Betulin

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Betulin
Betulin Betulin.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-475-5
KEGG
PubChem CID
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 Yes check.svgY
    Key: FVWJYYTZTCVBKE-ROUWMTJPSA-N Yes check.svgY
  • 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
Appearancesolid 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [2] It is also found in birch sap. [3] Inonotus obliquus contains betulin. [4]

Contents

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.

History

Betulin was discovered in 1788 by German-Russian chemist Johann Tobias Lowitz. [5] [6]

Chemistry

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

See also

References

  1. 1 2 3 Haynes, William M.; Lide, David R.; Bruno, Thomas J. (2014). "3". CRC Handbook of Chemistry and Physics (95th ed.). Boca Raton, Florida: CRC Press. p. 340. ISBN   9781482208689. OCLC   908078665.
  2. ↑ Green, Brian; Bentley, Michael D.; Chung, Bong Y.; Lynch, Nicholas G.; Jensen, Bruce L. (2007-12-01). "Isolation of Betulin and Rearrangement to Allobetulin. A Biomimetic Natural Product Synthesis". Journal of Chemical Education. 84 (12): 1985. Bibcode:2007JChEd..84.1985G. doi:10.1021/ed084p1985.
  3. ↑ Alakurtti, Sami; Mäkelä, Taru; Koskimies, Salme; Yli-Kauhaluoma, Jari (2006-09-01). "Pharmacological properties of the ubiquitous natural product betulin" . European Journal of Pharmaceutical Sciences. 29 (1): 1–13. doi:10.1016/j.ejps.2006.04.006. ISSN   0928-0987.
  4. ↑ Gao, Yuan; Xu, Hongyu; Lu, Zhenming; Xu, Zhenghong (November 2009). "Quantitative determination of steroids in the fruiting bodies and submerged-cultured mycelia of Inonotus obliquus". Se Pu. 27 (6): 745–749. ISSN   1000-8713. PMID   20352924.
  5. ↑ Lowitz, J. T. (1788). "Űber eine neue, fast benzoeartige substanz der briken". Crell's Chem. Ann. 1: 312–317.
  6. ↑ Król, Sylwia Katarzyna; Kiełbus, Michał; Rivero-Müller, Adolfo; Stepulak, Andrzej (2015). "Comprehensive Review on Betulin as a Potent Anticancer Agent". BioMed Research International. 2015: 584189. doi: 10.1155/2015/584189 . PMC   4383233 . PMID   25866796.
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