11-Oxoursolic acid acetate

Base Information

• Chemical Name: 11-Oxoursolic acid acetate
• CAS No.: 35959-01-4
• Molecular Formula: C32H48O5
• Molecular Weight: 512.7205
• NSC Number: 33403
• UNII: 2JV36G5X6D
• DSSTox Substance ID: DTXSID80957366
• Nikkaji Number: J2.420.539H
• Wikidata: Q82937689
• ChEMBL ID: CHEMBL601891
• Mol file: 35959-01-4.mol

Synonyms:11-OXOURSOLIC ACID ACETATE;35959-01-4;(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-acetyloxy-1,2,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,5,6,6a,7,8,8a,10,11,12,14b-tetradecahydropicene-4a-carboxylic acid;CHEMBL601891;NSC-33403;3-acetyl-11-keto-ursolic acid;NSC33403;2JV36G5X6D;3-O-acetyl-11-oxoursolic acid;DTXSID80957366;CHEBI:192396;BDBM50307109;AKOS016036264;PD181222;3-(Acetyloxy)-11-oxours-12-en-28-oic acid;(3beta)-3-(Acetyloxy)-11-oxours-12-en-28-oic acid;Urs-12-en-28-oic acid, 3beta-hydroxy-11-oxo-, acetate;Urs-12-en-28-oic acid, 3-(acetyloxy)-11-oxo-, (3beta)-;(1S,2R,4AS,6AS,6BR,8AR,10S,12AS,12BR,14BS)-10-(ACETYLOXY)-1,2,6A,6B,9,9,12A-HEPTAMETHYL-13-OXO-1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A,12B,13,14B-ICOSAHYDROPICENE-4A-CARBOXYLIC ACID

Chemical Property of 11-Oxoursolic acid acetate

Chemical Property:

• Vapor Pressure: 5.3E-16mmHg at 25°C
• Boiling Point: 601.1°Cat760mmHg
• Flash Point: 184.7°C
• Density: 1.13g/cm³
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 512.35017463
• Heavy Atom Count: 37
• Complexity: 1060

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(CCC3(C(=CC(=O)C4C3(CCC5C4(CCC(C5(C)C)OC(=O)C)C)C)C2C1C)C)C(=O)O
• Isomeric SMILES: C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC(=O)[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OC(=O)C)C)C)[C@@H]2[C@H]1C)C)C(=O)O

Technology Process of 11-Oxoursolic acid acetate

There total 9 articles about 11-Oxoursolic acid acetate 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: 83.0%

(3β)-3-acetoxy-urs-12-en-28-carboxylic acid (915-79-7,7372-30-7,94482-46-9,105452-47-9,121470-75-5) → 11-oxo-ursolic acid acetate (71623-71-7,35959-01-4)

Guidance literature:

With potassium permanganate; iron(III) sulfate hydrate; In dichloromethane; water; tert-butyl alcohol; at 20 ℃; for 23h;

DOI:10.1016/j.bmc.2012.08.010

Reference yield: 15.0%

(3β)-3-acetoxy-urs-12-en-28-carboxylic acid (915-79-7,7372-30-7,94482-46-9,105452-47-9,121470-75-5) → 3-O-acetyl-20β-hydroxy-urs-11-en-28,13-olide + 11-oxo-ursolic acid acetate (71623-71-7,35959-01-4) + 3β-acetoxyurs-11-en-28,13-olide (35959-08-1,108448-74-4)

Guidance literature:

With 3,3-dimethyldioxirane; In chloroform; at 20 ℃;

DOI:10.1248/cpb.55.247

Reference yield:

ursolic acid (77-52-1) → 11-oxo-ursolic acid acetate (71623-71-7,35959-01-4)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap / tetrahydrofuran / 20 °C

2: iron(III) sulfate hydrate; potassium permanganate / water; dichloromethane; tert-butyl alcohol / 23 h / 20 °C

With dmap; potassium permanganate; iron(III) sulfate hydrate; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/j.bmc.2012.08.010

upstream raw materials:

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

ursolic acid

acetylmethyl ursolic acid

Refernces

• 1、 Manson,Spring. "". . p. 3332,3334. Retrieved 1951.
• 2、 Leal, Ana S.,Wang, Rui,Salvador, Jorge A.R.,Jing, Yongkui. "Synthesis of novel ursolic acid heterocyclic derivatives with improved abilities of antiproliferation and induction of p53, p21waf1 and NOXA in pancreatic cancer cells". . p. 5774 - 5786. Retrieved 2012/11/06.
• 3、 Ogawa, Shoujiro,Hosoi, Keiji,Ikeda, Noriaki,Makino, Mitsuko,Fujimoto, Yasuo,Iida, Takashi. "Oxyfunctionalization products of terpenoids with dimethyldioxirane and their biological activity". . p. 247 - 250. Retrieved 2007/10/03.