Betulin

Title: Betulin
CAS Registry Number: 473-98-3
CAS Name: (3b)-Lup-20(29)-ene-3,28-diol
Additional Names: lup-20(30)-ene-3b,28-diol; trochol; betulinol; betulol
Molecular Formula: C30H50O2
Molecular Weight: 442.72
Percent Composition: C 81.39%, H 11.38%, O 7.23%
Literature References: In the outer portion of the bark of white birch (up to 24%), in other barks, and in lignite. Isoln: Lowitz, Crell's Chem. Ann. 1, 312 (1788); L. Ruzicka, O. Isler, Helv. Chim. Acta 19, 506 (1936); and botanical distribution: Steiner, Molisch Festschrift (1936). Isoln from Lemaireocereus griseus Britton et Rose, Cactaceae: C. Djerassi et al., J. Am. Chem. Soc. 78, 2312 (1956). Structure: Ames et al., J. Chem. Soc. 1951, 450; Davy et al., ibid. 1951, 2696, 2702. Stereochemistry: Guider et al., ibid. 1953, 3024; Das, Chem. Ind. (London) 1971, 1331. Reviews: J. Simonsen, W. C. J. Ross, The Terpenes vol. IV (Cambridge Univ. Press, 1957) pp 187-328; E. W. H. Hayek et al., Phytochemistry 28, 2229-2242 (1989).
Properties: Crystals from methanol-chloroform, mp 248-251°; sublimes at 240° at 0.01 mm. Solvated needles from alc contg one mol EtOH. After drying sublimes at 170-180° (bath temp) at 0.08 mm. uv max (H2SO4): 316 nm. [a]D15 +20° (c = 2 in pyridine). Sparingly sol in cold water, petr ether, carbon disulfide. One part is sol in 149 parts alc, 251 ether, 113 chloroform, 417 benzene. Sol in acetic acid.
Melting point: mp 248-251°
Optical Rotation: [a]D15 +20° (c = 2 in pyridine)
Absorption maximum: uv max (H2SO4): 316 nm
Derivative Type: Diacetate
CAS Registry Number: 1721-69-3
Molecular Formula: C34H54O4
Molecular Weight: 526.79
Percent Composition: C 77.52%, H 10.33%, O 12.15%
Properties: mp 223-224°. [a]D20 +22° (c = 1.2 in CHCl3). d4228.5 0.9635; nD228.5 1.4661.
Melting point: mp 223-224°
Optical Rotation: [a]D20 +22° (c = 1.2 in CHCl3)
Index of refraction: nD228.5 1.4661
Density: d4228.5 0.9635
Use: Light stabilizer for cellulose and wood pulp. In mfr of resins, laquers, emulsifiers and polyurethanes. Cosmetics additive.
Betulinic Acid Bevantolol Bevonium Methyl Sulfate Bexarotene Bezafibrate

Betulin
Betulin
Identifiers
CAS number 473-98-3 YesY
PubChem 72326
ChemSpider 65272 YesY
EC-number 207-475-5
KEGG C08618 YesY
ChEMBL CHEMBL23236 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C30H50O2
Molar mass 442.72 g mol−1
Melting point 256–257 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Betulin (lup-20(29)-ene-3β,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.[1] 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.