Kermesic Acid

Base Information

• Chemical Name: Kermesic Acid
• CAS No.: 18499-92-8
• Molecular Formula: C16H10O8
• Molecular Weight: 330.251
• UNII: 2A580G9V9I
• DSSTox Substance ID: DTXSID40471199
• Nikkaji Number: J15.513F
• Wikidata: Q27162385
• Mol file: 18499-92-8.mol

Synonyms:Kermesic Acid;18499-92-8;C.I. Natural Red 3;Kermesic acid [MI];1-Methyl-2-carboxy-3,5,6,8-tetrahydroxyanthraquinone;C.I. 75460;2A580G9V9I;3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid;2-Anthracenecarboxylic acid, 9,10-dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-;3,5,6,8-TETRAHYDROXY-1-METHYL-9,10-DIOXO-9,10-DIHYDROANTHRACENE-2-CARBOXYLIC ACID;Kermes;9,10-Dihydro-9,10-dioxo-1-methyl-3,5,6,8-tetrahydroxyanthracene-2-carboxylic acid;UNII-2A580G9V9I;natural red 3;SCHEMBL33762;CHEBI:90183;DTXSID40471199;FT-0670608;Q27162385;3,5,6,8-TETRAHYDROXY-1-METHYL-9,10-DIOXO-9,10-DIHYDROANTHRACENE-2-CARBOXYLICACID

Chemical Property of Kermesic Acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >320° (dec)
• Boiling Point: 679.8°Cat760mmHg
• Flash Point: 378.9°C
• PSA: 152.36000
• Density: 1.818g/cm³
• LogP: 1.29100
• XLogP3: 3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 330.03756727
• Heavy Atom Count: 24
• Complexity: 574

Purity/Quality:

98%Min ^*data from raw suppliers

KermesicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C(=CC(=C1C(=O)O)O)C(=O)C3=C(C2=O)C(=CC(=C3O)O)O
• Uses: Principle constituent of kermes, one of the oldest known insect dyes. Kermesic acid is used as brilliant scarlet dye. As brilliant scarlet dye. Kermesic Acid is a principle constituent of kermes, one of the oldest known insect dyes. Used as brilliant scarlet dye.

Technology Process of Kermesic Acid

There total 10 articles about Kermesic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methyl 3,5,6,8-tetrahydroxy-1-methyl-9,10-anthraquinone-2-carboxylate (80750-89-6) → 2-carboxy-1-methyl-3,5,6,8-tetrahydroxy-anthraquinone (18499-92-8)

Guidance literature:

With hydrogenchloride; In acetic acid; Heating;

DOI:10.1039/b002591g

Reference yield: 8.0%

Methyl 3,5,6,8-tetramethoxy-1-methylanthra-9,10-quinone-2-carboxylate (69119-28-4) → 2-carboxy-1-methyl-3,5,6,8-tetrahydroxy-anthraquinone (18499-92-8) + methyl 3,5,6,8-tetrahydroxy-1-methyl-9,10-anthraquinone-2-carboxylate (80750-89-6)

Guidance literature:

With aluminium trichloride; sodium chloride; at 180 ℃; for 0.05h;

Reference yield:

1-methyl-3,6,8-trihydroxy-9,10-anthracenedione-2-carboxylic acid (18499-84-8) → 2-carboxy-1-methyl-3,5,6,8-tetrahydroxy-anthraquinone (18499-92-8)

Guidance literature:

With aklavinone 12-hydroxylase (DnrF) from Streptomyces peucetius; NADPH; In aq. buffer; at 37 ℃; for 16h; pH=7.5; Reagent/catalyst; Enzymatic reaction;

DOI:10.1021/jacs.0c12406

upstream raw materials:

Methyl 3,5,6,8-tetramethoxy-1-methylanthra-9,10-quinone-2-carboxylate

9,10-dioxo-6-hydroxy-1-methyl-3,5,8-trimethoxyanthracene-2-carboxylic acid methyl ester

methyl 3,5,6,8-tetrahydroxy-1-methyl-9,10-anthraquinone-2-carboxylate

Methyl 5,6-diacetoxy-3,8-dihydroxy-1-methylanthra-9,10-quinone-2-carboxylate