≥98%, ~10 mg/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.
Butaprost is a structural analog of prostaglandin E2 (PGE2) with good selectivity for the EP2 receptor subtype. Butaprost has frequently been used to pharmacologically define the EP receptor expression profile of various human and animal tissues and cells . Serious confusion as to the structure of butaprost was generated by Gardiner in 1986,2 when he reported that the epimer of butaprost showing this selective activity was the C-16 (R)-epimer. In order to increase the binding affinity of (R)-butaprost for prostanoid receptors, we removed the methyl ester of (R)-butaprost and re-established the natural C-1 carboxylic acid. Prostaglandin free acids generally bind to their cognate receptors with 10 to 100 times the affinity of the corresponding ester derivative. The pharmacology of (R)-butaprost has not been carefully studied, but it is generally considered to be the less active C-16 epimer. (NOTE: In the Gardiner paper in the 1986 British Journal of Pharmacology, butaprost appears on page 46 where it is given the name TR 4979. The structure as drawn is incorrect, in that the author was using and referring to the more active C-16 epimer, which is actually 16(S). The structure on page 46 shows the structure as 16(R). It was not until the late 1990's that careful studies both in the US and Japan correctly identified the actual configuration of C-16 in the compound called butaprost is 16(S).
| Pubchem Sid | 504770120 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/504770120 |
| Sonrisas canónicas | CCCC1(CCC1)C(CC=CC2C(CC(=O)C2CCCCCCC(=O)O)O)O |
| IUPAC Name | 7-[(1R,2R,3R)-3-hydroxy-2-[(E,4R)-4-hydroxy-4-(1-propylcyclobutyl)but-1-enyl]-5-oxocyclopentyl]heptanoic acid |
| InChIKey | PAYNQYXOKJDXAV-NMXQQJQMSA-N |
| INCHI | 1S/C23H38O5/c1-2-13-23(14-8-15-23)21(26)11-7-10-18-17(19(24)16-20(18)25)9-5-3-4-6-12-22(27)28/h7,10,17-18,20-21,25-26H,2-6,8-9,11-16H2,1H3,(H,27,28)/b10-7+/t17-,18-,20-,21-/m1/s1 |
| Isómeros SMILES | CCCC1(CCC1)[C@@H](C/C=C/[C@H]2[C@@H](CC(=O)[C@@H]2CCCCCCC(=O)O)O)O |
| PubChem CID | 35021645 |
| Peso molecular | 394.6 |
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 |
| Clase | Fatty Acyls |
| Subclass | Eicosanoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Prostaglandins and related compounds |
| Alternative Parents | Long-chain fatty acids Hydroxy fatty acids Cyclopentanols Cyclic 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 - Cyclic alcohol - Cyclic ketone - Secondary alcohol - Ketone - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic homomonocyclic compound |
| Descripción | 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 | Not available |
| Sensibilidad | Moisture sensitive;heat sensitive |
|---|---|
| Peso molecular | 394.500 g/mol |
| XLogP3 | 3.900 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 13 |
| Exact Mass | 394.272 Da |
| Monoisotopic Mass | 394.272 Da |
| Topological Polar Surface Area | 94.800 Ų |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Complexity | 537.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 1 |
| Covalently-Bonded Unit Count | 1 |
B2302560