Betulin

Betulin

Chembox new
Name = Betulin
ImageFile = Betulin.svg
ImageName = Betulin
IUPACName = 3a-Hydroxymethyl-1-isopropenyl
-5a,5b,8,8,11a-pentamethyl-
icosahydro-cyclopenta [a] chrysen-9-ol
OtherNames = lup-20(29)-ene-3β,28-diol
Section1 = Chembox Identifiers
CASNo = 473-98-3
Section2 = Chembox Properties
C=30|H=50|O=2
MeltingPt = 256-257 °C

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 ["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] . 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.

Chemistry

Chemically betulin is a triterpenoid of lupane structure. It has a pentacyclic ring structure, and hydroxyl groups in positions C3 and C28.

Biological activities

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, an HIV protein needed for the invasion of the virus into the cell.

Recent clinical studies have verified that red alder "(Alnus rubra)" contains betulin and lupeol, compounds shown to be effective against a variety of tumors. Native Americans used Red Alder bark to treat poison oak, insect bites, and skin irritations. Blackfeet indians used an infusion made from the bark of Red Alder to treat lymphatic disorders and tuberculosis. [Edible and Medicinal Plants of the West, Gregory L. Tilford, ISBN 0-87842-359-1]

There has been extensive research done on this chemical at the University of Minnesota, Duluth among other educational institutions.

Manufacturers

* [http://www.betulin.ca "Betulin Producers"] - Betulin Producers of Canada and United States

References


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Look at other dictionaries:

  • Betulin — Bet u*lin, n. [L. betula birch tree.] (Chem.) a term originally applied to a substance obtained as a resin or tar by extraction from the outer bark of the common European white birch ({Betula alba}); now referring to the chemical compound… …   The Collaborative International Dictionary of English

  • Betŭlin — Betŭlin, von Lowitz 1788 in der Oberrinde der Birke als eigene Substanz ausgeschieden, von John 1811 als eigener Pflanzenstoff aufgestellt. Man erhält ihn durch Ausschwitzen aus, bis zum Dämpfen erhitzter Birkenrinde, als ein Gespinnst von weißer …   Pierer's Universal-Lexikon

  • Betulin — Strukturformel Allgemeines Name Betulin Andere Namen Betulinol …   Deutsch Wikipedia

  • betulin — ˈbechələ̇n noun ( s) Etymology: International Scientific Vocabulary betul (from New Latin Betula, genus name of Betula alba) + in : betulinol * * * betulin ( …   Useful english dictionary

  • betulin — noun A naturally abundant triterpene, commonly isolated from the bark of birch trees, that can be converted to betulinic acid …   Wiktionary

  • betulin — bet·u·lin …   English syllables

  • betulin(ol) —   n. resinous extract of birch bark; birch camphor …   Dictionary of difficult words

  • Betula alba — Betulin Bet u*lin, n. [L. betula birch tree.] (Chem.) a term originally applied to a substance obtained as a resin or tar by extraction from the outer bark of the common European white birch ({Betula alba}); now referring to the chemical compound …   The Collaborative International Dictionary of English

  • birch camphor — Betulin Bet u*lin, n. [L. betula birch tree.] (Chem.) a term originally applied to a substance obtained as a resin or tar by extraction from the outer bark of the common European white birch ({Betula alba}); now referring to the chemical compound …   The Collaborative International Dictionary of English

  • C30H50O2 — Betulin Bet u*lin, n. [L. betula birch tree.] (Chem.) a term originally applied to a substance obtained as a resin or tar by extraction from the outer bark of the common European white birch ({Betula alba}); now referring to the chemical compound …   The Collaborative International Dictionary of English

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