Quinovic acid

Base Information

• Chemical Name: Quinovic acid
• CAS No.: 465-74-7
• Molecular Formula: C30H46O5
• Molecular Weight: 486.692
• UNII: 9JP167T0ZN
• DSSTox Substance ID: DTXSID10963591
• Nikkaji Number: J12.650K
• Wikidata: Q27272637
• ChEMBL ID: CHEMBL4463264
• Mol file: 465-74-7.mol

Synonyms:(3beta)-3-hydroxyurs-12-ene-27,28-dioic acid;quinovic acid

Chemical Property of Quinovic acid

Chemical Property:

• Vapor Pressure: 4.52E-18mmHg at 25°C
• Melting Point: 298°C (rough estimate)
• Refractive Index: 1.5800 (estimate)
• Boiling Point: 621.9°Cat760mmHg
• Flash Point: 343.9°C
• PSA: 94.83000
• Density: 1.18g/cm³
• LogP: 6.15420
• Storage Temp.: 2-8°C
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 486.33452456
• Heavy Atom Count: 35
• Complexity: 968

Purity/Quality:

98%min ^*data from raw suppliers

Quinovicacid 95+% ^*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(C5(C)C)O)C)C)C2C1C)C(=O)O)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(CC[C@@H](C5(C)C)O)C)C)[C@@H]2[C@H]1C)C(=O)O)C(=O)O
• Uses: Quinovic Acid can be used to mediate anti-cancer effects.

Technology Process of Quinovic acid

There total 1 articles about Quinovic 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:

(3β)-3-[(2-O-sulfo-β-D-mannopyranosyl)oxy]urs-12-ene-27,28-dioic acid (1360864-83-0) + 1-O-[(3β)-27-hydroxy-3-(β-D-mannopyranosyloxy)-27,28-dioxours-12-en-28-yl]-β-D-glucopyranose (1360864-82-9) → D-Mannose (3458-28-4) + D-glucose (50-99-7) + quinovic acid (465-74-7)

Guidance literature:

With trifluoroacetic acid; In methanol; water; at 90 ℃; for 4h;

DOI:10.1002/hlca.201100261

Reference yield:

quinovic acid (465-74-7) → 2,9-dimethyl-picene (1679-02-3) + 2,9,10-trimethyl-picene

Guidance literature:

at 340 ℃;

DOI:10.1002/hlca.19430260134

Reference yield:

quinovic acid (465-74-7) → 3β-hydroxy-27-[(E)-4′-(O-tert-butyldimethylsilyl)feruloyloxy]urs-12-en-28-aldehyde

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C

2: diisobutylaluminium hydride / dichloromethane; hexane / 0 - 20 °C

3: potassium bromide; sodium hydrogencarbonate; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; water / 1.33 h / 20 °C

4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / 1,2-dichloro-ethane / 48 h / 40 °C

With dmap; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium bromide; In hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 4: |Steglich Esterification;

DOI:10.1021/acs.jnatprod.6b00392

upstream raw materials:

(3β)-3-[(2-O-sulfo-β-D-mannopyranosyl)oxy]urs-12-ene-27,28-dioic acid

1-O-[(3β)-27-hydroxy-3-(β-D-mannopyranosyloxy)-27,28-dioxours-12-en-28-yl]-β-D-glucopyranose

Downstream raw materials:

benzoic acid-(3-benzoyloxy-urs-12-ene-27,28-dioic acid )-anhydride

2,9-dimethyl-picene

3-benzoyloxy-urs-12-ene-27,28-dioic acid dimethyl ester

Refernces