Phorbol
From Wikipedia, the free encyclopedia
| Phorbol | |
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| Chemical name | 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 |
| Chemical formula | C20H28O6 |
| Molecular mass | 364.44 g/mol |
| CAS number | [17673-25-5] |
| Melting point | 250-251 °C |
| SMILES | OCC1=C[C@]([C@@](C(C)4C)([H]) [C@]4(O)[C@H](O)[C@H]2C)([H]) [C@]2(O)[C@@](C=C(C)C3=O) ([H])[C@@]3(O)C1 |
| Disclaimer and references | |
Phorbol is a natural, plant-derived organic compound. It is a member of the tigliane family of diterpenes. It was first isolated in 1934 as the hydrolysis product of croton oil which is derived from the seeds of Croton tiglium. It is well soluble in most polar organic solvents and in water.
Various esters of phorbol have important biological properties. The most notable physiological property of phorbol esters is their capacity to act as tumor promoters. They mimic diacylglycerols, glycerol derivatives in which two hydroxyl groups are substituted by fatty acids to form esters. The most common phorbol ester is 12-O-tetradecanoylphorbol-13-acetate (TPA), also called phorbol-12-myristate-13-acetate (PMA), which is used as biomedical research tool in models of carcinogenesis.
[edit] References
- Merck Index, 11th Edition, 7306
