Carmine (Carmine red) is a natural red dye found in the dried female insect Dactylopius coccus var. Costa (cochineal). Carmine is a extensively used food additive. Carmine can cause hypersensitivity reactions.

Physicochemical Properties

Molecular Formula	C22H20O13
Molecular Weight	492.3864
Exact Mass	492.09
CAS #	1390-65-4
PubChem CID	10255083
Appearance	Brown to red solid powder
Density	1.9±0.1 g/cm3
Boiling Point	907.6±65.0 °C at 760 mmHg
Melting Point	136ºC dec
Flash Point	316.1±27.8 °C
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.792
LogP	4.8
Hydrogen Bond Donor Count	9
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	3
Heavy Atom Count	35
Complexity	864
Defined Atom Stereocenter Count	5
SMILES	CC1=C2C(=CC(=C1C(=O)O)O)C(=O)C3=C(C2=O)C(=C(C(=C3O)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
InChi Key	DGQLVPJVXFOQEV-JNVSTXMASA-N
InChi Code	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
Chemical Name	3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-7-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracene-2-carboxylic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Depending on the formulation, carmine has been employed in biological staining to show nuclei, chromosomes, or mucins selectively[2].
References	[1]. Contact Dermatitis to Carmine. Dermatitis. Sep/Oct 2018;29(5):244-249. [2]. The history, chemistry and modes of action of carmine and related dyes. Biotech Histochem. 2007 Aug;82(4-5):173-87. [3]. Occupational asthma and food allergy due to carmine. Allergy. 1998 Sep;53(9):897-901.
Additional Infomation	Carminic acid appears as 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. (NTP, 1992) Carminic acid is 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. It has a role as an animal metabolite and a histological dye. It is a tetrahydroxyanthraquinone, a monocarboxylic acid and a C-glycosyl compound. It is a conjugate acid of a carminate(2-). Coloring matter from the insect Coccus cacti L. It is used in foods, pharmaceuticals, toiletries, etc., as a dye, and also has use as a microscopic stain and biological marker. See also: Cochineal (annotation moved to). Mechanism of Action The food coloring carminic acid redox cycles to produce free radicals. These radicals, in the presence of trace amounts of iron salts, readily damage membrane lipid and degrade the carbohydrate deoxyribose. Damage to membrane lipid appears to involve mainly organic oxygen radicals such as alkoxy and peroxy radicals, whereas that to deoxyribose implicates the hydroxyl radical formed in a Fenton-type reaction. Antioxidants and iron chelators prevent such damage. The antitumor agent carminic acid did not bind to DNA but nicked it slowly, more rapidly when reduced in situ, & still more when prereduced at the quinone moiety.

Solubility Data

Solubility (In Vitro)

H2O: 125 mg/mL

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.0309 mL	10.1546 mL	20.3091 mL
	5 mM	0.4062 mL	2.0309 mL	4.0618 mL
	10 mM	0.2031 mL	1.0155 mL	2.0309 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.