CHEBI:78310 - carminic acid

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ChEBI Name carminic acid
ChEBI ID CHEBI:78310
Definition A tetrahydroxyanthraquinone that is that is 1,3,4,6-tetrahydroxy-9,10-anthraquinone substituted by a methyl group at position 8, a carboxy group at position 7 and a 1,5-anhydro-D-glucitol moiety at position 2 via a C-glycosidic linkage. It is a natural dye isolated from several insects such as Dactylopius coccus.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3422
Supplier Information ChemicalBook:CB1454369, eMolecules:520938, ZINC000000001669
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Formula C22H20O13
Net Charge 0
Average Mass 492.389
Monoisotopic Mass 492.09039
InChI InChI=1S/C22H20O13/c1-4-8-5(2-6(24)9(4)22(33)34)13(25)10-11(15(8)27)16(28)12(18(30)17(10)29)21-20(32)19(31)14(26)7(3-23)35-21/h2,7,14,19-21,23-24,26,28-32H,3H2,1H3,(H,33,34)/t7-,14-,19+,20-,21+/m1/s1
InChIKey DGQLVPJVXFOQEV-JNVSTXMASA-N
SMILES C=1(C(=C2C(C3=C(C=C(O)C(C(O)=O)=C3C)C(C2=C(O)C1O)=O)=O)O)[C@@H]4O[C@@H]([C@H]([C@@H]([C@H]4O)O)O)CO
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): histological dye
A dye used in microscopic or electron microscopic examination of cells and tissues to give contrast and to highlight particular features of interest, such as nuclei and cytoplasm.
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ChEBI Ontology
Outgoing carminic acid (CHEBI:78310) has role animal metabolite (CHEBI:75767)
carminic acid (CHEBI:78310) has role histological dye (CHEBI:77178)
carminic acid (CHEBI:78310) is a C-glycosyl compound (CHEBI:20857)
carminic acid (CHEBI:78310) is a monocarboxylic acid (CHEBI:25384)
carminic acid (CHEBI:78310) is a tetrahydroxyanthraquinone (CHEBI:37496)
carminic acid (CHEBI:78310) is conjugate acid of carminate(2−) (CHEBI:149531)
Incoming carminate(2−) (CHEBI:149531) is conjugate base of carminic acid (CHEBI:78310)
IUPAC Name
(1S)-1,5-anhydro-1-(7-carboxy-1,3,4,6-tetrahydroxy-8-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)-D-glucitol
Synonyms Sources
C.I. 75470 ChEBI
C.I. Natural Red 4 HMDB
Carmine KEGG COMPOUND
Carmine red HMDB
Coccinellin ChemIDplus
Coccus cacti extract ChemIDplus
Cochineal ChEBI
Cochineal extract ChemIDplus
Cochineal tincture ChemIDplus
Natural red 4 HMDB
Sanred 1 ChemIDplus
Sun Red 1 HMDB
Sun Red No. 1 ChemIDplus
Manual Xrefs Databases
C11254 KEGG COMPOUND
Carminic_acid Wikipedia
FDB002568 FooDB
HMDB0030658 HMDB
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Registry Numbers Types Sources
1260-17-9 CAS Registry Number KEGG COMPOUND
1260-17-9 CAS Registry Number ChemIDplus
1414932 Reaxys Registry Number Reaxys
Citations Types Sources
24415463 PubMed citation Europe PMC
24731378 PubMed citation Europe PMC
24733592 PubMed citation Europe PMC
29551461 PubMed citation Europe PMC
32319483 PubMed citation Europe PMC
Last Modified
19 May 2020
General Comment
2020-05-19 It was previously thought that it contains α-D-glucopyranosyl residue which was later redetermined to be the β-D-glucopyranosyl anomer. See J.Org.Chem. 1981, 46, 7, 1511.