60857-08-1

Basic information

• Product Name: 12-DEOXYPHORBOL 13-ACETATE
• Synonyms: Prostatin >99%;12-Deoxyphorbol 13-Acetate, dPAc;(1aR,1bS,4aR,7aS,7bR,8R,9aS)-9a-(Acetyloxy)-1,1a,1b,4,4a,7a,7b,8,9,9a -decahydro-4a,7b-dihydroxy-3-(hydroxyMethyl)-1,1,6,8-tetraMethyl-;13-O-Acetyl-12-deoxyphorbol;SA 101A;CCRIS 6292;12-DEOXYPHORBOL 13-ACETATE;PROSTRATIN
• CAS NO: 60857-08-1
• Molecular Formula: C₂₂H₃₀O₆
• Molecular Weight: 390.47
• Product Categories: Activator;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Protein Kinase Inhibitors and Activators
• Mol File: 60857-08-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 216-219℃
• Boiling Point: 550.5 ºC at 760 mmHg
• Flash Point: 188.7 ºC
• Appearance: White to off-white powder.
• Density: 1.31
• Vapor Pressure: 2.06E-14mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: ?20°C
• Solubility: Soluble in DMSO at 30mg/ml
• PKA: 11.40±0.70(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
• CAS DataBase Reference: 12-DEOXYPHORBOL 13-ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 12-DEOXYPHORBOL 13-ACETATE(60857-08-1)
• EPA Substance Registry System: 12-DEOXYPHORBOL 13-ACETATE(60857-08-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 60857-08-1(Hazardous Substances Data)

Usage

Description

Activation of latent reservoirs of HIV-infected cells is a treatment strategy designed to reduce viral load and eliminate the perpetuation of retroviral infection. Prostratin is a non-tumor promoting phorbol ester that potently induces HIV-1 reactivation in latent reservoirs of infected Jurkat-LAT-GFP cells with an IC50 value of ~0.5 μM. Originally, prostratin was isolated from plant sources including P. prostrata, E. cornigera, and H. nutans. The effects of prostratin are mediated through activation of NF-κB via protein kinase C and by downregulation of HIV-1 receptor CD4 expression and its co-receptors CXCR4 and CCR5.

Uses

Different sources of media describe the Uses of 60857-08-1 differently. You can refer to the following data:
1. It is a protein kinase C activator found in the bark of the mamala tree of Samoa, Homalanthus nutans (Euphorbiaceae). Research indicated that prostratin has potential to be useful in the treatment of HIV as it flushes viral reservoirs in latently infected CD4+ T-cells.
2. Activation of latent reservoirs of HIV-infected cells is a treatment strategy designed to reduce viral load and eliminate the perpetuation of retroviral infection. Prostratin is a non-tumor promoting phorbol ester that potently induces HIV-1 reactivation in latent reservoirs of infected Jurkat-LAT-GFP cells . [Cayman Chemical]

Biochem/physiol Actions

Prostratin, an unusual non-tumorigenic phorbol ester, is an activator of protein kinase C (PKC) and also an activator of nuclear factor KB (NF-KB) mediated through activation of the IKKs (IKB kinases). Prostratin exhibits potent in vitro activity by inducing HIV expression in latently infected cell lines and primary cells, thus antagonizing HIV latency. Activation of PKC and NF-kB has been proposed as the mechanism of action. Prostratin also inhibits HIV entry into target cells by down-regulating CD4 and CXCR4 receptors.

References

1) Cashmore et al. (1976), The structure of prostratin: a toxic tetracyclic diterpene ester from Pimelea Prostrata; Tetrahedron Lett., 17 1737 2) Miana et al. (2015), Prostratin: An Overview; Mini Rev. Med. Chem., 15 1122 3) Shen et al. (2015), The protein kinase C agonist prostratin induces differentiation of human myeloid leukemia cells and enhances cellular differentiation by chemotherapeutic agents; Cancer Lett., 356 (2 Pt. B) 686 4) Biancotto et al. (2004), Dual role of prostratin in inhibition of infection and reactivation of human immunodeficiency virus from latency in primary blood lymphocytes and lymphoid tissue; J. Virol., 78 10507 5) Geribaldi-Doldan et al. (2015), 12-Deoxyphorbols Promote Adult Neurogenesis by Inducing Neural Progenitor Cell Proliferation via PKC activation ; Int. J, Neuropsychopharmacol., 19 pyv085

InChI:InChI=1/C22H30O6/c1-11-6-16-20(26,18(11)25)9-14(10-23)7-15-17-19(4,5)21(17,28-13(3)24)8-12(2)22(15,16)27/h6-7,12,15-17,23,26-27H,8-10H2,1-5H3/t12-,15+,16-,17-,20-,21+,22-/m1/s1

Downstream Products

• 1173884-74-6 C₂₀-O-trityl-prostratin 
• 112379-17-6 phorbol 13-acetate 12,20-dibenzoate 

Relevant articles and documents

Pharmaceutical potential of phorbol esters from Jatropha curcas oil

Phorbol esters (PEs) are diterpenes present in Jatropha curcas L. seeds and have a myriad of biological activities. Since PEs are toxic, they are considered to be futile in Jatropha-based biodiesel production chain. In the present study, the extracted PEs from Jatropha oil were used as a starting material to synthesise pharmacologically important compound, prostratin. The prostratin synthesised from Jatropha showed identical mass with that of the reference standard prostratin, as determined by Nano-LC-ESI-MS/MS. Considering the rapid growth in Jatropha biodiesel industry, potential exists to harness large amount of PEs which can be further utilised to synthesise prostratin as a value added product.

Chemical total-synthesis preparation method of prostratin

The invention discloses a chemical total-synthesis preparation method for prostratin. The chemical total-synthesis preparation method is characterized in that an easily prepared 5-(hydroxymethyl)-2-cyclopentene-1-alcohol is taken as a raw material, light oxidization de-arylation reaction is performed, addition is induced in molecules, olefin double decomposition reaction is performed, and a targetproduct is finally obtained through functional group conversion. The preparation method is simple and convenient in operation, and is gentle in condition, and the synthesized products are consistentwith spectral data of natural products.