≥95%, 100 μg/ml in ethanol for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
(±)5,6-DHET, or (±)5,6-dihydroxyeicosatetraenoic acid, cataloged under CAS number 213382-49-1, is a metabolite derived from the oxidative metabolism of arachidonic acid, specifically through the action of cytochrome P450 enzymes. This compound is part of a larger group of eicosanoids, which are oxidized derivatives of twenty-carbon fatty acids and play significant roles in various biochemical pathways. In research settings, (±)5,6-DHET is utilized to study the enzymatic pathways involved in the metabolism of arachidonic acid and to understand the role of cytochrome P450 enzymes in the generation of eicosanoids. This metabolite is particularly interesting because it provides insights into the non-enzymatic and enzymatic processes that regulate the levels and activity of eicosanoids, which are crucial for cellular signaling mechanisms that govern physiological responses. By studying (±)5,6-DHET, researchers can explore how cells respond to oxidative stress and how they regulate inflammatory processes at a molecular level. This research has significant implications for understanding the biochemical cascades that underpin various cellular behaviors and responses without directly focusing on therapeutic applications. Moreover, (±)5,6-DHET serves as a biochemical tool to assess the impact of oxidative enzymes on lipid signaling pathways, contributing to a deeper understanding of lipidomics and its relevance to cellular health and disease.
Product Description
Epoxide hydrolases convert the EETs into vicinal diols, with concurrent loss of much of their biological activity. It is a substrate for sheep seminal vesicle COX, producing 5,6-dihydroxy prostaglandin E1 and F1α metabolites in vitro.
Product Application
(±)-5,6-Dihydroxy-8Z,11Z,14Z-eicosatrienoic Acid ((±)5,6-DHET) is associated with abnormal lipoprotein oxylipins and metabolic disorders and may contribute to chronic inflammation.
| Canonical Smiles | CCCCCC=CCC=CCC=CCC(C(CCCC(=O)O)O)O |
|---|---|
| IUPAC Name | (8Z,11Z,14Z)-5,6-dihydroxyicosa-8,11,14-trienoic acid |
| InChIKey | GFNYAPAJUNPMGH-QNEBEIHSSA-N |
| INCHI | 1S/C20H34O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18(21)19(22)16-14-17-20(23)24/h6-7,9-10,12-13,18-19,21-22H,2-5,8,11,14-17H2,1H3,(H,23,24)/b7-6-,10-9-,13-12- |
| Isomeric SMILES | CCCCC/C=C\C/C=C\C/C=C\CC(C(CCCC(=O)O)O)O |
| UN Number | 1170 |
| Packing Group | II |
| Molecular Weight | 338.48 |
| Reaxy-Rn | 8580625 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8580625&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Fatty Acyls |
| Subclass | Eicosanoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Hydroxyeicosatrienoic acids |
| Alternative Parents | Long-chain fatty acids Hydroxy fatty acids Unsaturated fatty acids Secondary alcohols 1,2-diols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Hydroxyeicosatrienoic acid - Long-chain fatty acid - Hydroxy fatty acid - Unsaturated fatty acid - Fatty acid - Secondary alcohol - 1,2-diol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Carbonyl group - Alcohol - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds. |
| External Descriptors | Hydroxy/hydroperoxyeicosatrienoic acids |
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
 F2612365 | Certificate of Analysis | Jun 02, 2026 | D343076 |
| F2612360 | Certificate of Analysis | Jun 02, 2026 | D343076 |
| I2523334 | Certificate of Analysis | Sep 12, 2025 | D343076 |
| G2522318 | Certificate of Analysis | Jul 12, 2025 | D343076 |
| I2405403 | Certificate of Analysis | Aug 29, 2024 | D343076 |
| I2405402 | Certificate of Analysis | Aug 29, 2024 | D343076 |
| I2219326 | Certificate of Analysis | Jul 07, 2022 | D343076 |
| I2219327 | Certificate of Analysis | Jul 07, 2022 | D343076 |
| Solubility | Soluble in DMSO (~50 mg/ml), DMF (~50 mg/ml), and PBS (pH 7.2) (~1 mg/ml). |
|---|---|
| Sensitivity | Moisture sensitive |
| Molecular Weight | 338.500 g/mol |
| XLogP3 | 4.500 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 15 |
| Exact Mass | 338.246 Da |
| Monoisotopic Mass | 338.246 Da |
| Topological Polar Surface Area | 77.800 Ų |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Complexity | 385.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 2 |
| Defined Bond Stereocenter Count | 3 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 3 |
| Covalently-Bonded Unit Count | 1 |
