Phorbol

Phorbol[1]
Phorbol
Names
Preferred IUPAC name
(1aR,1bS,4aR,7aS,9bS,8R,9R,9aS)-4a,7b,9,9a-Tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5H-cyclopropa[3,4]benzo[1,2-e]azulen-5-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.162.035 Edit this at Wikidata
UNII
  • InChI=1S/C20H28O6/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3/t10-,12+,13-,14-,16-,18-,19-,20-/m1/s1 ☒N
    Key: QGVLYPPODPLXMB-UBTYZVCOSA-N ☒N
  • InChI=1/C20H28O6/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3/t10-,12+,13-,14-,16-,18-,19-,20-/m1/s1
    Key: QGVLYPPODPLXMB-UBTYZVCOBR
  • 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
Properties
C20H28O6
Molar mass 364.438 g·mol−1
Melting point 250 to 251 °C (482 to 484 °F; 523 to 524 K)
Soluble in DMSO (25mg/ml), 100% ethanol (25mg/ml), acetone, ether or dimethyl formamide; almost insoluble in aqueous buffers.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phorbol is a natural, plant-derived organic compound. It is a member of the tigliane family of diterpenes. Phorbol was first isolated in 1934 as the hydrolysis product of croton oil, which is derived from the seeds of the purging croton, Croton tiglium.[2][3][4][5][6] The structure of phorbol was determined in 1967.[7][8] 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.[9] They mimic diacylglycerols, glycerol derivatives in which two hydroxyl groups have reacted with fatty acids to form esters. The most common and potent phorbol ester is 12-O-tetradecanoylphorbol-13-acetate (TPA), also called phorbol-12-myristate-13-acetate (PMA), which is used as a biomedical research tool in contexts such as models of carcinogenesis.

  1. ^ Merck Index, 11th Edition, 7306
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ Tseng SS, van Duuren BL, Solomon JJ (1977). "Synthesis of 4aα-Phorbol 9-Myristate 9a-Acetate and Related Esters". J. Org. Chem. 42 (33): 3645–3649. doi:10.1021/jo00443a002. PMID 915585.
  7. ^ Hecker E; Bartsch H; Bresch H; Gschwendt M; Härle B; Kreibich G; Kubinyi H; Schairer HU; v. Szczepanski C; 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.
  8. ^ 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. 1967 (14): 716–717. doi:10.1039/C19670000716.
  9. ^ Blumberg PM (1988). "Protein Kinase C as the Receptor for the Phorbol Ester Tumor Promoters: Sixth Rhoads Memorial Award Lecture" (PDF). Cancer Res. 48 (1): 1–8. PMID 3275491.