(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3R)-3-hydroxy-4,4-dimethyloct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid

• ChemBase ID: 133549
• Molecular Formular: C22H36O5
• Molecular Mass: 380.51824
• Monoisotopic Mass: 380.25627425
• SMILES: CCCCC(C)(C)[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O)O
• Canonical SMILES: CCCCC([C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O)(C)C
• InChI: InChI=1S/C22H36O5/c1-4-5-14-22(2,3)20(25)13-12-17-16(18(23)15-19(17)24)10-8-6-7-9-11-21(26)27/h6,8,12-13,16-17,19-20,24-25H,4-5,7,9-11,14-15H2,1-3H3,(H,26,27)/b8-6-,13-12+/t16-,17-,19-,20-/m1/s1
• InChIKey: QAOBBBBDJSWHMU-WMBBNPMCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3R)-3-hydroxy-4,4-dimethyloct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: 16,16-dimethyl-PGE2
• Synonyms: 16,16-Dimethylprostaglandin E2

Database IDs

• CAS Number: 39746-25-3
• MDL Number: MFCD00151141
• PubChem SID: 24893214; 162227826
• PubChem CID: 5283066

CALCULATED PROPERTIES

• Acid pKa: 4.303361
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.7468438
• LogD (pH = 7.4): 1.0076984
• Log P: 3.9682438
• Molar Refractivity: 108.3048 cm^3
• Polarizability: 41.864788 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: methyl acetate solution

Safety Information

• European Hazard Symbols: Irritant (Xi)
• UN Number: 1231
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 36-66-67
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319-H336
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1231 3/PG 2
• Supplemental Hazard Statements: Repeated exposure may cause skin dryness or cracking.
• Storage Temperature: -20°C

Product Information

• Concentration: ~10 mg/mL
• Shipped in: wet ice

DETAILS

Sigma Aldrich - D0160

Preparation Note
Agitation or brief ultrasonication may be necessary for restoration of solutions which have been precipitated due to freezing. The methyl acetate can be removed using N2 or vacuum. Stock solutions of 1-5 mg/ml in absolute alcohol may be prepared and diluted with isotonic saline.