kermesic acid (CHEBI:90183)

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ChEBI Name	kermesic acid

ChEBI ID	CHEBI:90183

Definition	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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C16H10O8

Net Charge

Average Mass

330.246

Monoisotopic Mass

330.03757

InChI

InChI=1S/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)

InChIKey

CXORMDKZEUMQHX-UHFFFAOYSA-N

SMILES

C=1C(=C2C(C3=C(C=C(O)C(C(O)=O)=C3C)C(C2=C(O)C1O)=O)=O)O

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	animal metabolite Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.

Application(s):	dye

ChEBI Ontology
Outgoing	kermesic acid (CHEBI:90183) has role animal metabolite (CHEBI:75767) kermesic acid (CHEBI:90183) has role dye (CHEBI:37958) kermesic acid (CHEBI:90183) is a monocarboxylic acid (CHEBI:25384) kermesic acid (CHEBI:90183) is a tetrahydroxyanthraquinone (CHEBI:37496) kermesic acid (CHEBI:90183) is conjugate acid of kermesate (CHEBI:149530)

Incoming	kermesate (CHEBI:149530) is conjugate base of kermesic acid (CHEBI:90183)

IUPAC Name

3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Synonyms	Sources
1-Methyl-2-carboxy-3,5,6,8-tetrahydroxyanthraquinone	ChemIDplus
C.I. 75460	ChEBI
C.I. Natural Red 3	ChemIDplus
kermes	ChEBI
natural red 3	ChEBI

Citation	Type	Source
26515013	PubMed citation	Europe PMC

Last Modified

03 November 2015