Carminic acid

CAS# 1260-17-9

Carminic acid

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Chemical structure

Carminic acid

3D structure

Chemical Properties of Carminic acid

Cas No. 1260-17-9 SDF Download SDF
PubChem ID 14749 Appearance Red-black powder
Formula C22H20O13 M.Wt 492.39
Type of Compound Anthraquinones Storage Desiccate at -20°C
Synonyms Cochineal Red PWD; Sun Red 1
Solubility Soluble in methan
Chemical Name 3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-7-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracene-2-carboxylic acid
SMILES CC1=C2C(=CC(=C1C(=O)O)O)C(=O)C3=C(C2=O)C(=C(C(=C3O)O)C4C(C(C(C(O4)CO)O)O)O)O
Standard InChIKey DGQLVPJVXFOQEV-NGOCYOHBSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Carminic acid

The cochineal insects (Dactylopius spp.)

Biological Activity of Carminic acid

DescriptionCarminic acid, the well-known red dyestuff from cochineal insects (Dactylopius spp.), is a potent feeding deterrent to ants. Carminic acid is an antioxidant to protect erythrocytes and DNA against radical‐induced oxidation, it also has antitumor activity.
TargetsROS
In vitro

Red cochineal dye (carminic acid): Its role in nature.[Pubmed: 17779027]

Science. 1980 May 30;208(4447):1039-42.

Carminic acid, the well-known red dyestuff from cochineal insects (Dactylopius spp.), is a potent feeding deterrent to ants. This deterrency may be indicative of the natural function of the compound, which may have evolved in cochineals as a chemical weapon against predation. The behavior of an unusual predator is described-the carnivorous caterpillar of a pyralid moth (Laetilia coccidivora)-which is undeterred by Carminic acid and feeds on cochineals.
CONCLUSIONS:
The animal has the remarkable habit of utilizing the ingested Carminic acid for defensive purposes of its own.

Carminic acid: An antioxidant to protect erythrocytes and DNA against radical-induced oxidation[Reference: WebLink]

Journal of Physical Organic Chemistry, 2009 , 22 (9) :883-7.

This work explored the antioxidant effect of Carminic acid (CarOH) on the oxidation of DNA and erythrocytes induced by 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH).
METHODS AND RESULTS:
The half concentrations (IC50) of CarOH to scavenge radicals were measured by reacting with 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) radical cation (ABTS+•) and 2,2′-diphenyl-1-picrylhydrazyl (DPPH). The values of IC50 were 8.0 and 26.0 µM when CarOH reacted with ABTS+• and DPPH, respectively. CarOH was able to protect DNA against AAPH-induced oxidative damage by decreasing the formation rate of thiobarbituric acid reactive substance (TBARS). In addition, CarOH protected human erythrocytes against AAPH-induced hemolysis concentration dependently, during which one molecule of CarOH can trap almost three radicals. Moreover, quantum calculation revealed that the hydroxyl group at 6-position played major role in trapping radicals.

Protocol of Carminic acid

Structure Identification
Bioorganic Chemistry, 1979 , 8 (1) :17-24.

Reactions of the antitumor agent carminic acid and derivatives with DNA[Reference: WebLink]


METHODS AND RESULTS:
The antitumor agent Carminic acid 1a does not bind to DNA but nicks it slowly, more rapidly when reduced in situ, and still more rapidly when prereduced at the quinone moiety. The nicking process requires oxygen and is selectively inhibited by (i) superoxide dismutase, (ii) catalase, and (iii) free radical scavengers indicating the involvement of , and OH., respectively. The intermediacy of OH. was supported by spin trapping with N-t-butyl-α-phenylnitrone and epr of the radical produced via the Carminic acid semiquinone. The single strand scission of DNA by Carminic acid requires two adjacent hydroquinone moieties in the chromophore since reduced methyl tetra-O-methylcarminate 1b is without effect although it binds weakly to DNA. Polarographic redox potentials for the reversible (2e, 2H+) reduction of 1a and 1b are −0.736 ± 0.003 V and −0.56 ± 0.010 V against SCE, respectively.
CONCLUSIONS:
The fact that daunorubicin and adriamycin produce more extensive DNA strand scission than Carminic acid under comparable conditions of prereduction and on a molar basis is largely attributed to the assistance of intercalative binding afforded in the case of the anthracyclines.

Carminic acid Dilution Calculator

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Carminic acid Molarity Calculator

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Preparing Stock Solutions of Carminic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0309 mL 10.1546 mL 20.3091 mL 40.6182 mL 50.7728 mL
5 mM 0.4062 mL 2.0309 mL 4.0618 mL 8.1236 mL 10.1546 mL
10 mM 0.2031 mL 1.0155 mL 2.0309 mL 4.0618 mL 5.0773 mL
50 mM 0.0406 mL 0.2031 mL 0.4062 mL 0.8124 mL 1.0155 mL
100 mM 0.0203 mL 0.1015 mL 0.2031 mL 0.4062 mL 0.5077 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Carminic acid

Red cochineal dye (carminic Acid): its role in nature.[Pubmed:17779027]

Science. 1980 May 30;208(4447):1039-42.

Carminic acid, the well-known red dyestuff from cochineal insects (Dactylopius spp.), is a potent feeding deterrent to ants. This deterrency may be indicative of the natural function of the compound, which may have evolved in cochineals as a chemical weapon against predation. The behavior of an unusual predator is described-the carnivorous caterpillar of a pyralid moth (Laetilia coccidivora)-which is undeterred by Carminic acid and feeds on cochineals. The animal has the remarkable habit of utilizing the ingested Carminic acid for defensive purposes of its own.

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