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Phorbol

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Phorbol
Phorbol
Names
IUPAC names 1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-
4a,7b,9,9a-tetrahydroxy-3-
(hydroxymethyl)-1,1,6,8-tetramethyl-5H-
cyclopropabenzazulen-5-one
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.162.035 Edit this at Wikidata
CompTox Dashboard (EPA)
SMILES
  • OCC1=C((C(C)4C)()
    4(O)(O)2C)()
    2(O)(C=C(C)C3=O)
    ()3(O)C1
Properties
Chemical formula C20H28O6
Molar mass 364.44 g/mol
Melting point 250-251 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. Phorbol's structure was determined in 1967. 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. 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. PMA, together with ionomycin, can also be used to stimulate T-cell cytokine production, and is used in protocols for intracellular staining of these cytokines

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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.
  9. Template:Http://www.ebioscience.com/ebioscience/appls/FCI.htm
  • Merck Index, 11th Edition, 7306

External links

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