Pulegone
Title: Pulegone
CAS Registry Number: 89-82-7
CAS Name: (5R)-5-Methyl-2-(1-methylethylidene)cyclohexanone
Additional Names: R-(+)-p-menth-4(8)-en-3-one; 1-methyl-4-isopropylidene-3-cyclohexanone
Molecular Formula: C10H16O
Molecular Weight: 152.23
Percent Composition: C 78.90%, H 10.59%, O 10.51%
Literature References: Found in oils derived from plants of the Labiatae family as (+)-form. Readily isolated in quantity from the pennyroyal oils from Mentha pulegium L., M. longifolia (L.) Huds., and Hedeoma pulegioides (L.) Pers., Labiatae: Gildemeister, Hoffmann, Die ätherischen Ole Vol. I, p 560 (1928); Simonsen, The Terpenes Vol. I (2nd ed, 1947) p 370. Synthesis: Kuhn, Schinz, Helv. Chim. Acta 36, 161 (1953). Synthesis of the (±)-form: Black et al., J. Chem. Soc. 1956, 2971; Wolinsky et al., J. Org. Chem. 30, 3207 (1965); of the S(-)-form: E. J. Corey et al., ibid. 41, 380 (1976). Improved synthesis of the R(+)-form: T. Sato et al., Tetrahedron Lett. 1980, 3377. Conversion of the R(+) to the S(-)-form: H. E. Ensley, R. V. C. Carr, ibid. 1977, 513. Biosynthetic study: A. Akhila, D. V. Banthorpe, Z. Pflanzenphysiol. 99, 277 (1980), C.A. 94, 2073r (1981).
Properties: Oil. Pleasant odor, midway between peppermint and camphor. d415 0.9346. bp760 224°; bp100 151-153°; bp17 103°; bp6 84°. [a]D20 +21°; [a]20546 +28.2°. nD20 1.4894. Practically insol in water. Miscible with alcohol, ether, chloroform.
Boiling point: bp760 224°; bp100 151-153°; bp17 103°; bp6 84°
Optical Rotation: [a]D20 +21°; [a]20546 +28.2°
Index of refraction: nD20 1.4894
Density: d415 0.9346
 
Derivative Type: (±)-Form
Properties: Liquid. bp7 78-80°. nD16 1.4856. uv max (alc): 253.3 nm (log e 3.86).
Boiling point: bp7 78-80°
Index of refraction: nD16 1.4856
Absorption maximum: uv max (alc): 253.3 nm (log e 3.86)
 
Derivative Type: (-)-Form
Properties: Liquid. bp20 104-108°. [a]D23 -22.5° (neat).
Boiling point: bp20 104-108°
Optical Rotation: [a]D23 -22.5° (neat)

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