112246-15-8

Basic information

• Product 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
• Synonyms: (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;(3beta,12beta,20R)-12,20-Dihydroxydammar-24-en-3-yl beta-D-glucopyranoside;20(R)-Rh2;b-D-Glucopyranoside, (3b,12b,20R)-12,20-dihydroxydammar-24-en-3-yl;Ginsenoside Rh2, 20(R)-
• CAS NO: 112246-15-8
• Molecular Formula: C₃₆H₆₂O₈
• Molecular Weight: 622.87
• EINECS: 2017-001-1
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 112246-15-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 727.5°Cat760mmHg
• Flash Point: 393.8°C
• Appearance: /
• Density: 1.19
• Vapor Pressure: 1.94E-24mmHg at 25°C
• Refractive Index: 1.571
• PKA: 12.91±0.70(Predicted)
• CAS DataBase Reference: (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 DataBase Reference)
• NIST Chemistry Reference: (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(112246-15-8)
• EPA Substance Registry System: (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(112246-15-8)

Safety Data

• Hazardous Substances Data: 112246-15-8(Hazardous Substances Data)

Usage

Description

(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-2,3,5,6,7,8,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol is a complex organic compound with a unique molecular structure. It is characterized by its multiple stereocenters and hydroxyl groups, which may contribute to its potential biological activities and applications.

Uses

1. Used in Pharmaceutical Applications:
(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-2,3,5,6,7,8,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol is used as a potential therapeutic agent for various diseases due to its unique molecular structure and multiple hydroxyl groups, which may allow for interactions with biological targets.
2. Used in Drug Delivery Systems:
In the pharmaceutical industry, (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-2,3,5,6,7,8,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol can be used as a component in drug delivery systems, potentially enhancing the solubility, stability, and bioavailability of other therapeutic agents.
3. Used in Chemical Research:
(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-2,3,5,6,7,8,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol may also be utilized in chemical research for the synthesis of novel compounds or as a starting material for the development of new drugs with potential therapeutic applications.
Please note that the specific applications and uses mentioned above are hypothetical and based on the general properties of the compound. Further research and development would be required to validate these potential uses.

Physical form

Solid

Biochem/physiol Actions

20(R)-Ginsenoside Rh2, a matrix metalloproteinase (MMP) inhibitor, acts as a cell antiproliferator. It has anticancer effects via blocking cell proliferation and causing G1 phase arrest. 20(R)-Ginsenoside Rh2 induces apoptosis, and has anti-inflammatory and antioxidative activity. 20(R)-Ginsenoside Rh2 inhibits the replication and proliferation of mouse and human gammaherpesvirus 68 (MHV-68) with an IC50 of 2.77 μM for murine MHV-68. Ginsenoside Rh2 is a triterpene saponin found in Panax (ginseng) that exhibits immunomodulatory, neuroprotective, cognition enhancing, anti-inflammatory, antioxidative, and anticancer activities. In CD8+ T cells, ginsenoside Rh2 increases production of IFN-γ and activation of p38 MAPK and ERK, resulting in an increase in cell proliferation. In animals undergoing the Morris water maze test, ginsenoside Rh2 improves spatial learning and memory. This compound also modulates expression of inflammatory markers, decreasing expression of toll-like receptor 4 (TLR4), CD14, TNF-α, IL-1α and HIF-1α, and inhibiting degradation of IκB kinase and translocation of NF-κB across various cellular models.

InChI:InChI=1/C36H62O8/c1-20(2)10-9-14-36(8,42)35(7)17-16-34(6)21-11-12-25-32(3,4)26(13-15-33(25,5)22(21)18-23(38)30(34)35)44-31-29(41)28(40)27(39)24(19-37)43-31/h10,21-31,37-42H,9,11-19H2,1-8H3/t21?,22?,23-,24+,25?,26?,27+,28-,29+,30?,31-,33+,34+,35-,36+/m0/s1

Upstream product

• 127761-61-9 3β-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxy)-12β-acetoxydammar-24-en-20(S)-ol 
• 6892-79-1 Betulafolienetriol 
• 51116-90-6 12β,20(S)-Dammar-24-en-3-one 
• 127750-93-0 12β-Acetoxy-20(S)-hydroxydammar-24-en-3-one 
• 97869-56-2 12β-Acetoxydammar-24-en-3β,20(S)-diol 
• 108212-06-2 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)dammar-24-ene-3β,12β,20(S)-triol 
• 127761-61-9 (3β,12β,20S)-12-(acetyloxy)-20-hydroxydammar-24(25)-en-3-yl β-D-glucopyranoside-2,3,4,6-tetraacetate 
• 14197-60-5 ginsenoside Rg₃ 
• 6892-79-1 (20S)-dammar-24-ene-3α,12β,20-triol 
• 51116-90-6 12-β-O-hydroxy-20(S)-hydroxydammarane-24-ene-3-one 
• 127750-93-0 12-O-acetyl-dammar-24-ene-12β,20(S)-diol-3-one 
• 127750-92-9 12β-acethoxy-3β,20S-dihydroxydammar-24-ene 
• 6892-79-1 protopanaxadiol 
• 873850-51-2 C₆₉H₈₆O₁₃ 

Downstream Products

• 1357259-75-6 12,6'-dioctanoyl ginsenoside Rh₂ 
• 127761-61-9 (3β,12β,20S)-12-(acetyloxy)-20-hydroxydammar-24(25)-en-3-yl β-D-glucopyranoside-2,3,4,6-tetraacetate 
• 117666-46-3 3,12-di-O-β-D-glucopyranosyl-dammar-24-ene-3β,12β,20(S)-triol 

Relevant articles and documents

Hydrolysis of the outer β-(1,2)-d-glucose linkage at the C-3 position of ginsenosides by a commercial β-galactosidase and its use in the production of minor ginsenosides

Commercial β-galactosidase from Aspergillus oryzae (SUMILACT LTM) was used for the bioconversion of the ginsenosides Rb1, Rb2, Rc, Rd, and Rg3 to gypenoside-XVII, compound-O, compound-MC1, F2, and Rh2, respectively. The optimal conditions were

GLYCOSYLATION OF TRITERPENOIDS OF THE DAMMARANE SERIES. X. REGIO- AND STEREOSELECTIVE SYNTHESIS OF 20(S)-PROTOPANAXADIOL 3-O-β-D-GLUCOPYRANOSIDE (GINSENOSIDE Rh2)

The regio- and stereoselective synthesis of ginsenoside Rh2, which possesses anti-tumoral activity, has been effected by the glycosylation of 12β-acetoxydammar-24-ene-3β,20(S)-diol.Condensation with α-acetobromoglucose was carried out in the presence of silver oxide in dichloroethane at room temperature, and the yield of the desired glycoside amounted to 50percent.A method for the selective protection of the C-12-OH group of dammar-24-ene-3β,12β,20(S)-triol has been proposed.

Highly efficient biotransformation of ginsenoside Rb1 and Rg3 using β-galactosidase from Aspergillus sp.

A preliminary study on the enzymatic biotransformation of ginsenosides is evaluated. β-Galactosidase from Aspergillus sp. displayed β-glucosidase activity, which was responsible for its ability to transform major ginsenoside Rb1 to rare ginsenoside F2 via ginsenoside Rd. The Rb1 conversion, Rd and F2 yields reached 100%, 80.7% and 14.3% after 60 h at 60 °C, respectively. Ginsenoside Rg3 can be selectively hydrolyzed and only Rh2 was obtained with this β-galactosidase as well. Before hydrolysis, an Rg3 inclusion complex was prepared with hydroxypropyl-β-cyclodextrin (HP-β-CD) to improve the aqueous solubility. The solubility of Rg3 increased 74.6 fold, and the phase solubility curve displayed a typical AL-type, which indicates the formation of a 1 : 1 inclusion complex. Using an enzyme loading of 500 U g-1 Rg3, the highest Rg3 conversion of 90.6% and Rh2 yield of 88.5% were obtained after 24 h at 60 °C. These results indicate that β-galactosidase from Aspergillus sp. could be useful for the mass production of rare ginsenosides.

Synthesis of ginsenoside Rh2 and chikusetsusaponin-LT8 via gold(I)-catalyzed glycosylation with a glycosyl ortho-alkynylbenzoate as donor

Glycosylation of the acid labile protopanaxadiol derivatives was succeeded with a glycosyl ortho-hexynylbenzoate as donor under the catalysis of PPh 3AuNTf2, leading to the subsequent elaboration of ginsenoside Rh2 and chikusetsusaponin-LT8 in a concise manner.