Ginsenoside Rh2
Basic information
- CAS
78214-33-2- Standard SMILES
CC(C)=CCC[C@](C)(O)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(C)(C)[C@@H]3CC[C@]12C- InChIKey
CKUVNOCSBYYHIS-IRFFNABBSA-N- Molecular formula
- C36H62O8
- Average molar mass
- 622.9 g/mol
- Monoisotopic mass
- 622.44446893
Overview
(20S)-ginsenoside Rh2 is a ginsenoside found in Panax species 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-glucopyranoside, and in which a double bond has been introduced at the 24-25 position. It has a role as an antineoplastic agent, a bone density conservation agent, a hepatoprotective agent, an apoptosis inducer, a plant metabolite and a cardioprotective agent. It is a beta-D-glucoside, a tetracyclic triterpenoid, a 12beta-hydroxy steroid, a 20-hydroxy steroid and a ginsenoside. It derives from a hydride of a dammarane.
Names & identifiers
- Preferred name
- Ginsenoside Rh2
- IUPAC
- (2R,3R,4S,5S,6R)-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)oxane-3,4,5-triol
- English name
- Ginsenoside Rh2
- Molecular formula
- C36H62O8
- Molecular weight
- 622.88
Names & synonyms
Ginsenoside Rh278214-33-220(S)-Ginsenoside Rh2(20S)-ginsenoside Rh2Ginsenoside-Rh20JU44A5KWGCHEBI:77147DTXSID70999457(2R,3R,4S,5S,6R)-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)oxane-3,4,5-triolbeta-D-Glucopyranoside, (3beta,12beta)-12,20-dihydroxydammar-24-en-3-yl(2R,3R,4S,5S,6R)-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)oxane-3,4,5-triolRefChem:483868
Show more names
Rh220(S)-Rh2Ginsenoside Rh2-RMGinsenoside Rh2(P)GINSENOSIDE Rh2(SH)Ginsenoside Rh2(AS)Ginsenoside Rh2 ,98%3β-(β-D-Glucopyranosyl
Properties
Computed structural properties
- XLogP
- 5.6
- Topological polar surface area
- 140 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 7
- Heavy atoms
- 44
- Formal charge
- 0
- Complexity
- 1,070
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]
Physicochemical properties
- Melting point
- 139 · 139-144 °C
- Boiling point
- 726.4 · 726.4±60.0 °C(Predicted)
- Density
- 1.19 · 1.19±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- 10 mg/ml; · DMF: 10 mg/ml; DMSO: 10 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
- pka
- 12.91 · 12.91±0.70(Predicted)
- form
- Solid
- color
- White
- Major Application
- food and beverages
- InChIKey
- CKUVNOCSBYYHIS-IRFFNABBSA-N
- SMILES
- C\C(C)=C/CC[C@](C)(O)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]3[C@@]4(C)CC[C@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(C)(C)[C@@H]4CC[C@@]23C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- rtecs
- LZ5776539
- hs_code
- 29389090
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Applications
DescriptionGinsenoside Rh2 is a steroid glycoside found in plants of the genus Panax that has diverse biological activities. It inhibits release of β-hexosaminidase from RBL-2H3 cells (IC50 = 100 μM) and inhibits the IgE-dependent passive cutaneous anaphylaxis reaction in mice at a dose of 25 mg/kg. It inhibits growth of HRA ovarian and BxPC-3 pancreatic cancer cells in a dose-dependent manner. In vivo, ginsenoside Rh2 decreases immobility time in the forced swim test in a mouse model of colorectal carcinoma. Ginsenoside Rh2 also reduces infarct volume in a rat model of ischemia-reperfusion-induced brain injury.
Uses20(S)-Ginsenoside Rh2 is a bioactive metabolite of the ginsenoside component of Panax ginseng that has been shown to exhibit antibacterial effects in vitro.
Additional notes
DefinitionChEBI: A ginsenoside found in Panax species 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-glucopyranoside, and in which a double bond has been introduced at the 24-25 position.
Related reactions
0 records
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Compound notes
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