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Betulin



Betulin
IUPAC name 3a-Hydroxymethyl-1-isopropenyl
-5a,5b,8,8,11a-pentamethyl-
icosahydro-cyclopenta[a]chrysen-9-ol
Other names lup-20(29)-ene-3β,28-diol
Identifiers
CAS number 473-98-3
Properties
Molecular formula C30H50O2
Molar mass 442.72 g/mol
Melting point

256-257 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

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 [1]. 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.


Betulinic acid and its synthetic analogues exhibit anti-malarial, anti-inflamatory and anti-HIV activity as well as showing cytotoxicity towards a number of tumour cell lines. Even though betulin derivatives are most widely studied for their anticancer activity, also the anti-HIV effect is quite well characterized and it has been demonstrated that betulins can inhibit HIV entry to T cells by binding to the gp41, a HIV protein needed for the invasion of the virus into the cell.

References

  1. ^ Isolation of Betulin and Rearrangement to Allobetulin A Biomimetic Natural Product Synthesis Brian Green, Michael D. Bentley, Bong Y. Chung, Nicholas G. Lynch, and Bruce L. Jensen Journal of Chemical Education 1985 2007
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Betulin". A list of authors is available in Wikipedia.
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