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Betulinic Acid

Betulinic Acid

Product ID B1979
Cas No. 472-15-1
Purity ≥99%
Product Unit SizeCostQuantityStock
10 mg $45.30 In stock
50 mg $127.90 In stock
250 mg $338.00 In stock
Bulk Quote

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  • References
  • Description
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Description

Betulinic acid is a pentacyclic triterpene that exhibits antithrombotic, anti-atherosclerotic, antioxidative, anti-inflammatory, anti-angiogenic, and anticancer chemotherapeutic properties. Betulinic acid decreases expression of P-selectin and binding of PAC-1, preventing platelet aggregation. In macrophages, betulinic acid inhibits phosphorylation of IκB and p65 and prevents activation of NF-κB, promoting cholesterol efflux and decreasing cellular levels of cholesterol; in vivo, this leads to a decrease in atherosclerotic lesion size. In rat aortic tissue, betulinic acid induced relaxation through preventing increases in ROS, decreases in NO, and decreases in eNOS and superoxide dismutase (SOD) activity induced by superoxide anions. In animal models, this compound increases activity of superoxide dismutase (SOD), glutathione peroxidase, and glutathione reductase and also decreases expression of cyclooxygenase (COX-2), NO, TNF-α, and IL-1β, resulting in a decrease in paw edema. In adenocarcinoma cells, this betulinic acid inhibits collagen biosynthesis, decreases prolidase activity, and decreases expression of HIF-1α, VEGF, and α1/2 integrins. Betulinic acid decreases expression of cyclin D3 and Bcl-xl in vitro, inducing cell cycle arrest and apoptosis. Additionally, this compound downregulates expression of Sp1 protein, decreasing lung tumor growth in animal models.

Product Info

Cas No.

472-15-1

Purity

≥99%

Formula

C30H48O3

Formula Wt.

456.70

Chemical Name

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid

IUPAC Name

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8, 11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a, 13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid

Synonym

Mairin

Melting Point

296°C

Solubility

Soluble in ethanol (0.5 mg/mL). Soluble in DMSO (20 mg/mL). Soluble in DMF (15 mg/mL). Slightly soluble in methanol.

Appearance

White to off white powder

Shipping and Storage

Store Temp

Ambient

Ship Temp

Ambient

Downloads

MSDS

B1979 MSDS PDF

Info Sheet

B1979 Info Sheet PDF

References

Kim MJ, Kang HG, Jeon SB, et al. The antioxidant betulinic acid enhances porcine oocyte maturation through Nrf2/Keap1 signaling pathway modulation. PLoS One. 2024 Oct 10;19(10):e0311819. PMID: 39388445.

Zhao GJ, Tang SL, Lv YC, et al. Antagonism of Betulinic Acid on LPS-Mediated Inhibition of ABCA1 and Cholesterol Efflux through Inhibiting Nuclear Factor-kappaB Signaling Pathway and miR-33 Expression. PLoS One. 2013 Sep 25;8(9):e74782. PMID: 24086374.

Hsu TI, Wang MC, Chen SY, et al. Betulinic acid decreases specificity protein 1 (Sp1) level via increasing the sumoylation of sp1 to inhibit lung cancer growth. Mol Pharmacol. 2012 Dec;82(6):1115-28. PMID: 22956772.

Qian LB, Fu JY, Cai X, et al. Betulinic acid inhibits superoxide anion-mediated impairment of endothelium-dependent relaxation in rat aortas. Indian J Pharmacol. 2012 Sep-Oct;44(5):588-92. PMID: 23112419.

Tzakos AG, Kontogianni VG, Tsoumani M, et al. Exploration of the antiplatelet activity profile of betulinic acid on human platelets. J Agric Food Chem. 2012 Jul 18;60(28):6977-83. PMID: 22720759

Tsai JC, Peng WH, Chiu TH, et al. Anti-inflammatory effects of Scoparia dulcis L. and betulinic acid. Am J Chin Med. 2011;39(5):943-56. PMID: 21905284.

Karna E, Szoka L, Palka JA. Betulinic acid inhibits the expression of hypoxia-inducible factor 1alpha and vascular endothelial growth factor in human endometrial adenocarcinoma cells. Mol Cell Biochem. 2010 Jul;340(1-2):15-20. PMID: 20174965.

Chen Z, Wu Q, Chen Y, et al. Effects of betulinic acid on proliferation and apoptosis in Jurkat cells and its in vitro mechanism. J Huazhong Univ Sci Technolog Med Sci. 2008 Dec;28(6):634-8. PMID: 19107355.

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