481-73-2

Basic information

• Product Name: 1,3,8-trihydroxy-6-hydroxymethylanthraquinone
• Synonyms: 1,3,8-trihydroxy-6-hydroxymethylanthraquinone;1,3,8-Trihydroxy-6-(hydroxymethyl)anthracene-9,10-dione;1,3,8-Trihydroxy-6-hydroxymethyl-9,10-anthracenedione;ω-Hydroxyemodin
• CAS NO: 481-73-2
• Molecular Formula: C₁₅H₁₀O₆
• Molecular Weight: 286.2363
• Mol File: 481-73-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: 288 °C
• Boiling Point: 672.3°Cat760mmHg
• Flash Point: 374.4°C
• Appearance: /
• Density: 1.702g/cm³
• Vapor Pressure: 5.43E-19mmHg at 25°C
• Refractive Index: 1.783
• PKA: 6.23±0.20(Predicted)
• CAS DataBase Reference: 1,3,8-trihydroxy-6-hydroxymethylanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,8-trihydroxy-6-hydroxymethylanthraquinone(481-73-2)
• EPA Substance Registry System: 1,3,8-trihydroxy-6-hydroxymethylanthraquinone(481-73-2)

Safety Data

• Hazardous Substances Data: 481-73-2(Hazardous Substances Data)

Usage

General Description

1,3,8-Trihydroxy-6-hydroxymethylanthraquinone is a chemical compound that belongs to the class of organic compounds known as anthraquinones. Anthraquinones are organic compounds containing either anthracene or phenanthrene carrying two ketone groups at the 9- and 10- positions. This particular compound, as the name suggests, contains three hydroxy groups and one hydroxymethyl group attached to the anthraquinone structure. It is also known by its less complex IUPAC name, Trihydroxyhydroxymethylanthraquinone. However, little is known about the exact properties, uses, or safety concerns associated with this compound due to the limited research available.

InChI:InChI=1/C15H10O6/c16-5-6-1-8-12(10(18)2-6)15(21)13-9(14(8)20)3-7(17)4-11(13)19/h1-4,16-19H,5H2

Upstream product

• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 
• 478-35-3 6,8-dihydroxy-3-(hydroxymethyl)-1-methoxyanthra-9,10-quinone 
• 134070-56-7 3-bromomethyl-1,6,8-trihydroxy-anthraquinone 
• 132319-49-4 4,5,7-trimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde 
• 121210-61-5 3-(dibromomethyl)-1,6,8-trimethoxyanthracene-9,10-dione 
• 6414-42-2 1,3,8-trimethoxy-6-methyl-9,10-anthraquinone 
• 96822-98-9 1,3,8-triacetoxyanthracene-9,10-dione-6-carbaldehyde 
• 33770-95-5 6-formyl-1,3,8-trihydroxyanthracene-9,10-dione 
• 1373404-37-5 1,8-diacetoxy-3-hydroxyanthracene-9,10-dione-6-carbaldehyde 
• 61350-19-4 4,5,7-triacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid 
• 152039-23-1 3-(Acetoxymethyl)-1-hydroxy-6,8-dimethoxy-9,10-anthracenedione 
• 152039-16-2 4-(Acetyloxy)-6-chloro-5,8-dimethoxy-2-(acetoxymethyl)naphthalene 
• 152039-17-3 4-(Acetyloxy)-2-(acetoxymethyl)-6-chloro-5,8-naphthalenedione 
• 152039-18-4 2-(Acetoxymethyl)-6-chloro-4-hydroxy-5,8-naphthalenedione 

Downstream Products

• 569-05-1 1,8-dihydroxy-3-hydroxymethyl-6-methoxy-anthraquinone 
• 491-60-1 emodinanthrone 
• 481-72-1 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione 
• 35688-09-6 ω-hydroxyemodin-5-methyl ether 
• 478-35-3 6,8-dihydroxy-3-(hydroxymethyl)-1-methoxyanthra-9,10-quinone 
• 4517-57-1 4,5-dihydroxy-7-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde 
• 205391-53-3 3-Benzyloxy-6-bromomethyl-1,8-dihydroxy-anthraquinone 

Relevant articles and documents

A facile synthesis of emodin derivatives, emodin carbaldehyde, citreorosein, and their 10-deoxygenated derivatives and their inhibitory activities on μ-calpain

A new procedure for the preparation of emodin carbaldehyde and citreorosein was described, in which, ω,ω'-dibromomethylemodin triacetate was prepared as a key intermediate by NBSmediated bromination of 1,3,8-triacetylemodin. Reduction of emodin and citreorosein with SnCl 2 in a 1:1 mixture of HOAc and HCl afforded the corresponding anthrones in 90% and 92% yield, respectively, while the corresponding 10-desoxyemodin carbaldehyde was prepared by MnO2 oxidation of 10-desoxycitreorosein. 10-Desoxycitreorosein and emodin carbaldehyde showed feasible μ-calpain inhibitory activities with IC50 values of 20.15 and 25.77 M, respectively.

Chemoenzymatic, biomimetic total synthesis of (-)-rugulosin B, C and rugulin analogues and their biosynthetic implications

Herein, we report the chemoenzymatic synthesis of a heterodimeric (-)-rugulosin B, homodimeric (-)-rugulosin C, and several rugulin analogues in three to four steps starting from anthraquinones. This work supports dimerization between variously substituted putative monomeric intermediates during the biosynthesis of naturally occurring (+)-rugulosin B and C.

Identification and characterization of an anthrol reductase from: Talaromyces islandicus (Penicillium islandicum) WF-38-12

An NADPH-dependent oxidoreductase from Talaromyces islandicus WF-38-12 has been identified through genome analysis. It has been shown to catalyze a regio- and stereoselective reduction of anthrols (formed in situ by the reduction of anthraquinones in the presence of Na2S2O4) to (R)-dihydroanthracenones, with high enantiomeric excess (>99%). The implications of results on the biosynthesis of deoxygenated (bis)anthraquinones and modified (bis)anthraquinones are discussed.