(1S,2R,4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-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-carboxylic acid

• ChemBase ID: 72922
• Molecular Formular: C30H48O5
• Molecular Mass: 488.69912
• Monoisotopic Mass: 488.35017464
• SMILES: [C@@H]1([C@@H]([C@]([C@H]2[C@](C1)([C@@H]1[C@@](CC2)([C@]2(C(=CC1)[C@H]1[C@@](CC2)(CC[C@H]([C@@H]1C)C)C(=O)O)C)C)C)(CO)C)O)O
• Canonical SMILES: OC[C@]1(C)[C@@H](O)[C@H](O)C[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@@H](C)[C@@H](CC1)C)C(=O)O)C)C
• InChI: InChI=1S/C30H48O5/c1-17-9-12-30(25(34)35)14-13-28(5)19(23(30)18(17)2)7-8-22-26(3)15-20(32)24(33)27(4,16-31)21(26)10-11-29(22,28)6/h7,17-18,20-24,31-33H,8-16H2,1-6H3,(H,34,35)/t17-,18+,20-,21-,22-,23+,24+,26+,27+,28-,29-,30+/m1/s1
• InChIKey: JXSVIVRDWWRQRT-UYDOISQJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-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-carboxylic acid
• IUPAC Traditional name: asiatic acid
• Synonyms: 2α,23-Dihydroxyursolic acid; Dammarolic acid; NSC 166063; Asiatic acid; Asiatic acid; 2,3,23-Trihydroxy-12-ursen-28-oic acid; 亚细亚酸

Database IDs

• CAS Number: 464-92-6
• MDL Number: MFCD00238541
• PubChem SID: 162037842; 24878917
• PubChem CID: 119034

CALCULATED PROPERTIES

• Acid pKa: 4.7441254
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 3.4007869
• LogD (pH = 7.4): 1.6238283
• Log P: 4.2261305
• Molar Refractivity: 136.8342 cm^3
• Polarizability: 54.46818 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder
• Melting Point: 325-330 °C(lit.)

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C30H48O5
• Classification: Genuine Natural Compounds

DETAILS

Selleck Chemicals - S2266

Research Area: Cancer
Biological Activity:
Asiatic acid is the aglycone of asiaticoside isolated from the plant Centella asiatica, commonly used in wound healing. It is a neuroprotectant and inducer of apoptosis in HepG2 human hepatoma cells. It was likely to confine the breast cancer cells in the S-G2/M phase mainly through the p38 pathway, because both SB203580 and p38 small interfering RNA (siRNA) inhibition significantly attenuated the accumulation of inactive phospho-Cdc2 and phospho-Cdc25C proteins and the cell numbers of S-G2/M phase. [1]References on Asiatic acid[1] J Pharmacol Exp Ther., 2005 Apr, 313(1):333-44.

Sigma Aldrich - 546712

Biochem/physiol Actions
Asiatic acid is commonly used in wound healing. Asiatic acid has antioxidant, anti-inflammatory and neuroprotective properties.
Packaging
500 mg in glass bottle
Application
Starting material for asiatic acid derivative synthesis for use as:
• Anticancer agents1
• Glycogen phosphorylase inhibitors2
• Hepatoprotectants3,4,5

REFERENCES

• Hsu YL et al. J Pharmacol Exp Ther. 2005 Apr;313(1):333-44.