30636-90-9

Usage

Uses

Used in Pharmaceutical Industry:
PROTOPANAXDIOL is used as a therapeutic agent for the treatment of cerebral ischemic injury. It exhibits neuroprotective effects by reducing inflammation, oxidative stress, and cell death, thereby promoting the recovery of brain function after an ischemic event.
Additionally, PROTOPANAXDIOL is used as an antioxidant to reverse oxidative stress, which is a significant factor in the development of various diseases and conditions, including aging, neurodegenerative disorders, and cardiovascular diseases.
Used in Research and Development:
PROTOPANAXDIOL serves as a valuable compound in the development of novel AMP-activated protein kinase (AMPK) inhibitors. AMPK is a key regulator of cellular energy homeostasis, and its modulation can have significant implications for glucose and lipid metabolism. By studying the effects of PROTOPANAXDIOL on AMPK, researchers can gain insights into the development of new therapeutic strategies for metabolic disorders and other related conditions.

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 
• 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 
• 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 R_h2 
• 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 
• 51116-90-6 12-β-O-hydroxy-20(S)-hydroxydammarane-24-ene-3-one 
• 51116-90-6 12β,20(S)-dihydroxydammar-24-en-3-one 

Relevant academic research and scientific papers

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.