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Betulin

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Betulin
Betulin
Names
IUPAC name Lup-20(29)-ene-3β,28-diol
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.006.797 Edit this at Wikidata
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: FVWJYYTZTCVBKE-ROUWMTJPSA-N
  • 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/s1Key: FVWJYYTZTCVBKE-ROUWMTJPBQ
SMILES
  • O5CC4(3(2((1(CO)(CC1C(=C)C)CC2)CC3)C)(C)CC4C5(C)C)C
  • CC(=C)1CC2(13CC45(CC(C(5CC4(3(CC2)C)C)(C)C)O)C)CO
Properties
Chemical formula C30H50O2
Molar mass 442.728 g·mol
Melting point 256–257 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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

Inonotus obliquus contains betulin,

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.

References

  1. Green, Brian; Bentley, Michael D.; Chung, Bong Y.; Lynch, Nicholas G.; Jensen, Bruce L. (1985), "Isolation of Betulin and Rearrangement to Allobetulin A Biomimetic Natural Product Synthesis", J. Chem. Educ., 200: 7.
  2. Gao, Y; Xu, H; Lu, Z; Xu, Z (2009). "Quantitative determination of steroids in the fruiting bodies and submerged-cultured mycelia of Inonotus obliquus". Se pu. 27 (6): 745–9. PMID 20352924.
  3. Tilford, Gregory L. (1997), Edible and Medicinal Plants of the West, Missoula, MO: Mountain Press, ISBN 0-87842-359-1.

Literature

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