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

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

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

• 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 
• 52705-93-8 ginsenoside Rd 
• 11021-13-9 ginsenoside Rb₂ 
• 14197-60-5 ginsenoside Rg₃ 
• 51116-90-6 12-β-O-hydroxy-20(S)-hydroxydammarane-24-ene-3-one 
• 6892-79-1 (20S)-dammar-24-ene-3α,12β,20-triol 

Downstream Products

• 51116-90-6 12β,20(S)-Dammar-24-en-3-one 
• 67400-17-3 ginsenoside Rh₂ 
• 62025-49-4 ginsenoside F₂ 
• 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 
• 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 
• 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 

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

Microwave degradation of floatation-enriched ginsenoside extract from Panax quinquefolium L. Leaf

Even though the degradation of ginsenosides has been thoroughly studied in animals and in vitro using acids, enzymes, and intestinal bacteria, a new degradation method is established for obtaining the ginsenosides Rg3, Rh2 and their

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.

Metabolism of 20(S)- and 20(R)-ginsenoside Rg3 by human intestinal bacteria and its relation to in vitro biological activities.

When ginsenoside Rg3 was anaerobically incubated with human fecal microflora, all specimens metabolized ginsenoside Rg3 to ginsenoside Rh2 and protopanaxadiol. The main metabolite was ginsenoside Rh2. 20(S)-ginsenoside Rg3 was quickly transformed to 20(S)

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.

Isolation and characterization of ginsenoside-Rg2, 20R-prosapogenin, 20S-prosapogenin and Δ20-prosapogenin. Chemical studies on saponins of Panax ginseng C.A. Meyer, Third report

In the course of a chemical study on pure ginsenosides, a ginsenoside-Rg2 was isolated as colorless needles, from the lateral root of Panax ginseng C.A. Meyer. For the characterization of Rg2, a chikusetsusaponin-I (ginsenoside-Rg2) was isolated as colorless needles from rhizome of Panax japonicus C.A. Meyer. The optical rotation value of both saponins were opposite to the published data. On the large scale isolation of ginsenosides, trace amount of ginsenoside-Rg2 was isolated as crystals. Three compounds, A, B and C, were isolated from the reaction mixture on hydrolysis of ginsenoside-Rb1, Rb2 and Rc with 50% aq. acetic acid. A was 20R-prosapogenin and it was identical with Rg3. On the other hand, B was found to be 20S-prosapogenin. And C was estimated to be prosapogenin dehydrated at C20-OH and named as Δ20-prosapogenin. It was found that an equilibration is present among A, B and C at the earlier stage on acid hydrolysis.