Betulinaldehyde

Base Information

• Chemical Name: Betulinaldehyde
• CAS No.: 13159-28-9
• Molecular Formula: C30H48O2
• Molecular Weight: 440.71
• Nikkaji Number: J39.287A
• Wikidata: Q76009748
• Metabolomics Workbench ID: 141116
• ChEMBL ID: CHEMBL512622
• Mol file: 13159-28-9.mol

Synonyms:BETULINALDEHYDE;Betulinicaldehyde;13159-28-9;Betulinic aldehyde;Betulinal;Betunal;Betulin aldehyde;Lup-20(29)-en-28-al, 3beta-hydroxy-;Lup-20(29)-en-28-al, 3-hydroxy-, (3beta)-;(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbaldehyde;NSC 250423;SCHEMBL208983;CHEMBL512622;CHEBI:177424;FELCJAPFJOPHSD-ROUWMTJPSA-N;HY-N0084;BDBM50599935;MFCD12407180;s9153;AKOS016009535;CCG-269130;AC-34027;MS-27924;A888397;(1R,3aS,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-eicosahydro-cyclopenta[a]chrysene-3a-carbaldehyde;(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbaldehyde;3beta-Hydroxy-Lup-20(30)-en-28-al;Nsc 250423

Chemical Property of Betulinaldehyde

Chemical Property:

• Vapor Pressure: 1.04E-12mmHg at 25°C
• Melting Point: 183-187 °C(Solv: methanol (67-56-1))
• Refractive Index: 1.544
• Boiling Point: 513.909 °C at 760 mmHg
• PKA: 15.17±0.70(Predicted)
• Flash Point: 217.385 °C
• PSA: 37.30000
• Density: 1.042 g/cm³
• LogP: 7.20380
• XLogP3: 8.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 440.365430770
• Heavy Atom Count: 32
• Complexity: 814

Purity/Quality:

98% ^*data from raw suppliers

Betulinicaldehyde 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C=O
• Isomeric SMILES: CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)C=O

Technology Process of Betulinaldehyde

There total 24 articles about Betulinaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

betulin (473-98-3) → betulonic aldehyde (4439-98-9) + betulinic aldehyde (13159-28-9,92594-07-5)

Guidance literature:

With [bis(acetoxy)iodo]benzene; 1,5-dimethyl-9-azanoradamantane N-oxyl; In dichloromethane; at 25 ℃; for 0.75h; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/jo502426p

Reference yield: 97.0%

betulin (473-98-3) → betulinic aldehyde (13159-28-9,92594-07-5)

Guidance literature:

With N-chloro-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1128/AAC.02121-15

Reference yield: 89.0%

3-O-acetylbetulinal (27570-21-4) → betulinic aldehyde (13159-28-9,92594-07-5)

Guidance literature:

With methanol; potassium hydroxide; In tetrahydrofuran; at 20 ℃; Temperature;

upstream raw materials:

3-O-acetylbetulinal

Betulinic acid

betulin

(3β)-3-acetyloxy-N-methoxy-N-methyl-lup-20(29)-en-28-amide

Downstream raw materials:

Betulinic acid

(3β)-3-[4-(2-phenylmethoxycarbonyl)-3,3-dimethyl-1-oxobutoxy]lup-20(29)-en-28-al

4-fluoro-N-[[(3β)-3-hydroxylup-20(29)-en-28-yl]methyl]phenylacetamide

(3β)-28-[[(phenylcarbonyl)amino]methyl]lup-20(29)-en-3-ol; hydrogen 3,3-dimethylpentanedioate

Refernces

• 1、 Urano, Emiko,Ablan, Sherimay D.,Mandt, Rebecca,Pauly, Gary T.,Sigano, Dina M.,Schneider, Joel P.,Martin, David E.,Nitz, Theodore J.,Wild, Carl T.,Freed, Eric O.. "Alkyl amine bevirimat derivatives are potent and broadly active HIV-1 maturation inhibitors". . p. 190 - 197. Retrieved 2016.
• 2、 Sidoryk, Katarzyna,Korda, Anna,Rárová, Lucie,Okle??ková, Jana,Strnad, Miroslav,Cmoch, Piotr,Pakulski, Zbigniew,Gwardiak, Katarzyna,Karczewski, Romuald,Luboradzki, Roman. "Synthesis and biological activity of new homolupanes and homolupane saponins". . p. 2004 - 2012. Retrieved 2015.
• 3、 Holy, Jon,Kolomitsyna, Oksana,Krasutsky, Dmytro,Oliveira, Paulo J.,Perkins, Edward,Krasutsky, Pavel A.. "Dimethylaminopyridine derivatives of lupane triterpenoids are potent disruptors of mitochondrial structure and function". . p. 6080 - 6088. Retrieved 2010.
• 4、 Ruzicka,Rey. "-". . . Retrieved 1942.
• 5、 Kim, Darrick S. H. L.,Pezzuto, John M.,Pisha, Emily. "Synthesis of betulinic acid derivatives with activity against human melanoma". . p. 1707 - 1712. Retrieved 1998.
• 6、 Lugi?ina, Jevge?ija,Linden, Martin,Bazulis, Māris,Kumpi??, Viktors,Mishnev, Anatoly,Popov, Sergey A.,Golubeva, Tatiana S.,Waldvogel, Siegfried R.,Shults, Elvira E.,Turks, Māris. "Electrosynthesis of Stable Betulin-Derived Nitrile Oxides and their Application in Synthesis of Cytostatic Lupane-Type Triterpenoid-Isoxazole Conjugates". . p. 2557 - 2577. Retrieved 2021.
• 7、 Bu, Ming,Han, Yinglong,Lin, Yu,Liu, Jicheng,Wang, Haijun,Wang, Jiafeng,Wang, Jing,Wu, Jiale,Zhang, Jie. "Design and synthesis of novel betulin derivatives containing thio-/semicarbazone moieties as apoptotic inducers through mitochindria-related pathways". . . Retrieved 2021/11/01.