Betulin

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Betulin
Betulin
Identifiers
CAS number473-98-3 YesY
PubChem72326
ChemSpider65272 YesY
EC-number207-475-5
KEGGC08618 YesY
ChEMBLCHEMBL23236 YesY
Jmol-3D imagesImage 1
Image 2
Properties
Molecular formulaC30H50O2
Molar mass442.72 g mol−1
Melting point256–257 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references
 
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Betulin
Betulin
Identifiers
CAS number473-98-3 YesY
PubChem72326
ChemSpider65272 YesY
EC-number207-475-5
KEGGC08618 YesY
ChEMBLCHEMBL23236 YesY
Jmol-3D imagesImage 1
Image 2
Properties
Molecular formulaC30H50O2
Molar mass442.72 g mol−1
Melting point256–257 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox 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.

History[edit]

Betulin was discovered in 1788 by German-Russian chemist Johann Tobias Lowitz.

Chemistry[edit]

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

Biological activities[edit]

Inonotus obliquus contains betulin,[2]

Recent clinical studies[by whom?] 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.[3]

References[edit]

  1. ^ Green, Brian; Bentley, Michael D.; Chung, Bong Y.; Lynch, Nicholas G.; Jensen, Bruce L. (2007), "Isolation of Betulin and Rearrangement to Allobetulin A Biomimetic Natural Product Synthesis", J. Chem. Educ. 84: 1985, doi:10.1021/ed084p1985 .
  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 .