Betulin

• CAT Number: I003644
• CAS Number: 473-98-3
• Molecular Formula: C₃₀H₅₀O₂
• Molecular Weight: 442.72
• Purity: ≥95%
• Target: 14.5 μM (SREBP, K562 cell), 74.1 μM (SREBP, HeLa cell), 17.1 μM (SREBP, GOTO cell)[1], 21.09 μM (SREBP, 181P cell), 20.62 μM (SREBP, HeLa cell)[2].
• Solubility: DMSO
• Storage: Store at -20°C
• IUPAC Name: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-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]chrysen-9-ol
• InChI: InChI=1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1
• InChIKey: FVWJYYTZTCVBKE-ROUWMTJPSA-N
• SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)CO

Betulin (Cat.No:I003644) is a natural triterpene compound found in various plants, including birch bark and white mustard. It has been studied for its potential therapeutic properties, including anti-inflammatory, antioxidant, and anti-cancer effects. Betulin has shown to inhibit the growth of cancer cells in vitro and in vivo and has potential as a chemopreventive agent. It is considered safe for use in traditional medicine.

Reference

1:Betulin exhibits anti-inflammatory activity in LPS-stimulated macrophages and endotoxin-shocked mice through an AMPK/AKT/Nrf2-dependent mechanism. Ci X, Zhou J, Lv H, Yu Q, Peng L, Hua S.Cell Death Dis. 2017 May 18;8(5):e2798. doi: 10.1038/cddis.2017.39. PMID: 28518138 2:Neuroprotective Effects of Betulin in Pharmacological and Transgenic C. elegans Models of Parkinson/’s Disease. Tsai CW, Tsai RT, Liu SP, Chen CS, Tsai MC, Chien SH, Hung HS, Lin SZ, Shyu WC, Fu RH.Cell Transplant. 2017 Apr 26. doi: 10.3727/096368917X695425. [Epub ahead of print] PMID: 28447571 3:Synthesis of HIV-Maturation Inhibitor BMS-955176 from Betulin by an Enabling Oxidation Strategy. Ortiz A, Soumeillant M, Savage SA, Strotman NA, Haley M, Benkovics T, Nye J, Xu Z, Tan Y, Ayers S, Gao Q, Kiau S.J Org Chem. 2017 May 5;82(9):4958-4963. doi: 10.1021/acs.joc.7b00438. Epub 2017 Apr 19. PMID: 28406018 4:Accelerated re-epithelialization of partial-thickness skin wounds by a topical betulin gel: Results of a randomized phase III clinical trials program. Barret JP, Podmelle F, Lipový B, Rennekampff HO, Schumann H, Schwieger-Briel A, Zahn TR, Metelmann HR; BSH-12 and BSG-12 study groups..Burns. 2017 Apr 8. pii: S0305-4179(17)30149-3. doi: 10.1016/j.burns.2017.03.005. [Epub ahead of print] PMID: 28400148 5:Erratum to: Betulin suppressed interleukin-1b-induced gene expression, secretion and proteolytic activity of matrix metalloproteinase in cultured articular chondrocytes and production of matrix metalloproteinase in the knee joint of rat. Ra HJ, Lee HJ, Jo HS, Nam DC, Lee YB, Kang BH, Moon DK, Kim DH, Lee CJ, Hwang SC.Korean J Physiol Pharmacol. 2017 Mar;21(2):275. doi: 10.4196/kjpp.2017.21.2.275. Epub 2017 Feb 21. PMID: 28280422 Free PMC Article6:Betulin-loaded PEDOT films for regional chemotherapy. Krukiewicz K, Cichy M, Ruszkowski P, Turczyn R, Jarosz T, Zak JK, Lapkowski M, Bednarczyk-Cwynar B.Mater Sci Eng C Mater Biol Appl. 2017 Apr 1;73:611-615. doi: 10.1016/j.msec.2016.12.115. Epub 2016 Dec 28. PMID: 28183652 7:New acetylenic derivatives of betulin and betulone, synthesis and cytotoxic activity. Bębenek E, Kadela-Tomanek M, Chrobak E, Wietrzyk J, Sadowska J, Boryczka S.Med Chem Res. 2017;26(1):1-8. doi: 10.1007/s00044-016-1713-9. Epub 2016 Sep 1. Review. PMID: 28111514 Free PMC Article8:Betulin suppressed interleukin-1β-induced gene expression, secretion and proteolytic activity of matrix metalloproteinase in cultured articular chondrocytes and production of matrix metalloproteinase in the knee joint of rat. Ra HJ, Lee HJ, Jo HS, Nam DC, Lee YB, Kang BH, Moon DK, Kim DH, Lee CJ, Hwang SC.Korean J Physiol Pharmacol. 2017 Jan;21(1):19-26. doi: 10.4196/kjpp.2017.21.1.19. Epub 2016 Dec 21. Erratum in: Korean J Physiol Pharmacol. 2017 Mar;21(2):275. PMID: 28066137 Free PMC Article9:Anticancer properties of ester derivatives of betulin in human metastatic melanoma cells (Me-45). Drąg-Zalesińska M, Drąg M, Poręba M, Borska S, Kulbacka J, Saczko J.Cancer Cell Int. 2017 Jan 3;17:4. doi: 10.1186/s12935-016-0369-3. eCollection 2017. PMID: 28053599 Free PMC Article10:Structural and Computational Study of 4 New Solvatomorphs of Betulin: A Combined X-Ray, Hirshfeld Surface, and Thermal Analysis. Yang D, Gong N, Zhang L, Lu Y, Du G.J Pharm Sci. 2017 Mar;106(3):826-834. doi: 10.1016/j.xphs.2016.11.004. Epub 2016 Nov 22. PMID: 27989367