5,8-Dihydroxy-1,4-naphthoquinone

Base Information

• Chemical Name: 5,8-Dihydroxy-1,4-naphthoquinone
• CAS No.: 475-38-7
• Molecular Formula: C10H6O4
• Molecular Weight: 190.155
• Hs Code.: 2914690090
• European Community (EC) Number: 207-495-4
• NSC Number: 344555,26647
• UNII: S9IX5I5C0K
• DSSTox Substance ID: DTXSID00197161
• Nikkaji Number: J12.362E,J939.863E
• Wikipedia: Naphthazarin
• Wikidata: Q4639550
• Pharos Ligand ID: H26CYVULPP8Q
• Metabolomics Workbench ID: 129981
• ChEMBL ID: CHEMBL274056
• Mol file: 475-38-7.mol

Synonyms:5,8-dihydroxy-1,4-naphthoquinone;5,8-dioxy-1,4-naphthoquinone;naphthazarin

Chemical Property of 5,8-Dihydroxy-1,4-naphthoquinone

Chemical Property:

• Appearance/Colour: dark purple to brown-black powder
• Vapor Pressure: 1.51E-10mmHg at 25°C
• Melting Point: 220-230 °C
• Refractive Index: 1.71
• Boiling Point: 498.2 °C at 760 mmHg
• PKA: 6.98±0.20(Predicted)
• Flash Point: 269.2 °C
• PSA: 74.60000
• Density: 1.592g/cm³
• LogP: 1.03300
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Soluble in water (5520 mg/L 25.).
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 190.02660867
• Heavy Atom Count: 14
• Complexity: 277

Purity/Quality:

99% ^*data from raw suppliers

5,8-Dihydroxy-1,4-naphthoquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: C1=CC(=C2C(=O)C=CC(=O)C2=C1O)O

Technology Process of 5,8-Dihydroxy-1,4-naphthoquinone

There total 55 articles about 5,8-Dihydroxy-1,4-naphthoquinone 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: 98.0%

5,8-diacetoxy-1,4-naphthoquinone (14569-45-0) → 5,8-Dihydroxy-1,4-naphthoquinone (475-38-7)

Guidance literature:

With water; sodium hydroxide; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.3184/174751911X556710

Reference yield: 96.0%

1,4,5,8-tetramethoxynaphthalene (10075-68-0) → 5,8-Dihydroxy-1,4-naphthoquinone (475-38-7)

Guidance literature:

With lithium perchlorate; In water; acetonitrile; Electrochemical reaction;

DOI:10.1016/S0040-4039(00)01041-8

Reference yield: 93.0%

5,8-dihydroxy-2,3-dihydro-[1,4]naphthoquinone (4988-51-6) → 5,8-Dihydroxy-1,4-naphthoquinone (475-38-7)

Guidance literature:

5,8-dihydroxy-2,3-dihydro-[1,4]naphthoquinone; With sodium hydroxide; at 60 ℃; for 1.5h;

With hydrogenchloride; In water;

DOI:10.1007/s00044-016-1550-x

upstream raw materials:

maleic anhydride

hydroquinone

succinic acid anhydride

ethanol

Downstream raw materials:

5-(2',4'-dimethoxy-6'-methylbenzoyloxy)-8-hydroxy-1,4-naphthoquinone

4-(1-Cyclohexyl-ethoxy)-5,8-dihydroxy-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione

5,8-Dihydroxy-4-(2-phenyl-propoxy)-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione

5,8-Dihydroxy-4-(1-phenyl-propoxy)-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione

Refernces

• 1、 Bolton et al.. "-". . p. 169,170. Retrieved 1963.
• 2、 Zhang, Yi,Luo, Ying-Hua,Piao, Xian-Ji,Shen, Gui-Nan,Wang, Jia-Ru,Feng, Yu-Chao,Li, Jin-Qian,Xu, Wan-Ting,Zhang, Yu,Zhang, Tong,Wang, Chang-Yuan,Jin, Cheng-Hao. "The design of 1,4-naphthoquinone derivatives and mechanisms underlying apoptosis induction through ROS-dependent MAPK/Akt/STAT3 pathways in human lung cancer cells". . p. 1577 - 1587. Retrieved 2019/03/06.
• 3、 Wang, Jia-Ru,Shen, Gui-Nan,Luo, Ying-Hua,Piao, Xian-Ji,Shen, Meng,Liu, Chang,Wang, Yue,Meng, Ling-Qi,Zhang, Yi,Wang, Hao,Li, Jin-Qian,Xu, Wan-Ting,Liu, Yang,Sun, Hu-Nan,Han, Ying-Hao,Jin, Mei-Hua,Cao, Long-Kui,Jin, Cheng-Hao. "The compound 2-(naphthalene-2-thio)-5,8-dimethoxy-1,4-naphthoquinone induces apoptosis via reactive oxygen species-regulated mitogen-activated protein kinase, protein kinase B, and signal transducer and activator of transcription 3 signaling in human gastric cancer cells". . p. 295 - 306. Retrieved 2018/09/25.