Betulin
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 600117

CAS#: 473-98-3

Description: Betulin (lup-20(29)-ene-3β,28-diol) is an abundant, naturally occurring triterpene. It is commonly isolated from the bark of birch trees and forms up to 30% of the dry weight of the extractive. The purpose of the compound in the bark is not known. It can be converted to betulinic acid (the alcohol group replaced by a carboxylic acid group), which is biologically more active than betulin itself.


Price and Availability

Size
Price

500mg
USD 150
Size
Price

1g
USD 200
Size
Price

Betulin purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 600117
Name: Betulin
CAS#: 473-98-3
Chemical Formula: C30H50O2
Exact Mass: 442.38108
Molecular Weight: 442.72
Elemental Analysis: C, 81.39; H, 11.38; O, 7.23


Synonym:

IUPAC/Chemical Name: Lup-20(29)-ene-3β,28-diol

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]


Technical Data

Appearance:
Solid powder

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).

Harmonized System Code:
293490


References

1: Haque S, Nawrot DA, Alakurtti S, Ghemtio L, Yli-Kauhaluoma J, Tammela P. Screening and characterisation of antimicrobial properties of semisynthetic betulin derivatives. PLoS One. 2014 Jul 17;9(7):e102696. doi: 10.1371/journal.pone.0102696. eCollection 2014. PubMed PMID: 25032708.

2: Orchel A, Kulczycka A, Chodurek E, Bebenek E, Borkowska P, Boryczka S, Kowalski J, Dzierzewicz Z. Influence of betulin and 28-O-propynoylbetulin on proliferation and apoptosis of human melanoma cells (G-361). Postepy Hig Med Dosw (Online). 2014;68(0):191-7. PubMed PMID: 24988630.

3: Pettit GR, Melody N, Hempenstall F, Chapuis JC, Groy TL, Williams L. Antineoplastic agents. 595. Structural modifications of betulin and the X-ray crystal structure of an unusual betulin amine dimer. J Nat Prod. 2014 Apr 25;77(4):863-72. doi: 10.1021/np400947d. Epub 2014 Apr 2. PubMed PMID: 24694263; PubMed Central PMCID: PMC4010298.

4: Orchel A, Kulczycka A, Chodurek E, Bębenek E, Borkowska P, Boryczka S, Kowalski J, Dzierżewicz Z. Influence of betulin and 28-O-propynoylbetulin on proliferation and apoptosis of human melanoma cells (G-361). Postepy Hig Med Dosw (Online). 2014 Feb 6;68:191-7. PubMed PMID: 24662787.

5: Sousa MC, Varandas R, Santos RC, Santos-Rosa M, Alves V, Salvador JA. Antileishmanial activity of semisynthetic lupane triterpenoids betulin and betulinic acid derivatives: synergistic effects with miltefosine. PLoS One. 2014 Mar 18;9(3):e89939. doi: 10.1371/journal.pone.0089939. eCollection 2014. PubMed PMID: 24643019; PubMed Central PMCID: PMC3958361.

6: Jeromenok J, Böhlmann W, Jäger C, Weber J. Carbon dioxide adsorption in betulin-based micro- and macroporous polyurethanes. ChemistryOpen. 2013 Feb;2(1):17-20. doi: 10.1002/open.201200045. Epub 2013 Jan 18. PubMed PMID: 24551524; PubMed Central PMCID: PMC3594587.

7: Zhao X, Wang W, Zu Y, Zhang Y, Li Y, Sun W, Shan C, Ge Y. Preparation and characterization of betulin nanoparticles for oral hypoglycemic drug by antisolvent precipitation. Drug Deliv. 2014 Jan 30. [Epub ahead of print] PubMed PMID: 24479653.

8: Chowdhury S, Mukherjee T, Chowdhury SR, Sengupta S, Mukhopadhyay S, Jaisankar P, Majumder HK. Disuccinyl betulin triggers metacaspase-dependent endonuclease G-mediated cell death in unicellular protozoan parasite Leishmania donovani. Antimicrob Agents Chemother. 2014 Apr;58(4):2186-201. doi: 10.1128/AAC.02193-13. Epub 2014 Jan 27. PubMed PMID: 24468787; PubMed Central PMCID: PMC4023740.

9: Ilyina A, Arredondo-Valdés R, Farkhutdinov S, Segura-Ceniceros EP, Martínez-Hernández JL, Zaynullin R, Kunakova R. Effect of betulin-containing extract from birch tree bark on α-amylase activity in vitro and on weight gain of broiler chickens in vivo. Plant Foods Hum Nutr. 2014 Mar;69(1):65-70. doi: 10.1007/s11130-014-0404-2. PubMed PMID: 24445672.

10: Saudagar P, Dubey VK. Molecular mechanisms of in vitro betulin-induced apoptosis of Leishmania donovani. Am J Trop Med Hyg. 2014 Feb;90(2):354-60. doi: 10.4269/ajtmh.13-0320. Epub 2014 Jan 13. PubMed PMID: 24420777; PubMed Central PMCID: PMC3919248.