Caffeoquinone

Base Information

• Chemical Name: Caffeoquinone
• CAS No.: 15416-77-0
• Molecular Formula: C₉H₆O₄
• Molecular Weight: 178.144
• Nikkaji Number: J39.014C
• Wikidata: Q27149812
• Mol file: 15416-77-0.mol

Synonyms:Caffeoquinone;Caffeic acid quinone;15416-77-0;2-Propenoic acid, 3-(3,4-dioxo-1,5-cyclohexadien-1-yl)-;3-(2-propenoic acid)-o-benzoquinone;caffeic acid o-quinone;2-Propenoic acid,3-(3,4-dioxo-1,5-cyclohexadien-1-yl)-;CHEBI:133316;3-(3,4-dioxocyclohexa-1,5-dien-1-yl)acrylic acid;Q27149812;(2E)-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)prop-2-enoic acid

Chemical Property of Caffeoquinone

Chemical Property:

• Boiling Point: 350.2±42.0 °C(Predicted)
• PKA: 4.40±0.10(Predicted)
• PSA: 71.44000
• Density: 1.555±0.06 g/cm3(Predicted)
• LogP: 0.26160
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 178.02660867
• Heavy Atom Count: 13
• Complexity: 358

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)C(=O)C=C1C=CC(=O)O
• Isomeric SMILES: C1=CC(=O)C(=O)C=C1/C=C/C(=O)O

Technology Process of Caffeoquinone

There total 3 articles about Caffeoquinone 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:

caffeic acid (331-39-5,501-16-6) → caffeic acid o-quinone (15416-77-0,170931-44-9)

Guidance literature:

With ammonium cerium(IV) nitrate; In methanol; at -78 ℃; for 1h;

Reference yield:

caffeic acid (331-39-5,501-16-6) → caffeic acid o-quinone (15416-77-0,170931-44-9)

Guidance literature:

With oxygen; In water; at 25 ℃; Rate constant; inhibition by 6^A-deoxy-6^A-(methylamino)-β-cyclodextrin and other aminocyclodextrins; at pH 10.0;

DOI:10.1021/jo00080a049

Reference yield:

caffeic acid (331-39-5,501-16-6) → caffeic acid o-quinone (15416-77-0,170931-44-9) + 2,5-(3',4'-dihydroxyphenyl)tetrahydrofuran-3,4-dicarboxylic acid + 2,5-(3',4'-dihydroxyphenyl)tetrahydrofuran-3,4-dicarboxylic acid

Guidance literature:

With periodate form of Amberlite IRA 904; In water; at 20 ℃; for 4h; Product distribution; Mechanism; Rate constant; pH and solvent dependence;

DOI:10.1016/S0031-9422(00)94790-3

upstream raw materials:

caffeic acid

caffeic acid

Downstream raw materials:

caffeic acid

Refernces

• 1、 Eliseev,Yatsimirskii. "Dual effect of cyclodextrins on catechol autoxidation". . p. 264 - 265. Retrieved 1994.
• 2、 Ilesanmi, Olutosin Samuel,Ojopagogo, Yetunde Adedolapo,Adewale, Isaac Olusanjo. "Kinetic characteristics of purified tyrosinase from different species of Dioscorea (YAM) in aqueous and non-aqueous systems". . p. 111 - 117. Retrieved 2014.
• 3、 Zeng, Cheng-Chu,Ping, Da-Wei,Hu, Li-Ming,Song, Xiu-Qing,Zhong, Ru-Gang. "Anodic oxidation of catechols in the presence of α-oxoketene N,N-acetals with a tetrahydropyrimidine ring: Selective α-arylation reaction". scheme or table. p. 2465 - 2472. Retrieved 2010/07/06.