2-[(1S,2S)-3-oxo-2-[(2Z)-(5,5,5-2H3)pent-2-en-1-yl]cyclopentyl]acetic acid

• ChemBase ID: 172010
• Molecular Formular: C12H18O3
• Molecular Mass: 210.26952
• Monoisotopic Mass: 210.12559444
• SMILES: C1[C@H]([C@@H](C(=O)C1)C/C=C\CC)CC(=O)O
• Canonical SMILES: CC/C=C\C[C@H]1[C@@H](CCC1=O)CC(=O)O
• InChI: InChI=1S/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10-/m0/s1
• InChIKey: ZNJFBWYDHIGLCU-CMIOBCHKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S)-3-oxo-2-[(2Z)-(5,5,5-^2H₃)pent-2-en-1-yl]cyclopentyl]acetic acid
• IUPAC Traditional name: [(1S,2S)-3-oxo-2-[(2Z)-(5,5,5-^2H₃)pent-2-en-1-yl]cyclopentyl]acetic acid
• Synonyms: (1R,2R)-rel-3-Oxo-2-(2Z)-2-penten-1-ylcyclopentaneacetic Acid-d3; (+/-)-Jasmonic Acid-d3; [1α,2β(Z)]-3-Oxo-2-(2-pentenyl)cyclopentaneacetic Acid-d3; rac-trans Jasmonic Acid-d3

Database IDs

• CAS Number: 903510-51-0
• PubChem SID: 164227920
• PubChem CID: 71749649

CALCULATED PROPERTIES

• Acid pKa: 4.714082
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.5633299
• LogD (pH = 7.4): -0.21431588
• Log P: 2.414311
• Molar Refractivity: 58.5565 cm^3
• Polarizability: 22.455748 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - J210522

Labelled Jasmonic Acid. A major constituent of essential oil of Jasmine. Used by the fragrance industry. This product is a clear, colorless to very light yellow oil that adheres to the surface of the vial.

REFERENCES

• Hamberg, M., et al.: Biochim. Biophys Acta, 1165, 1 (1992)
• Tizio, R., et al.: Biocell, 20, 1 (1992)
• Farmer, E., et al.: Science, 276, 912 (1992)