2-O-β-D-Glucopyranosyl-(3β,12β)-20-(β-D-glucopyranosyloxy)-12-hydroxydammar-24-en-3-yl-β-D-glucopyranosid
Ginsenoside Rd
Grundinformationen
- CAS
52705-93-8- Standard-SMILES
CC(C)=CCC[C@](C)(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[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@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(C)(C)[C@@H]3CC[C@]12C- InChIKey
RLDVZILFNVRJTL-IWFVLDDISA-N- Summenformel
- C48H82O18
- Durchschnittliche Molmasse
- 947,2 g/mol
- Monoisotopische Masse
- 946,55011576
Überblick
Ginsenoside Rd is a ginsenoside found in Panax ginseng and Panax japonicus var. major that is (20S)-ginsenoside Rg3 in which the hydroxy group at position 20 has been converted to its beta-D-glucopyranoside. It has a role as an anti-inflammatory drug, an immunosuppressive agent, a neuroprotective agent, an apoptosis inducer, a vulnerary and a plant metabolite. It is a beta-D-glucoside, a tetracyclic triterpenoid and a ginsenoside. It is functionally related to a (20S)-ginsenoside Rg3.
Namen und Bezeichner
- Bevorzugter Name
- Ginsenoside Rd
- IUPAC
- (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-4,4,8,10,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
- Lokaler Name
- 2-O-β-D-Glucopyranosyl-(3β,12β)-20-(β-D-glucopyranosyloxy)-12-hydroxydammar-24-en-3-yl-β-D-glucopyranosid
- Englischer Name
- Ginsenoside Rd
- Summenformel
- C48H82O18
- Molmasse
- 947.15
Namen und Synonyme
Ginsenoside Rd52705-93-8Gypenoside VIIIChikusetsusaponin fk7CHEMBL473659WB232T95AVDTXSID301031221CHEBI:679882-O-beta-D-Glucopyranosyl-(3beta,12beta)-20-(beta-D-glucopyranosyloxy)-12-hydroxydammara-24-en-3-yl-beta-D-glucopyranosidebeta-D-Glucopyranoside, (3beta,12beta)-20-(beta-D-glucopyranosyloxy)-12-hydroxydammar-24-en-3-yl 2-O-beta-D-glucopyranosyl-(3beta,12beta)-20-(beta-D-glucopyranosyloxy)-12-hydroxydammar-24-en-3-yl 2-O-beta-D-glucopyranosyl-beta-D-glucopyranosideRefChem:37442
Weitere Namen anzeigen
ginsenosideRPanaxoside RdGINSENOOSIDERDSanchinoside RdRd Ginsenoside RdGinsenoside Rd-RMGinsenoside Rd(AS)
UNII-WB232T95AVGINSENOSIDE RD (CONSTITUENT OF AMERICAN GINSENG, ASIAN GINSENG, AND TIENCHI GINSENG)2-((2-(5-((4,5-dihydroxy-6-(hydroxymethyl)-3-((3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)oxan-2-yl)oxy)-16-hydroxy-2,6,6,10,11-pentamethyltetracyclo(8.7.0.02,7.011,15)heptadecan-14-yl)-6-methylhept-5-en-2-yl)oxy)-6-(hydroxymethyl)oxane-3,4,5-triol258-118-5(2S,3R,4S,5S,6R)-2-((2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(((3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((2S)-6-methyl-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyhept-5-en-2-yl)-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-3-yl)oxy)oxan-3-yl)oxy-6-(hydroxymethyl)oxane-3,4,5-triolginsenoside-RdNSC-308876GS-Rd
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,4
- Polarare Oberfläche (TPSA)
- 298 Ų
- H-Brücken-Donoren
- 12
- H-Brücken-Akzeptoren
- 18
- Frei drehbare Bindungen
- 13
- Schwere Atome
- 66
- Formalladung
- 0
- Komplexität
- 1.680
Experimentelle und physikochemische Eigenschaften
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]
Physikochemische Eigenschaften
- Schmelzpunkt
- 204 · 204~206℃
- Siedepunkt
- 1015.6 · 1015.6±65.0 °C(Predicted)
- Dichte
- 1.38 · 1.38±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- pka
- 12.85 · 12.85±0.70(Predicted)
- Farbe
- White to Off-White
- Stabilität
- Hygroscopic
- Kosmetik-Inhaltsstoffe Funktionen
- ANTIOXIDANT
- InChIKey
- FBFMBWCLBGQEBU-FIKSETHBNA-N
- LogP
- 3.11 · 3.110 (est)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 2.3% (1 of 43) of reports.
Warning
H302 (97.7%): 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 43 reports by companies from 2 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (97.7%)
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29389090
- risk_code
- 22
- hazard_code
- Xn
- safety_code
- 2-45
Chemie und Industrie
Anwendungen
BeschreibungGinsenosides 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 Rd is a protopanaxadiol which is more abundant in some Panax species (e.g., P. quinquefolium) than others. This ginsenoside has diverse in vitro and in vivo effects, including cardioprotective, neuroprotective, and anti-inflammatory actions. Notably, ginsenoside Rd is converted to other ginsenosides in response to steaming or heating plant materials, leading to loss of these activities.
VerwendenGinsenoside RD has been shown to attenuate tau protein phosphorylation via the PI3K/AKT/GSK-3β pathway after forebrain ischemia. This could be used to counter the risk of developing post-stroke dementia.
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