ethyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoate

• ChemBase ID: 133512
• Molecular Formular: C22H38O5
• Molecular Mass: 382.53412
• Monoisotopic Mass: 382.27192432
• SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)OCC)O)O)O
• Canonical SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)OCC)O)O
• InChI: InChI=1S/C22H38O5/c1-3-5-8-11-17(23)14-15-19-18(20(24)16-21(19)25)12-9-6-7-10-13-22(26)27-4-2/h6,9,14-15,17-21,23-25H,3-5,7-8,10-13,16H2,1-2H3/b9-6-,15-14+/t17-,18+,19+,20-,21+/m0/s1
• InChIKey: KRDFNHLEMLCWKD-GWSKAPOCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoate
• IUPAC Traditional name: ethyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoate
• Synonyms: Prostaglandin F2α methyl ester

Database IDs

• CAS Number: 33854-16-9
• EC Number: 201-185-2
• MDL Number: MFCD00133790
• PubChem SID: 162227789; 24898094
• PubChem CID: 6436137

CALCULATED PROPERTIES

• Acid pKa: 14.513965
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.1137564
• LogD (pH = 7.4): 3.1137564
• Log P: 3.1137564
• Molar Refractivity: 109.9884 cm^3
• Polarizability: 42.66191 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 15.8 °F; -9 °C

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1231
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-36-66-67
• Safety Statements: 16-26-29-33
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H319-H336
• GHS Precautionary statements: P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1231 3/PG 2
• Supplemental Hazard Statements: Repeated exposure may cause skin dryness or cracking.
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Concentration: ~5 mg/mL in methyl acetate

DETAILS

Sigma Aldrich - P0314

Biochem/physiol Actions
Constricts an isolated human smooth muscle; methyl ester form of prostaglandin F2α which is a luteolytic prostaglandin (induces parturition; pulmonary vasoconstrictor).
包装
Packaged under Argon.