3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one

• ChemBase ID: 139868
• Molecular Formular: C11H16O
• Molecular Mass: 164.24414
• Monoisotopic Mass: 164.12011513
• SMILES: CC/C=C\CC1=C(CCC1=O)C
• Canonical SMILES: CC/C=C\CC1=C(C)CCC1=O
• InChI: InChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4-
• InChIKey: XMLSXPIVAXONDL-PLNGDYQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one
• IUPAC Traditional name: jasmone; 3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one
• Synonyms: cis-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one; Jasmone; cis-Jasmone; 3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one; (Z)-3-甲基-2-(2-戊烯基)-2-环戊烯-1-酮; 茉莉酮; 顺式茉莉酮; 顺-茉莉酮

Database IDs

• CAS Number: 488-10-8
• EC Number: 207-668-4
• MDL Number: MFCD00001402
• Beilstein Number: 1907713
• Merck Index: 145259
• PubChem SID: 162234116; 24901546
• PubChem CID: 1549018
• FEMA ID: 3196
• Flavis Number: 7.094

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.0967138
• LogD (pH = 7.4): 3.0967138
• Log P: 3.0967138
• Molar Refractivity: 52.8994 cm^3
• Polarizability: 19.869722 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 134-135 °C/12 mmHg(lit.); 134-135°C/12mm
• Flash Point: 107 °C; 107°C(224°F); 224.6 °F
• Density: 0.94 g/mL at 25 °C(lit.); 0.940
• Refractive Index: 1.4990; n20/D 1.498(lit.)
• Organoleptic: jasmine; fruity

Safety Information

• RTECS: GY7301000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H315-H319-H335-H303
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Regulation Compliance: FDA 21 CFR (172.515)

Pharmacology Properties

• Allergens: no known allergens, no known allergens
• Mechanism of Action: mediated through cAMP; Postsynaptic; Spasmolytic

Product Information

• Purity: ≥85%; 94%
• Grade: Halal; Kosher; NI
• Biological Source: Occurs in orange and jasmin leaves. Also in peppermint oil, green tea and bergamot oranges (Citrus bergamia)
• Application(s): Attractant or repellent for various insects; Spasmolytic
• Empirical Formula (Hill Notation): C11H16O

DETAILS

Sigma Aldrich - W319600

Packaging
1 kg in glass bottle
1 sample in glass bottle
100 g in glass bottle
5 kg in steel drum

REFERENCES

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 689A, (nmr)
• Aldrich Library of FT-IR Spectra: Vapor Phase, 1989, 3, 534A, (ir)
• Birch, A.J. et al., Aust. J. Chem., 1973, 26, 2671, (synth)
• McMurry, J.E. et al., J.O.C., 1973, 38, 4367, (synth)
• Ellison, R.A., Synthesis, 1973, 397, (synth, rev)
• Pattenden, G. et al., J.C.S. Perkin 1, 1974, 1603, (synth)
• Joulain, D., Parfums, Cosmet., Aromes, 1975, 33, (synth, rev)
• Bulat, J.A. et al., Can. J. Chem., 1976, 54, 3869, (synth)
• Opdyke, D.L.J., Food Cosmet. Toxicol., 1976, 14, 845, (rev, tox)
• Bazulkis, P. et al., J.O.C., 1977, 42, 2362
• Sato, T. et al., Bull. Chem. Soc. Jpn., 1981, 54, 505, (synth)
• Takahashi, T. et al., Chem. Lett., 1981, 1189, (synth)
• Furuhata, A. et al., Agric. Biol. Chem., 1982, 46, 1757, (synth)
• Watanabe, S. et al., Aust. J. Chem., 1982, 35, 1739, (synth)
• Yoshida, T. et al., Bull. Chem. Soc. Jpn., 1982, 55, 3931, (synth)
• Piers, E. et al., Can. J. Chem., 1982, 60, 1256, (synth)
• Ogura, F. et al., Bull. Chem. Soc. Jpn., 1984, 57, 1691, (synth)
• Mikolajczyk, M. et al., Z. Naturforsch., B, 1986, 41, 263, (synth)
• Ohta, S. et al., Heterocycles, 1987, 26, 141, (synth)
• Welsh, S.C. et al., J.O.C., 1987, 52, 1440, (synth)
• Billington, D.C. et al., J. Chem. Res., Miniprint, 1988, 2601, (synth)
• Mathew, J. et al., Chem. Comm., 1990, 684, (synth)
• Sarkar, A.K. et al., J. Chem. Res., Synop., 1992, 418, (synth)
• Tsukasa, H., Biosci., Biotechnol., Biochem., 1994, 58, 1181, (synth, bibl)
• Islam, M.S. et al., Tet. Lett., 1996, 37, 5735, (synth)