Carminic acid

Carminic acid^[1]
Names
	IUPAC names 7-α-D-Glucopyranosyl-9,10-dihydro-; 3,5,6,8-tetrahydroxy-1-methyl-9,10-; dioxoanthracenecarboxylic acid[citation needed]
	Other names Carminic acid; C.I. Natural Red 4; C.I. 75470
Identifiers
CAS Number	1260-17-9
ChEBI	CHEBI:78310
ChEMBL	ChEMBL263094
ChemSpider	14068
Jmol 3D model	Interactive image
KEGG	C11254
UNII	CID8Z8N95N
	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 Key: DGQLVPJVXFOQEV-NGOCYOHBSA-N ; InChI=1/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 Key: DGQLVPJVXFOQEV-NGOCYOHBBS ;
	SMILES O=C(O)c2c(c3C(=O)c1c(O)c(c(O)c(O)c1C(=O)c3cc2O)[C@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)CO)C ;
Properties
Chemical formula	C22H20O13
Molar mass	492.38 g/mol
Density	? g/cm3
Melting point	120 °C (248 °F; 393 K) (decomposes)
Acidity (pKa)	3.39, 5.78, 8.35, 10.27, 11.51
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

Carminic acid (C₂₂H₂₀O₁₃) is a red glucosidal hydroxyanthrapurin that occurs naturally in some scale insects, such as the cochineal, Armenian cochineal, and Polish cochineal. The insects produce the acid as a deterrent to predators. Carminic acid is the colouring agent in carmine. Synonyms are C.I. 75470 and C.I. Natural Red 4.

The chemical structure of carminic acid consists of a core anthraquinone structure linked to a glucose sugar unit. Carminic acid was first synthesized by organic chemists in 1991.^[3]

References

↑ Merck Index, 11th Edition, 1850.
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[1] Merck Index, 11th Edition, 1850.

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v t e Glycosides
Bond	O-glycosidic bond N-glycosidic bond S-glycosidic bond C-glycosidic bond
Geometry	α-Glycoside β-Glycoside 1,4-Glycoside 1,6-Glycoside
Glycone	Fructoside Galactoside Glucoside Glucuronide Rhamnoside Riboside
Aglycone	Alcoholic glycoside Cardiac glycoside Bufadienolide Cardenolide Cyanogenic glycoside Glycosylamine Phenolic glycoside Anthraquinone glycoside Coumarin glycoside Flavonoid glycoside Saponin Steviol glycoside Thioglycoside

Carminic acid

References

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Names


IUPAC names 7-α-D-Glucopyranosyl-9,10-dihydro- 3,5,6,8-tetrahydroxy-1-methyl-9,10- dioxoanthracenecarboxylic acid^{[citation needed]}
Other names Carminic acid C.I. Natural Red 4 C.I. 75470
Identifiers
CAS Number	1260-17-9^Y
ChEBI	CHEBI:78310^N
ChEMBL	ChEMBL263094^N
ChemSpider	14068^Y
Jmol 3D model	Interactive image
KEGG	C11254^Y
UNII	CID8Z8N95N^Y
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^Y Key: DGQLVPJVXFOQEV-NGOCYOHBSA-N^Y InChI=1/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 Key: DGQLVPJVXFOQEV-NGOCYOHBBS
SMILES O=C(O)c2c(c3C(=O)c1c(O)c(c(O)c(O)c1C(=O)c3cc2O)[C@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)CO)C
Properties
Chemical formula	C₂₂H₂₀O₁₃
Molar mass	492.38 g/mol
Density	? g/cm³
Melting point	120 °C (248 °F; 393 K) (decomposes)
Acidity (pK_a)	3.39, 5.78, 8.35, 10.27, 11.51^[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references