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

• 58976-97-9 6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacene-quinone 
• 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 
• 65271-75-2 1,4-(dihydroxypentylamino)anthracene-9,10-dione 
• 134774-69-9 2-((S)-2-Benzyloxy-4,5-dihydroxy-2-methyl-pentyl)-1,4-dihydroxy-anthraquinone 
• 67905-17-3 N-[4-[(4-hydroxyanthraquinone-1-yl)amino]phenyl]ethanamide 
• 81-48-1 1-hydroxy-4-(4-methylphenylamino)-9,10-anthraquinone 

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.

Anthraquinone-oligodeoxynucleotide conjugates as triple helix stabilizing agents

A number of anthraquinones have been synthesized and linked to a 10-mer homopyrimidine oligodeoxynucleotide. All the anthraquinone-oligodeoxynucleotide conjugates exhibited sequence specific triple helix formation when tested by DNase I footprinting. Neither the presence of an ionizable side chain nor the position of substitution of the anthraquinone appeared to affect triplex stability.