| Identification | More | [Name]
Asiatic acid | [CAS]
464-92-6 | [Synonyms]
(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
2,3,23-TRIHYDROXY-12-URSEN-28-OIC ACID
ASIATIC ACID
URS-12-EN-28-OIC ACID, 2,3,23-TRIHYDROXY-, (2A,3B,4A)-
ASIATICACID:URS-12-EN-28-OICACID, 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)-
(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
2α,3β,23-Trihydroxyurs-12-en-28-oicacid
(4R)-2α,3β,23-Trihydroxyurs-12-en-28-oic acid
2α,3β,23-Trihydroxyurs-12-ene-28-oic acid
Asiantic acid | [EINECS(EC#)]
482-720-9 | [Molecular Formula]
C30H48O5 | [MDL Number]
MFCD00238541 | [Molecular Weight]
488.7 | [MOL File]
464-92-6.mol |
| Chemical Properties | Back Directory | [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 | [InChIKey]
JXSVIVRDWWRQRT-UYDOISQJSA-N | [LogP]
5.748 (est) | [CAS DataBase Reference]
464-92-6(CAS DataBase Reference) |
| Hazard Information | Back Directory | [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]
wound healing, experimental carcinogen | [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 and
Vateria 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]
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 |
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