betulin

{{Chembox

| Watchedfields = changed

| verifiedrevid = 441829253

| Name = Betulin

| ImageFile = Betulin.svg

| ImageName = Betulin

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

| SystematicName = (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

| 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

| 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

| InChIKey = FVWJYYTZTCVBKE-ROUWMTJPBQ

| SMILES1 = 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FVWJYYTZTCVBKE-ROUWMTJPSA-N

| CASNo = 473-98-3

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

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

| UNII = 6W70HN7X7O

| EC_number = 207-475-5

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

| ChemSpiderID = 65272

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

| KEGG = C08618

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| Section2 = {{Chembox Properties

| Appearance = solid with needle-like crystals{{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}}

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

| MeltingPtC = 256 to 257

| Solubility = insoluble

| SolubleOther = slightly soluble in ethanol and benzene; soluble in diethyl ether, ethyl acetate and ligroin

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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.{{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}} It is also found in birch sap.{{Cite journal |last=Alakurtti |first=Sami |last2=Mäkelä |first2=Taru |last3=Koskimies |first3=Salme |last4=Yli-Kauhaluoma |first4=Jari |date=2006-09-01 |title=Pharmacological properties of the ubiquitous natural product betulin |url=https://www.sciencedirect.com/science/article/abs/pii/S0928098706001102 |journal=European Journal of Pharmaceutical Sciences |volume=29 |issue=1 |pages=1–13 |doi=10.1016/j.ejps.2006.04.006 |issn=0928-0987}} Inonotus obliquus contains betulin.{{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}}

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.