7-[(1R,4S,5R,6R)-6-[(3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoic acid

• ChemBase ID: 153684
• Molecular Formular: C20H34O6
• Molecular Mass: 370.48036
• Monoisotopic Mass: 370.23553881
• SMILES: CCCCC[C@@H](C=C[C@H]1[C@H]2C[C@@H]([C@@H]1CCCCCCC(=O)O)OO2)OO
• Canonical SMILES: CCCCC[C@@H](C=C[C@H]1[C@@H]2OO[C@H]([C@@H]1CCCCCCC(=O)O)C2)OO
• InChI: InChI=1S/C20H34O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h12-13,15-19,23H,2-11,14H2,1H3,(H,21,22)/t15-,16+,17+,18-,19+/m0/s1
• InChIKey: QXCRWNZYEVOQMB-BRIYLRKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,4S,5R,6R)-6-[(3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoic acid
• IUPAC Traditional name: 7-[(1R,4S,5R,6R)-6-[(3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoic acid
• Synonyms: 15-Hydroperoxyprostaglandin R1; 8,11-Epidioxy-15-hydroperoxy-(9α,11α, 13E,15)-prost-13-ene-1-oic acid; PGG1; Prostaglandin G1

Database IDs

• CAS Number: 52162-11-5
• EC Number: 200-662-2
• MDL Number: MFCD04974503
• PubChem SID: 162247823
• PubChem CID: 71311715

CALCULATED PROPERTIES

• Acid pKa: 4.4051266
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.6413295
• LogD (pH = 7.4): 1.8841186
• Log P: 4.7681847
• Molar Refractivity: 98.2755 cm^3
• Polarizability: 39.11424 Å^3
• Polar Surface Area: 85.22 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: acetone solution
• Flash Point: 1.4 °F; -17 °C

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1090
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-36-66-67
• Safety Statements: 9-16-26
• 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), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1090 3/PG 2
• Supplemental Hazard Statements: Repeated exposure may cause skin dryness or cracking.
• Storage Temperature: -70°C

Product Information

• Purity: >95% (HPLC)
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C20H34O6

DETAILS

Sigma Aldrich - P7617

Application
Used in studies of prostacylcin synthetase