32752-29-7

Basic information

• Product Name: PHORBOL 13-ACETATE
• Synonyms: PHORBOL 13-ACETATE;PHORBOL 13-MONOACETATE;1,6,8-alpha-tetramethyl-l-19a-acetate;(1aR)-1,1,6,8α-Tetramethyl-3-(hydroxymethyl)-4aβ,7bα,9β-trihydroxy-9aα-acetoxy-1,1aα,1bβ,4,4a,7aα,7b,8,9,9a-decahydro-5H-cyclopropa[3,4]benzo[1,2-e]azulene-5-one;(1aR)-9aα-Acetyloxy-1,1aα,1bβ,4,4a,7aα,7b,8,9,9a-decahydro-4aβ,7bα,9β-trihydroxy-3-hydroxymethyl-1,1,6,8α-tetramethyl-5H-cyclopropa[3,4]benz[1,2-e]azulen-5-one;5H-Cyclopropa(3,4)benz(1,2-E)azulen-5-one, 1,1A-alpha,1B-beta,4,4A,7A-alpha,7B,8,9,9A-decahydro-4A-alpha,7B-alpha,9-beta,9A-alpha-tetrahydroxy-3-hydroxymethyl-1,1,6,8-alpha-tetramethyl-, 9A-acetate;5H-Cyclopropa(3,4)benz(1,2-E)azulen-5-one, 9A-(acetyloxy)-1,1A,1B,4,4A,7A,7B,8,9,9A-decahydro-4A,7B,9-trihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-, (1ar-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-;Phorbol 13-Acetate >99%
• CAS NO: 32752-29-7
• Molecular Formula: C22H30O7
• Molecular Weight: 406.47
• Product Categories: metabolite
• Mol File: 32752-29-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 582.4 ºC at 760 mmHg
• Flash Point: 200.2ºC
• Appearance: White to off-white powder.
• Density: 1.37 g/cm³
• Vapor Pressure: 5.44E-16mmHg at 25°C
• Refractive Index: 1.616
• Storage Temp.: −20°C
• CAS DataBase Reference: PHORBOL 13-ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: PHORBOL 13-ACETATE(32752-29-7)
• EPA Substance Registry System: PHORBOL 13-ACETATE(32752-29-7)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28-36/37/38
• Safety Statements: 26-27-36/37/39-45
• RTECS: GZ0612000
• Hazardous Substances Data: 32752-29-7(Hazardous Substances Data)

Usage

General Description

Phorbol 13-acetate, also known as TPA, is a potent tumor promoter and a pharmacological agent derived from the croton plant. It is a strong activator of protein kinase C (PKC), a key enzyme involved in cell signaling processes. TPA has been widely studied for its ability to induce the proliferation of cancer cells and has been used in research to understand the mechanisms of tumor promotion and cancer development. In addition, TPA has been investigated for its potential as a treatment for certain skin conditions, such as psoriasis and eczema, due to its ability to induce differentiation and inhibit inflammation in skin cells. However, its potent tumor-promoting effects have limited its clinical use.

InChI:InChI=1/C22H30O7/c1-10-6-15-20(27,17(10)25)8-13(9-23)7-14-16-19(4,5)22(16,29-12(3)24)18(26)11(2)21(14,15)28/h6-7,11,14-16,18,23,26-28H,8-9H2,1-5H3/t11-,14+,15-,16-,18-,20-,21-,22-/m1/s1

Upstream product

• 250268-53-2 13-O-acetylphorbol-20-linoleate 
• 41621-85-6 Phorbol 13,20-diacetate 

Relevant articles and documents

Differential effects of phorbol-13-monoesters on human immunodeficiency virus reactivation

The persistence of latent reservoirs of HIV-1 represents a major barrier to virus eradication in patients treated with antiretrovirals. Prostratin is a non-tumor promoting 12-deoxyphorbol monoester capable of up-regulating viral expression from latent provirus and therefore is potentially useful for HIV adjuvant therapy and similar properties might be elicited by related non-tumor promoting phorboids. We have therefore investigated a series of phorbol 13-monoesters for their capacity to reactivate HIV latency. Using a Jurkat T cell line containing latent HIV proviruses, we found that prostratin and phorbol-13-stearate effectively activate HIV-1 gene expression in these latently infected cells, with phorbol-13-stearate being at least 10-fold more potent than prostratin, and its activity rapidly decreasing with a shortening of the acyl side chain. We further demonstrated that phorbol-13-stearate and prostratin stimulate IKK-dependent phosphorylation and degradation of IκBα, leading to activation of NF-κB. Moreover, prostratin, phorbol-13-hexanoate and phorbol-13-stearate also activate the JNK and ERK pathways. Studies with isoform-specific PKC inhibitors suggest that the classical PKCs play a prominent role in the responses elicited by phorbol-13-stearate. Nevertheless, this compound induces a translocation pattern of the PKC isotypes α and δ to cellular compartments distinctly different from that elicited by prostratin and PMA.

Synthesis of 4aalpha-phorbol 9-myristate 9a-acetate and related esters.

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