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

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

Downstream Products

• 24928-15-2 Phorbol 12,13-diacetate 
• 70470-59-6 phorbol 12-acetate 
• 22376-31-4 4-O-Methyl-phorbol-12,13-diacetat 
• 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 
• 17673-25-5 Phorbol 
• 123380-74-5 C₃₇H₄₄O₈ 
• 123358-24-7 C₄₄H₄₈O₉ 
• 123358-25-8 C₄₄H₅₀O₉Si 
• 123358-26-9 C₄₄H₄₈O₉Si 
• 31365-46-5 phorbol-12-acetate-13-myristate 
• 20839-16-1 12-O-acetylphorbol 13-dodecanoate 

Relevant articles and documents

New phorbol ester derivatives as potent anti-HIV agents

Tigliane esters show many biological activities, including anti-HIV-1 activity. Our aim in this study was to establish structure-anti-HIV activity relationships for four series of tigliane-type diterpenoids. We synthesized and evaluated 29 new phorbol ester derivatives for anti-HIV activity and for cytotoxicity against human tumor cell lines. Among them, three derivatives, two phorbol-13-monoesters (5d and 5e) and a phorbol-12,13-diester (6a), showed significant anti-HIV activity. We found that better anti-HIV activity was often associated with a shorter acyl ester at C-13. Particularly, compounds with a phenyl ring in the ester side chain exhibited excellent anti-HIV activity and had good safety indexes. Due to its significant anti-HIV potency with a high selectivity index, phorbol-12,13-dicinnamoate (6a) was chosen as the potential candidate for further preclinical trials.

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.

Phorbol derivatives having antivirus activity

An antiviral agent comprising as an active ingredient a phorbol derivative of formula (I): (wherein R1, R2, R3, R4, and R5, independently one another, represent a hydrogen atom, an aliphatic carboxylic acid residue, or an aromatic carboxylic acid residue) having a ratio r=CC0/IC100, i.e., ratio of concentration CC0at which survival of MT-4 cells is decreased upon cell proliferation tests to concentration IC100at which HIV-1-induced cytopathic effect (CPE) on MT-4 cells is inhibited by 100%, of 2 or more and having a protein kinase C(PKC) activation of 30% or less at a concentration of 10 ng/mL. The agent is useful as an anti-HIV agent.