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betulin
Sign in to saveAlso known as Trochol, Betulinol, Betuline, Betulol
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. It is also found in birch sap. Inonotus obliquus contains betulin.
Chemical data
- Formula
- C30H50O2
- Molecular weight
- 442.7 g/mol
- 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-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
- SMILES
- 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
- InChIKey
- FVWJYYTZTCVBKE-ROUWMTJPSA-N
- XLogP
- 8.3
- Polar surface area
- 40.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
2,968 papers- Methods of Betulin Extraction from Birch Bark.Molecules (Basel, Switzerland) · 2022
- Pharmacological Potential of Betulin as a Multitarget Compound.Biomolecules · 2023
- Betulin and its derivatives as novel compounds with different pharmacological effects.Biotechnology advances · 2020
- Betulin-betulinic acid natural product based analogs as anti-cancer agents.Anti-cancer agents in medicinal chemistry · 2013
- Shenling Baizhu Powder and Betulin attenuate sepsis-induced intestinal injury by targeting GADD45B/TAOK1/p38 MAPK pathway.Journal of ethnopharmacology · 2025
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 442.381
Show 7 more facts
- found in taxon
- broad bean
- melting point
- 251
- chemical formula
- C₃₀H₅₀O₂
- Commons category
- Betulin
- canonical SMILES
- CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)CO
- solubility
- 0.0001
- isomeric SMILES
- 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
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- History
- Chemistry
- See also
- References
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. It is also found in birch sap. Inonotus obliquus contains betulin.
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.
Excerpted from Wikipedia’s “betulin” article, available under the CC BY-SA 4.0 licence.