7755-01-3

Basic information

• Product Name: Protopanaxadiol
• Synonyms: Protopanaxadiol;20R-Betulafolienetriol;(20R)-5α-Dammar-24-ene-3β,12β,20-triol;(20R)-Dammar-24-ene-3β,12β,20-triol;(20R)-Protopanaxadiol;20R-Protopanaxadiol;PROTOVERATRINE A+B (RG)(CALL);Protopanaxadiol, 98%, from Panax ginseng C. A. Mey.
• CAS NO: 7755-01-3
• Molecular Formula: C₃₀H₅₂O₃
• Molecular Weight: 460.73208
• Product Categories: Miscellaneous Natural Products;Ginseng series
• Mol File: 7755-01-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 559.5 °C at 760 mmHg
• Flash Point: 226.1 °C
• Appearance: /
• Density: 1.036 g/cm³
• Vapor Pressure: 7.57E-15mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: 2-8°C
• PKA: 14.96±0.70(Predicted)
• CAS DataBase Reference: Protopanaxadiol(CAS DataBase Reference)
• NIST Chemistry Reference: Protopanaxadiol(7755-01-3)
• EPA Substance Registry System: Protopanaxadiol(7755-01-3)

Safety Data

• Hazardous Substances Data: 7755-01-3(Hazardous Substances Data)

Usage

Description

(20)R-Protopanaxadiol is a sapogenin that has been found in P. ginseng and has anticancer and antibacterial activities. It has a cytotoxic concentration (CC50) value of 6.1 μM in MT-4 human T cell leukemia cells and inhibits the growth of several additional cancer cell lines, including A549 human lung carcinoma, SKOV3 human ovarian adenocarcinoma, SK-Mel-2 human melanoma, P388 and L1210 murine leukemia, and K562 human chronic leukemia cells (ED50s = 11-26 μM). (20)R-protopanaxadiol also inhibits the growth of H. pylori in vitro (MICs = 50-100 μg/ml).

Uses

20(R)-Protopanaxdiol is a saponin ginsenoside which is a signature phytochemical of Ginseng, an herbaceous plant. Anti-cancer agent.

Definition

ChEBI: A diastereomer of protopanaxadiol in which the 20-hydroxy substituent has been introduced at the pro-R position.

InChI:InChI=1/C30H52O3/c1-19(2)10-9-14-30(8,33)20-11-16-29(7)25(20)21(31)18-23-27(5)15-13-24(32)26(3,4)22(27)12-17-28(23,29)6/h10,20-25,31-33H,9,11-18H2,1-8H3/t20-,21+,22?,23+,24-,25-,27-,28+,29-,30+/m0/s1

Upstream product

• 51116-90-6 12-β-O-hydroxy-20(S)-hydroxydammarane-24-ene-3-one 
• 14197-60-5 ginsenoside Rg₃ 
• 6892-79-1 (20S)-dammar-24-ene-3α,12β,20-triol 
• 1268481-62-4 (20S)-protopanaxadiol 3-O-(6-O-malonyl-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside) 20-O-β-D-xylopyranosyl-(1->3)-β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside 
• 11021-13-9 ginsenoside Rb₂ 
• 52705-93-8 ginsenoside Rd 

Downstream Products

• 51116-90-6 12β,20(S)-dihydroxydammar-24-en-3-one 
• 873850-44-3 12-benzoyl-protopanaxdiol 
• 873850-47-6 12-t-butyl-diphenylsilyl-protopanaxdiol 
• 1444554-63-5 (3S,8R,10R,12R,14R,17S)-17-((S)-2-hydroxy-5-((4-methoxyphenyl)amino)pentan-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol 
• 1444554-67-9 (3S,8R,10R,12R,14R,17S)-17-((S)-5-(benzylamino)-2-hydroxypentan-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol 
• 1444554-79-3 (3S,8R,10R,12R,14R,17S)-17-((S)-5-((4-fluorobenzyl)amino)-2-hydroxypentan-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol 
• 1444554-83-9 (3S,8R,10R,12R,14R,17S)-17-((S)-5-((4-chlorobenzyl)amino)-2-hydroxypentan-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol 
• 1444554-87-3 (3S,8R,10R,12R,14R,17S)-17-((S)-5-((3,4-dimethoxybenzyl)amino)-2-hydroxypentan-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol 
• 1444554-91-9 (3S,8R,10R,12R,14R,17S)-17-((S)-2-hydroxy-5-(phenethylamino)pentan-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol 
• 1444554-99-7 (3S,8R,10R,12R,14R,17S)-17-((S)-2-hydroxy-5-((4-nitrophenethyl)amino)pentan-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol 
• 1444555-03-6 (3S,8R,10R,12R,14R,17S)-17-((S)-5-((3,4-dimethoxyphenethyl)amino)-2-hydroxypentan-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol 
• 1444555-12-7 (3S,8R,10R,12R,14R,17S)-17-((S)-2-hydroxy-5-((3-phenylpropyl)amino)pentan-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol 
• 67-64-1 acetone 

Relevant articles and documents

Isolation and characterization of a new ginsenoside from the fresh root of panax ginseng

A new saponin, malonylginsenoside Ra3, was isolated from the fresh root of Panax ginseng, along with four known ginsenosides. The new compound was identified as (20S)-protopanaxadiol-3-O-(6-O-malonyl-ss-D-glucopyranosyl(1- 2)-ss-D-glucopyranoside -20-O-ss-D-xylopyranosyl(1?3)-ss-D- glucopyranosyl(1?6)-ss-D-glucopyranoside on the basis of extensive 1D and 2D NMR as well as HRESI-MS spectroscopic data analysis. Copyright

Synthesis of 3β,20S-dihydroxydammar-24-en-12-one 3,20-DI-O-β-D- glucopyranoside (chikusetsusaponin-LT8), a glycoside from Panax japonicus

A method for preparative production of 3β,20S-dihydroxydammar-24-en- 12-one 3,20-di-O-β-D-glucopyranoside (1), a glycoside from Panax japonicus, chikusetsusaponin-LT8 was developed. Chemical transformation of betulafolientriol, a component of Betula leaves extract, produced the 12-keto-20S-protopanaxadiol (3β,20S-dihydroxydammar-24-en-12-one) (2), exhaustive glycosylation of which by 2,3,4,6-tetra-O-acetyl-α-D- glucopyranosylbromide (3) under Koenigs - Knorr reaction conditions with subsequent removal of protecting groups formed 3β,20S-dihydroxydammar-24- en-12-one3,20-di-Q-β-D-glucopyranoside (1). The principal glycosylation product was 3β,20S-dihydroxydammar-24-en-12-one 3-O-β-D- glucopyranoside if equimolar amounts of (2) and (3) were used. 2006 Springer Science+Business Media, Inc.

SEMISYNTHETIC ANALOGUES OF GINSENOSIDES, GLYCOSIDES FROM GINSENG

Glycosylation of the dammar-24-ene-3,12β,20(S)-triols with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (A) in the presence of silver oxide in dichloromethane gives a mixture of the acetylated 3-, 12-, 20-, 3,12-di-, and 3,20-di-O-β-D-glucopyranosyl derivatives in a total yield of 83-84.5percent.Under similar conditions, the 3-O-acetyl derivatives of dammar-24-ene-3,12β,20(S)-triols give a mixture of 12- and 20-O-β-D-glucopyranosyl derivatives.Condensation of betulafolienetriol both with the glycosyl bromide A in the presence of mercuric cyanide in nitromethane and with 3,4,6,-tri-O-acetyl-β-D-glucopyranose 1,2-(tert-butyl ortoacetate) in the presence of 2,4,6-trimethyl-pyridinium perchlorate in chlorobenzene under azeotropic distillation results in dehydration and 20-dehydroxyglucosides are formed.