43124-92-1

Basic information

• Product Name: Dihydrobetulindiacetate
• Synonyms: Dihydrobetulindiacetate
• CAS NO: 43124-92-1
• Molecular Formula: C₃₄H₅₆O₄
• Molecular Weight: 526.79016
• Mol File: 43124-92-1.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Dihydrobetulindiacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydrobetulindiacetate(43124-92-1)
• EPA Substance Registry System: Dihydrobetulindiacetate(43124-92-1)

Safety Data

• Hazardous Substances Data: 43124-92-1(Hazardous Substances Data)

Upstream product

• 55029-05-5 lupane-3β,28-diol 
• 108-24-7 acetic anhydride 
• 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 
• 7372-31-8 Dihydrobetulin 
• 1721-69-3 betulin diacetate 
• 473-98-3 betulin 
• 71-41-0 pentan-1-ol 
• 28161-06-0 3β,28-diacetoxy-29-oxolupane 
• 7803-57-8 hydrazine hydrate 
• 1721-69-3 betulin diacetate 

Downstream Products

• 203576-62-9 benzyl (3β)-3-hydroxylupan-28-oate 
• 619292-61-4 benzyl 3,O-didehydro-20,29-dihydrobetulinate 
• 134501-93-2 17α(H)-28-Norlupane 
• 134501-93-2 17β(H)-28-Norlupane 
• 134502-04-8 3-Oxolupane tosylhydrazone 
• 25576-27-6 Lupanon-⁽³⁾-carbonsaeure-⁽²⁸⁾ 
• 464-99-3 Lupane 
• 3186-72-9 3-Oxolupane 
• 3186-86-5 3β-Hydroxy-28-lupane 
• 139255-68-8 3β,28-dihydroxy-21,22-secolup-18(19)-ene-21,22-dioic anhydride acetate 
• 25488-54-4 (1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetoxy-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid 
• 38736-78-6 dihydrobetulinic acid 
• 7372-31-8 Dihydrobetulin 
• 53900-05-3 3β-Acetoxy-28-lupanol 

Relevant articles and documents

First conjugate of glucuronic acid with triterpenoid dihydrobetulin

3β-O-Acetyl-28-O-succinyl-(2,3,4-tri-O-acetyl-5-methoxycarbonyl-β-D-glucopyranosyl)dihydrobetulin was synthesized.

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.

Synthesis of cytotoxic 2,2-difluoroderivatives of dihydrobetulinic acid and allobetulin and study of their impact on cancer cells

In this article, we describe the preparation and cytotoxic properties of a small focused library of lupane and 18plusmn;-oleanane triterpenoids that contain a combination of two structural motifs known to enhance the biological activities. First, we introduced two fluorine atoms to position 2 of the skeleton. Second, we synthesized a set of hemiester prodrugs, which were intended to increase the solubility and activity. Starting from betulin, we obtained two hydroxyketones (derivatives of dihydrobetulinic acid and allobetulin) and their fluorination using DAST provided 2,2-difluoro-3-oxo-compounds as the main products. Then the 3-oxo group in each derivative was reduced by NaBH4 to obtain 32-hydroxy compounds suitable for modifying by various hemiesters. We prepared 21 compounds, 11 of them new, their cytotoxicity was tested on T lymphoblastic leukemia CCRF-CEM cells first and the most active derivatives were selected for screening on another six tumor and two non-tumor cell lines. All of them showed selectivity against cancer lines with therapeutic index between 2 and 8. All hemiesters had activity in the same range as the free hydroxyl derivatives and they would be suitable prodrugs for future in vivo experiments. Interestingly, all hemiesters of 2,2-difluorodihydrobetulonic acid had higher activity against p53 knock-out p53g'/g' cancer cell line than against the non-mutated analog. In active derivatives, the cell cycle was analyzed by flow cytometry and several compounds slowed down cell cycle progression through G0/G1 or S-phase.