Betulin

Betulin
Compound Structure:
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:

72326

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]

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

442.7 g/mol

XLogP3-AA

8.3

Hydrogen Bond Donor Count

2

Hydrogen Bond Acceptor Count

2

Rotatable Bond Count

2

Exact Mass

442.381080833 g/mol

Monoisotopic Mass

442.381080833 g/mol

Topological Polar Surface Area

40.5Ų

Heavy Atom Count

32

Formal Charge

0

Complexity

786

Isotope Atom Count

0

Defined Atom Stereocenter Count

10

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Solid

Boiling Point

284.00 to 288.00 °C. @ 743.00 mm Hg

Melting Point

251 - 252 °C

Source: PubChem

Source Species: Entada africana
Erythrophleum suaveolens
Parinari curatellaefolia
Download SDF