Scytalone

Base Information

• Chemical Name: Scytalone
• CAS No.: 49598-85-8
• Molecular Formula: C10H10O4
• Molecular Weight: 194.184
• UNII: 1MQ5L1414D
• Nikkaji Number: J20.775F
• Wikidata: Q105245472
• ChEMBL ID: CHEMBL4081370
• Mol file: 49598-85-8.mol

Synonyms:3,4-dihydro-3,6,8-trihydroxy-1(2H)naphthalenone;3,4-dihydro-3,6,8-trihydroxy-1-(2H)-naphthalenone;scytalone;scytolone

Chemical Property of Scytalone

Chemical Property:

• Vapor Pressure: 6.76E-10mmHg at 25°C
• Boiling Point: 476.7°Cat760mmHg
• Flash Point: 256.2°C
• PSA: 77.76000
• Density: 1.533g/cm³
• LogP: 0.58760
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 240

Purity/Quality:

98%min ^*data from raw suppliers

(3R)-3,4-DIHYDRO-3,6,8-TRIHYDROXY-1(2H)-NAPHTHALENONE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(CC(=O)C2=C1C=C(C=C2O)O)O
• Isomeric SMILES: C1[C@H](CC(=O)C2=C1C=C(C=C2O)O)O

Technology Process of Scytalone

There total 18 articles about Scytalone 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: 36.0%

1,3,6,8-Tetrahydroxynaphthalene (18512-30-6) → 3,6,8-Trihydroxy-3,4-dihydronaphthalen-1(2H)-one (49598-85-8,59872-10-5,144068-45-1)

Guidance literature:

With Verticillium dahliae brm-1 mutant (ATCC 44571); In ethanol; at 30 ℃; for 14h; Enzymatic reaction;

Reference yield: 36.0%

1,3,6,8-Tetrahydroxynaphthalene (18512-30-6) → scytalone (49598-85-8,59872-10-5,144068-45-1)

Guidance literature:

With glucose dehydrogenase; β-nicotinamide adenine dinucleotide phosphate disodium salt; D-glucose; recombinant oxidoreductase from Talaromyces islandicus WF-38-12; In aq. phosphate buffer; for 12h; stereoselective reaction; Inert atmosphere; Enzymatic reaction;

DOI:10.1039/c9gc03072g

Reference yield: 25.0%

1,3,6,8-Tetrahydroxynaphthalene (18512-30-6) → 3,6,8-Trihydroxy-3,4-dihydronaphthalen-1(2H)-one (49598-85-8,59872-10-5,144068-45-1) + flaviolin (479-05-0)

Guidance literature:

With sodium tetrahydroborate; sodium methylate; In methanol; Mechanism;

upstream raw materials:

1,3,6,8-Tetrahydroxynaphthalene

methyl 2-(2-acetyl-3,5-dihydroxyphenyl)acetate

1-carbomethoxy-3,5-dihydroxybenzene

methyl 3,5-bis(benzyloxy)benzoate

Downstream raw materials:

flaviolin

2-Hydroxyjuglon

1,3,6,8-Tetrahydroxynaphthalene

Refernces

• 1、 Singh, Shailesh Kumar,Mondal, Amit,Saha, Nirmal,Husain, Syed Masood. "Identification and characterization of an anthrol reductase from: Talaromyces islandicus (Penicillium islandicum) WF-38-12". supporting information. p. 6594 - 6599. Retrieved 2019/12/26.
• 2、 Ichinose,Ebizuka,Sankawa. "Mechanistic studies on the biomimetic reduction of tetrahydroxynaphthalene, a key intermediate in melanin biosynthesis". . p. 192 - 196. Retrieved 2007/10/03.