Phorbol
Title: Phorbol
CAS Registry Number: 17673-25-5
CAS Name: [1aR-(1aa,1bb,4ab,7aa,7ba,8a,9b,9aa)]-1,1a,1b,4,4a,7a,7b,8,9,9a-Decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5H-cyclopropa[3,4]benz[1,2-e]azulen-5-one
Molecular Formula: C20H28O6
Molecular Weight: 364.43
Percent Composition: C 65.91%, H 7.74%, O 26.34%
Literature References: Parent alcohol of the tumor promoting compounds in croton oil, q.v., the oil expressed from the seeds of Croton tiglium L., Euphorbiaceae. Phorbol has a structural skeleton based on cyclopropabenzazulene. Isoln: Flaschenträger, Wigner, Helv. Chim. Acta 25, 569 (1942); Kauffmann, Neumann, Ber. 92, 1715 (1959); S. Tseng et al., J. Org. Chem. 42, 3645 (1977). Structure and stereochemistry: Hecker et al., Tetrahedron Lett. 1967, 3165; Pettersen, Ferguson, Chem. Commun. 1967, 716. Unlike its diesters, phorbol does not appear to be co-carcinogenic or enhance chemically-induced mutagenesis: C. J. Soper, F. J. Evans, Cancer Res. 37, 2487 (1977). Mechanism of action study on phorbol esters: A. S. Kraft, W. B. Anderson, Nature 301, 621 (1983). Comprehensive review of phorbol and its esters: Hecker, Schmidt, Fortschr. Chem. Org. Naturst. 31, 377-467 (1974); P. M. Blumberg, Crit. Rev. Toxicol. 8, 199-234 (1981).
Properties: Anhydr crystals, dec 250-251°. Two forms of solvated crystals from ethyl acetate: mp 162-163° and 233-234°. Solvated crystals from methanol or ethanol; mp 249-250°. [a]D24 +102° (water). [a]D20 +118° (c = 0.4 in dioxane). uv max (ethanol): 235, 334 nm (e 5200, 70). Quite sol in polar solvents, including water.
Melting point: mp 162-163° and 233-234°; mp 249-250°
Optical Rotation: [a]D24 +102° (water); [a]D20 +118° (c = 0.4 in dioxane)
Absorption maximum: uv max (ethanol): 235, 334 nm (e 5200, 70)
 
Derivative Type: 12-Myristate 13-acetate diester
Additional Names: 12-O-Tetradecanoylphorbol-13-acetate; TPA; croton oil factor A1
Molecular Formula: C36H56O8
Molecular Weight: 616.83
Percent Composition: C 70.10%, H 9.15%, O 20.75%
Properties: uv max (ethanol): 232, 333 nm (e 5400, 73). Differentiation of human leukemia cells: J. B. Weinberg, Science 213, 655 (1981).
Absorption maximum: uv max (ethanol): 232, 333 nm (e 5400, 73)

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