≥97%, ~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.
(±)18-HEPE is produced by non-enzymatic oxidation of eicosapentaenoic acid. 18-HEPE levels are increased in the plasma and heart, as well as in the supernatant of cultured peritoneal macrophages isolated from fat-1 transgenic mice that are capable of endogenously producing ω-3 fatty acids from ω-6 fatty acids. It reduces increases in cardiac fibrosis and the expression of Nppa, Col1a1, Tgfb1, Cx3cl1, and Adgre1 induced by transverse aortic constriction in a mouse model of cardiac hypertrophy when administered at doses of 1 and 5 µg.
| Canonical Smiles | CCC(C=CC=CCC=CCC=CCC=CCCCC(=O)O)O |
|---|---|
| IUPAC Name | (5Z,8Z,11Z,14Z,16E)-18-hydroxyicosa-5,8,11,14,16-pentaenoic acid |
| InChIKey | LRWYBGFSVUBWMO-UXNZXXPISA-N |
| INCHI | 1S/C20H30O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,15,17,19,21H,2-3,8-9,14,16,18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11-,17-15+ |
| Isomeric SMILES | CCC(/C=C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O |
| Molecular Weight | 318.45 |
| Reaxy-Rn | 29757820 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=29757820&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 | Hydroxyeicosapentaenoic acids |
| Alternative Parents | Long-chain fatty acids Hydroxy fatty acids Unsaturated fatty acids Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Hydroxyeicosapentaenoic acid - Long-chain fatty acid - Hydroxy fatty acid - Fatty acid - Unsaturated fatty acid - Secondary alcohol - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic oxide - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Carbonyl group - Organooxygen compound - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds. |
| External Descriptors | Hydroxy/hydroperoxyeicosapentaenoic acids |
| Solubility | Soluble in DMSO (~50 mg/ml), DMF (~50 mg/ml), PBS (pH 7.2) (~1 mg/ml), and ethanol. |
|---|---|
| Refractive Index | n20D1.53 (Predicted) |
| Boil Point(°C) | 78° C |
| Molecular Weight | 318.400 g/mol |
| XLogP3 | 4.600 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 13 |
| Exact Mass | 318.219 Da |
| Monoisotopic Mass | 318.219 Da |
| Topological Polar Surface Area | 57.500 Ų |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Complexity | 428.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 5 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 5 |
| Covalently-Bonded Unit Count | 1 |
G2529349