Betulin

Betulin
Names
IUPAC name
Lup-20(29)-ene-3β,28-diol
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
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.006.797
EC Number
  • 207-475-5
KEGG
UNII
  • 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 Y
    Key: FVWJYYTZTCVBKE-ROUWMTJPSA-N Y
  • InChI=1/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
    Key: FVWJYYTZTCVBKE-ROUWMTJPBQ
  • O[C@H]5CC[C@@]4([C@@H]3[C@@]([C@]2([C@@H]([C@@H]1[C@](CO)(CC[C@H]1C(=C)C)CC2)CC3)C)(C)CC[C@H]4C5(C)C)C
  • CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)CO
Properties
C30H50O2
Molar mass 442.728 g·mol−1
Appearance solid with needle-like crystals
Melting point 256 to 257 °C (493 to 495 °F; 529 to 530 K)
insoluble
Solubility slightly soluble in ethanol and benzene; soluble in diethyl ether, ethyl acetate and ligroin
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

Betulin is an abundant, naturally occurring triterpene. It is commonly isolated from the bark of birch trees, hence its name, from betula. It forms up to 30% of the dry weight of silver birch bark. It is also found in birch sap. Inonotus obliquus contains betulin.

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.