Corosolic acid

Base Information

• Chemical Name: Corosolic acid
• CAS No.: 4547-24-4
• Molecular Formula: C₃₀H₄₈O₄
• Molecular Weight: 472.709
• Hs Code.: 2918195000
• European Community (EC) Number: 610-253-4
• UNII: AMX2I57A98
• DSSTox Substance ID: DTXSID70904142
• Nikkaji Number: J14.066J
• Wikipedia: Corosolic_acid
• Wikidata: Q5172335
• Pharos Ligand ID: X5XG53ZWLS5D
• Metabolomics Workbench ID: 133423
• ChEMBL ID: CHEMBL391533
• Mol file: 4547-24-4.mol

Synonyms:2alpha-hydroxyursoloic acid;corosolic acid;Glucosol

Chemical Property of Corosolic acid

Chemical Property:

• Appearance/Colour: Fine-Brown Yellow Powder
• Vapor Pressure: 1.56E-15mmHg at 25°C
• Melting Point: 243～245℃
• Refractive Index: 1.566
• Boiling Point: 573.3 °C at 760 mmHg
• PKA: 4.67±0.70(Predicted)
• Flash Point: 314.6 °C
• PSA: 77.76000
• Density: 1.14 g/cm³
• LogP: 6.06030
• Storage Temp.: 2-8°C
• Solubility.: methanol: soluble1mg/mL, clear, colorless
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 472.35526001
• Heavy Atom Count: 34
• Complexity: 908

Purity/Quality:

5%, ^*data from raw suppliers

Corosolic 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(CC(C(C5(C)C)O)O)C)C)C2C1C)C)C(=O)O
• Isomeric SMILES: C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(C[C@H]([C@@H](C5(C)C)O)O)C)C)[C@@H]2[C@H]1C)C)C(=O)O
• Description: Corosolic acid is a triterpenoid that has been found in L. speciosa leaves and has diverse biological activities, including anticancer, anti-inflammatory, antidiabetic, antihypertensive, antihyperlipidemic, and antioxidant properties. It is cytotoxic to HepG2, A549, SNU-C4, HeLa S3, and K562 cells (EC50s = 4.8, 5, 0.4, 1, and 4.3 μg/ml, respectively). Corosolic acid inhibits ear edema in mice induced by phorbol 12-myristate 13-acetate (TPA; ) with an ID50 value of 0.09 mg/ear. It reduces blood glucose levels in an insulin tolerance test in a KKAy mouse model of type 2 diabetes when administered at doses of 2 and 10 mg/kg. Corosolic acid (0.072% in the diet) reduces systolic blood pressure and serum levels of free fatty acids, the oxidative stress markers thiobarbituric acid-reactive substances (TBARS) and 8-hydroxy-2’-deoxyguanosine (8-OHdG), and the myeloperoxidase markers 3-nitrotyrosine and 3-chlorotyrosine in an SHR/NDmcr-cp (cp/cp) rat model of metabolic syndrome.
• Uses: (2α,3β)-2,3-Dihydroxy-urs-12-en-28-oic Acid influences inflammatory gene expression regarding inflammatory bowel disease. In addition, its extracted from the plants Gentiana farreri and shows anti-tumor activity (2α,3β)-2,3-Dihydroxy-urs-12-en-28-oic Acid influences inflammatory gene expression regarding inflammatory bowel disease. In addition, its extracted from the plants Gentiana farreri and shows anti-tum or activity

Technology Process of Corosolic acid

There total 14 articles about Corosolic 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%

benzyl-2α,3β-dihydroxyurs-12-en-28-oic acid (869788-73-8) → corosolic acid (4547-24-4,52213-27-1,72881-13-1,87205-98-9,114580-53-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmcl.2005.08.026

Reference yield: 85.0%

2α-hydroxy-3-oxourosolic acid (132473-94-0) → 2α-hydroxy-ursolic acid (4547-24-4,52213-27-1,72881-13-1,87205-98-9,114580-53-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃;

Reference yield:

(2α,3β)-2,3-bis(acetyloxy)-urs-12-en-28-oic acid (57498-76-7) → corosolic acid (4547-24-4,52213-27-1,72881-13-1,87205-98-9,114580-53-9)

Guidance literature:

With methanol; potassium hydroxide; at 20 ℃; for 2h;

upstream raw materials:

methyl corosolate

2α,3α-diacetoxyurs-12-en-28-oic acid

methyl 2α,3β-diacetoxyurs-12-en-28-oate

benzyl-2α,3β-dihydroxyurs-12-en-28-oic acid

Downstream raw materials:

methyl 2α,3β-diacetoxyurs-12-en-28-oate

benzyl-2α,3β-dihydroxyurs-12-en-28-oic acid

3β-acetoxy-2α-hydroxyurs-12-en-28-oic acid

2α,3α-diacetoxyurs-12-en-28-oic acid

Refernces

• 1、 Fu, Shaobin,Meng, Qingfeng,Long, Shu-An,Zhang, Yun,Sun, Di-An,Wei, Gang. "Biocatalytic Synthesis of the Anti-diabetes Agent-corosolic Acid by Whole Cells of Microorganisms". . p. 871 - 874. Retrieved 2015/10/29.
• 2、 -. "Process for preparing high purity corosolic acid and high purity ursolic acid". Page/Page column 5-6. . Retrieved 2008/12/04.