EPIPOLYGODIAL

Base Information

• Chemical Name: EPIPOLYGODIAL
• CAS No.: 5956-39-8
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.338
• Mol file: 5956-39-8.mol

Synonyms:EPIPOLYGODIAL

Chemical Property of EPIPOLYGODIAL

Chemical Property:

• Vapor Pressure: 0.000163mmHg at 25°C
• Boiling Point: 330.7°C at 760 mmHg
• Flash Point: 124°C
• PSA: 34.14000
• Density: 1.094g/cm³
• LogP: 3.16310

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Epipolygodial has been shown to be effective against drug resistant cancer cells and other proliferative diseases.

Technology Process of EPIPOLYGODIAL

There total 16 articles about EPIPOLYGODIAL 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: 50.0%

Polygodial (6754-20-7,72581-70-5) → Isopolygodial (5956-39-8,72581-70-5)

Guidance literature:

With potassium hydroxide; In methanol;

DOI:10.1039/a702743e

Reference yield: 20.0%

((1S,4aR,8aS)-2-Hydroxymethyl-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-methanol (22567-27-7,34437-62-2,79732-75-5,90581-65-0,94942-39-9,106622-50-8,146276-81-5) → (1S,4aR,8aS)-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarbaldehyde (5956-39-8,6752-77-8,6754-20-7,33118-34-2,71536-99-7,90581-66-1,90581-67-2,94372-44-8,109838-20-2,109838-21-3,119238-51-6,126188-20-3,72581-70-5)

Guidance literature:

With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; at -60 ℃;

DOI:10.1016/S0040-4039(01)80095-2

Reference yield:

dimethyl 3,5,6,7,8,8a-hexahydro-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate (71557-96-5) → (1S,4aR,8aS)-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarbaldehyde (5956-39-8,6752-77-8,6754-20-7,33118-34-2,71536-99-7,90581-66-1,90581-67-2,94372-44-8,109838-20-2,109838-21-3,119238-51-6,126188-20-3,72581-70-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / 1,5 diazabicyclo<5.4.0>undecene-5 / toluene / 48 h / Heating

2: H₂ / Pd/C / methanol / 760 Torr

3: LiAlH₄

4: 20 percent / trifluoroacetic anhydride, triethylamine, DMSO / -60 °C

With lithium aluminium tetrahydride; hydrogen; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; 1,5-Diazabicyclo[5.4.0]undec-5-ene; palladium on activated charcoal; In methanol; toluene;

DOI:10.1016/S0040-4039(01)80095-2

upstream raw materials:

(1S,4aS)-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarboxylic acid dimethyl ester

dimethyl 3,5,6,7,8,8a-hexahydro-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate

(S)-5,5,8a-Trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1,2-dicarboxylic acid dimethyl ester

pu'ulenal

Downstream raw materials:

(1R,4aR,8aS)-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarbaldehyde

(4aS,8aR)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-2(1H)-naphthalenone

Refernces

• 1、 Garcia, Diogo Gomes,Gon?alves-de-Albuquerque, Cassiano Felippe,da Silva, Camila Ignácio,Kiss, Robert,Dasari, Ramesh,Chandra, Sunena,Kornienko, Alexander,Burth, Patricia. "Effect of polygodial and its direct derivatives on the mammalian Na+/K+-ATPase activity". . p. 1 - 8. Retrieved 2018.
• 2、 Dasari, Subramanyam,Samy, Angela Lincy Prem Antony,Narvekar, Parnal,Dontaraju, Venkata Satish,Dasari, Ramesh,Kornienko, Alexander,Munirathinam, Gnanasekar. "Polygodial analog induces apoptosis in LNCaP prostate cancer cells". . p. 154 - 162. Retrieved 2018.
• 3、 Dasari, Ramesh,De Carvalho, Annelise,Medellin, Derek C.,Middleton, Kelsey N.,Hague, Frédéric,Volmar, Marie N. M.,Frolova, Liliya V.,Rossato, Mateus F.,De La Chapa, Jorge J.,Dybdal-Hargreaves, Nicholas F.,Pillai, Akshita,Mathieu, Véronique,Rogelj, Snezna,Gonzales, Cara B.,Calixto, Jo?o B.,Evidente, Antonio,Gautier, Mathieu,Munirathinam, Gnanasekar,Glass, Rainer,Burth, Patricia,Pelly, Stephen C.,Van Otterlo, Willem A. L.,Kiss, Robert,Kornienko, Alexander. "Synthetic and Biological Studies of Sesquiterpene Polygodial: Activity of 9-Epipolygodial against Drug-Resistant Cancer Cells". . p. 2014 - 2026. Retrieved 2015.