Acetobetulinic acid

Base Information

• Chemical Name: Acetobetulinic acid
• CAS No.: 10376-50-8
• Molecular Formula: C₃₂H₅₀O₄
• Molecular Weight: 498.747
• Nikkaji Number: J123.034D
• Wikidata: Q104909346
• Metabolomics Workbench ID: 130540
• ChEMBL ID: CHEMBL312687
• Mol file: 10376-50-8.mol

Synonyms:Acetobetulinic acid;3-acetylbetulinic acid;10376-50-8;3-O-Acetyl Betulinic Acid;Betulinic Acid 3-O-Acetate;(3-O-Acetyl)Betulinic Acid;CHEMBL312687;3-O-Acetyl-betulinic acid;(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetoxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid;Lup-20(29)-en-28-oic acid, 3-(acetyloxy)-, (3b)-;(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetoxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylicacid;(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-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-carboxylic acid;Lup-20(29)-en-28-oic acid, 3.beta.-hydroxy-, acetate;Lup-20(29)-en-28-oic acid, 3-(acetyloxy)-, (3.beta.)-;SCHEMBL962020;ACWNTJJUZAIOLW-BWXYOZBYSA-N;BDBM50103967;3beta-acetoxylup-20(29)-en-28-oic acid;(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetoxy-5a,5b,8,8,11a-pentamethyl1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylicacid;9-Acetoxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carboxylic acid

Chemical Property of Acetobetulinic acid

Chemical Property:

• Appearance/Colour: White to off-white solid.
• Vapor Pressure: 4.6E-14mmHg at 25°C
• Refractive Index: 1.54
• Boiling Point: 561.1 °C at 760 mmHg
• Flash Point: 169.1 °C
• PSA: 63.60000
• Density: 1.09 g/cm³
• LogP: 7.66030
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 8.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 498.37091007
• Heavy Atom Count: 36
• Complexity: 967

Purity/Quality:

98%,99%, ^*data from raw 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)OC(=O)C)C)C(=O)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)OC(=O)C)C)C(=O)O
• Uses: 3-O-Acetyl-betulinic acid is a betulinic acid derivative that shows cytotoxic activity on human cancer cell lines. Anti-cancer.

Technology Process of Acetobetulinic acid

There total 25 articles about Acetobetulinic acid 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%

Betulinic acid (472-15-1) + acetic anhydride (108-24-7) → 3-O-acetylbetulinic acid (10376-50-8,38736-81-1)

Guidance literature:

Betulinic acid; acetic anhydride; With dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 65 ℃; for 2h;

With hydrogenchloride; water; at 100 ℃; for 0.5h;

Reference yield: 87.0%

acetic anhydride (108-24-7) → 3-O-acetylbetulinic acid (10376-50-8,38736-81-1)

Guidance literature:

With pyridine; at 20 ℃;

Reference yield: 81.0%

3-O-acetylbetulinal (27570-21-4) → 3-O-acetylbetulinic acid (10376-50-8,38736-81-1)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; In various solvents; at 0 - 20 ℃; for 1.25h;

DOI:10.1016/j.bmc.2007.06.033

upstream raw materials:

betulin monoacetate

Betulinic acid

acetic anhydride

acetic acid

Downstream raw materials:

1-O-(3β-acetoxy-lup-20(29)-ene-28-oyl)-2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl

C₄₄H₆₇NO₅

C₄₅H₆₉NO₆

C₄₄H₆₆FNO₅

Refernces

• 1、 Petrenko,Elantseva,Petukhova,Shakirov,Shul'ts,Tolstikov. "Synthesis of betulonic acid derivatives containing amino-acid fragments". . p. 331 - 339. Retrieved 2002.
• 2、 Sidova, Veronika,Zoufaly, Pavel,Pokorny, Jan,Dzubak, Petr,Hajduch, Marian,Popa, Igor,Urban, Milan. "Cytotoxic conjugates of betulinic acid and substituted triazoles prepared by Huisgen Cycloaddition from 30-azidoderivatives". . . Retrieved 2017.
• 3、 Cargnin, Simone Tasca,Staudt, Andressa Finkler,Medeiros, Patrícia,de Medeiros Sol Sol, Daniel,de Azevedo dos Santos, Ana Paula,Zanchi, Fernando Berton,Gosmann, Grace,Puyet, Antonio,Garcia Teles, Carolina Bioni,Gnoatto, Simone Baggio. "Semisynthesis, cytotoxicity, antimalarial evaluation and structure-activity relationship of two series of triterpene derivatives". . p. 265 - 272. Retrieved 2018.
• 4、 Minassi, Alberto,Rogati, Federica,Cruz, Cristina,Prados, M. Eugenia,Galera, Nuria,Jinénez, Carla,Appendino, Giovanni,Bellido, M. Luz,Calzado, Marco A,Caprioglio, Diego,Mu?oz, Eduardo. "Triterpenoid Hydroxamates as HIF Prolyl Hydrolase Inhibitors". . p. 2235 - 2243. Retrieved 2018.
• 5、 Mukherjee, Rama,Jaggi, Manu,Siddiqui, Mohammad J. A.,Srivastava, Sanjay K.,Rajendran, Praveen,Vardhan, Anand,Burman, Anand C.. "Synthesis and cytotoxic activity of 3-O-acyl/3-hydrazine/2-bromo/20,29- dibromo betulinic acid derivatives". . p. 4087 - 4091. Retrieved 2004.
• 6、 Spivak, Anna Yu.,Nedopekina, Darya A.,Gubaidullin, Rinat R.,Davletshin, Eldar V.,Tukhbatullin, Adis A.,D’yakonov, Vladimir A.,Yunusbaeva, Milyausha M.,Dzhemileva, Lilya U.,Dzhemilev, Usein M.. "Pentacyclic triterpene acid conjugated with mitochondria-targeting cation F16: Synthesis and evaluation of cytotoxic activities". . p. 940 - 951. Retrieved 2021.
• 7、 Qian, Keduo,Yu, Donglei,Chen, Chin-Ho,Huang, Li,Morris-Natschke, Susan L.,Nitz, Theodore J.,Salzwedel, Karl,Reddick, Mary,Allaway, Graham P.,Lee, Kuo-Hsiung. "Anti-AIDS agents. 78. Design, synthesis, metabolic stability assessment, and antiviral evaluation of novel betulinic acid derivatives as potent anti-human immunodeficiency virus (HIV) agents". . p. 3248 - 3258. Retrieved 2009.
• 8、 Chouna, Jean Rodolphe,Dongmo, Appolinaire Kene,Frese, Marcel,Kaaniche, Fatma,Lenta, Bruno Ndjakou,Mawabo, Isabelle Kamga,Ngnokam, David,Nkenfou, Celine Nguefeu,Nkeng-Efouet-Alango, Pépin,Nono, Raymond Ngansop,Sewald, Norbert. "A-type doubly linked proanthocyanidin trimer and other metabolites from Canthium venosum fruits, and their biological activities". . p. 134 - 138. Retrieved 2020.
• 9、 Bildziukevich, Uladzimir,Rárová, Lucie,Janovská, Lucie,?aman, David,Wimmer, Zdeněk. "Enhancing effect of cystamine in its amides with betulinic acid as antimicrobial and antitumor agent in vitro". . p. 91 - 98. Retrieved 2019.
• 10、 Bruckner,Kovacs,Koczka. "-". . p. 948,950. Retrieved 1948.