Cas no 84414-40-4 (23-Hydroxybetulin)

23-Hydroxybetulin structure
23-Hydroxybetulin structure
Product Name:23-Hydroxybetulin
CAS No:84414-40-4
MF:C30H50O3
MW:458.716209888458
CID:1080641
PubChem ID:14605681
Update Time:2025-11-02

23-Hydroxybetulin Chemical and Physical Properties

Names and Identifiers

    • 23-Hydroxybetulin
    • (3β,4α)-Lup-20(29)-ene-3,23,28-triol (ACI)
    • 3aH-Cyclopenta[a]chrysene, lup-20(29)-ene-3,23,28-triol deriv. (ZCI)
    • Lup-20(30)-ene-3β,23,28-triol (6CI)
    • 84414-40-4
    • AKOS040761030
    • (1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-3a,8-bis(hydroxymethyl)-5a,5b,8,11a-tetramethyl-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
    • CHEMBL3815071
    • (1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-3a,8-bis(hydroxymethyl)-5a,5b,8,11a-tetramethyl-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
    • Inchi: 1S/C30H50O3/c1-19(2)20-9-14-30(18-32)16-15-28(5)21(25(20)30)7-8-23-26(3)12-11-24(33)27(4,17-31)22(26)10-13-29(23,28)6/h20-25,31-33H,1,7-18H2,2-6H3/t20-,21+,22+,23+,24-,25+,26-,27-,28+,29+,30+/m0/s1
    • InChI Key: PHMKDBZGQWXPAZ-MZFJGDBOSA-N
    • SMILES: C([C@]12CC[C@@H](C(=C)C)[C@@H]1[C@H]1CC[C@@H]3[C@]4(CC[C@H](O)[C@@](C)(CO)[C@@H]4CC[C@@]3(C)[C@@]1(CC2)C)C)O

Computed Properties

  • Exact Mass: 458.37600
  • Monoisotopic Mass: 458.37599545g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 33
  • Rotatable Bond Count: 3
  • Complexity: 808
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 11
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 7.6
  • Topological Polar Surface Area: 60.7?2

Experimental Properties

  • Color/Form: Powder
  • Density: 1.057±0.06 g/cm3 (20 oC 760 Torr),
  • Boiling Point: 273.6±0.0 °C at 760 mmHg
  • Flash Point: 131.6±19.0 °C
  • Solubility: Insuluble (3.6E-4 g/L) (25 oC),
  • PSA: 60.69000
  • LogP: 5.96960
  • Vapor Pressure: 0.0±0.5 mmHg at 25°C

23-Hydroxybetulin Security Information

23-Hydroxybetulin Pricemore >>

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23-Hydroxybetulin Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Ethyl bromide ,  Potassium carbonate Solvents: Dimethylformamide
1.2 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran
Reference
Terpenoids. III: Synthesis and biological evaluation of 23-hydroxybetulinic acid derivatives as novel inhibitors of glycogen phosphorylase
Zhu, Peiqing; et al, Bioorganic & Medicinal Chemistry Letters, 2009, 19(24), 6966-6969

23-Hydroxybetulin Raw materials

23-Hydroxybetulin Preparation Products

Additional information on 23-Hydroxybetulin

Recent Advances in the Study of 23-Hydroxybetulin (CAS: 84414-40-4): A Promising Triterpenoid with Therapeutic Potential

23-Hydroxybetulin (CAS: 84414-40-4), a naturally occurring triterpenoid derived from the bark of birch trees (Betula spp.), has recently garnered significant attention in the field of chemical biology and medicinal chemistry due to its diverse pharmacological properties. This research brief synthesizes the latest findings on 23-Hydroxybetulin, focusing on its molecular mechanisms, therapeutic applications, and recent advancements in its synthesis and formulation.

Recent studies have elucidated the anti-inflammatory and anticancer properties of 23-Hydroxybetulin. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that 23-Hydroxybetulin exhibits potent inhibitory effects on NF-κB signaling pathways, thereby reducing inflammation in vitro and in vivo. Another study in the European Journal of Pharmacology (2024) highlighted its ability to induce apoptosis in various cancer cell lines, including breast and lung cancer, through the modulation of Bcl-2 family proteins and caspase activation.

In addition to its anticancer and anti-inflammatory effects, 23-Hydroxybetulin has shown promise in the treatment of metabolic disorders. A preclinical study published in Biochemical Pharmacology (2023) reported that 23-Hydroxybetulin improves insulin sensitivity and reduces hepatic steatosis in obese mouse models, suggesting its potential as a therapeutic agent for type 2 diabetes and non-alcoholic fatty liver disease (NAFLD).

Advances in the synthetic chemistry of 23-Hydroxybetulin have also been reported. A 2024 study in Organic Letters described a novel semi-synthetic route to produce 23-Hydroxybetulin derivatives with enhanced bioavailability and reduced cytotoxicity. This breakthrough opens new avenues for the development of optimized analogs with improved pharmacokinetic profiles.

Despite these promising findings, challenges remain in the clinical translation of 23-Hydroxybetulin. Issues such as poor solubility, limited oral bioavailability, and potential off-target effects need to be addressed through further research. Recent efforts in nanotechnology-based drug delivery systems, as reported in the International Journal of Pharmaceutics (2024), offer potential solutions to these challenges.

In conclusion, 23-Hydroxybetulin (CAS: 84414-40-4) represents a multifaceted compound with significant therapeutic potential across various disease areas. Ongoing research continues to uncover its molecular mechanisms and explore strategies to overcome its limitations. The integration of synthetic chemistry, pharmacology, and drug delivery technologies will be crucial for the future development of 23-Hydroxybetulin-based therapeutics.

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