16830-15-2

Basic information

• Product Name: Asiaticoside
• Synonyms: 2-alpha,3-beta,23-trihydroxy-urs-12-en-28-oicacio-6-deoxy-alpha-l-mannopy;asiaticosid;blastoestimulina;dermatologico;ranosyl-(1-4)-o-beta-d-glucopyranosyl-(1-6)-o-beta-d-glucopyranosylester;[6-[[3,4-Dihydroxy-6-(hydroxymethyl)-5-(3,4,5-trihydroxy-6-methyl-oxan-2-yl)oxy-oxan-2-yl]oxymethyl]-3,4,5-trihydroxy-oxan-2-yl] (1S,2R,4aS,6aS,6bR,9S,10R,11R,12aS,14bR)-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;CENTELASE;ASIATICOSIDE
• CAS NO: 16830-15-2
• Molecular Formula: C₄₈H₇₈O₁₉
• Molecular Weight: 959.12
• EINECS: 240-851-7
• Product Categories: Saponins;Alkaloids;Natural Plant Extract;The group of Asiaticoside;Herb extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 16830-15-2.mol
• Article Data: 0

Chemical Properties

• Melting Point: 235-238°C
• Boiling Point: 949.4 °C at 760 mmHg
• Flash Point: 268.4 °C
• Appearance: powder
• Density: 1.35 g/cm³
• Vapor Pressure: 0.001Pa at 160℃
• Refractive Index: 1.606
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Ethanol (Slightly, Heated, Sonicated), Methanol (Slightly)
• PKA: 12.50±0.70(Predicted)
• Water Solubility: 99mg/L
• CAS DataBase Reference: Asiaticoside(CAS DataBase Reference)
• NIST Chemistry Reference: Asiaticoside(16830-15-2)
• EPA Substance Registry System: Asiaticoside(16830-15-2)

Safety Data

• Safety Statements: 24/25
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• RTECS: YU9625000
• F: 1-10
• Hazardous Substances Data: 16830-15-2(Hazardous Substances Data)

Usage

Description

Asiaticoside 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.

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 16830-15-2 differently. You can refer to the following data:
1. wound healing, anxiolytic
2. Asiatic 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.

Flammability and Explosibility

Notclassified

Safety Profile

Questionable carcinogen withexperimental tumorigenic data. When heated todecomposition it emits acrid smoke and fumes. Promoteshealing of wounds.

InChI:InChI=1/C48H78O16/c1-22-12-17-48(19-18-46(7)25(30(48)23(22)2)10-11-29-45(6)15-9-14-44(4,5)28(45)13-16-47(29,46)8)43(58)64-42-37(56)34(53)32(51)27(62-42)21-59-40-38(57)35(54)39(26(20-49)61-40)63-41-36(55)33(52)31(50)24(3)60-41/h10,22-24,26-42,49-57H,9,11-21H2,1-8H3/t22-,23+,24+,26-,27-,28+,29-,30+,31+,32-,33-,34+,35-,36-,37-,38-,39-,40-,41+,42+,45+,46-,47-,48+/m1/s1

Synthetic route

asiaticoside (16830-15-2) → asiatic acid (464-92-6, 89786-83-4, 103974-74-9, 106327-64-4, 114580-55-1, 116348-15-3, 143839-02-5)

Conditions	Yield
With water; sodium dodecyl-sulfate; sodium hydroxide at 20℃; under 760.051 Torr; for 0.25h;	93.08%
Stage #1: asiaticoside With ethanol; sodium hydroxide at 80℃; Stage #2: With hydrogenchloride; water In ethanol pH=4 - 5;
With hydrogenchloride; sodium hydroxide In water
With sodium hydroxide In methanol Reflux;
With methanol; sodium hydroxide Reflux;

asiaticoside (16830-15-2) → (4aR,6aR,6bS,8aS,11R,12S,12aS,14bR,16R,16aR)-(2-ethoxy-2-oxoethyl)-16-hydroxy-2,2,4a,6a,6b,11,12,14b-octamethyl-4a,4b,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b,15,16,16a-icosahydro-4H-piceno[3,4-d][1,3]dioxine-8a-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; hydrogenchloride / water 2: potassium carbonate; triethylamine; potassium iodide 3: perchloric acid / N,N-dimethyl-formamide View Scheme

asiaticoside (16830-15-2) → (1S,2R,4aS,6aS,6bR,9R,10R,11R,12aR,14bS) (2-hydrazinyl(2-oxoethyl))-10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; hydrogenchloride / water 2: potassium carbonate; triethylamine; potassium iodide 3: hydrazine; ammonia / ethanol View Scheme

asiaticoside (16830-15-2) → (ethoxycarbonyl)methyl 2α,3β,23-trihydroxyurs-12-en-28-oate (1195758-14-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; hydrogenchloride / water 2: potassium carbonate; triethylamine; potassium iodide View Scheme

asiaticoside (16830-15-2) → (1S,2R,4aS,6aS,6bR,9R,10R,11R,12aR,14bS)-(2-(ethylamino)-2-oxoethyl)-10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; hydrogenchloride / water 2: potassium carbonate; triethylamine; potassium iodide 3: ammonia / ethanol View Scheme

asiaticoside (16830-15-2) → (1S,2R,4aS,6aS,6bR,9R,10R,11R,12aR,14bS)-(2-oxo-2-(propylamino)ethyl)-10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; hydrogenchloride / water 2: potassium carbonate; triethylamine; potassium iodide 3: ammonia / ethanol View Scheme

asiaticoside (16830-15-2) → (1S,2R,4aS,6aS,6bR,9R,10R,11R,12aR,14bS)-(2-(butylamino)-2-oxoethyl)-10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; hydrogenchloride / water 2: potassium carbonate; triethylamine; potassium iodide 3: ammonia / ethanol View Scheme

asiaticoside (16830-15-2) → (1S,2R,4aS,6aS,6bR,9R,10R,11R,12aR,14bS)-(2-(isopropylamino)-2-oxoethyl)-10,11-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; hydrogenchloride / water 2: potassium carbonate; triethylamine; potassium iodide 3: ammonia / ethanol View Scheme

asiaticoside (16830-15-2) → (2R,4aR,6aR,6bS,8aS,11R,12S,12aS,14bR,16R,16aR)-(2-ethoxy-2-oxoethyl)-16-hydroxy-4a,6a,6b,11,12,14b-hexamethyl-2-phenyl-4a,4b,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b,15,16,16a-icosahydro-4H-piceno[3,4-d][1,3]dioxine-8a-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; hydrogenchloride / water 2: potassium carbonate; triethylamine; potassium iodide 3: perchloric acid / N,N-dimethyl-formamide View Scheme

asiaticoside (16830-15-2) → (2R,4aR,6aR,6bS,8aS,11R,12S,12aS,14bR,16R,16aR)-(2-ethoxy-2-oxoethyl)-2-ethyl-16-hydroxy-4a,6a,6b,11,12,14b-hexamethyl-4a,4b,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b,15,16,16a-icosahydro-4H-piceno[3,4-d][1,3]dioxine-8a-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; hydrogenchloride / water 2: potassium carbonate; triethylamine; potassium iodide 3: perchloric acid / N,N-dimethyl-formamide View Scheme

asiaticoside (16830-15-2) → (2R,4aR,6aR,6bS,8aS,11R,12S,12aS,14bR,16R,16aR)-(2-ethoxy-2-oxoethyl)-16-hydroxy-2-(4-hydroxyphenyl)-4a,6a,6b,11,12,14b-hexamethyl-4a,4b,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b,15,16,16a-icosahydro-4H-piceno[3,4-d][1,3]dioxine-8a-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; hydrogenchloride / water 2: potassium carbonate; triethylamine; potassium iodide 3: perchloric acid / N,N-dimethyl-formamide View Scheme

asiaticoside (16830-15-2) → (2R,4aR,6aR,6bS,8aS,11R,12S,12aS,14bR,16R,16aR)-(2-ethoxy-2-oxoethyl)-16-hydroxy-2-(4-methoxyphenyl)-4a,6a,6b,11,12,14b-hexamethyl-4a,4b,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b,15,16,16a-icosahydro-4H-piceno[3,4-d][1,3]dioxine-8a-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; hydrogenchloride / water 2: potassium carbonate; triethylamine; potassium iodide 3: perchloric acid / N,N-dimethyl-formamide View Scheme

asiaticoside (16830-15-2) → (2R,4aR,6aR,6bS,8aS,11R,12S,12aS,14bR,16R,16aR)-(2-ethoxy-2-oxoethyl)-16-hydroxy-4a,6a,6b,11,12,14b-hexamethyl-2-(4-nitrophenyl)-4a,4b,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b,15,16,16a-icosahydro-4H-piceno[3,4-d][1,3]dioxine-8a-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; hydrogenchloride / water 2: potassium carbonate; triethylamine; potassium iodide 3: perchloric acid / N,N-dimethyl-formamide View Scheme

asiaticoside (16830-15-2) → 2α-hydroxy-3β,23-isopropylidenedioxy-urs-12-ene-28-oic acid (139610-49-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol / Reflux 2: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C View Scheme

asiaticoside (16830-15-2) → methyl 2α-O-carboxypropionyl-3β,23-isopropylidenedioxyurs-12-ene-28-oate (1575689-18-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide / methanol / Reflux 2: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 20 °C 4: dmap / dichloromethane / 8 h / Reflux View Scheme

asiaticoside (16830-15-2) → methyl 2-α-O-[4-(4-tert-butoxycarbonyl-1-piperazinyl)-4-oxobutyryl]-3β,23-isopropylidenedioxyurs-12-ene-28-oate

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium hydroxide / methanol / Reflux 2: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 20 °C 4: dmap / dichloromethane / 8 h / Reflux 5: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 0 °C View Scheme

asiaticoside (16830-15-2) → methyl 2-α-O-[4-(1-piperazinyl)-4-oxobutyryl]-3β,23-isopropylidenedioxyurs-12-ene-28-oate

Conditions	Yield
Multi-step reaction with 6 steps 1: sodium hydroxide / methanol / Reflux 2: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 20 °C 4: dmap / dichloromethane / 8 h / Reflux 5: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 0 °C 6: trifluoroacetic acid / dichloromethane / 2 h / 0 °C View Scheme

asiaticoside (16830-15-2) → methyl 2α-hydroxy-3β,23-isopropylidenedioxyurs-12-ene-28-oate (19533-98-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / methanol / Reflux 2: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 20 °C View Scheme

asiaticoside (16830-15-2) → 2α,3β,24-triacetyloxy-urs-12-en-28-oic acid (57688-73-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; methanol / Reflux 2: pyridine / 8 h / 20 °C View Scheme

asiaticoside (16830-15-2) → O,O'-diethyl{N-[2α,3β,23-triacetoxyurs-12-ene-28-oyl]-(3-bromophenyl)methyl}phosphonate

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; methanol / Reflux 2: pyridine / 8 h / 20 °C 3: oxalyl dichloride; triethylamine / dichloromethane / 8 h / 0 - 20 °C 4: dichloromethane / 4 h / 20 °C View Scheme

asiaticoside (16830-15-2) → O,O'-diethyl{N-[2α,3β,23-triacetoxyurs-12-ene-28-oyl]-(4-bromophenyl)methyl}phosphonate

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; methanol / Reflux 2: pyridine / 8 h / 20 °C 3: oxalyl dichloride; triethylamine / dichloromethane / 8 h / 0 - 20 °C 4: dichloromethane / 4 h / 20 °C View Scheme

asiaticoside (16830-15-2) → O,O'-diethyl{N-[2α,3β,23-triacetoxyurs-12-ene-28-oyl]-(2-methylphenyl)methyl}phosphonate

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; methanol / Reflux 2: pyridine / 8 h / 20 °C 3: oxalyl dichloride; triethylamine / dichloromethane / 8 h / 0 - 20 °C 4: dichloromethane / 4 h / 20 °C View Scheme

asiaticoside (16830-15-2) → O,O'-diethyl{N-[2α,3β,23-triacetoxyurs-12-ene-28-oyl]-(3-methylphenyl)methyl}phosphonate

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; methanol / Reflux 2: pyridine / 8 h / 20 °C 3: oxalyl dichloride; triethylamine / dichloromethane / 8 h / 0 - 20 °C 4: dichloromethane / 4 h / 20 °C View Scheme

asiaticoside (16830-15-2) → O,O'-diethyl{N-[2α,3β,23-triacetoxyurs-12-ene-28-oyl]-(4-methylphenyl)methyl}phosphonate

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; methanol / Reflux 2: pyridine / 8 h / 20 °C 3: oxalyl dichloride; triethylamine / dichloromethane / 8 h / 0 - 20 °C 4: dichloromethane / 4 h / 20 °C View Scheme

asiaticoside (16830-15-2) → O,O'-diethyl{N-[2α,3β,23-triacetoxyurs-12-ene-28-oyl]-(2-methoxyphenyl)methyl}phosphonate

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; methanol / Reflux 2: pyridine / 8 h / 20 °C 3: oxalyl dichloride; triethylamine / dichloromethane / 8 h / 0 - 20 °C 4: dichloromethane / 4 h / 20 °C View Scheme

asiaticoside (16830-15-2) → O,O'-diethyl{N-[2α,3β,23-triacetoxyurs-12-ene-28-oyl]-(3-methoxyphenyl)methyl}phosphonate

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; methanol / Reflux 2: pyridine / 8 h / 20 °C 3: oxalyl dichloride; triethylamine / dichloromethane / 8 h / 0 - 20 °C 4: dichloromethane / 4 h / 20 °C View Scheme

asiaticoside (16830-15-2) → O,O'-diethyl{N-[2α,3β,23-triacetoxyurs-12-ene-28-oyl]-(4-methoxyphenyl)methyl}phosphonate

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; methanol / Reflux 2: pyridine / 8 h / 20 °C 3: oxalyl dichloride; triethylamine / dichloromethane / 8 h / 0 - 20 °C 4: dichloromethane / 4 h / 20 °C View Scheme

asiaticoside (16830-15-2) → O,O'-diethyl{N-[2α,3β,23-triacetoxyurs-12-ene-28-oyl]-(1-naphthyl)methyl}phosphonate

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; methanol / Reflux 2: pyridine / 8 h / 20 °C 3: oxalyl dichloride; triethylamine / dichloromethane / 8 h / 0 - 20 °C 4: dichloromethane / 4 h / 20 °C View Scheme

asiaticoside (16830-15-2) → O,O'-diethyl{N-[2α,3β,23-triacetoxyurs-12-ene-28-oyl]-(2-naphthyl)methyl}phosphonate

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; methanol / Reflux 2: pyridine / 8 h / 20 °C 3: oxalyl dichloride; triethylamine / dichloromethane / 8 h / 0 - 20 °C 4: dichloromethane / 4 h / 20 °C View Scheme

Downstream Products

• 57688-73-0 2α,3β,24-triacetyloxy-urs-12-en-28-oic acid 
• 19533-98-3 methyl 2α-hydroxy-3β,23-isopropylidenedioxyurs-12-ene-28-oate