7372-31-8

Basic information

• Product Name: Dihydrobetulin
• Synonyms: Dihydrobetulin;Lupane-3β,28-diol
• CAS NO: 7372-31-8
• Molecular Formula: C₃₀H₅₂O₂
• Molecular Weight: 442.7168
• Mol File: 7372-31-8.mol
• Article Data: 21

Chemical Properties

• Melting Point: 277 °C
• Boiling Point: 520.1±23.0 °C(Predicted)
• Appearance: /
• Density: 1.006±0.06 g/cm3(Predicted)
• PKA: 15.10±0.10(Predicted)
• CAS DataBase Reference: Dihydrobetulin(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydrobetulin(7372-31-8)
• EPA Substance Registry System: Dihydrobetulin(7372-31-8)

Safety Data

• Hazardous Substances Data: 7372-31-8(Hazardous Substances Data)

Upstream product

• 43124-92-1 (?)-3β,28-diacetoxydihydrobetulin 
• 54145-78-7 (1S,3a5,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-9-oxoicosahydro-1H-cyclopenta[a]chrysene-3a-carbaldehyde 
• 79875-75-5 6β,28-diacetoxylup-20(29)-en-3-one 
• 81346-04-5 3β,28-lupanediol 28-acetate 
• 1072913-62-2 (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol 
• 1721-69-3 betulin diacetate 
• 473-98-3 betulin 
• 43124-92-1 3β,28-Diacetoxylupane 
• 1721-69-3 betulin diacetate 
• 79875-65-3 6β,28-dihydroxy-3-oxolup-20(29)-ene 

Downstream Products

• 25576-27-6 3-oxolupan-28-ic acid 
• 43124-92-1 (?)-3β,28-diacetoxydihydrobetulin 
• 81346-04-5 3β,28-lupanediol 28-acetate 
• 1393571-37-3 3-O,28-O-diphthaloyl dihydrobetulin 
• 1007345-51-8 C₄₉H₇₆N₂O₅ 
• 20066-05-1 methyl dihydrobetulonate 
• 134501-93-2 17α(H)-28-Norlupane 
• 134501-93-2 17β(H)-28-Norlupane 
• 134502-04-8 3-Oxolupane tosylhydrazone 
• 464-99-3 Lupane 
• 3186-72-9 3-Oxolupane 
• 3186-86-5 3β-Hydroxy-28-lupane 
• 38736-78-6 dihydrobetulinic acid 
• 43124-92-1 3β,28-Diacetoxylupane 

Relevant articles and documents

Electrosynthesis of Stable Betulin-Derived Nitrile Oxides and their Application in Synthesis of Cytostatic Lupane-Type Triterpenoid-Isoxazole Conjugates

Novel lupane-type triterpenoid-isoxazole conjugates were designed by direct placing of isoxazole linker at C(17) of triterpenoid. The suggested synthetic sequence demonstrates successful combination of electro-organic synthesis and conventional approaches. TEMPO-mediated electrooxidation of betulin to betulinal was developed and optimized at boron-doped diamond anodes with potassium acetate as inexpensive supporting electrolyte. Betulinal-derived oxime was further selectively electro-oxidized at a graphite anode to nitrile oxide, which proved to be stable and isolable species. The same reaction sequence was performed with 3β-lupane-3,28-diol. Nitrile oxides were characterized by 15N NMR and X-ray crystallography. The isolable nitrile oxides allowed creation of isoxazole library by 1,3-dipolar cycloaddition reactions with various alkynes. Some of the title conjugates exhibit cytostatic properties against breast cancer cell line MCF7, glioblastoma multiform cell line U-87 MG and lung carcinoma cell line A549 with growth inhibition (GI50) concentrations up to 11 μm, while being harmless to immortalized human fibroblasts hTERT (GI50 >100 μm).

Synthesis and Antimicrobial Activity of Dihydrobetulin N-Acetylglucosaminides

Dihydrobetulin N-acetylglucosaminides were synthesized for the first time. A study of their antimicrobial activity against a standard set of Gram-positive and Gram-negative bacteria and fungi showed highly selective bacteriostatic activity for glycosides 9 and 13 against Staphylococcus aureus ATCC 209p.

EXTENDED BETULINIC ACID ANALOGS

Compounds having drug and bio-affecting properties, their pharmaceutical compositions and methods of use are set forth. In particular, betulinic acid derivatives that possess unique antiviral activity are provided as HIV maturation inhibitors, as represen