Synonym
AI3-62999, Betulin, Betuline, Betulinol, Betulol, Trochol; (+)-Betulin; NSC 4644; NSC4644; NSC-4644; Lup-20(29)-ene-3β,28-diol
IUPAC/Chemical 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)icosahydro-1H-cyclopenta[a]chrysen-9-ol
InChi Key
FVWJYYTZTCVBKE-ROUWMTJPSA-N
InChi Code
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
SMILES Code
CC1(C)[C@@H](O)CC[C@]2(C)[C@@]3([H])CC[C@]4([H])[C@@]5([H])[C@H](C(C)=C)CC[C@@](CO)5CC[C@](C)4[C@@](C)3CC[C@@]12[H]
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
442.72
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Ci X, Zhou J, Lv H, Yu Q, Peng L, Hua S. Betulin exhibits anti-inflammatory activity in LPS-stimulated macrophages and endotoxin-shocked mice through an AMPK/AKT/Nrf2-dependent mechanism. Cell Death Dis. 2017 May 18;8(5):e2798. doi: 10.1038/cddis.2017.39. PubMed PMID: 28518138; PubMed Central PMCID: PMC5520743.
2: Ra HJ, Lee HJ, Jo HS, Nam DC, Lee YB, Kang BH, Moon DK, Kim DH, Lee CJ, Hwang SC. 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. 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. PubMed PMID: 28066137; PubMed Central PMCID: PMC5214907.
3: Cheng W, Ji S, Zhang H, Han Z, Liu Q, Wang J, Ping H. mTOR activation is critical for betulin treatment in renal cell carcinoma cells. Biochem Biophys Res Commun. 2017 Jan 22;482(4):1030-1036. doi: 10.1016/j.bbrc.2016.11.153. Epub 2016 Nov 28. PubMed PMID: 27908730.
4: Zhou YQ, Weng XF, Dou R, Tan XS, Zhang TT, Fang JB, Wu XW. Betulin from Hedyotis hedyotidea ameliorates concanavalin A-induced and T cell-mediated autoimmune hepatitis in mice. Acta Pharmacol Sin. 2017 Feb;38(2):201-210. doi: 10.1038/aps.2016.102. Epub 2016 Oct 31. PubMed PMID: 27796295; PubMed Central PMCID: PMC5309748.
5: Gui YZ, Yan H, Gao F, Xi C, Li HH, Wang YP. Betulin attenuates atherosclerosis in apoE(-/-) mice by up-regulating ABCA1 and ABCG1. Acta Pharmacol Sin. 2016 Sep;37(10):1337-1348. doi: 10.1038/aps.2016.46. Epub 2016 Jul 4. PubMed PMID: 27374487; PubMed Central PMCID: PMC5057233.
