Phorbol

Chembox new
Name = Phorbol
ImageFile = Phorbol.png ImageName = Phorbol
IUPACName = 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
Section1 = Chembox Identifiers
CASNo = 17673-25-5
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
Section2 = Chembox Properties
Formula = C₂₀H₂₈O₆
MolarMass = 364.44 g/mol
MeltingPt = 250-251 °C

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".cite journal | author = Flaschenträger B, v. Wolffersdorff R | title = Über den Giftstoff des Crotonöles. 1. Die Säuren des Crotonöles | journal = Helvetica Chimica Acta | volume = 17 | issue = 1 | pages = 1444–1452 | year = 1934 | pmid = | doi = 10.1002/hlca.193401701179 | issn = ] cite journal | author = Flaschenträger B, Wigner G | title = Über den Giftstoff des Crotonöles. V. Die Gewinnung von Crotonharz, Dünnem Öl und Phorbol aus dem Crotonöl durch Alkoholyse | journal = Helvetica Chimica Acta | volume = 25 | issue = 3 | pages = 569–581 | year = 1942 | pmid = | doi = 10.1002/hlca.19420250315 | issn = ] cite journal | author = Kauffmann T, Neumann H, Lenhardt K | title = Zur Konstitution des Phorbols, I. Über die reduzierende Gruppe des Phorbols | journal = Chemische Berichte | volume = 92 | issue = 8 | pages = 1715–1726 | year = 1959 | pmid = | doi = 10.1002/cber.19590920802 | issn = ] cite journal | author = Kauffmann T, Eisinger A, Jasching W, Lenhardt K | title = Zur Konstitution des Phorbols, I. Über die reduzierende Gruppe des Phorbols | journal = Chemische Berichte | volume = 92 | issue = 8 | pages = 1727–1738 | year = 1959 | pmid = | doi = 10.1002/cber.19590920803 | issn = ] cite journal | author = Tseng S-S, Van Duuren BL, Solomon JJ | title = Synthesis of 4a.alpha.-phorbol 9-myristate 9a-acetate and related esters | journal = J. Org. Chem. | volume = 42 | issue = 33 | pages = 3645–3649 | year = 1977 | pmid = | doi = 10.1021/jo00443a002 | issn = ] and its structure was determined in 1967.cite journal | author = Hecker E, Bartsch H, Bresch H, Gschwendt M, Härle B, Kreibich G, Kubinyi H, Schairer HU, Szczepanski Ch v, Thielmann HW | title = Structure and stereochemistry of the tetracyclic diterpene phorbol from croton tiglium L | journal = Tetrahedron Letters | volume = 8 | issue = 33 | pages = 3165–3170 | year = 1967| pmid = | doi = 10.1016/S0040-4039(01)89890-7 | issn = ] cite journal | author = Pettersen RC, Ferguson G, Crombie L, Games ML, Pointer DJ | title = The structure and stereochemistry of phorbol, diterpene parent of co-carcinogens of croton oil | journal = Chem. Commun. (London) | volume = | issue = | pages = 716 | year = 1967 | pmid = | doi =10.1039/C19670000716 | issn = ] It is very soluble in most polar organic solvents, as well as in water.

Various esters of phorbol have important biological properties, the most notable of which is the capacity to act as tumor promoters through activation of protein kinase C.cite journal | author = Blumberg PM | title = Protein kinase C as the receptor for the phorbol ester tumor promoters: sixth Rhoads memorial award lecture | journal = Cancer Res. | volume = 48 | issue = 1 | pages = 1–8 | year = 1988 | pmid = 3275491 | doi = | issn = ] 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

External links

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