Betulin
Compound Structure: |
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Synonyms: | Betulin;Betulinol;Betuline;Trochol;Betulol;Lup-20(29)-ene-3b,28-diol;Betulinic alcohol;Lup-20(29)-ene-3beta,28-diol;(+)-betulin;Lup-20(30)-ene-3beta,28-diol | ||||||||||||||||||||||||||||||||||||||||||||
Compound ID: | NMPC-667 | ||||||||||||||||||||||||||||||||||||||||||||
PubChem ID: | |||||||||||||||||||||||||||||||||||||||||||||
Molecular Formula: | C30H50O2 | ||||||||||||||||||||||||||||||||||||||||||||
Canonical SMILES: | CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)CO | ||||||||||||||||||||||||||||||||||||||||||||
InChIKey: | FVWJYYTZTCVBKE-ROUWMTJPSA-N | ||||||||||||||||||||||||||||||||||||||||||||
About the compound: | Betulin, a pentacyclic triterpenoid, is distinguished by its unique structure: it is a lupane with a double bond at the 20(29) position and has two specific substituents, a 3beta-hydroxy group and a 28-hydroxymethyl group. This compound is multifunctional, serving roles as a metabolite, an antiviral agent, an analgesic, an anti-inflammatory agent, and an antineoplastic agent. Chemically, it is classified as both a pentacyclic triterpenoid and a diol, and it is derived from a hydride of lupane. Betulin is an abundant and naturally occurring triterpene, most commonly isolated from the bark of birch trees. It constitutes a significant portion of birch bark, forming up to 30% of the dry weight of silver birch bark. It is also present in birch sap. In addition, Inonotus obliquus, a species of fungus, contains betulin. One of the notable functions of betulin in nature is its contribution to the white color of birch tree bark. This white coloration serves a protective function for the tree, especially against mid-winter overheating caused by the sun. This adaptation is significant as it allows birches to thrive as one of the northernmost occurring deciduous trees. The presence of betulin in the bark thus plays a crucial role in the ecological adaptation and survival of birch trees in cold climates. GHS Hazard Statements • H302 (33.33%): Harmful if swallowed [Warning Acute toxicity, oral] • H312 (33.33%): Harmful in contact with skin [Warning Acute toxicity, dermal] • H315 (33.33%): Causes skin irritation [Warning Skin corrosion/irritation] • H319 (33.33%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] • H332 (33.33%): Harmful if inhaled [Warning Acute toxicity, inhalation] • H335 (33.33%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] • H371 (33.33%): May cause damage to organs [Warning Specific target organ toxicity, single exposure] |
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Properties: |
Chemical and Physical Properties
Source:
PubChem |
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Source Species: |
Entada africana Erythrophleum suaveolens Parinari curatellaefolia |