90906-40-4

Usage

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

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

Downstream Products

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

Relevant academic research and scientific papers

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

THERAPEUTIC AGENT FOR ULCERATIVE COLITIS AND/OR CROHN'S DISEASE

Disclosed is an agent for preventing or treating ulcerative colitis, Crohn's disease, and/or Behcet's disease. A therapeutic agent for ulcerative colitis, Crohn's disease, and/or Behcet's disease, comprising a polyunsaturated fatty acid derivative represented by the following formula (1) as an active ingredient.

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.

Synthesis of polyconjugated fatty acids

The present invention relates to fatty acids. In particular, the present invention provides polyconjugated fatty acids, and methods of their synthesis and their use.

Synthesis of long chain n-3 and n-6 fatty acids having a photoactive conjugated tetraene group

Fatty acids of the n-3 and n-6 families containing a photoactive conjugated tetraene group near the carboxylate were prepared from several naturally occurring fatty acids by sequential iodolactonization and treatment with excess 1,8-diazabicyclo[5.4.0]undec-7-ene. The new conjugated fatty acids include 5E,7E,9E,11Z,14Z- and 5E,7E,9E,11E,14Z-eicosapentaenoic acids derived from arachidonic acid; 5E,7E,9E,11Z,14Z,17Z- and 5E,7E,9E,11E,14Z,17Z-eicosahexaenoic acids from eicosapentaenoic acid; and 4E,6E,8E,10Z,13Z,16Z,19Z- and 4E,6E,8E,10E,13Z,16Z,19Z-docosaheptaenoic acids from docosahexaenoic acid. All of the newly synthesized fatty acids were characterized by UV, 1H NMR and mass spectroscopy. These new products represent the first examples of directed conjugation of methylene interrupted double bond systems. The products can be synthesized in gram quantities and in high yields (>50%). Interestingly, it did not prove possible to synthesize fatty acids having a triene group near the carboxyl group even using mild conditions and different synthetic approaches. Once initiated, the isomerization always continued until a tetraene group was formed. Because of the sensitivity of the tetraene group to light, these fatty acids have the potential for being used in tracking fatty acid movements in cells employing fluorescence techniques and in UV light-induced cross linking to membrane proteins.