Asiaticoside
Grundinformationen
- CAS
16830-15-2- Standard-SMILES
C[C@H]1[C@H](C)CC[C@]2(C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@H]12- InChIKey
WYQVAPGDARQUBT-FGWHUCSPSA-N- Summenformel
- C48H78O19
- Durchschnittliche Molmasse
- 959,1 g/mol
- Monoisotopische Masse
- 958,51373025
Überblick
Asiaticoside is a triterpenoid saponin that is a trisaccharide derivative of asiatic acid. Isolated from Centella asiatica, it exhibits anti-inflammatory, antioxidant and wound-healing properties. It has a role as an antioxidant, an antifibrotic agent, an antidepressant, an antineoplastic agent, a neuroprotective agent, an anti-inflammatory agent, a vulnerary and a plant metabolite. It is a pentacyclic triterpenoid, a carboxylic ester, a triterpenoid saponin and a trisaccharide derivative. It is functionally related to an asiatic acid.
Namen und Bezeichner
- Bevorzugter Name
- Asiaticoside
- IUPAC
- [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (1S,2R,4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
- Englischer Name
- Asiaticoside
- Summenformel
- C48H78O19
- Molmasse
- 959.12
Namen und Synonyme
Asiaticoside16830-15-2MadecassolCentelaseAsiaticosidEmdecassolPKO39VY215DTXSID30937476BA-2742NSC-36002NSC-166062RefChem:28503
Weitere Namen anzeigen
Asiaticosidesdermatologicoblastoestimulina2-alpha,3-beta,23-trihydroxy-urs-12-en-28-oicacio-6-deoxy-alpha-l-mannopyMADECASOLMeal snow
DTXCID201777735(6-((3,4-dihydroxy-6-(hydroxymethyl)-5-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxymethyl)-3,4,5-trihydroxyoxan-2-yl) 10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate(2alpha,3beta)-2,3,23-Trihydroxyurs-12-en-28-oic acid, O-6-deoxy-alpha-L-mannopyranosyl-(1-4)-O-beta-D-glucopyranosyl-(1-6)-O-beta-D-glucopyranosyl Ester240-851-7((2S,3R,4S,5S,6R)-6-(((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-((2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxymethyl)-3,4,5-trihydroxyoxan-2-yl) (1S,2R,4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate((2S,3R,4S,5S,6R)-6-(((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxymethyl)-3,4,5-trihydroxyoxan-2-yl) (1S,2R,4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylateAsiaticoside (>90%)Asiaticoside CRS
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,1
- Polarare Oberfläche (TPSA)
- 315 Ų
- H-Brücken-Donoren
- 12
- H-Brücken-Akzeptoren
- 19
- Frei drehbare Bindungen
- 10
- Schwere Atome
- 67
- Formalladung
- 0
- Komplexität
- 1.820
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Physikochemische Eigenschaften
- Schmelzpunkt
- 235 · 235-238°C
- Siedepunkt
- 1017.5 · 1017.5±65.0 °C(Predicted)
- Dichte
- 1.44 · 1.44±0.1 g/cm3(Predicted)
- Dampfdruck
- 0.001 Pa · 0.001Pa at 160℃
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- Löslichkeit
- DMSO (Slightly), Ethanol (Slightly, Heated, Sonicated), Methanol (Slightly)
- pka
- 12.5 · 12.50±0.70(Predicted)
- Aggregatzustand
- Solid
- Farbe
- Crystals
- Wasserlöslichkeit
- 99 mg/L · 99mg/L
- Major Application
- food and beverages
- Kosmetik-Inhaltsstoffe Funktionen
- ANTIOXIDANTSKIN CONDITIONINGPERFUMING
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 100% (108 of 108) of all reports.
Not Classified
Aggregated GHS information provided per 108 reports by companies from 1 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Regulatory Information
REACH registered substance: O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl (2α,3β,4α)-2,3,23-trihydroxyurs-12-en-28-oate (EC: 240-851-7)
Urs-12-en-28-oic acid, 2,3,23-trihydroxy-, O-6-deoxy-.alpha.-L-mannopyranosyl-(1â4)-O-.beta.-D-glucopyranosyl-(1â6)-.beta.-D-glucopyranosyl ester, (2.alpha.,3.beta.,4.alpha.)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesNot Classified
Sicherheitsdaten
- F
- 1-10
- wgk
- 3
- ridadr
- UN 2811 6.1 / PGIII
- hs_code
- 29389090
- RTECS-Nr.
- YU9625000
- safety_code
- 24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological ClassificationSubstances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Anwendungen
BeschreibungAsiaticoside is the main saponin constituent of C. asiatica, a plant long used in the Ayurvedic system of medicine to treat a variety of ailments including dermatitis, diabetes, cough, cataract, hypertension, as well as for wound healing and improving memory. In various wound healing models, topical application (0.2-0.4%), injection (1 mg), or ingestion (1 mg/kg) of asiaticoside has been shown to increase hydroxyproline content, improve tensile strength, increase collagen synthesis and remodeling of the collagen matrix, promote epithelialization, stimulate glycosaminoglycan synthesis, and elevate antioxidant levels.
VerwendenAsiatic Acid is a terpenoid saponin component isolated from Centella asiatica with antioxidant and anti-inflammatory activities. Asiaticoside has been shown to possess strong wound-healing properties and reduces scar formation.
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