90906-40-4

Basic information

• Product Name: (+/-)4-HDOHE
• Synonyms: 4-HYDROXY DOCOSAHEXAENOIC ACID;(+/-)4-HDOHE;(+/-)4-HYDROXY-5E,7Z,10Z,13Z,16Z,19Z-DOCOSAHEXAENOIC ACID;(±)4-HDHA;IFRKCNPQVIJFAQ-PQVBWYSWSA-N
• CAS NO: 90906-40-4
• Molecular Formula: C₂₂H₃₂O₃
• Molecular Weight: 344.48768
• Mol File: 90906-40-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 502.3±50.0 °C(Predicted)
• Appearance: /
• Density: 0.995±0.06 g/cm3(Predicted)
• PKA: 4.57±0.10(Predicted)
• CAS DataBase Reference: (+/-)4-HDOHE(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)4-HDOHE(90906-40-4)
• EPA Substance Registry System: (+/-)4-HDOHE(90906-40-4)

Safety Data

• Hazardous Substances Data: 90906-40-4(Hazardous Substances Data)

Usage

Description

(+/-)4-HDOHE, also known as 4-hydroxy-2 docosahexaenoic acid, is an autoxidation product of docosahexaenoic acid (DHA) that can be produced in vitro and in biological systems such as rat liver, brain, and intestinal microsomes. It is also generated through enzymatic transformation of DHA by RBL-1 cells, with the S-isomer being the most likely enzymatic product. (+/-)4-HDOHE serves as a potential marker of oxidative stress in the brain and retina, where DHA is a prevalent polyunsaturated fatty acid.

Uses

Used in Neurological Applications:
(+/-)4-HDOHE is used as a biomarker for oxidative stress in the brain, helping to identify and monitor the presence of oxidative stress in neurological conditions and diseases.
Used in Ophthalmological Applications:
(+/-)4-HDOHE is used as a biomarker for oxidative stress in the retina, assisting in the detection and assessment of oxidative stress-related eye conditions and potential retinal damage.
Used in Research and Diagnostics:
(+/-)4-HDOHE is utilized in scientific research to study the role of oxidative stress in various physiological and pathological processes, as well as in the development of diagnostic tools and methods for assessing oxidative stress levels in biological samples.

Upstream product

• 825632-99-3 5-((1E,3Z,6Z,9Z,12Z,15Z)-Octadeca-1,3,6,9,12,15-hexaen-1-yl)dihydrofuran-2(3H)-one 
• 6217-54-5 docosahexaenoic acid 
• 78144-19-1 5-[(3Z,6Z,9Z,12Z,15Z)-1-iodooctadeca-3,6,9,12,15-pentaenyl]dihydro-2(3H)-furanone 

Downstream Products

• 845673-74-7 (5E,7Z,10Z,13Z,16Z,19Z)-4-oxodocosa-5,7,10,13,16,19-hexaenoic acid 

Relevant articles and documents

SYNTHESIS OF RESOLVINS AND INTERMEDIATES, COMPOUNDS PREPARED THEREBY, AND USES THEREOF

Methods are disclosed for the preparation of a new class of lipid mediators known as resolvins, with Resolvin D6 (4,17-dihydroxy-5E,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid) being exemplary. Also disclosed are methods for the efficient synthesis of key int

Synthesis of docosahexaenoic acid derivatives designed as novel PPARγ agonists and antidiabetic agents

To discover novel peroxisome proliferator-activated receptor γ (PPARγ) agonists that could be used as antidiabetic agents, we designed docosahexaenoic acid (DHA) derivatives (2 and 3), which have a hydrophilic substituent at the C(4)-position, based on the crystal structure of the ligand-binding pocket of PPARγ. These compounds were synthesized via iodolactone as a key intermediate. We found that both DHA derivatives (2 and 3) showed PPARγ transactivation higher than, or comparable to, that of pioglitazone, which is a TZD derivative used as an antidiabetic agent. DHA derivatives related to these potent compounds 2 and 3 were also synthesized to study structure-activity relationships. Furthermore, 4-OH DHA 2, which shows strong PPARγ transcriptional activity, was separated as an optically pure form.

Identification of putative metabolites of docosahexaenoic acid as potent PPARγ agonists and antidiabetic agents

We found that putative metabolites of docosahexaenoic acid (DHA) are strong PPARγ activators and potential antidiabetic agents. We designed DHA derivatives based on the crystal structure of PPARγ, synthesized them and evaluated their activities in vitro and in vivo. The efficacy of 5E-4-hydroxy-DHA 2a as a PPARγ activator was about fourfold stronger than that of pioglitazone. Furthermore, the 4-keto derivative (10b) showed antidiabetic activity in animal models without producing undesirable effects such as obesity and hepatotoxicity.