1260-17-9 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 1260-17-9 differently. You can refer to the following data:
1. red to dark red crystalline powder
2. Cochineal extract is a concentrated solution obtained after removing alcohol from an aqueous–alcoholic extract of
cochineal (Dactylopius coccus Costa, also called Coccus cati L.). This extract is used as a color additive, the primary colorant being
carminic acid.
History
CI Natural Red 4(CI 75470), is a red dye occurring as a glycoside in the body of the cochineal insect Dactylopius coccus of the order Homoptera, family Coccidae. This insect is native to Central and South America. The Aztecs had extracted the dye from the insect centuries before the coming of the Spaniards. For breeding purposes, the insects were collected in the autumn and carefully protected during the winter months. Cochineal was harvested after three months, and then the bugs were killed by immersion in hot water, by placing in hot ovens, or by exposure to the hot sun. The latter method produced the highest quality dye. At present, Peru and the Canary Islands are the main source of the dye. Until the advent of synthetic dyes, the principal use for carminic acid was for dyeing tin-mordanted wool or silk. Its aluminum lake, carmine, finds use in the coloring of foods.
Uses
Different sources of media describe the Uses of 1260-17-9 differently. You can refer to the following data:
1. Carminic acid (C.I. 75470) For staining nuclei in histological sections. Used to prepare staining solutions. CAS 1260-17-9, pH 1.6 (10?g/l, H?O, 20?°C).
2. A red glucosidal hydroxyanthrapurin, it is produced naturally within some insects as a defense mechanism.
3. antineoplastic, glucosyltransferase inhibitor
Definition
ChEBI: 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-gly
osidic linkage. It is a natural dye isolated from several insects such as Dactylopius coccus.
General Description
Dark purplish-brown mass or bright red or dark red powder. Darkens at 248°F. Deep red color in water. Yellow to violet in acidic aqueous solutions.
Reactivity Profile
CARMINE neutralizes bases in exothermic reactions. Incompatible with strong oxidizing agents.
Fire Hazard
Flash point data for CARMINE are not available. CARMINE is probably combustible.
Purification Methods
Carminic acid forms red prisms from EtOH. It gives a red colour in Ac2O and yellow to violet in acidic solution. UV: max (H2O) 500nm ( 6,800); (0.02N HCl) 490-500nm ( 5,800) and (0.0001N NaOH) 540nm ( 3,450). IR: max (Nujol) 1708s, 1693s, 1677m, 1648m, 1632m, 1606s, 1566s, 1509 cm-1. Periodate oxidation is complete after 4hours at 0o with the consumption of 6.2 mols. The tetra-O-methyl carminate has m 186-188o (yellow needles from *C6H6/pet ether). [IR: Ali & Haynes J Chem Soc 1033 1959, Bhatia & Venkataraman Indian J Chem 3 (2) 92 1965, Synthesis: Davis & Smith Biochemical Preparations 4 38 1955, Beilstein 18 III/1V 6697.]
Check Digit Verification of cas no
The CAS Registry Mumber 1260-17-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,6 and 0 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1260-17:
(6*1)+(5*2)+(4*6)+(3*0)+(2*1)+(1*7)=49
49 % 10 = 9
So 1260-17-9 is a valid CAS Registry Number.
InChI: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
1260-17-9Relevant articles and documents
Production of Carminic Acid by Metabolically Engineered Escherichia coli
Yang, Dongsoo,Jang, Woo Dae,Lee, Sang Yup
, p. 5364 - 5377 (2021)
Carminic acid is an aromatic polyketide found in scale insects (i.e., Dactylopius coccus) and is a widely used natural red colorant. It has long been produced by the cumbersome farming of insects followed by multistep purification processes. Thus, there has been much interest in producing carminic acid by the fermentation of engineered bacteria. Here we report the complete biosynthesis of carminic acid from glucose in engineered Escherichia coli. We first optimized the type II polyketide synthase machinery from Photorhabdus luminescens, enabling a high-level production of flavokermesic acid upon coexpression of the cyclases ZhuI and ZhuJ from Streptomyces sp. R1128. To discover the enzymes responsible for the remaining two reactions (hydroxylation and C-glucosylation), biochemical reaction analyses were performed by testing enzyme candidates reported to perform similar reactions. The two identified enzymes, aklavinone 12-hydroxylase (DnrF) from Streptomyces peucetius and C-glucosyltransferase (GtCGT) from Gentiana triflora, could successfully perform hydroxylation and C-glucosylation of flavokermesic acid, respectively. Then, homology modeling and docking simulations were performed to enhance the activities of these two enzymes, leading to the generation of beneficial mutants with 2-5-fold enhanced conversion efficiencies. In addition, the GtCGT mutant was found to be a generally applicable C-glucosyltransferase in E. coli, as was showcased by the successful production of aloesin found in Aloe vera. Simple metabolic engineering followed by fed-batch fermentation resulted in 0.63 ± 0.02 mg/L of carminic acid production from glucose. The strategies described here will be useful for the design and construction of biosynthetic pathways involving unknown enzymes and consequently the production of diverse industrially important natural products.
Synthesis of carminic acid, the colourant principle of cochineal
Allevi, Pietro,Anastasia, Mario,Bingham, Steve,Ciuffreda, Pierangela,Fiecchi, Alberto,Cighetti, Giuliana,Muir, Max,Scala, Antonio,Tyman, John
, p. 575 - 582 (2007/10/03)
The first synthesis of carminic acid (7β-D-glucopyranosyl-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-9,10- dihydroanthracene-2-carboxylic acid) is described. Selective C-glycosylation at the 7-position of ethyl and benzyl 3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylates with 2,3,4,6-tetra-O-benzyl-1-trifluoroacetyl-α-D-glucopyranose afforded intermediates which were oxidised to ethyl and benzyl 3,5,8-trimethoxy-1-methyl-9,10-dioxo-7-(2′,3′,4′,6′- tetra-O-benzyl-β-D-glucopyranosyl)-9,10-dihydroanthracene-2-carboxylate respectively. The benzyl compound was hydrogenolysed and the ethyl analogue hydrogenolysed and hydrolysed to give the same product, which was tetraacetylated and demethylated to afford 6-deoxycarminic acid tetraacetate, 3,5,8-trihydroxy-1-methyl-9,10-dioxo-7-(2′,3′,4′,6′- tetra-O-acetyl-β-D-glucopyranosyl)-9,10-dihydroanthracene-2-carboxylic acid. The pentamethoxy intermediates were obtained from 2-chloronaphthazarin by Diels-Alder addition to 3-alkoxycarbonyl-2,4-bis(trimethylsiloxy)penta-2,4-dienes to give alkyl 6-deoxykermesates. Methylation afforded the corresponding trimethyl ethers, which by reductive methylation gave the required pentamethoxy compounds. By known steps 6-deoxycarminic acid tetraacetate was converted into the 5,8,9,10-bisquinone, acetoxylation of which gave carminic acid octaacetate. Acidic hydrolysis afforded carminic acid.
