L-dopaquinone

Base Information

• Chemical Name: L-dopaquinone
• CAS No.: 4430-97-1
• Molecular Formula: C9H9 N O4
• Molecular Weight: 195.175
• Hs Code.: 2922509090
• UNII: 5P7FHT9NL7
• DSSTox Substance ID: DTXSID80863397
• Nikkaji Number: J943.581F
• Wikipedia: L-Dopaquinone
• Wikidata: Q106315140
• ChEMBL ID: CHEMBL1743218
• Mol file: 4430-97-1.mol

Synonyms:4-(2-carboxy-2-aminoethyl)-1,2-benzoquinone;dopaquinone;dopaquinone, (S)-isomer;o-dopaquinone

Chemical Property of L-dopaquinone

Chemical Property:

• Vapor Pressure: 3.25E-08mmHg at 25°C
• Boiling Point: 419.5°Cat760mmHg
• Flash Point: 207.5°C
• PSA: 97.46000
• Density: 1.426g/cm³
• LogP: 0.12310
• XLogP3: -3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 195.05315777
• Heavy Atom Count: 14
• Complexity: 354

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)C(=O)C=C1CC(C(=O)O)N

Technology Process of L-dopaquinone

There total 10 articles about L-dopaquinone 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: 88.0%

→ Dopaquinone (4430-97-1)

Guidance literature:

Reference yield:

?Tyr (556-02-5,556-03-6,34537-57-0,55520-40-6,96946-98-4,60-18-4,18875-48-4,25619-78-7,30704-25-7) → dopa (63-84-3,90638-38-3) + 3,3'-dityrosine (980-21-2) + Dopaquinone (4430-97-1)

Guidance literature:

With ozone; In water; Product distribution;

DOI:10.1007/BF00657696

Reference yield:

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → levodopa (59-92-7,90638-38-3) + L-dopaquinone (4430-97-1,25520-73-4,39801-65-5,77942-59-7)

Guidance literature:

With mushroom tyrosinase; In aq. phosphate buffer; dimethyl sulfoxide; for 0.5h; Enzymatic reaction;

DOI:10.1016/j.bioorg.2020.104108

upstream raw materials:

dopa

levodopa

?Tyr

3-O-methyldopa

Downstream raw materials:

5-S-G-L-D

3-<(R)-2-amino-2-carboxyethylthio>-5-<(S)-2-amino-2-carboxyethyl>-1,2-dihydroxybenzene

levodopa

leucodopachromene

Refernces

• 1、 Chila, Victor K. F.,Sorilaga, Manuel P.,Hubbard, Arthur T.,Anderson, Stanley E.. "Electrochemistry of Chemisorbed Molecules. 4.The Effect of Chirality on the Orientation and Electrochemical Oxidation of l - and dl-DOPA". . p. 232 - 235. Retrieved 1983.
• 2、 George, Augustine,Indhu, Mohan,Ashokraj, Sundarapandian,Shanmugam, Ganesh,Ganesan, Ponesakki,Kamini, Numbi Ramudu,Ayyadurai, Niraikulam. "Genetically encoded dihydroxyphenylalanine coupled with tyrosinase for strain promoted labeling". supporting information. . Retrieved 2021/11/08.
• 3、 Liu, Lu-Lu,Ren, Yuan-Jing,Song, Wei,Wei, Shu-Dong,Yang, Hai-Bo. "Inhibitory effects and molecular mechanism on mushroom tyrosinase by condensed tannins isolation from the fruit of Ziziphus jujuba Mill. var. spinosa (Bunge) Hu ex H. F. Chow". . p. 1813 - 1821. Retrieved 2020/11/03.