methyl 2-[(1S,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetate

• ChemBase ID: 172012
• Molecular Formular: C13H20O3
• Molecular Mass: 224.2961
• Monoisotopic Mass: 224.1412445
• SMILES: C1[C@H]([C@@H](C(=O)C1)C/C=C\CC)CC(=O)OC
• Canonical SMILES: CC/C=C\C[C@H]1[C@@H](CCC1=O)CC(=O)OC
• InChI: InChI=1S/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4-/t10-,11-/m0/s1
• InChIKey: GEWDNTWNSAZUDX-XXJOZFEBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-[(1S,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetate
• IUPAC Traditional name: methyl 2-[(1S,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetate
• Synonyms: (1R,2R)-rel-3-Oxo-2-(2Z)-2-penten-1-ylcyclopentaneacetic Acid Methyl Ester; (Z)-trans-(+/-)-3-Oxo-2-(2Z)-2-penten-1-ylcyclopentaneacetic Acid Methyl Ester; (+/-)-Methyl Jasmonate; [1α,2β(Z)]-3-Oxo-2-(2-pentenyl)cyclopentaneacetic Acid Methyl Ester; Jasmoneige; Methyl DL-Jasmonate; rac-trans Jasmonic Acid Methyl Ester

Database IDs

• CAS Number: 20073-13-6
• PubChem SID: 164227922
• PubChem CID: 6428089

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.560205
• LogD (pH = 7.4): 2.560205
• Log P: 2.560205
• Molar Refractivity: 63.3256 cm^3
• Polarizability: 24.543266 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - J210530

Jasmonic acid (J210520) analog, a constituent of essential oil of Jasmine.

REFERENCES

• Ishii, Y., et al.: Leukemia, 18, 1413 (2004)
• Ito, Y., et al.: J. Agric. Food Chem., 50, 4878 (2004)