Asiatic acid CAS 464-92-6
Asiatic acid Basic information
| Product Name: | Asiatic acid |
| Synonyms: | 2,3,23-TRIHYDROXY-12-URSEN-28-OIC ACID;(1s,2r,4as,6ar,6as,6br,8ar,9s,10s,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-carboxylic acid;ASIATIC ACID;URS-12-EN-28-OIC ACID, 2,3,23-TRIHYDROXY-, (2A,3B,4A)-;Urs-12-en-28-oic acid, 2,3,23-trihydroxy-, (2.alpha.,3.beta.,4.alpha.)-;ASIATIC ACID(P);Urs-12-en-28-oic acid, 2,3,23-trihydroxy-, (2α,3β,4α)-;ASIATICACID:URS-12-EN-28-OICACID, 2,3,23-TRIHYDROXY-, (2A,3B,4A)-, |
| CAS: | 464-92-6 |
| MF: | C30H48O5 |
| MW: | 488.7 |
| EINECS: | 482-720-9 |
| Product Categories: | Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Antineoplastic;Steroids;The group of Asiaticoside;Pentacyclic Triterpenes;C13 to C42+;Carbonyl Compounds;Carboxylic Acids;464-92-6;API |
| Mol File: | 464-92-6.mol |
Asiatic acid Chemical Properties
| Melting point | 325-330 °C(lit.) |
| Boiling point | 609.4±55.0 °C(Predicted) |
| density | 1.18±0.1 g/cm3(Predicted) |
| RTECS | YU9580000 |
| storage temp. | 2-8°C |
| solubility | methanol: soluble1mg/mL, clear, colorless |
| form | powder |
| pka | 4.66±0.70(Predicted) |
| color | white |
| biological source | Centella asiatica |
| Water Solubility | Soluble in dimethyl sulfoxide, ethanol and dimethylformamide. Sparingly soluble in water |
| Cosmetics Ingredients Functions | SKIN CONDITIONING LIGHT STABILIZER |
| InChIKey | JXSVIVRDWWRQRT-UYDOISQJSA-N |
| SMILES | C[C@@H]1CC[C@@]2(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@@]34C)[C@@H]2[C@H]1C)C(O)=O |
| LogP | 5.748 (est) |
| CAS DataBase Reference | 464-92-6(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| WGK Germany | 3 |
| HS Code | 29181990 |
| Storage Class | 11 - Combustible Solids |
| Hazardous Substances Data | 464-92-6(Hazardous Substances Data) |
| Chemical Properties | White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, from the whole grass of Centella asiatica (Centella asiatica), a plant of the genus Leiogangen, family Umbelliferae. |
| Uses | wound healing, experimental carcinogen |
| Uses | Asiatic Acid is a terpenoid with an ursane skeleton isolated from Centella asiatica. Asiatic Acid is a neuroprotectant and induces of apoptosis in HepG2 human hepatoma cells. |
| Uses | Asiatic acid is commonly used in wound healing. Asiatic acid has antioxidant, anti-inflammatory and neuroprotective properties. It is a starting material for asiatic acid derivative synthesis for use as anticancer agents, glycogen phosphorylase inhibitors and and hepatoprotectants. |
| Definition | ChEBI: A pentacyclic triterpenoid that is ursane substituted by a carboxy group at position 28 and hydroxy groups at positions 2, 3 and 23 (the 2alpha,3beta stereoisomer). It is isolated from Symplocos lancifolia andVateria indica and exhibits anti-angiogenic activity. |
| General Description | Asiatic acid is a naturally occurring pentacyclic triterpenoid, obtained from Centella asiatica. |
| Biochem/physiol Actions | Asiatic acid is commonly used in wound healing. Asiatic acid has antioxidant, anti-inflammatory and neuroprotective properties. |
| Synthesis | 16830-15-2 464-92-6 1) 1 g of (2α,3β,4α)-3,4-dihydroxy-6-(hydroxymethyl)-5-((3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl 10,11-dihydroxy-9-(hydroxymethyl)-hexamethyl- Eicosanoid-4a-carboxylic acid ester (asiaticoside), 4.3×10^-2 mol sodium dodecyl sulfate and 0.02 mol NaOH were mixed, water was added to 1 L, and stirred until completely dissolved to obtain a mixed solution. The hydrolysis reaction was carried out at room temperature (25°C) and atmospheric pressure (1 atm) for 15 min to obtain the hydrolysate.2) The pH of the hydrolysate was adjusted to 5.0 with 1 M HCl solution and allowed to stand for 30 min, followed by filtration and collection of the precipitate.3) The precipitate was dissolved in 70% (v/v) aqueous ethanol at a ratio of 1 g:30 mL and filtered to remove insoluble matter. Crystallization was carried out by adding 16 times the volume of distilled water to the filtrate and allowed to stand overnight for complete crystallization. The crystallized product was collected by filtration and dried to constant weight in a vacuum drying oven at 40°C to obtain cumaric acid white crystals of 0.445 g. The product was analyzed by high-performance liquid chromatography (HPLC) with a purity of 95.8% and a yield of 93.08%. |
| target | TNF-α | IFN-γ | IL Receptor | Caspase | p21 | NOS | NADPH-oxidase | NO | HMG-CoA reductase | COX |
| References | [1] Patent: CN106349319, 2017, A. Location in patent: Paragraph 0017-0032 [2] Patent: WO2009/89365, 2009, A2. Location in patent: Page/Page column 6-7 [3] Steroids, 2015, vol. 96, p. 44 - 49 [4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 20, p. 4500 - 4504 [5] RSC Advances, 2016, vol. 6, # 67, p. 62890 - 62906 |
Asiatic acid Preparation Products And Raw materials
| Raw materials | Asiaticoside |
