(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS No.: 14197-60-5
• Molecular Formula: C₄₂H₇₂O₁₃
• Molecular Weight: 785.026
• Hs Code.: 29389090
• Metabolomics Workbench ID: 133493
• Wikidata: Q105246825
• Mol file: 14197-60-5.mol

Synonyms:Ginsenoside Rg3(S-FORM);ginsenoside-rg3;(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;2-((4,5-dihydroxy-2-((12-hydroxy-17-(2-hydroxy-6-methylhept-5-en-2-yl)-4,4,8,10,14-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;MFCD11045225;11019-45-7;SCHEMBL12400395;BS-42403;SY075378;NS00018302;2-[4,5-dihydroxy-2-[[12-hydroxy-17-(2-hydroxy-6-methylhept-5-en-2-yl)-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Chemical Property of (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Chemical Property:

• Melting Point: 315-318 °C
• Boiling Point: 885.017 °C at 760 mmHg
• PKA: 12.85±0.70(Predicted)
• Flash Point: 489.041 °C
• PSA: 218.99000
• Density: 1.303 g/cm³
• LogP: 2.14900
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥5mg/mL
• XLogP3: 4
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 10
• Exact Mass: 784.49729235
• Heavy Atom Count: 55
• Complexity: 1370

Purity/Quality:

Ginsenoside Rg3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C)C)O)C)O)C
• Description: Ginsenosides are pharmacologically active natural constituents of ginseng and other plants of the genus Panax. Structurally, they are steroid glycosides derived from the triterpene squalene. Ginsenoside Rg3 is a panaxadiol found in white and red P. ginseng. This ginsenoside has diverse in vitro and in vivo effects, including anti-cancer, neuroprotective, anti-hypertensive, and anti-inflammatory actions. Ginsenoside Rg3 induces apoptosis and inhibits angiogenesis in a variety of cancer models. Notably, this ginsenoside can be produced by heating other ginsenosides, leading to elevated levels in steamed or dried ginseng preparations.
• Uses: Ginsenoside Rg3 has been used to investigate its modulatory effects on delayed rectifier potassium current (IKr) channels in long QT syndrome (LQTS)2-human induced pluripotent stem cells (hiPSC-CMs). Ginsenoside Rg3 shows a synergistic antitumor effect with cisplatin in cisplatin-resistant bladder tumor cell lines and is considered to be an anti-tumor agent.

Technology Process of (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

There total 24 articles about (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

ginsenoside Rd (52705-93-8) → ginsenoside Rg3 (14197-60-5,38243-03-7,126252-51-5)

Guidance literature:

With Flavobacterium sp. BGS₃₆; In water; at 30 ℃; for 24h; Microbiological reaction;

DOI:10.1007/s10600-014-0907-y

Reference yield: 35.7%

C58H88O21 → ginsenoside Rg3 (14197-60-5,38243-03-7,126252-51-5) + C42H72O13 (201540-22-9)

Guidance literature:

With sodium methylate; In methanol; Ambient temperature;

DOI:10.1016/S0008-6215(97)00217-6

Reference yield:

ginsenoside Rd (52705-93-8) → protopanaxadiol (6892-79-1,7755-01-3,30636-90-9,38243-15-1,53368-76-6,103834-30-6) + ginsenoside Rg3 (14197-60-5,38243-03-7,126252-51-5)

Guidance literature:

With water; sodium hydroxide; at 165 ℃; for 0.0833333h;

DOI:10.1021/jf902153a

upstream raw materials:

C₄₆H₇₆O₁₆

malonyl-ginsenoside Rb₂

malonyl-ginsenoside Rc

C₅₇H₉₄O₂₅

Downstream raw materials:

ginsenoside Rh₂

protopanaxadiol

ginsenoside Rs3

Refernces

• 1、 -. "Manufacturing method for mass-production of 20(S)-ginsenoside Rg3". Paragraph 0029; 0031-0043. . Retrieved 2018/08/30.
• 2、 Ten,Chae,Yoo. "Biotransformation of ginsenoside Rd into 20(S)-Rg3 by bacterium flavobacterium sp. BGS36". . p. 181 - 183. Retrieved 2014/06/09.