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

• ChemBase ID: 134416
• Molecular Formular: C12H18O3
• Molecular Mass: 210.26952
• Monoisotopic Mass: 210.12559444
• SMILES: CC/C=C\C[C@H]1[C@@H](CCC1=O)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)-pent-2-en-1-yl]cyclopentyl]acetic acid
• IUPAC Traditional name: (+)-jasmonic acid
• Synonyms: (±)-1α,2β-3-Oxo-2-(cis-2-pentenyl)cyclopentaneacetic acid; (±)-Jasmonic acid; (1R,2R)-rel-3-Oxo-2-(2Z)-2-penten-1-ylcyclopentaneacetic Acid; (+/-)-Jasmonic Acid; [1α,2β(Z)]-3-Oxo-2-(2-pentenyl)cyclopentaneacetic Acid; trans-Jasmonic Acid

Database IDs

• CAS Number: 77026-92-7
• MDL Number: MFCD04221274
• PubChem SID: 162228692; 24896192
• PubChem CID: 7251180

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

PROPERTIES

Physical Property

• Apperance: liquid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Suitability: plant cell culture tested

DETAILS

Sigma Aldrich - J2500

Frequently Asked Questions
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Other Notes
Note: This product is a clear, colorless to very light yellow oil that adheres to the surface of the vial.
Application
Jasmonic acid (JA) is a plant hormone derived from linolenic acid. Jasmonic acid is involved in plant cell signaling responses to abiotic and biotic stress. JA is involved in the regulation of processes that include growth inhibition, senescence, flower development, leaf abscission and tendril coiling. JA is also involved in wound healing of plants and systemic acquired resistance to attack by insects.

Toronto Research Chemicals - J210520

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)