≥98%, 10mg/ml in methyl acetate 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.
15-Keto-prostaglandin F2α is the first metabolite of PGF2α, biosynthesized by 15-hydroxy prostaglandin dehydrogenase (15-hydroxy PGDH). This compound is believed to be one of the critical components in the postovulatory pheromone for goldfish and Atlantic salmon, and has been shown to stimulate their olfactory receptors. 15-Keto-prostaglandin F2α is reportedly 10-folds less active than PGF2α at decreasing rabbit intraocular pressure; however, prostaglandin metabolites may have important biological functions due to an increased half-life under physiological conditions.
| Canonical Smiles | CCCCCC(=O)C=CC1C(CC(C1CC=CCCCC(=O)O)O)O |
|---|---|
| IUPAC Name | (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-oxooct-1-enyl]cyclopentyl]hept-5-enoic acid |
| InChIKey | LOLJEILMPWPILA-AMFHKTBMSA-N |
| INCHI | 1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,16-19,22-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17-,18+,19-/m1/s1 |
| Isomeric SMILES | CCCCCC(=O)/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O |
| Molecular Weight | 352.5 |
| Reaxy-Rn | 34893641 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=34893641&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 | Prostaglandins and related compounds |
| Alternative Parents | Long-chain fatty acids Hydroxy fatty acids Unsaturated fatty acids Cyclopentanols Enones Acryloyl compounds Ketones Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aliphatic homomonocyclic compounds |
| Substituents | Prostaglandin skeleton - Long-chain fatty acid - Hydroxy fatty acid - Cyclopentanol - Unsaturated fatty acid - Fatty acid - Enone - Acryloyl-group - Cyclic alcohol - Alpha,beta-unsaturated ketone - Secondary alcohol - Ketone - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Organic oxygen compound - Carbonyl group - Alcohol - Aliphatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. |
| External Descriptors | Prostaglandins |
| Solubility | Soluble in ethanol, water (10 mg/ml) at 25° C, PBS pH 7.2, DMF, and DMSO. |
|---|---|
| Refractive Index | n20D1.56 |
| Molecular Weight | 352.500 g/mol |
| XLogP3 | 2.600 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 12 |
| Exact Mass | 352.225 Da |
| Monoisotopic Mass | 352.225 Da |
| Topological Polar Surface Area | 94.800 Ų |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Complexity | 469.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 2 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 2 |
| Covalently-Bonded Unit Count | 1 |
K2405563