For research use only. Not for therapeutic Use.
Betulin（Cat No.:I003644）is a naturally occurring triterpene found in the bark of birch trees, valued for its wide range of biological activities, including anti-inflammatory, antiviral, and anticancer effects. Known for its ability to modulate oxidative stress and inflammation, betulin has shown promise in wound healing and skin health applications. It also serves as a precursor for betulinic acid, a compound with notable anticancer potential. With its antioxidant properties and ability to inhibit certain cancer cell lines, betulin is being explored in pharmaceutical and nutraceutical research for therapeutic applications.
| Catalog Number | I003644 |
| CAS Number | 473-98-3 |
| Synonyms | NSC 4644;Trochol |
| Molecular Formula | C₃₀H₅₀O₂ |
| Purity | ≥95% |
| Target | 14.5 μM (SREBP, K562 cell), 74.1 μM (SREBP, HeLa cell), 17.1 μM (SREBP, GOTO cell), 21.09 μM (SREBP, 181P cell), 20.62 μM (SREBP, HeLa cell). |
| 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)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)CO |
| Reference | </br>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 </br>2:Neuroprotective Effects of Betulin in Pharmacological and Transgenic <i>C. elegans</i> 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 </br>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 </br>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 </br>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 Article</br>6: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 </br>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 Article</br>8: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 Article</br>9: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 Article</br>10: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 |
