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Urs-12-en-28-oic acid,2,3,23-trihydroxy-, (2a,3b,4a)-(CAS No. 464-92-6)

Urs-12-en-28-oic acid,2,3,23-trihydroxy-, (2a,3b,4a)- C30H48O5 (cas 464-92-6) Molecular Structure

464-92-6 Structure

Identification and Related Records

Urs-12-en-28-oic acid,2,3,23-trihydroxy-, (2a,3b,4a)-
【Iupac name】
7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
【CAS Registry number】
Asiaticacid (6CI)
Urs-12-en-28-oic acid, 2a,3b,23-trihydroxy- (7CI,8CI)
2a,23-Dihydroxyursolic acid
NSC 166063
【Molecular Formula】
C30H48O5 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【Isomers smiles】
【MOL File】

Chemical and Physical Properties

White powder
1.18 g/cm3
【Melting Point】
【Boiling Point】
609.4 °C at 760 mmHg
2.13E-17mmHg at 25°C
【Refractive Index】
【Flash Point】
336.4 °C
In water, 5.98X10-2 mg/L at 25 deg C (est)
【Computed Properties】
Molecular Weight:488.69912 [g/mol]
Molecular Formula:C30H48O5
H-Bond Donor:4
H-Bond Acceptor:5
Rotatable Bond Count:2
Exact Mass:488.350175
MonoIsotopic Mass:488.350175
Topological Polar Surface Area:98
Heavy Atom Count:35
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:12
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:5
Feature 3D Donor Count:3
Feature 3D Anion Count:1
Feature 3D Ring Count:5
Effective Rotor Count:4.6
Conformer Sampling RMSD:0.8
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
Xi: Irritant;

Safety Information of Asiatic acid (CAS NO.464-92-6):
Hazard Codes: XiIrritant

The drug "Titrated Extract from Centella asiatica" (TECA), used for its stimulating properties on the healing of wounds, is a mixture of 3 terpenes extracted from a tropical plant: asiatic acid (30%, w/w), madecassic acid (30%, w/w) and asiaticoside (40%, w/w). [Maquart FX et al; Connect Tissue Res 24 (2): 107-20 (1990)] PubMed Abstract

 Asiatic acid ,its CAS NO. is 464-92-6,the synonyms is Urs-12en-28-oic acid, 2,3,23-trihydroxy-, (2alpha, 3beta,
4alpha)- ; HSDB 7662 ; NSC 166063 .

【Octanol/Water Partition Coefficient】
log Kow = 5.32 (est)
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Isolated from Syzygium claviflorum

Biomedical Effects and Toxicity

【Therapeutic Uses】
Titrated extract of Centella asiatica (TECA) contains three principal ingredients, asiaticoside (AS), asiatic acid (AA), and madecassic acid (MA). These components are known to be clinically effective on systemic scleroderma, abnormal scar formation, and keloids. ... [Hong SS et al; Arch Pharm Res 28 (4): 502-8 (2005)]
【Biomedical Effects and Toxicity】
A new HPLC assay method was used to investigate the pharmacokinetics of asiatic acid after oral administration of the total triterpenic fraction of Centella asiatica in single doses (30 or 60 mg) and after a 7-day treatment (30 or 60 mg twice daily). Twelve healthy volunteers received each treatment following a randomized cross-over design with trials separated by a 3-week interval. The time of peak plasma concentration was not affected by dosage difference or by treatment scheme. Differences in peak plasma concentration and area under the concentration vs. time curve from 0 to 24 hr (AUC0-24) calculated after 30 or 60 mg administration (single dose) were accounted for by the different dose regimen. However, after chronic treatment with both 30 and 60 mg, peak plasma concentrations, AUC0-24 and half-life were significantly higher than those observed after the corresponding single dose administration. This phenomenon could be explained by a metabolic interaction between asiatic acid and asiaticoside, which is transformed into asiatic acid in vivo. [Grimaldi R et al; J Ethnopharmacol 28 (2): 235-41 (1990)] PubMed Abstract
The comparative steady-state bioavailability of asiatic acid was studied in 12 healthy male and female volunteers following oral administration of approximately equimolar doses of either asiatic acid (12 mg) or the glycoside derivative of asiatic acid, asiaticoside (24 mg). Both asiatic acid and asiaticoside are constituents of the marketed dermatological product Madecassol. Asiaticoside is converted in vivo to asiatic acid by hydrolytic cleavage of the sugar moiety. Steady-state AUC0-12hr values for asiatic acid on either regimen were similar (614 +/- 250 following asiatic acid compared to 606 +/- 316 following asiaticoside) indicating comparable bioavailability for asiatic acid with the two ingredients at approximately equimolar doses. Since asiatic acid is considered to be the most therapeutically active ingredient of Madecassol, the current data suggest that the therapeutic effects of asiaticoside may be mediated through conversion to asiatic acid. [Rush WR et al; Eur J Drug Metab Pharmacokinet 18 (4): 323-6 (1993)] PubMed Abstract

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