4439-98-9

Basic information

• Product Name: Lup-20(29)-en-28-al,3-oxo-
• Synonyms: Lup-20(30)-en-28-al,3-oxo- (6CI,7CI); 1H-Cyclopenta[a]chrysene, lup-20(29)-en-28-al deriv.;(+)-Betulonal; Betulonal; Betulonaldehyde; Betulonic aldehyde; Liquidambronal
• CAS NO: 4439-98-9
• Molecular Formula: C30H46 O2
• Molecular Weight: 438.694
• Mol File: 4439-98-9.mol
• Article Data: 43

Chemical Properties

• CAS DataBase Reference: Lup-20(29)-en-28-al,3-oxo-(CAS DataBase Reference)
• NIST Chemistry Reference: Lup-20(29)-en-28-al,3-oxo-(4439-98-9)
• EPA Substance Registry System: Lup-20(29)-en-28-al,3-oxo-(4439-98-9)

Safety Data

• Hazardous Substances Data: 4439-98-9(Hazardous Substances Data)

Upstream product

• 473-98-3 betulin 
• 64-19-7 acetic acid 
• 27686-35-7 28-acetoxybetulin 
• 7020-34-0 betulone 
• 136587-07-0 28-acetyloxy-lup-20⁽²⁹⁾-en-3-one 
• 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 
• 212708-99-1 O,O'-bis-(trimethylsilyl)-betulin 
• 407-25-0 trifluoroacetic anhydride 
• 556-91-2 aluminum tri-tert-butoxide 
• 106-51-4 p-benzoquinone 
• 71-43-2 benzene 

Downstream Products

• 473-98-3 betulin 
• 4481-62-3 betulonic acid 
• 1350915-20-6 (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-benzyl 5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-9-(((trifluoromethyl)sulfonyl)oxy)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate 
• 203576-71-0 benzyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-oxo-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate 
• 1392315-12-6 (1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(3-fluoro-4-(methoxycarbonyl)phenyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid 
• 1392315-11-5 (1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-benzyl 9-(3-fluoro-4-(methoxycarbonyl)phenyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate 
• 192211-42-0 benzyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate 
• 2259-06-5 methyl betulinate 
• 1392314-32-7 methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate 
• 1392113-47-1 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((hydroxyimino)methyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate 
• 1392113-46-0 methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-formyl-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate 
• 1392312-45-6 4-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-[[2-(1,1-dioxido-4-thiomorpholinyl)ethyl]amino]-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13boctadecahydro-5a,5b,8,8,11a-pentamethyl-1-(1-methylethenyl)-1H-cyclopenta[a]chrysen-9-yl]-benzoic acid 
• 1392314-60-1 methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxido-4-thiomorpholinyl)ethyl)amino)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate 

Relevant articles and documents

Catalytic oxidative transformation of betulin to its valuable oxo-derivatives over gold supported catalysts: Effect of support nature

Liquid-phase oxidation of betulin extracted from birch bark was studied over gold catalysts supported on a range of supports (hydrotalcite, ZrO2, ZnO, MgO, CeO2, La2O3, HMS and various alumina) with different morphology and properties. Gold catalysts as well as the corresponding supports were characterized by XRD, BET, ICP-OES, XPS and TEM. It was found that the nature of the support plays a decisive role in betulin oxidation over gold-based catalysts, expressed in the influence on the average size and distribution of gold nanoparticles and, thereby, on their catalytic performance (activity and selectivity) in betulin oxidation. Moreover, it was revealed that betulin oxidation catalyzed by gold is a structure sensitive reaction, requiring an optimal size of gold nanoparticles of ca. 3.3 nm. The most suitable support for gold was found to be alumina. Kinetic studies allowed determination of reaction orders and conditions favorable for selective formation of a particular oxo-derivative of betulin (betulone, betulinic and betulonic aldehydes, betulinic acid).

Synthesis of 3-O-Acetylbetulinic and betulonic aldehydes according to svern and the pharmacological activity of related oximes

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Oxidation of betulin and its monoacetates by "activated" DMSO

The oxidation of betulin and its 3-O- and 28-O-acetates by "activated" dimethylsulfoxide was investigated.

Chemical transformations of betulonic aldehyde

Chemical transformations of 3-oxolup-20(29)-en-28-al in oxidation, reduction, reductive amination, aldol crotonic condensation, cyclopropanation, Grignard, and Wittig reactions were investigated. The structure of reaction products was established by X-ray diffraction (XRD) analysis.

Enhancement of the antioxidant and skin permeation properties of betulin and its derivatives

This study investigated the antioxidant activity DPPH, ABTS, and Folin–Ciocalteu methods of betulin (compound 1) and its derivatives (compounds 2–11). Skin permeability and accumulation associated with compounds 1 and 8 were also examined. Identification of the obtained products (compound 2–11) and betulin isolated from plant material was based on the analysis of1H-NMR and13C-NMR spectra. The partition coefficient was calculated to determine the lipophilicity of all compounds. In the next stage, the penetration through pig skin and its accumulation in the skin were evaluated of ethanol vehicles containing compound 8 (at a concentration of 0.226 mmol/dm3), which was characterized by the highest antioxidant activity. For comparison, penetration studies of betulin itself were also carried out. Poor solubility and the bioavailability of pure compounds are major constraints in combination therapy. However, we observed that the ethanol vehicle was an enhancer of skin permeation for both the initial betulin and compound 8. The betulin 8 derivative showed increased permeability through biological membranes compared to the parent betulin. The paper presents the transformation of polycyclic compounds to produce novel derivatives with marked antioxidant activities and as valuable intermediates for the pharmaceutical industry. Moreover, the compounds contained in the vehicles, due to their mechanism of action, can have a beneficial effect on the balance between oxidants and antioxidants in the body, minimizing the effects of oxidative stress. The results of this work may contribute to knowledge regarding vehicles with antioxidant potential. The use of vehicles for this type of research is therefore justified.

Anti-tumor betulinol derivative and preparation method thereof

The invention discloses an anti-tumor betulin derivative and a preparation method thereof. The preparation method comprises the following steps: adding betulin into a reactor, oxidizing hydroxyl by using a mixed solution of sodium dichromate and sulfuric acid, carrying out acylating chlorination on thionyl chloride, carrying out aminolysis under an alkaline condition, and finally crystallizing by using ethanol to obtain the betulin derivative with a novel structure. Pathological experiments show that compared with cis-platinum which is commonly used at present, the betulin derivative has remarkable inhibitory activity on breast cancer cells, human ovarian cancer cells, human lung cancer cells and human liver cancer cells. The method is simple in route, simple to operate and high in yield, the used reagents are common reagents, and particularly, the preparation cost of the technical route of the preparation method is obviously reduced, and the reaction conditions are mild.