Carminic acid

Carminic acid: Carminic acid^[1]

IUPAC name

7-α-D-Glucopyranosyl-9,10-dihydro-
3,5,6,8-tetrahydroxy-1-methyl-9,10-
dioxoanthracenecarboxylic acid

Other names

Carminic acid
C.I. Natural Red 4
C.I. 75470

Identifiers

CAS number 1260-17-9^Y

ChemSpider 14068^Y

UNII CID8Z8N95N^Y

KEGG C11254^Y

Jmol-3D images Image 1

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

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

Properties

Molecular formula C₂₂H₂₀O₁₃

Molar mass 492.38 g/mol

Density ? g/cm³

Melting point
120 °C (decomp.)

Y acid (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Carminic acid (C₂₂H₂₀O₁₃) is a red glucosidal hydroxyanthrapurin that occurs naturally in some scale insects, such as the cochineal and the 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.^[2]

References

^ Merck Index, 11th Edition, 1850.

^ Allevi, P. et al. (1991). "The 1st Total Synthesis of Carminic Acid". Journal of the Chemical Society-Chemical Communications 18: 1319–1320.

v · Glycosides

Bond
N-glycosidic bond · O-glycosidic bond · S-glycosidic bond

Geometry
α-Glycoside · β-Glycoside · 1,4-Glycoside · 1,6-Glycoside

Glycone
Glucoside · Fructoside · Glucuronide · Riboside

Aglycone
Alcoholic glycoside · Anthraquinone glycoside · Cardiac glycoside (Bufadienolide, Cardenolide) · Coumarin glycoside · Cyanogenic glycoside · Flavonoid glycoside · Glycosylamine · Phenolic glycoside · Saponin · Steviol glycoside · Thioglycoside

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i

Categories:
Anthraquinone dyes
Anthraquinone glycosides
Hydroxyquinols
Glucosides

Carminic acid^[1]


IUPAC name 7-α-D-Glucopyranosyl-9,10-dihydro- 3,5,6,8-tetrahydroxy-1-methyl-9,10- dioxoanthracenecarboxylic acid
Other names Carminic acid C.I. Natural Red 4 C.I. 75470
Identifiers
CAS number	1260-17-9^Y
ChemSpider	14068^Y
UNII	CID8Z8N95N^Y
KEGG	C11254^Y
Jmol-3D images	Image 1
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
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
Properties
Molecular formula	C₂₂H₂₀O₁₃
Molar mass	492.38 g/mol
Density	? g/cm³
Melting point	120 °C (decomp.)
Y acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Carminic acid — Carminic Car*min ic, a. Of or pertaining to, or derived from, carmine. [1913 Webster] {Carminic acid}. Same as {Carmine}, 3. [1913 Webster] … The Collaborative International Dictionary of English
carminic acid — noun Etymology: International Scientific Vocabulary carminic + acid : a red crystalline anthraquinone dye C22H20O13 best known as the essential coloring matter of cochineal and used chiefly as a biological stain * * * carminic acid, a purplish… … Useful english dictionary
carminic acid — Carmine Car mine, n. [F. carmin (cf. Sp. carmin, It. carminio), contr. from LL. carmesinus purple color. See {Crimson}.] 1. A rich red or crimson color with a shade of purple. [1913 Webster] 2. A beautiful pigment, or a lake, of this color,… … The Collaborative International Dictionary of English
carminic acid — karmino rūgštis statusas T sritis chemija apibrėžtis Polihidroksiantrachinonkarboksirūgšties junginys su gliukoze. formulė C₂₂H₂₀O₁₃ atitikmenys: angl. carminic acid rus. карминовая кислота … Chemijos terminų aiškinamasis žodynas
carminic acid — A glucoside of an anthracenequinone carboxylic acid; the essential constituent of carmine. * * * car·min·ic acid kär .min ik n a red crystalline anthraquinone dye C22H20O13 best known as the essential coloring matter of cochineal and used chiefly … Medical dictionary
carminic acid — noun a phenolic quinone that is the main constituent of cochineal Syn: carmine, E120 … Wiktionary
carminic — CARMÍNIC adj.m. Acid carminic = acid extras din coşenilă. [< fr. carminique]. Trimis de LauraGellner, 13.09.2007. Sursa: DN CARMÍNIC adj. acid carminic = acid extras din coşenilă. (< fr. carminique) Trimis de raduborza, 15.09.2007. Sursa … Dicționar Român
Carminic — Car*min ic, a. Of or pertaining to, or derived from, carmine. [1913 Webster] {Carminic acid}. Same as {Carmine}, 3. [1913 Webster] … The Collaborative International Dictionary of English
Carmine — This article is about the pigment. For other uses, see Carmine (disambiguation). Carmine Carmine ( /ˈ … Wikipedia
Cochineal — Female (left) and male (right) Cochineals. Scientific classification Domain: Eukaryota … Wikipedia

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Carminic acid

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