476-60-8

Basic information

• Product Name: Anthracene-1,4,9,10-tetraol
• Synonyms: 2,3-DIHYDRO-9,10-DIHYDROXY-1,4-ANTHRAQUINONE;1,4-DIHYDROXYANTHRAHYDROQUINONE;1,4-DIHYDROXY ANTHRAQUINONE LEUCO COMPOUND;1,4,9,10-TETRAHYDROXYANTHRACENE;1,4,9,10-ANTHRACENETETROL;ANTHRACENE-1,4,9,10-TETRAOL;LEUCOQUINIZARIN;LEUCO QUINIZARINE
• CAS NO: 476-60-8
• Molecular Formula: C₁₄H₁₀O₄
• Molecular Weight: 242.23
• EINECS: 207-507-8
• Product Categories: Anthracenes
• Mol File: 476-60-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 151 °C
• Boiling Point: 305.05°C (rough estimate)
• Flash Point: 322.7 °C
• Appearance: Light yellow powder.
• Density: 1.1478 (rough estimate)
• Vapor Pressure: 4.74E-17mmHg at 25°C
• Refractive Index: 1.5190 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.11±0.30(Predicted)
• CAS DataBase Reference: Anthracene-1,4,9,10-tetraol(CAS DataBase Reference)
• NIST Chemistry Reference: Anthracene-1,4,9,10-tetraol(476-60-8)
• EPA Substance Registry System: Anthracene-1,4,9,10-tetraol(476-60-8)

Safety Data

• RTECS: OH4742000
• Hazardous Substances Data: 476-60-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 19, p. 2937, 1978 DOI: 10.1016/S0040-4039(01)94905-6

InChI:InChI=1/C14H10O4/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6,15-18H

Upstream product

• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 59637-76-2 semiquinone of 1,4-dihydroxy-anthracene-9,10-dione 

Downstream Products

• 67905-17-3 N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]ethanamide 
• 81-48-1 1-hydroxy-4-(4-methylphenylamino)-9,10-anthraquinone 
• 134774-69-9 2-((S)-2-Benzyloxy-4,5-dihydroxy-2-methyl-pentyl)-1,4-dihydroxy-anthraquinone 
• 65271-75-2 1,4-(dihydroxypentylamino)anthracene-9,10-dione 
• 132000-22-7 (5R)-3-O-Benzyl-1,2-O-isopropylidene-3-C-methyl-5-(9',10'-dihydro-1',4'-dihydroxy-9',10'-dioxo-2'-anthryl)-α-D-ribofuranose 
• 132000-20-5 (5S)-3-O-Benzyl-1,2-O-isopropylidene-3-C-methyl-5-(9',10'-dihydro-1',4'-dihydroxy-9',10'-dioxo-2'-anthryl)-α-D-ribofuranose 
• 58976-97-9 6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacene-quinone 

Relevant articles and documents

Synthesis of mono- and bis-substituted anthraquinones as inhibitors of human telomerase

A number of anthraquinone derivatives have been synthesized in good yield and tested for their ability to inhibit the enzymes telomerase and Taq polymerase using a modified telomeric repeat amplification protocol. In addition, all the synthesized compounds were screened against a panel of ovarian carcinoma cell lines (A2780, CH1 and SKOV-3) to determine their cytotoxicity. All compounds tested inhibited telomerase at a concentration of 10 μM, but showed negligible inhibition of Taq polymerase. None of the compounds tested displayed significant general cell toxicity in ovarian cancer cell lines. The synthesized compounds are potential selective inhibitors of human telomerase.

Near-IR region absorbing 1,4-diaminoanthracene-9,10-dione motif?based?ratiometric chemosensors for Cu2+

1,4-Bis[2-aminoethylamino]anthracene-9,10-diones selectively bind with Cu2+ to form complexes with unusual selectivity under basic conditions. The deprotonation of the aryl amine NH in the case of these chemosensors causes a bathochromic shift in the absorption band from 585 nm and 635 nm to 725 nm and enables ratiometric estimation of Cu2+ between pH 8 and 12.

Thermodynamics of semiquinone disproportionation in aqueous buffer

The thermodynamic parameters, Kdisp, ΔH° and ΔS°, controlling the disproportionation of semiquinones derived from 1,4-benzoquinone (BQ), 1,4-naphthoquinone (NQ), 2-methylbenzoquinone (MBQ), menadione (MNQ), naphthazarin (NZQ) and quinizarin (QNZ), have been determined. Smaller disproportionation constants, Kdisp, are observed upon addition of a fused benzene ring to the semiquinone structure. Negative enthalpies and positive entropies of disproportionation govern the disproportionation equilibria. Addition of OH groups to the 5 and 8 positions in NQ?- displaces the disproportionation equilibrium to the semiquinone probably due to intramolecular hydrogen bonding.