2961-04-8

Basic information

• Product Name: 1,4,5-TRIHYDROXYANTHRAQUINONE
• Synonyms: 1,4,5-TRIHYDROXYANTHRAQUINONE;1,4,8-TRIHYDROXYANTHRAQUINONE;1,4,5-trihydroxy-9,10-anthraquinone;1,4,5-trihydroxyanthracene-9,10-dione
• CAS NO: 2961-04-8
• Molecular Formula: C₁₄H₈O₅
• Molecular Weight: 256.21032
• EINECS: 220-992-0
• Mol File: 2961-04-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 254-256 °C (decomp)
• Boiling Point: 503.4°Cat760mmHg
• Flash Point: 272.3°C
• Appearance: /
• Density: 1.659g/cm³
• Vapor Pressure: 9.35E-11mmHg at 25°C
• Refractive Index: 1.772
• PKA: 6.36±0.20(Predicted)
• CAS DataBase Reference: 1,4,5-TRIHYDROXYANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,5-TRIHYDROXYANTHRAQUINONE(2961-04-8)
• EPA Substance Registry System: 1,4,5-TRIHYDROXYANTHRAQUINONE(2961-04-8)

Safety Data

• Hazardous Substances Data: 2961-04-8(Hazardous Substances Data)

Usage

Family

Anthraquinone

Type

Naturally occurring organic compound

Color

Red pigment

Natural Sources

Various plants, lichens, and fungi

Industrial Use

Dyeing and coloring in the textile industry

Chemical Structure

Three hydroxyl groups attached to an anthraquinone core

Pharmacological Properties

a. Antioxidant
b. Anti-inflammatory
c. Anticancer effects

Traditional Medicine Uses

a. Laxative
b. Diuretic

InChI:InChI=1/C14H8O5/c15-7-3-1-2-6-10(7)14(19)12-9(17)5-4-8(16)11(12)13(6)18/h1-5,15-17H

Upstream product

• 117-10-2 1,8-dihydroxy-9,10-anthracenedione 
• 1594-64-5 1,4,8-Trichloroanthraquinone 
• 496-64-0 3-hydroxy-2-pyrone 
• 475-38-7 5,8-Dihydroxy-1,4-naphthoquinone 
• 104901-38-4 5-methoxy-9-hydroxy-10-chloro-1,4-anthraquinone 
• 86278-83-3 4-ethylenedioxy-(3-nitromethyl)-pentanal 
• 69043-83-0 1,4-dioxo-1,2,3,4-tetrahydro-5,9,10-trihydroxyanthracene(leuco 1,4,5-trihydroxy-9,10-anthraquinone) 
• 64831-62-5 2-<2,5-Dimethoxy-benzoyl>-6-methoxy-benzoesaeure 
• 64831-67-0 1,4-dihydroxy-5-methoxy-9,10-anthracenedione 
• 86911-88-8 3-(2,5-Dimethoxy-phenyl)-7-methoxy-3H-isobenzofuran-1-one 
• 86911-85-5 ethyl 4-(2,5-dimethoxyphenyl)-4-hydroxy-2-butynoate 
• 78048-06-3 (4α,4aβ,9aβ)-9a-chloro-8-hydroxy-1,1,4-trimethoxy-1,4,4a,9a-tetrahydroanthraquinone 
• 84399-87-1 (4α,4aβ,9aβ)-8-hydroxy-1,1,4-trimethoxy-1,4,4a,9a-tetrahydroanthraquinone 
• 18855-92-0 3-chlorojuglone 

Downstream Products

• 81-60-7 1,4,5,8-tetrahydroxy-anthraquinone 
• 132000-36-3 (5S)-3-O-Benzyl-3-C-methyl-1,2-O-isopropylidene-5-(9',10'-dihydro-1',4',5'-trihydroxy-9',10'-dioxo-2'-anthryl)-α-D-ribofuranose 
• 132024-68-1 (5R)-3-O-benzyl-3-C-methyl-1,2-O-isopropylidene-5-(9',10'-dihydro-1',4',5'-trihydroxy-9',10'-dioxo-2'-anthryl)-α-D-ribofuranose hemihydrate 
• 132000-34-1 (5S)-3-O-Benzyl-3-C-methyl-5-(9',10'-dihydro-1',4',5'-trihydroxy-9',10'-dioxo-2-anthryl)-α,β-D-ribopyranose 
• 132000-34-1 (5R)-3-O-Benzyl-3-C-methyl-5-(9',10'-dihydro-1',4',5'-trihydroxy-9',10'-dioxo-2'-anthryl)-α-β-D-ribopyranose 
• 132000-30-7 (4R)-2-O-Benzyl-2-C-methyl-3-O-formyl-4-(9',10'-dihydro-1',4',5'-trihydroxy-9',10'-dioxo-2'-anthryl)-α(β)-D-erythro-tetrafuranose hemihydrate 
• 132000-30-7 (4S)-2-O-Benzyl-2-C-methyl-3-O-formyl-4-(9',10'-dihydro-1',4',5'-trihydroxy-9',10'-dioxo-2-anthryl)-α,β-D-erythro-tetrafuranose 
• 132000-29-4 5-Deoxy-3-O-benzyl-3-C-methyl-1,2-O-isopropylidene-5-(9',10',-dihydro-1',4',5'-trihydroxy-9',10'-dioxo-2'-anthryl)-α-D-ribofuranose hemihydrate 
• 117-10-2 1,8-dihydroxy-9,10-anthracenedione 
• 117-12-4 1,5-dihydroxyanthraquinone 
• 476-56-2 islandicin 

Relevant articles and documents

1,4-Anthraquinonoid dienophiles applicable to synthesis of linear tetracycles

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Synthesis and activity of substituted anthraquinones against a human filarial parasite, Brugia malayi

Lymphatic filariasis (elephantiasis) is a global public health problem caused by the parasitic nematodes Wuchereria bancrofti and Brugia malayi. We have previously reported anthraquinones from daylily roots with potent activity against pathogenic trematode Schistosoma mansoni. Here we report the synthesis of novel anthraquinones A-S and their antifilrarial activity. Anthraquinones A-S were synthesized by a single-step Friedel-Crafts acylation reaction between phthalic anhydrides and substituted benzenes. The antifilarial properties of these synthetic anthraquinones were tested against microfilaria as well as adult male and female worms of B. malayi. The most active anthraquinone was K, which showed 100% mortality within 1, 5, and 3 days, respectively, against microfilaria and adult male and female worms at 5 ppm concentration. Albendazole, an oral drug currently used to treat parasitic infections, was used as a positive control. Methylated products of anthraquinones did not affect the microfilaria. Histological examination of treated adult female parasites showed most of the anthraquinones caused marked effects on intrauterine embryos.

REGIOSELECTIVE REACTIONS OF 9-HYDROXY-10-CHLORO-1,4-ANTHRAQUINONE. SYNTHESIS OF DIGITOPURPONE AND ISLANDICIN

9-Hydroxy-10-chloro-1,4-anthraquinone, obtained in the reaction of 1,4-dihydroxy-9,10-anthraquinone with thionyl chloride, is nitrated selectively at the peri position to the chlorine atom and is converted into 5-nitro-9-hydroxy-10-chloro-1,4-anthraquinone.The isomeric 8-nitro-9-hydroxy-10-chloro-1,4-anthraquinone is formed during the hydrolysis of the nitration product and the subsequent reaction of 5-nitro-1,4-dihydroxy-9,10-anthraquinone with thionyl chloride.The reaction of 9-hydroxy-10-chloro-1,4-anthraquinone and its nitro derivatives with the carbanion generated from malonic ester leads to selective alkylation at position 3.Together, the indicated reactions make it possible to realize the regioselective synthesis of 2-methyl-1,4,8- and 2-methyl-1,4,5-trihydroxy-9,10-anthraquinones.