3-Oxo-12-ursen-28-oic acid

Base Information

• Chemical Name: 3-Oxo-12-ursen-28-oic acid
• CAS No.: 6246-46-4
• Molecular Formula: C₃₀H₄₆O₃
• Molecular Weight: 454.693
• Hs Code.: 2918300090
• Wikidata: Q104172071
• Mol file: 6246-46-4.mol

Synonyms:3-oxo-12-ursen-28-oic acid

Chemical Property of 3-Oxo-12-ursen-28-oic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 284-285 °C
• Refractive Index: 1.55
• Boiling Point: 555.078 °C at 760 mmHg
• PKA: 4.68±0.70(Predicted)
• Flash Point: 303.558 °C
• PSA: 54.37000
• Density: 1.097 g/cm³
• LogP: 7.29770
• Storage Temp.: 2-8°C
• XLogP3: 7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 454.34469533
• Heavy Atom Count: 33
• Complexity: 916

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-oxo-urs-12-en-28-oic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(=O)C5(C)C)C)C)C2C1C)C)C(=O)O
• Uses: Ursonic acid (UNA) is a phytochemical which can be also extracted from a great variety of traditional medicinal herbs. It can be used as a cosmetics additive and serve as a starting material for synthesis of more potent bioactive derivatives, such as experimental antitumor agents. Ursonic acid induces the apoptosis of human cancer cells through multiple signaling pathways.

Technology Process of 3-Oxo-12-ursen-28-oic acid

There total 8 articles about 3-Oxo-12-ursen-28-oic 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%

ursolic acid (77-52-1) → ursonic acid (94482-51-6,6246-46-4)

Guidance literature:

With Jones reagent; silica gel; In acetone; at 0 ℃; for 0.5h;

DOI:10.1016/j.ejmech.2016.04.051

Reference yield: 91.0%

ursolic acid (77-52-1,989-30-0,26532-58-1,74984-66-0,121467-37-6) → 3-oxo-urs-12-en-28-oic acid (6246-46-4,94482-51-6)

Guidance literature:

With Jones reagent; In acetone; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.ejmech.2013.05.029

Reference yield: 6.23%

ursolic acid (77-52-1) → ursonic acid (94482-51-6,6246-46-4) + 1β,11α-dihydroxy-3-oxo-urs-12-en-28-oic acid + 1β-hydroxy-3-oxo-urs-12-en-28,13-lactone + 1β,3β,11α-trihydroxyurs-12-en-28-oic acid + 1β,11α-dihydroxy-3-oxo-urs-12-en-28-o-β-D-glucopyranoside

Guidance literature:

Microbiological reaction;

DOI:10.1016/j.bmcl.2017.03.076

upstream raw materials:

ursolic acid

ursolic acid

urs-12-en-3,28-diol

(3β)-3-acetoxy-urs-12-en-28-carboxylic acid

Refernces

• 1、 Jin, Chun-Mei,Jin, Chunmei,Jin, Li-Li,Liu, Fang,Wei, Zhi-Yu,Zhang, Lin-Hao. "Evaluation of ursolic acid derivatives with potential anti-Toxoplasma gondii activity". . . Retrieved 2020.
• 2、 Wu, Jie,Zhang, Zhi-Hong,Zhang, Lin-Hao,Jin, Xue-Jun,Ma, Juan,Piao, Hu-Ri. "Design, synthesis, and screening of novel ursolic acid derivatives as potential anti-cancer agents that target the HIF-1α pathway". . p. 853 - 858. Retrieved 2019.
• 3、 Zhang, Te,He, Baoen,Yuan, Huan,Feng, Gaili,Chen, Fenglian,Wu, Aizhi,Zhang, Lili,Lin, Huiran,Zhuo, Zhenjian,Wang, Tao. "Synthesis and Antitumor Evaluation in Vitro of NO-Donating Ursolic Acid-Benzylidene Derivatives". . . Retrieved 2019.
• 4、 Meng, Yan-Qiu,Zhang, Liang-Feng,Liu, Dong-Ying,Liu, Li-Wei,Zhang, Yi,Zhao, Min-Jie. "Synthesis and antitumor activity evaluation of novel ursolic acid derivatives". . p. 280 - 288. Retrieved 2016.
• 5、 Fu, Hai-Jian,Zhao, Yang,Zhou, Yu-Ren,Bao, Bei-Hua,Du, Yun,Li, Jian-Xin. "Ursolic acid derivatives as bone anabolic agents targeted to tryptophan hydroxylase 1 (Tph-1)". . p. 33 - 47. Retrieved 2015.
• 6、 Li, A-Liang,Hao, Yun,Wang, Wen-Yan,Liu, Qing-Song,Sun, Yue,Gu, Wen. "Design, synthesis, and anticancer evaluation of novel indole derivatives of ursolic acid as potential topoisomerase II inhibitors". . . Retrieved 2020.
• 7、 Chen, Yingyu,Li, Cailong,Zheng, Yunquan,Gao, Yu,Hu, Jianda,Chen, Haijun. "Discovery of FZU-03,010 as a self-assembling anticancer amphiphile for acute myeloid leukemia". . p. 1007 - 1011. Retrieved 2017.
• 8、 Kashiwada,Nagao,Hashimoto,Ikeshiro,Okabe,Cosentino,Lee. "Anti-AIDS agents 38. Anti-HIV activity of 3-O-acyl ursolic acid derivatives". . p. 1619 - 1622. Retrieved 2000.
• 9、 Dar, Bilal Ahmad,Lone, Ali Mohd,Shah, Wajaht Amin,Qurishi, Mushtaq Ahmad. "Synthesis and screening of ursolic acid-benzylidine derivatives as potential anti-cancer agents". . p. 26 - 32. Retrieved 2016.
• 10、 He, Rong-Jing,Huo, Hong,Li, Yan-Ran,Pan, Qiu-Sha,Qian, Xing-Kai,Sun, Cheng-Gong,Sun, Lei,Wang, Le-Tian,Wang, Ya-Jie,Yang, Ling,Zhang, Jing,Zhou, Xiang-Lu,Zou, Li-Wei. "Discovery of triterpenoids as potent dual inhibitors of pancreatic lipase and human carboxylesterase 1". . p. 629 - 640. Retrieved 2022/02/09.