(2R,3R,4S,5R,6R)-2-[[(10S,12S,14R,17S)-12-hydroxy-17-[(2R)-2-hydroxy-6 -methyl-hept-5-en-2-yl]-4,4,10,14,17-pentamethyl-2,3,5,6,7,8,9,11,12,1 3,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxyme thyl)oxane-3,4,5-triol

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-2-[[(10S,12S,14R,17S)-12-hydroxy-17-[(2R)-2-hydroxy-6 -methyl-hept-5-en-2-yl]-4,4,10,14,17-pentamethyl-2,3,5,6,7,8,9,11,12,1 3,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxyme thyl)oxane-3,4,5-triol
• CAS No.: 112246-15-8
• Molecular Formula: C₃₆H₆₂O₈
• Molecular Weight: 622.883
• Mol file: 112246-15-8.mol

Synonyms:20(R)-GinsenosideRh2; 20(R)-Rh2

Chemical Property of (2R,3R,4S,5R,6R)-2-[[(10S,12S,14R,17S)-12-hydroxy-17-[(2R)-2-hydroxy-6 -methyl-hept-5-en-2-yl]-4,4,10,14,17-pentamethyl-2,3,5,6,7,8,9,11,12,1 3,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxyme thyl)oxane-3,4,5-triol

Chemical Property:

• Vapor Pressure: 1.94E-24mmHg at 25°C
• Boiling Point: 727.5°Cat760mmHg
• PKA: 12.91±0.70(Predicted)
• Flash Point: 393.8°C
• PSA: 139.84000
• Density: 1.19g/cm³
• LogP: 4.32480

Purity/Quality:

98% ^*data from raw suppliers

20(R)-GinsenosideRh2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 20(R)-Ginsenoside Rh2 is a matrix metalloproteinase (MMP) inhibitor that acts as a cell antiproliferator. It was originally isolated from the Panax Ginseng root. (20R)Ginsenoside Rh2, a natural compound found in Panax ginseng, which is a plant glycoside with a dammarane skeloton resembling a steroid skeleton. It shows antiviral and anticancer activities. It has an anti-cancer proliferation, differentiation and chemopreventive effects in certain cancer cell types. It is a matrix metalloproteinase (MMP) inhibitor.

Technology Process of (2R,3R,4S,5R,6R)-2-[[(10S,12S,14R,17S)-12-hydroxy-17-[(2R)-2-hydroxy-6 -methyl-hept-5-en-2-yl]-4,4,10,14,17-pentamethyl-2,3,5,6,7,8,9,11,12,1 3,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxyme thyl)oxane-3,4,5-triol

There total 19 articles about (2R,3R,4S,5R,6R)-2-[[(10S,12S,14R,17S)-12-hydroxy-17-[(2R)-2-hydroxy-6 -methyl-hept-5-en-2-yl]-4,4,10,14,17-pentamethyl-2,3,5,6,7,8,9,11,12,1 3,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxyme thyl)oxane-3,4,5-triol 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: 90.0%

3β-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxy)-12β-acetoxydammar-24-en-20(S)-ol (127761-61-9) → Ginsenoside Rh2 (67400-17-3,78214-33-2,88156-29-0,112246-15-8,117708-91-5)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1007/BF00598267

Reference yield: 85.5%

β-cyclodextrin → ginsenoside Rh2 (67400-17-3,78214-33-2,88156-29-0,112246-15-8,117708-91-5)

Guidance literature:

With β-galactosidase from Aspergillus saponins; water; at 60 ℃; for 48h;

DOI:10.1039/c5ra11519a

Reference yield: 76.0%

C69H86O13 (873850-51-2) → ginsenoside Rh2 (67400-17-3,78214-33-2,88156-29-0,112246-15-8,117708-91-5)

Guidance literature:

With methanol; potassium hydroxide; at 20 ℃;

DOI:10.1016/j.tetlet.2011.04.003

upstream raw materials:

3β-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxy)-12β-acetoxydammar-24-en-20(S)-ol

Betulafolienetriol

12β,20(S)-Dammar-24-en-3-one

12β-Acetoxy-20(S)-hydroxydammar-24-en-3-one

Downstream raw materials:

3,12-di-O-β-D-glucopyranosyl-dammar-24-ene-3β,12β,20(S)-triol

(3β,12β,20S)-12-(acetyloxy)-20-hydroxydammar-24(25)-en-3-yl β-D-glucopyranoside-2,3,4,6-tetraacetate

12,6'-dioctanoyl ginsenoside Rh₂

Refernces

• 1、 Atopkina, Lyubov N.,Uvarova, Nina I.,Elyakov, Georgi B.. "Simplified preparation of the ginsenoside-Rh2 minor saponin from ginseng". . p. 449 - 451. Retrieved 1997.
• 2、 Dai, Longhai,Liu, Can,Li, Jiao,Dong, Caixia,Yang, Jiangang,Dai, Zhubo,Zhang, Xueli,Sun, Yuanxia. "One-Pot Synthesis of Ginsenoside Rh2 and Bioactive Unnatural Ginsenoside by Coupling Promiscuous Glycosyltransferase from Bacillus subtilis 168 to Sucrose Synthase". . p. 2830 - 2837. Retrieved 2018/03/26.
• 3、 -. "METHOD FOR PREPARING NOVEL PROCESSED GINSENG OR AN EXTRACT THEREOF, THE USUALLY MINUTE GINSENOSIDE CONTENT OF WHICH IS INCREASED". Paragraph 0049; 0050; 0051. . Retrieved 2013/03/28.