174721-08-5

Basic information

• Product Name: ginsenoside Rh(4)
• Synonyms: ginsenoside Rh(4);(3beta,6alpha,12beta,20E)-3,12-Dihydroxydammara-20(22),24-dien-6-yl-beta-D-glucopyranoside
• CAS NO: 174721-08-5
• Molecular Formula: C36H60O8
• Molecular Weight: 620.85700
• Mol File: 174721-08-5.mol

Chemical Properties

• Boiling Point: 723.449oC at 760 mmHg
• Flash Point: 391.328oC
• Appearance: /
• Density: 1.21
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: -20°C Freezer
• Solubility: Methanol (Slightly), Pyridine (Slightly)
• PKA: 12.91±0.70(Predicted)
• CAS DataBase Reference: ginsenoside Rh(4)(CAS DataBase Reference)
• NIST Chemistry Reference: ginsenoside Rh(4)(174721-08-5)
• EPA Substance Registry System: ginsenoside Rh(4)(174721-08-5)

Safety Data

• Hazardous Substances Data: 174721-08-5(Hazardous Substances Data)

Usage

Uses

Ginsenoside Rh4 possesses inhibitory and antifungal activity.

InChI:InChI=1/C36H60O8/c1-19(2)10-9-11-20(3)21-12-15-35(7)27(21)22(38)16-25-34(6)14-13-26(39)33(4,5)31(34)23(17-36(25,35)8)43-32-30(42)29(41)28(40)24(18-37)44-32/h10-11,21-32,37-42H,9,12-18H2,1-8H3/b20-11+/t21-,22-,23+,24-,25-,26+,27+,28-,29+,30-,31+,32-,34-,35-,36-/m1/s1

Upstream product

• 22427-39-0 ginsenoside-Rg₁ 
• 52286-59-6 ginsenoside Re 

Relevant articles and documents

Microbial transformation of 20(S)-protopanaxatriol-type saponins by Absidia coerulea

Three 20(S)-protopanaxatriol-type saponins, ginsenoside-Rg1 (1), notoginsenoside-R1 (2), and ginsenoside-Re (3), were transformed by the fungus Absidia coerulea (AS 3.3389). Compound 1 was converted into five metabolites, ginsenoside-Rh4 (4), 3β,2β,25- trihydroxydammar-(E)-20(22)-ene-6-O-β-D-glucopyranoside (5), 20(S)-ginsenoside-Rh1 (6), 20(R)-ginsenoside-Rh1 (7), and a mixture of 25-hydroxy-20(S)-ginsenoside-Rh1 and its C-20(R) epimer (8). Compound 2 was converted into 10 metabolites, 20(S)-notoginsenoside-R 2 (9), 20(R)-notoginsenoside-R2 (10), 3β,12β,25- trihydroxydammar-(E)-20(22)-ene-6-O-β-D-xylopyranosyl-(1→2) -β-D-glucopyranoside (11), 3β,12β-dihydroxydammar-(E)-20(22),24- diene-6-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranoside (12), 3β,12β,20,25-tetrahydroxydammaran-6-O-β-D-xylopyranosyl- (1→2)-β-D-glucopyranoside (13), and compounds 4-8. Compound 3 was metabolized to 20(S)-ginsenoside-Rg2 (14), 20(R)-ginsenoside-Rg 2 (15), 3β,12β,25-trihydroxydammar-(E)-20(22)-ene-6-O- α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (16), 3β,12β-dihydroxydammar-(E)-20(22),24-diene-6-O-α-L- rhamnopyranosyl-(1→2)-β-D-glucopyranoside (17), 3β,12β,20, 25-tetrahydroxydammaran-6-O-α-L-rhamnopyranosyl-(1→2) -β-D-glucopyranoside (18), and compounds 4-8. The structures of five new metabolites, 10-13 and 16, were established by spectroscopic methods.

Synthesis of Δ20-Ginsenosides Rh4, (20E)-Rh3, Rg6, and Rk1: A General Approach to Access Dehydrated Ginsenosides

Four representative Δ20-ginsenosides, namely, ginsenosides Rh4 (1), (20E)-Rh3 (2), Rg6 (3), and Rk1 (4) from Panax Ginseng, were chemically synthesized for the first time. Dehydration of the naturally occurring 20(S)-protopanaxatriol and 20(S)-protopanaxadiol provided all types of Δ20-sapogenins, which were separated due to a judicious choice of protecting groups. The Δ20-sapogenins were then directly glycosylated with glycosyl ortho-alkynylbenzoate donors under the catalysis of Ph3PAuNTf2 as key steps. The neutral conditions of the glycosylations were crucial to prevent the acid-labile Δ20,21 double bond from isomerization.

Manufacturing method for mass-production of ginsenoside Rh4

The present invention relates to a method for mass-producing Ginsenoside-Re, and more specifically, to a method for mass-producing Ginsenoside-Re in which organic acid is mixed with Ginsenoside-Re and the mixture is treated under high temperature and high pressure, to produce Ginsenoside-Rh4. Ginsenoside-Rh4 exists in a small amount, only in red ginseng and black ginseng but not in white ginseng, and the conventional means to extract Ginsenoside-Rh4 by treating a ginseng extract and a red ginseng extract is not only ineffective in isolating and purifying Ginsenoside-Rh4, due to the presence of various other ginsenosides having similar chemical structures and molecular weights, but also results in a very low yield of isolated and purified Ginsenoside-Rh4, because Ginsenoside-Rh4 is present only in a miniscule amount in such extracts. On the other hand, the present invention produces Ginsenoside-Rh4 only by using Ginsenoside-Re capable of being easily isolated from ginseng leaves. Therefore, the isolation and purification of Ginsenoside-Rh4 is easier than when using extracts, and the mass-production of the same is markedly easy. Also, since Ginsenoside-Rh4 isolated and purified by the conventional means is costly, the method for mass-producing Ginsenoside-Rh4 according to the present invention, which enables Ginsenoside-Rh4 to be produced inexpensively, can generate higher value-added.COPYRIGHT KIPO 2016

TREATMENT AND PREVENTION OF CANCER WITH NEW GINSENOSIDE DERIVATIVES

The present invention relates to ginsenoside derivatives effective in prevention and treatment of cancer. More specifically, the present invention relates to ginsenoside derivatives with novel structures effective in prevention and treatment of cancers, method of their preparation, and a pharmaceutical composition comprising the above novel compounds as active ingredients.