18499-92-8

Basic information

• Product Name: 9,10-Dihydro-9,10-dioxo-1-methyl-3,5,6,8-tetrahydroxyanthracene-2-carboxylic acid
• Synonyms: 9,10-Dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic acid;9,10-Dihydro-9,10-dioxo-1-methyl-3,5,6,8-tetrahydroxyanthracene-2-carboxylic acid;Kermesic acid;1-Methyl-2-carboxy-3,5,6,8-tetrahydroxyanthraquinone;C.I. Natural Red 3;KerMes;KerMes (dye)
• CAS NO: 18499-92-8
• Molecular Formula: C₁₆H₁₀O₈
• Molecular Weight: 330.2458
• Product Categories: Aromatics
• Mol File: 18499-92-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: >320° (dec)
• Boiling Point: 679.8°Cat760mmHg
• Flash Point: 378.9°C
• Appearance: /
• Density: 1.818g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.805
• CAS DataBase Reference: 9,10-Dihydro-9,10-dioxo-1-methyl-3,5,6,8-tetrahydroxyanthracene-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-Dihydro-9,10-dioxo-1-methyl-3,5,6,8-tetrahydroxyanthracene-2-carboxylic acid(18499-92-8)
• EPA Substance Registry System: 9,10-Dihydro-9,10-dioxo-1-methyl-3,5,6,8-tetrahydroxyanthracene-2-carboxylic acid(18499-92-8)

Safety Data

• Hazardous Substances Data: 18499-92-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 18499-92-8 differently. You can refer to the following data:
1. Principle constituent of kermes, one of the oldest known insect dyes. Kermesic acid is used as brilliant scarlet dye.
2. As brilliant scarlet dye.
3. Kermesic Acid is a principle constituent of kermes, one of the oldest known insect dyes. Used as brilliant scarlet dye.

Definition

ChEBI: A tetrahydroxyanthraquinone that is that is 3,5,6,8-tetrahydroxy-9,10-anthraquinone substituted by methyl and carboxy groups at positions 1 and 2 respectively. It is a natural dye isolated from the insect species Kermes ilices .

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

• 110551-57-0 9,10-dioxo-6-hydroxy-1-methyl-3,5,8-trimethoxyanthracene-2-carboxylic acid methyl ester 
• 80750-89-6 methyl 3,5,6,8-tetrahydroxy-1-methyl-9,10-anthraquinone-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 
• 69119-28-4 Methyl 3,5,6,8-tetramethoxy-1-methylanthra-9,10-quinone-2-carboxylate 

Relevant articles and documents

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

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

A Simple Transformation of Carminic Acid into Kermesic Acid

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