Betulin: Difference between revisions

(83 intermediate revisions by 42 users not shown)

Line 1:

{{~~chembox~~

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = ~~407684162~~

| verifiedrevid = 441829253

| Name = Betulin

| ImageFile = Betulin.~~png~~

| ImageFile = Betulin.svg

| ImageName = Betulin

| IUPACName = Lup-20(29)-ene-3βべーた,28-diol

| 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''-cyclopenta[''a'']chrysen-9-ol

| OtherNames =

| OtherNames = Betulinol, betuline, betulol, betulinic alcohol, trochol

| Section1 = {{Chembox Identifiers

| 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

| PubChem = 72326

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 23236

Line 21:

| StdInChIKey = FVWJYYTZTCVBKE-ROUWMTJPSA-N

| CASNo = 473-98-3

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

⚫

| ~~EC-number~~ = 207-475-5

| UNII = 6W70HN7X7O

⚫

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

⚫

| EC_number = 207-475-5

⚫

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 65272

| KEGG_Ref = {{keggcite|~~changed~~|kegg}}

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C08618

}}

| Section2 = {{Chembox Properties

| 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>

| C=30|H=50|O=2

| C=30 | H=50 | O=2

| MeltingPt = 256–257 °C

| MeltingPtC = 256 to 257

| Solubility = insoluble<ref name=":crc" />

| SolubleOther = slightly soluble in [[ethanol]] and [[benzene]]; soluble in [[diethyl ether]], [[ethyl acetate]] and [[ligroin]]<ref name=":crc" />

}}

| Section3 =

| Section4 =

| Section5 =

| Section6 =

}}

'''Betulin''' (lup-20(29)-ene-3βべーた,28-diol) is an abundant naturally occurring [[triterpene]]. It is commonly isolated from the [[bark]] of [[birch]] 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 [[betulinic acid]] (the [[alcohol]] group replaced by a [[carboxylic acid]] group), which is biologically more active than betulin itself.

'''Betulin''' is an abundant, naturally occurring [[triterpene]]. It is commonly isolated from the [[Bark (botany)|bark]] of [[birch]] trees. It forms up to 30% of the dry weight of [[Betula pendula|silver birch]] 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 [[birch sap]].{{Citation needed|date=April 2018}} ''[[Inonotus obliquus]]'' 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>

The compound in the bark gives the tree its white color which appears to protect the tree from [[Midwinter|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 [[Germany|German]]-[[Russian Empire|Russian]] chemist [[Johann Tobias Lowitz]].<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>

==Chemistry==

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

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

== See also ==

==Biological activities==

''[[Inonotus obliquus]]'' 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>

* [[Abietic acid]]

Recent clinical studies{{By whom|date=August 2010}} have verified that [[red alder]] ''([[Alnus rubra]])'' contains betulin and [[lupeol]], compounds shown to be effective against a variety of [[tumor]]s. [[Indigenous peoples of the Americas|Native Americans]] used red alder bark to treat [[poison oak]], [[insect bite]]s, and [[Irritation#Skin|skin irritations]]. [[Blackfeet Indians]] used an [[infusion]] made from the bark of red alder to treat [[Lymphatic disease|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>

* [[Stanol ester]]

* [[Phytosterol]]s

==References==

==Literature==

* Franziska B. Mullauer, Jan H. Kessler, Jan Paul Medema [http://chaga.us.oriveda.com/resources.php ''Betulin Is a Potent Anti-Tumor Agent that Is Enhanced by Cholesterol''], 2009

[[Category:Triterpenes]]

[[Category:Isopropenyl compounds]]

[[ar:بتيولين]]

[[cs:Betulin]]

[[de:Betulin]]

[[es:Betulinol]]

[[nl:Betuline]]

[[pl:Betulina]]

[[ru:Бетулин]]

[[fi:Betuliini]]