19891-05-5

Basic information

• Product Name: PHORBOL 12,13,20-TRIACETATE, 4BETA
• Synonyms: 8,9,9a-decahydro-3-(hydroxymethyl)-4a-beta,7b-alpha,9-beta,9a-alpha-tetrahydro;PHORBOL-12,13,20-TRIACETATE;PHORBOL 12,13,20-TRIACETATE, 4BETA;6,8-alpha-tetramethyl-,3,9,9a-triacetate,(+)-xy-1
• CAS NO: 19891-05-5
• Molecular Formula: C₂₆H₃₄O₉
• Molecular Weight: 490.54
• Mol File: 19891-05-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 589.6°Cat760mmHg
• Flash Point: 191.1°C
• Appearance: white/
• Density: 1.32g/cm³
• Vapor Pressure: 2.33E-16mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: −20°C
• CAS DataBase Reference: PHORBOL 12,13,20-TRIACETATE, 4BETA(CAS DataBase Reference)
• NIST Chemistry Reference: PHORBOL 12,13,20-TRIACETATE, 4BETA(19891-05-5)
• EPA Substance Registry System: PHORBOL 12,13,20-TRIACETATE, 4BETA(19891-05-5)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28-36/37/38
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: GZ0591950
• Hazardous Substances Data: 19891-05-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C26H34O9/c1-12-8-19-24(31,21(12)30)10-17(11-33-14(3)27)9-18-20-23(6,7)26(20,35-16(5)29)22(34-15(4)28)13(2)25(18,19)32/h8-9,13,18-20,22,31-32H,10-11H2,1-7H3/t13-,18+,19-,20-,22-,24-,25-,26?/m1/s1

Upstream product

• 17673-25-5 phorbol 
• 108-24-7 acetic anhydride 
• 371759-56-7 Phorbol-3-ol-12,13,20-triacetat 
• 64-19-7 acetic acid 

Downstream Products

• 22376-31-4 4-O-Methyl-phorbol-12,13-diacetat 
• 123358-26-9 C₄₄H₄₈O₉Si 
• 123358-25-8 C₄₄H₅₀O₉Si 
• 123358-24-7 C₄₄H₄₈O₉ 
• 123380-74-5 C₃₇H₄₄O₈ 
• 31365-46-5 phorbol-12-acetate-13-myristate 
• 20839-16-1 12-O-acetylphorbol 13-dodecanoate 
• 70470-59-6 phorbol 12-acetate 
• 24928-15-2 Phorbol 12,13-diacetate 
• 17673-25-5 Phorbol 
• 77646-25-4 Acetic acid (1aS,1bR,4aS,5R,7aR,7bR,8S,9S,9aR)-9-acetoxy-3-acetoxymethyl-4a,5,7b-trihydroxy-1,1,6,8-tetramethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester 

Relevant articles and documents

On the active substances of croton oil. VII. Phorbol

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Inhibition of cytopathic effect of human immunodeficiency virus type-1 by various phorbol derivatives

Forty-eight derivatives of phorbol (9) and isophorbol (14) were evaluated for their inhibition of human immunodeficiency virus (HIV)-1 induced cytopathic effects (CPE) on MT-4 cells, as well as their activation of protein kinase C (PKC), as indices of anti-HIV-1 and tumor promoting activities, respectively. Of these compounds, the most potent inhibition of CPE was observed in 12-O-tetradecanoylphorbol 13-acetate (8) and 12-O-acetylphorbol 13-decanoate (6). The former also showed the strongest PKC activation activity, while the latter showed no activity at 10 ng/ml. Both activities were generally observed in those phorbol derivatives with an A/B trans configuration, but not in the isophorbol derivatives with an A/B cis configuration. Acetylation of 20-OH in the phorbol derivatives significantly reduced the inhibition of CPE, as shown in 12-O-, 20-O-diacetylphorbol 13-decanoate (6a) (IC100=15.6 μg/ml) vs. compound 6 (IC100=0.0076 μg/ml), and 12-O-tetradecanoylphorbol 13,20-diacetate (8a) (IC100=15.6 μg/ml) vs. 12-O- tetradecanoylphorbol 13-acetate (8) (IC100=0.00048 μg/ml), except in the case of 12-O-decanoylphorbol 13-(2-methylbutyrate) (4) and phorbol 12,13-diacetate (9c). The reduction of a carbonyl group at C-3 abruptly reduced the inhibition of CPE, as observed in 3β-hydroxyphorbol 12,13,20-triacetate (9f) (IC100=500 μg/ml) vs. phorbol 12,13,20-triacetate (9d) (IC100=62.5 μg/ml). Although 8 was equipotent in the inhibition of CPE, and activation of PKC, both activities were abruptly decreased by the acetylation of 20-OH and methylation of 4-OH [as in 8a and 4-O-methyl-12-O- tetradecanoylphorbol 13,20-diacetate (8b), respectively]. On the other hand, its positional isomer (12-O-acetylphorbol 13-tetradecanoate (8c) showed neither activities. The removal of a long acyl group in 8 led to a substantial loss of both activities, as shown in phorbol 13-acetate (9b). Of the 12-O-acetyl-13-O-acylphorbol derivatives, the highest inhibition of CPE was observed in 6, which has a dodecanoyl residue at C-13. Both an increase and decrease in the number of fatty acid carbon chains resulted in significant reduction of the inhibition of CPE.

The first formal asymmetry synthesis of phorbol

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