mode of lipoxygenase (LOX) obtained from infected rice plants, typical unsaturated fatty acids (3-8) were treated with LOX and oxygen. It was observed that ω-10 and ω-6 positions of unsaturated fatty acids were oxidized predominantly in the cases of exotic ω-6 (4 and 5) and ω-3 (7 and 8) series, respectively. In the case of endogenous fatty acids (3 and 6), oxidation at ω-6 position predominated. All the allylic alcohols obtained by reduction of the oxidation products with NaBH4 possess S-configuration.