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. It forms up to 30% of the dry weight of silver birch bark.^[2] It is also found in birch sap.^{[citation needed]} Inonotus obliquus contains betulin.^[3]

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.^[4]^[5]

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.
^ 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] 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.

[4] Lowitz, J. T. (1788). "Űber eine neue, fast benzoeartige substanz der briken". Crell's Chem. Ann. 1: 312–317.

[5] 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.

[1]

[2]

[3]

[4]

[5]

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^Y
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL23236^Y
ChemSpider	65272^Y
ECHA InfoCard	100.006.797
EC Number	207-475-5
KEGG	C08618^Y
PubChem CID	72326
UNII	6W70HN7X7O^Y
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^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
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^[1]
Melting point	256 to 257 °C (493 to 495 °F; 529 to 530 K)
Solubility in water	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). Y verify (what is ^YN ?) Infobox references

Betulin

History

Chemistry

See also

References

€4.95