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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]
PubChem PubChem 442070
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.[1][2][3][4][5] and its structure was determined in 1967.[6][7] 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.[8] 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

  1. ^ Flaschenträger B, v. Wolffersdorff R (1934). "Über den Giftstoff des Crotonöles. 1. Die Säuren des Crotonöles". Helvetica Chimica Acta 17 (1): 1444-1452. doi:10.1002/hlca.193401701179.
  2. ^ Flaschenträger B, Wigner G (1942). "Über den Giftstoff des Crotonöles. V. Die Gewinnung von Crotonharz, Dünnem Öl und Phorbol aus dem Crotonöl durch Alkoholyse". Helvetica Chimica Acta 25 (3): 569-581. doi:10.1002/hlca.19420250315.
  3. ^ Kauffmann T, Neumann H, Lenhardt K (1959). "Zur Konstitution des Phorbols, I. Über die reduzierende Gruppe des Phorbols". Chemische Berichte 92 (8): 1715-1726. doi:10.1002/cber.19590920802.
  4. ^ Kauffmann T, Eisinger A, Jasching W, Lenhardt K (1959). "Zur Konstitution des Phorbols, I. Über die reduzierende Gruppe des Phorbols". Chemische Berichte 92 (8): 1727-1738. doi:10.1002/cber.19590920803.
  5. ^ Tseng S-S, Van Duuren BL, Solomon JJ (1977). "Synthesis of 4a.alpha.-phorbol 9-myristate 9a-acetate and related esters". J. Org. Chem. 42 (33): 3645-3649. doi:10.1021/jo00443a002.
  6. ^ Hecker E, Bartsch H, Bresch H, Gschwendt M, Härle B, Kreibich G, Kubinyi H, Schairer HU, Szczepanski Ch v, Thielmann HW (1967). "Structure and stereochemistry of the tetracyclic diterpene phorbol from croton tiglium L". Tetrahedron Letters 8 (33): 3165-3170. doi:10.1016/S0040-4039(01)89890-7.
  7. ^ Pettersen RC, Ferguson G, Crombie L, Games ML, Pointer DJ (1967). "The structure and stereochemistry of phorbol, diterpene parent of co-carcinogens of croton oil". Chem. Commun. (London): 716. doi:10.1039/C19670000716.
  8. ^ Blumberg PM (1988). "Protein kinase C as the receptor for the phorbol ester tumor promoters: sixth Rhoads memorial award lecture". Cancer Res. 48 (1): 1–8. PMID 3275491.
  • Merck Index, 11th Edition, 7306
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Phorbol". A list of authors is available in Wikipedia.
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