| Revision as of 17:03, 13 January 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified fields - updated 'UNII_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoBot|bugs← Previous edit |
Latest revision as of 06:15, 12 July 2024 edit undoحسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 edits added Category:Secondary alcohols using HotCat |
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{{chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 401927530 |
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| verifiedrevid = 441829253 |
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| Name = Betulin |
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| Name = Betulin |
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| ImageFile = Betulin.png |
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| ImageFile = Betulin.svg |
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| ImageName = Betulin |
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| ImageName = Betulin |
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| IUPACName = Lup-20(29)-ene-3β,28-diol |
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| IUPACName = Lup-20(29)-ene-3β,28-diol |
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| SystematicName = (1''R'',3a''S'',5a''R'',5b''R'',7a''R'',9''S'',11a''R'',11b''R'',13a''R'',13b''R'')-3a-(Hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1''H''-cyclopentachrysen-9-ol |
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| OtherNames = |
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| OtherNames = Betulinol, betuline, betulol, betulinic alcohol, trochol |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| 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 |
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| 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 |
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| PubChem = 72326 |
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| PubChem = 72326 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 23236 |
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| ChEMBL = 23236 |
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| SMILES = O5CC4(3(2((1(CO)(CC1C(=C)\C)CC2)CC3)C)(C)CC4C5(C)C)C |
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| SMILES = O5CC4(3(2((1(CO)(CC1C(=C)C)CC2)CC3)C)(C)CC4C5(C)C)C |
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| InChIKey = FVWJYYTZTCVBKE-ROUWMTJPBQ |
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| InChIKey = FVWJYYTZTCVBKE-ROUWMTJPBQ |
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| SMILES1 = CC(=C)1CC2(13CC45(CC(C(5CC4(3(CC2)C)C)(C)C)O)C)CO |
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| SMILES1 = CC(=C)1CC2(13CC45(CC(C(5CC4(3(CC2)C)C)(C)C)O)C)CO |
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| StdInChIKey = FVWJYYTZTCVBKE-ROUWMTJPSA-N |
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| StdInChIKey = FVWJYYTZTCVBKE-ROUWMTJPSA-N |
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| CASNo = 473-98-3 |
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| CASNo = 473-98-3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| EC-number = 207-475-5 |
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| UNII = 6W70HN7X7O |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| EC_number = 207-475-5 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 65272 |
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| ChemSpiderID = 65272 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C08618 |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Appearance = solid with needle-like crystals<ref name=":crc">{{Cite book|chapter-url=https://books.google.com/books?id=bNDMBQAAQBAJ&pg=SA7-PA|title=CRC Handbook of Chemistry and Physics|last1=Haynes|first1=William M.|last2=Lide|first2=David R.|last3=Bruno|first3=Thomas J.|publisher=CRC Press|year=2014|isbn=9781482208689|edition=95th|location=Boca Raton, Florida|pages=340|chapter=3|oclc=908078665}}</ref> |
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| C=30|H=50|O=2 |
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| C=30 | H=50 | O=2 |
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| MeltingPt = 256–257 °C |
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| MeltingPtC = 256 to 257 |
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| Solubility = insoluble<ref name=":crc" /> |
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| SolubleOther = slightly soluble in ] and ]; soluble in ], ] and ]<ref name=":crc" /> |
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| Section3 = |
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| Section4 = |
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| Section5 = |
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| Section6 = |
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'''Betulin''' (lup-20(29)-ene-3β,28-diol) is an abundant naturally occurring ]. It is commonly isolated from the ] of ] trees and forms up to 30% of the dry weight of the extractive <ref>{{citation | title = Isolation of Betulin and Rearrangement to Allobetulin A Biomimetic Natural Product Synthesis | first1 = Brian | last1 = Green | first2 = Michael D. | last2 = Bentley | first3 = Bong Y. | last3 = Chung | first4 = Nicholas G. | last4 = Lynch | first5 = Bruce L. | last5 = Jensen | journal = J. Chem. Educ. | year = 1985 | volume = 200 | pages = 7}}.</ref>. The purpose of the compound in the bark is not known. It can be converted to ] (the ] group replaced by a ] group), which is biologically more active than betulin itself. |
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'''Betulin''' is an abundant, naturally occurring ]. It is commonly isolated from the ] of ] trees. It forms up to 30% of the dry weight of ] bark.<ref>{{Cite journal|last1=Green|first1=Brian|last2=Bentley|first2=Michael D.|last3=Chung|first3=Bong Y.|last4=Lynch|first4=Nicholas G.|last5=Jensen|first5=Bruce L.|date=2007-12-01|title=Isolation of Betulin and Rearrangement to Allobetulin. A Biomimetic Natural Product Synthesis|journal=Journal of Chemical Education|language=EN|volume=84|issue=12|pages=1985|doi=10.1021/ed084p1985|bibcode=2007JChEd..84.1985G}}</ref> It is also found in ].{{Citation needed|date=April 2018}} '']'' contains betulin.<ref>{{Cite journal|last1=Gao|first1=Yuan|last2=Xu|first2=Hongyu|last3=Lu|first3=Zhenming|last4=Xu|first4=Zhenghong|date=November 2009|title=Quantitative determination of steroids in the fruiting bodies and submerged-cultured mycelia of ''Inonotus obliquus''|journal=Se Pu |volume=27|issue=6|pages=745–749|issn=1000-8713|pmid=20352924}}</ref> |
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The compound in the bark gives the tree its white color which appears to protect the tree from ] overheating by the ]. As a result, birches are some of the northernmost occurring deciduous trees. |
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==History== |
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Betulin was discovered in ] by ]-] chemist ].<ref>{{Cite journal|last=Lowitz|first=J. T.|date=1788|title=Űber eine neue, fast benzoeartige substanz der briken|journal=Crell's Chem. Ann.|volume=1|pages=312–317}}</ref><ref>{{Cite journal|last1=Król|first1=Sylwia Katarzyna|last2=Kiełbus|first2=Michał|last3=Rivero-Müller|first3=Adolfo|last4=Stepulak|first4=Andrzej|date=2015|title=Comprehensive Review on Betulin as a Potent Anticancer Agent |journal=BioMed Research International|volume=2015|page=584189 |doi=10.1155/2015/584189 |pmc=4383233|pmid=25866796|doi-access=free }}</ref> |
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==Chemistry== |
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==Chemistry== |
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Chemically, betulin is a triterpenoid of ] structure. It has a pentacyclic ring structure, and hydroxyl groups in positions C3 and C28. |
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Chemically, betulin is a triterpenoid of ] structure. It has a pentacyclic ring structure, and hydroxyl groups in positions C3 and C28. |
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== See also == |
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==Biological activities== |
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Recent clinical studies{{By whom|date=August 2010}} have verified that ] ''(])'' contains betulin and ], 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.<ref>{{citation | first = Gregory L. | last = Tilford | title = Edible and Medicinal Plants of the West | publisher = Mountain Press | location = Missoula, MO | year = 1997 | isbn = 0-87842-359-1}}.</ref> |
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==References== |
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==References== |
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{{Reflist}} |
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{{Reflist}} |
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==Literature== |
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* Franziska B. Mullauer, Jan H. Kessler, Jan Paul Medema , 2009 |
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