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Ginsenoside Rg3

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Ginsenoside Rg3 Basic information

Product Name:
Ginsenoside Rg3
Synonyms:
  • beta-d-glucopyranoside,(3-beta,12-beta)-12,20-dihydroxydammar-24-en-3-yl2-o-b
  • dammar-24-ene-12-beta,20-diol,3-beta-((2-o-beta-d-glucopyranosyl-beta-d-gluc
  • eta-d-glucopyranosyl-
  • gensenoside RG3
  • (3β,12β)-12,20-Dihydroxydammar-24-en-3-yl 2-O-β-D-glucopyranosyl-β-D-glucopyranoside
  • 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
  • Ginsenoside Rg3, 98%, from Panax ginseng C. A. Mey.
CAS:
14197-60-5
MF:
C42H72O13
MW:
785.03
Product Categories:
  • chemical reagent
  • pharmaceutical intermediate
  • Ginsenoside series
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Saponins
  • The group of Ginsenosides
Mol File:
14197-60-5.mol
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Ginsenoside Rg3 Chemical Properties

Melting point:
315-318°C
Boiling point:
885.0±65.0 °C(Predicted)
Density 
1.30
storage temp. 
2-8°C
solubility 
DMSO: ≥5mg/mL
pka
12.85±0.70(Predicted)
form 
powder
color 
white to beige
optical activity
[α]/D +10 to +20°, c = 1 in methanol
InChIKey
RWXIFXNRCLMQCD-JBVRGBGGSA-N
CAS DataBase Reference
14197-60-5(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
RTECS 
LY9537300
HS Code 
29389090
Toxicity
mouse,LD50,intraperitoneal,1250mg/kg (1250mg/kg),Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 343, 1975.
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Ginsenoside Rg3 Usage And Synthesis

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).

Uses

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.

Definition

ChEBI: (20S)-ginsenoside Rg3 is a ginsenoside found in Panax ginseng and Panax japonicus var. major that is dammarane which is substituted by hydroxy groups at the 3beta, 12beta and 20 pro-S positions, in which the hydroxy group at position 3 has been converted to the corresponding beta-D-glucopyranosyl-beta-D-glucopyranoside, and in which a double bond has been introduced at the 24-25 position. It has a role as an apoptosis inducer, an antineoplastic agent, a plant metabolite and an angiogenesis modulating agent. It is a ginsenoside, a tetracyclic triterpenoid and a glycoside. It is functionally related to a (20S)-protopanaxadiol. It derives from a hydride of a dammarane.

Biochem/physiol Actions

Ginsenoside Rg3 is a natural product isolated from Panax ginseng. Similar to other ginsenosides it exhibits cardio protective effects. Ginsenoside Rg3 enhances cardiac, hERG (IKr) and KCNQ (Iks), channel currents by interaction with the channel pore entryway. It also inhibits the palmitate-induced apoptosis of MIN6N8 mouse insulinoma beta-cells through modulating p44/42 MAPK activation. Ginsenoside Rg3 increases the level of the transcription factor Nrf2 and induces the mRNA levels of multidrug resistance-associated protein (Mrp) 1 and Mrp3. Rg3 modulate neuroinflammation by attenuating the activation of microglia in response to systemic LPS treatment. It activates AMPK in HepG2 cells and reduces the lipid accumulation thereby decreasing the risk of cardiovascular disease due to dyslipidemia.

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