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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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| verifiedrevid = 407684162 |
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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|correct|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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| 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|changed|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C08618 |
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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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'''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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'']'' contains betulin,<ref name="pmid20352924">{{cite journal |last1=Gao |first1=Y |last2=Xu |first2=H |last3=Lu |first3=Z |last4=Xu |first4=Z |title=Quantitative determination of steroids in the fruiting bodies and submerged-cultured mycelia of Inonotus obliquus |journal=Se pu |volume=27 |issue=6 |pages=745–9 |year=2009 |pmid=20352924}}</ref> |
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* ] |
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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 ]s. ] used red alder bark to treat ], ]s, and ]. ] used an ] made from the bark of red alder to treat ] and ].<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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* ] |
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* ]s |
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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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