12-DEOXYPHORBOL 13-ACETATE

Base Information

• Chemical Name: 12-DEOXYPHORBOL 13-ACETATE
• CAS No.: 60857-08-1
• Molecular Formula: C22H30O6
• Molecular Weight: 390.477
• Hs Code.: 2916200090
• Mol file: 60857-08-1.mol

Synonyms: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-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-,[1aR-(1aa,1bb,4ab,7aa,7ba,8a,9aa)]-;12-Deoxyphorbol 13-acetate;13-O-Acetyl-12-deoxyphorbol;NSC 623310;SA 101A;Stillingia factorS7;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-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-,(1aR,1bS,4aR,7aS,7bR,8R,9aS)-;

Chemical Property of 12-DEOXYPHORBOL 13-ACETATE

Chemical Property:

• Appearance/Colour: White to off-white powder.
• Vapor Pressure: 2.06E-14mmHg at 25°C
• Melting Point: 216-219℃
• Refractive Index: 1.599
• Boiling Point: 550.5 ºC at 760 mmHg
• PKA: 11.40±0.70(Predicted)
• Flash Point: 188.7 ºC
• PSA: 104.06000
• Density: 1.31 g/cm³
• LogP: 1.53010
• Storage Temp.: ?20°C
• Solubility.: Soluble in DMSO at 30mg/ml

Purity/Quality:

99%min ^*data from raw suppliers

Prostratin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• 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: 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. 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]

Technology Process of 12-DEOXYPHORBOL 13-ACETATE

There total 36 articles about 12-DEOXYPHORBOL 13-ACETATE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

C22H30N2O6 (1035455-44-7) → prostratin (60857-08-1)

Guidance literature:

In ethyl acetate; benzene; at 20 ℃; for 0.333333h; Product distribution / selectivity; UV-irradiation;

Reference yield: 86.0%

12-deoxyphorbaldehyde-13-acetate → prostratin (60857-08-1)

Guidance literature:

With sodium tetrahydroborate; at -50 ℃; for 0.25h; Reagent/catalyst;

Reference yield: 36.0%

C20-O-trityl-prostratin (1173884-74-6) → prostratin (60857-08-1)

Guidance literature:

C₂₀-O-trityl-prostratin; With methanol; perchloric acid; water; at 20 ℃; for 0.251389h;

With water; sodium hydrogencarbonate; In methanol; at 20 ℃; for 0.0833333h; Product distribution / selectivity;

upstream raw materials:

C₂₂H₃₀N₂O₆

C₂₀-O-trityl-prostratin

(3aR,6aS,7R,10R,10aR,10bS)-3a,10a-dihydroxy-5-(hydroxymethyl)-2,10-dimethyl-7-(prop-1-en-2-yl)-3a,4,6a,7,10,10a-hexahydrobenzo[e]azulene-3,8(9H,10bH)-dione

(1R,5R)-5-hydroxymethyl-2-cyclopenten-1-ol

Refernces

• 1、 Hirose, Akira,Watanabe, Ayumu,Ogino, Kohei,Nagatomo, Masanori,Inoue, Masayuki. "Unified Total Syntheses of Rhamnofolane, Tigliane, and Daphnane Diterpenoids". . p. 12387 - 12396. Retrieved 2021.
• 2、 -. "Process to Produce Prostratin and Structural or Functional Analogs Thereof". Page/Page column 11. . Retrieved 2009/07/25.