Betulin is an abundant, naturally occurring triterpene. It is commonly isolated from the bark of birch trees. It forms up to 30% of the dry weight of silver birch bark.[2] It is also found in birch sap.[citation needed] Inonotus obliquus contains betulin.[3]
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IUPAC name
Lup-20(29)-ene-3β,28-diol
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Systematic 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)icosahydro-1H-cyclopenta[a]chrysen-9-ol | |
Other names
Betulinol, betuline, betulol, betulinic alcohol, trochol
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3D model (JSmol)
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ECHA InfoCard | 100.006.797 |
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PubChem CID
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Properties | |
C30H50O2 | |
Molar mass | 442.728 g·mol−1 |
Appearance | solid with needle-like crystals[1] |
Melting point | 256 to 257 °C (493 to 495 °F; 529 to 530 K) |
insoluble[1] | |
Solubility | slightly soluble in ethanol and benzene; soluble in diethyl ether, ethyl acetate and ligroin[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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The compound in the bark gives the tree its white color which appears to protect the tree from mid-winter overheating by the sun. As a result, birches are some of the northernmost occurring deciduous trees.
Betulin was discovered in 1788 by German-Russian chemist Johann Tobias Lowitz.[4][5]
Chemically, betulin is a triterpenoid of lupane structure. It has a pentacyclic ring structure, and hydroxyl groups in positions C3 and C28.