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

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

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

Upstream product

• 1035455-44-7 C₂₂H₃₀N₂O₆ 
• 1173884-74-6 C₂₀-O-trityl-prostratin 

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.

Unified Total Syntheses of Rhamnofolane, Tigliane, and Daphnane Diterpenoids

Rhamnofolane, tigliane, and daphnane diterpenoids are structurally complex natural products with multiple oxygen functionalities, making them synthetically challenging. While these diterpenoids share a 5/7/6-trans-fused ring system (ABC-ring), the three-carbon substitutions at the C13- and C14-positions on the C-ring and appending oxygen functional groups differ among them, accounting for the disparate biological activities of these natural products. Here, we developed a new, unified strategy for expeditious total syntheses of five representative members of these three families, crotophorbolone (1), langduin A (2), prostratin (3), resiniferatoxin (4), and tinyatoxin (5). Retrosynthetically, 1-5 were simplified into their common ABC-ring 6 by detaching the three-carbon units and the oxygen-appended groups. Intermediate 6 with six stereocenters was assembled from four achiral fragments in 12 steps by integrating three powerful transformations, as follows: (i) asymmetric Diels-Alder reaction to induce formation of the C-ring; (ii) π-allyl Stille coupling reaction to set the trisubstituted E-olefin of the B-ring; and (iii) Eu(fod)3-promoted 7-endo cyclization of the B-ring via the generation of a bridgehead radical. Then 6 was diversified into 1-5 by selective installation of the different functional groups. Attachment of the C14-β-isopropenyl and isopropyl groups led to 1 and 2, respectively, while oxidative acetoxylation and C13,14-β-dimethylcyclopropane formation gave rise to 3. Finally, formation of an α-oriented caged orthoester by C13-stereochemical inversion and esterification with two different homovanillic acids delivered 4 and 5 with a C13-β-isopropenyl group. This unified synthetic route to 1-5 required only 16-20 total steps, demonstrating the exceptional efficiency of the present strategy.

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.

Process to Produce Prostratin and Structural or Functional Analogs Thereof

This invention concerns a process to convert a hydroxyl group (bold in R3C—OH) in a tigliane-type compound to a hydrogen (bold in R3C—H) to obtain deoxytigliane-type compounds or structural or functional analogs thereof. The process has wide application particularly to produce specific biologically active compounds in quantity for use as pharmaceuticals. In particular the process can be used to convert phorbol to a 12-deoxytigliane (prostrating which is a therapeutic lead for the treatment of AIDS. New compositions of matter are also disclosed.