Betulonic acid

Base Information

• Chemical Name: Betulonic acid
• CAS No.: 4481-62-3
• Molecular Formula: C30H46O3
• Molecular Weight: 454.693
• Hs Code.: 29389090
• UNII: 7C1UV6ITF5
• Nikkaji Number: J14.452E
• Wikidata: Q104395269
• Metabolomics Workbench ID: 133981
• ChEMBL ID: CHEMBL431525
• Mol file: 4481-62-3.mol

Synonyms:betulonic acid

Chemical Property of Betulonic acid

Chemical Property:

• Vapor Pressure: 1.83E-13mmHg at 25°C
• Melting Point: 253 °C
• Refractive Index: 1.527
• Boiling Point: 548.1 °C at 760 mmHg
• PKA: 4.62±0.70(Predicted)
• Flash Point: 299.4 °C
• PSA: 54.37000
• Density: 1.061 g/cm³
• LogP: 7.29770
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 7.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 454.34469533
• Heavy Atom Count: 33
• Complexity: 902

Purity/Quality:

Liquidambaric acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(=O)C(C5CCC4(C3(CC2)C)C)(C)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(CCC(=O)C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)C)C(=O)O
• Uses: (+)-Betulonic Acid shows potent cytotoxic activities against PC3, MGC-803, Bcap-37, and MCF-7 cell lines.

Technology Process of Betulonic acid

There total 20 articles about Betulonic 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: 100.0%

betulonic aldehyde (4439-98-9) → betulonic acid (4481-62-3)

Guidance literature:

With sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20 ℃; for 2h; Inert atmosphere;

Reference yield: 96.0%

cyclohexylammonium betulonate → betulonic acid (4481-62-3)

Guidance literature:

With phosphoric acid; In dichloromethane; water;

DOI:10.1016/j.steroids.2016.08.002

Reference yield: 93.0%

Betulinic acid (472-15-1) → betulonic acid (4481-62-3)

Guidance literature:

With pyridinium chlorochromate; In chloroform; for 2h; Ambient temperature;

DOI:10.1016/S0031-9422(98)00167-8

upstream raw materials:

betulonic aldehyde

Betulinic acid

betulin

acetic acid

Downstream raw materials:

3-oxolupan-28-ic acid

dihydrobetulinic acid

3α-20,29-dihydrobetulunic acid

(S)-2-tert-Butoxycarbonylamino-6-[((1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-icosahydro-cyclopenta[a]chrysene-3a-carbonyl)-amino]-hexanoic acid methyl ester

Refernces

• 1、 Ayers, Sloan,Benkovics, Tamas,Marshall, Jonathan,Tan, Yichen,Strotman, Neil A.,Kiau, Susanne. "Autoxidation Products of Betulonaldehyde". . p. 2758 - 2761. Retrieved 2016.
• 2、 Cui, Hai-Wei,He, Yuan,Wang, Jinhua,Gao, Wei,Liu, Ting,Qin, Min,Wang, Xue,Gao, Cheng,Wang, Yan,Liu, Ming-Yao,Yi, Zhengfang,Qiu, Wen-Wei. "Synthesis of heterocycle-modified betulinic acid derivatives as antitumor agents". . p. 240 - 248. Retrieved 2015.
• 3、 H?rm?, Ville,Haavikko, Raisa,Virtanen, Johannes,Ahonen, Ilmari,Schukov, Hannu-Pekka,Alakurtti, Sami,Purev, Enkhee,Rischer, Heiko,Yli-Kauhaluoma, Jari,Moreira, Vania M.,Nees, Matthias,Oksman-Caldentey, Kirsi-Marja. "Optimization of invasion-specific effects of betulin derivatives on prostate cancer cells through lead development". . . Retrieved 2015.
• 4、 Chen, Yingying,Li, Man,Ma, Wenxiao,Ran, Fuxiang,Xiao, Sulong,Yuan, Lan,Zhang, Lihe,Zhou, Demin. "Rhodamine B-based fluorescent probes for molecular mechanism study of the anti-influenza activity of pentacyclic triterpenes". . . Retrieved 2020.
• 5、 Bastos, Denise Z.L.,Pimentel, Ida C.,de Jesus, Daniel A.,de Oliveira, Bras H.. "Biotransformation of betulinic and betulonic acids by fungi". . p. 834 - 839. Retrieved 2007.
• 6、 Tolmacheva,Grishko,Boreko,Savinova,Pavlova. "Synthesis and antiviralactivity of 2,3-seco-derivatives of betulonic acid". . p. 673 - 676. Retrieved 2009.
• 7、 da Silva, Elenilson F.,de Vargas, Artur S.,Willig, Julia B.,de Oliveira, Cristiane B.,Zimmer, Aline R.,Pilger, Diogo A.,Buffon, Andréia,Gnoatto, Simone C.B.. "Synthesis and antileukemic activity of an ursolic acid derivative: A potential co-drug in combination with imatinib". . . Retrieved 2021.
• 8、 Bebenek, Ewa,Chrobak, Elwira,Wietrzyk, Joanna,Kadela, Monika,Chrobak, Artur,Kusz, Joachim,Ksiazek, Maria,Jastrzebska, Maria,Boryczka, Stanislaw. "Synthesis, structure and cytotoxic activity of acetylenic derivatives of betulonic and betulinic acids". . p. 210 - 219. Retrieved 2016.
• 9、 Gupta, Nidhi,Rath, Santosh K.,Singh, Jasvinder,Qayum, Arem,Singh, Shashank,Sangwan, Payare L.. "Synthesis of novel benzylidene analogues of betulinic acid as potent cytotoxic agents". . p. 517 - 530. Retrieved 2017.
• 10、 Yang, Sheng-Jie,Liu, Ming-Chuan,Zhao, Qi,Hu, De-Yu,Xue, Wei,Yang, Song. "Synthesis and biological evaluation of betulonic acid derivatives as antitumor agents". . p. 58 - 65. Retrieved 2015.