Humulene CAS Registry Number: 6753-98-6 α-石竹烯

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Literature References: Sesquiterpenoid isomer of caryophyllene, q.v. occurring in many essential oils, especially oil of hops (Humulus lupulus L. Moraceae) and leaves of Lindera strychnifolia (F.) Will Lauraceae. Occurs in nature as a mixture with b-humulene. Isolation of mixture: A. C. Chapman, J. Chem. Soc. 67, 54, 780 (1895). Identity with a-caryophyllene: F. Sorm et al., Collect. Czech. Chem. Commun. 14, 693, 699, 716 (1949). Structure: F. Sorm et al., ibid. 19, 570 (1954). Stereochemistry: A. T. McPhail, G. A. Sim, J. Chem. Soc. B 1966, 112. Synthesis: E. J. Corey, E. Hanamaka, J. Am. Chem. Soc. 89, 2758 (1967). Stereoselective synthesis: Y. Kitagawa et al., ibid. 99, 3864 (1977); E. J. Corey et al., Tetrahedron Lett. 34, 3675 (1993). Chromatographic conversion to b-humulene: V. Benesova et al., Collect. Czech. Chem. Commun. 26, 1832 (1961). Reviews: F. Sorm in Fortschr. Chem. Org. Naturst. 19, 1-32 (1961); Rodd's Chemistry of Carbon Compounds vol. IIC, S. Coffey, Ed., (Elsevier, New York, 2nd ed., 1969) pp 282-283.