18499-92-8

Usage

Uses

Used in Textile Industry:
9,10-Dihydro-9,10-dioxo-1-methyl-3,5,6,8-tetrahydroxyanthracene-2-carboxylic acid is used as a dye for [providing brilliant scarlet color] because of its natural dye properties and historical significance in the textile industry.
Used in Historical and Cultural Preservation:
9,10-Dihydro-9,10-dioxo-1-methyl-3,5,6,8-tetrahydroxyanthracene-2-carboxylic acid is used as a historical dye for [preserving and restoring ancient textiles and artifacts] due to its role as a principle constituent of kermes, one of the oldest known insect dyes.

InChI:InChI=1/C16H10O8/c1-4-9-5(2-6(17)10(4)16(23)24)13(20)12-11(15(9)22)7(18)3-8(19)14(12)21/h2-3,17-19,21H,1H3,(H,23,24)

Upstream product

• 69119-28-4 Methyl 3,5,6,8-tetramethoxy-1-methylanthra-9,10-quinone-2-carboxylate 
• 18499-84-8 1-methyl-3,6,8-trihydroxy-9,10-anthracenedione-2-carboxylic acid 
• 50-99-7 D-glucose 
• 80750-87-4 methyl 5-bromo-3,6,8-trimethoxy-1-methylanthraquinone-2-carboxylate 
• 110551-55-8 6-methyl-4,8,11-trimethoxyanthra<2,3-b>furan-5,10-dione 
• 110551-56-9 9,10-dioxo-7-formyl-6-hydroxy-1-methyl-3,5,8-trimethoxyanthracene-2-carboxylic acid methyl ester 
• 286931-58-6 Methyl 5,6-diacetoxy-3,8-dihydroxy-1-methylanthra-9,10-quinone-2-carboxylate 
• 80750-89-6 methyl 3,5,6,8-tetrahydroxy-1-methyl-9,10-anthraquinone-2-carboxylate 
• 110551-57-0 9,10-dioxo-6-hydroxy-1-methyl-3,5,8-trimethoxyanthracene-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Production of Carminic Acid by Metabolically Engineered Escherichia coli

Carminic acid is an aromatic polyketide found in scale insects (i.e., Dactylopius coccus) and is a widely used natural red colorant. It has long been produced by the cumbersome farming of insects followed by multistep purification processes. Thus, there has been much interest in producing carminic acid by the fermentation of engineered bacteria. Here we report the complete biosynthesis of carminic acid from glucose in engineered Escherichia coli. We first optimized the type II polyketide synthase machinery from Photorhabdus luminescens, enabling a high-level production of flavokermesic acid upon coexpression of the cyclases ZhuI and ZhuJ from Streptomyces sp. R1128. To discover the enzymes responsible for the remaining two reactions (hydroxylation and C-glucosylation), biochemical reaction analyses were performed by testing enzyme candidates reported to perform similar reactions. The two identified enzymes, aklavinone 12-hydroxylase (DnrF) from Streptomyces peucetius and C-glucosyltransferase (GtCGT) from Gentiana triflora, could successfully perform hydroxylation and C-glucosylation of flavokermesic acid, respectively. Then, homology modeling and docking simulations were performed to enhance the activities of these two enzymes, leading to the generation of beneficial mutants with 2-5-fold enhanced conversion efficiencies. In addition, the GtCGT mutant was found to be a generally applicable C-glucosyltransferase in E. coli, as was showcased by the successful production of aloesin found in Aloe vera. Simple metabolic engineering followed by fed-batch fermentation resulted in 0.63 ± 0.02 mg/L of carminic acid production from glucose. The strategies described here will be useful for the design and construction of biosynthetic pathways involving unknown enzymes and consequently the production of diverse industrially important natural products.

The synthesis of kermesic acid by acetylation-aided tautomerism of 6-chloro-2,5,8-trihydroxynaphtho-1,4-quinone

Methodology has been sought towards obtaining a 2-chloro-1,4-naphthoquinone bearing hydroxyl groups in the adjoining ring for obtaining either kermesic or carminic acids. In the first of these objectives, kermesic acid has been synthesised from 6-chloro-2,5,8-trihydroxynaphtho-1,4-quinone by the regioselective cycloaddition of the 1,2-diacetate formed by its acetylation-aided tautomerism and cycloaddition with (E)- and (Z)-3-alkoxycarbonyl-2,4-bis(trimethylsilyloxy)penta-1,3-dienes. The parent unacetylated quinone resists cycloaddition.

The synthesis of kermesic acid by acetylation-aided tautomerism of 6- chloro-2,5,8-trihydroxynaphtho-1,4-quinone

6-Chloro-2,5,8-trihydroxynaphtho-1,4-quinone does not undergo cycloaddition reactions but the 1,2-diacetate, 2-chloro-5,6-diacetoxy-8- hydroxynaphtho-1,4-quinone, formed by acetylation-aided tautomerism added (E)- and (Z)-3-alkoxycarbonyl-2,4-bis(trimethy

Method for dyeing keratinous fibres using a monohydroxyindole or dihydroxyindole and a non-oxidizing aromatic carbonyl derivative and dyeing agent

The present invention relates to a method for dyeing keratinous fibers, characterized in that the following are applied to the fibers: a) a composition (A) containing, in a medium appropriate for dyeing, at least one monohydroxyindole or dihydroxyindole, this application being preceded or followed by the application of b) a composition (B) containing, in a medium appropriate for dyeing, at least one aromatic carbonyl derivative chosen from hydroxyacetophenones, hydroxybenzophenones, 2-hydroxy-1,4-benzoquinones, hydroxy-1,4-naphthoquinones,amino-1,4-naphthoquinones,hydroxy-9,10-anthraquinones and amino-9,10-anthraquinones. It also relates to the dyeing agents for carrying it out.

Chemistry of the Coccoidea. VIII. Synthesis of the Ancient Dyestuff Kermesic Acid and of Related Anthraquinones

The insect anthraquinones kermesic acid (3) and laccaic acid D (2) have been synthesized efficiently, as have the plant anthraquinones aloesaponarin-I (4) and -II (33).The syntheses were based on regiospecific Diels-Alder addition of the silyloxy dienes (10) and (11) to simpler quinones.Regiospecificity was controlled by 2(3)-chloro groups in the dienophiles or, for addition to certain naphthoquinones, by a hydroxy group peri to carbonyl.