Betulin

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
CAS Number	473-98-3 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL23236 ;
ChemSpider	65272 ;
ECHA InfoCard	100.006.797
EC Number	207-475-5;
KEGG	C08618 ;
PubChem CID	72326;
UNII	6W70HN7X7O ;
CompTox Dashboard (EPA)	DTXSID101019934 ;
	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/s1 Key: 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/s1 Key: FVWJYYTZTCVBKE-ROUWMTJPBQ;
	SMILES 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
Chemical formula	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)
Solubility in water	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). verify (what is ?) 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.^[2] It is also found in birch sap.^[3] Inonotus obliquus contains betulin.^[4]

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.

References

^ ^a ^b ^c 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.
^ 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.
^ 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.
^ 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.
^ Lowitz, J. T. (1788). "Űber eine neue, fast benzoeartige substanz der briken". Crell's Chem. Ann. 1: 312–317.
^ 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.

[:crc-1] 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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History

Chemistry

See also

References