Phorbol

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Phorbol
Phorbol
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 have reacted with 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.

References

  • Merck Index, 11th Edition, 7306


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