1,2-dihydroxy-9,10-dihydroanthracene-9,10-dione

• ChemBase ID: 72622
• Molecular Formular: C14H8O4
• Molecular Mass: 240.21092
• Monoisotopic Mass: 240.04225874
• SMILES: c1ccc2c(c1)C(=O)c1c(C2=O)ccc(c1O)O
• Canonical SMILES: O=C1c2ccccc2C(=O)c2c1ccc(c2O)O
• InChI: InChI=1S/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H
• InChIKey: RGCKGOZRHPZPFP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,2-dihydroxy-9,10-dihydroanthracene-9,10-dione
• IUPAC Traditional name: alizarin; 1,2-dihydroxy-9,10-dihydroanthracene-9,10-dione
• Synonyms: Turkey ree; Mordant red 11, Alizarin e; Alizarin red; 1,2-dihydroxyanthracene-9,10-dione; Mordant Red 11; 1,2-Dihydroxyanthraquinone; Rubia; alizarin crimson; crimson madder; rose madder; Alizarin; Alizarin; ALIZARIN RED; Madder; Lizarinic acid; 1,2-dihydroxy anthraquinone; 1,2-dihydroxy-9,10-anthracenedione; 1,2-二羟基蒽醌; 媒染红 11; 茜素

Database IDs

• CAS Number: 72-48-0
• EC Number: 200-782-5
• MDL Number: MFCD00001201
• Beilstein Number: 1914037
• Merck Index: 14251
• PubChem SID: 162037547; 24845856; 24847507; 24859562; 24860109
• PubChem CID: 6293
• CHEBI ID: 16866
• CHEMBL: 55814
• Chemspider ID: 6056
• KEGG ID: C01474
• Unique Ingredient Identifier: 60MEW57T9G
• Wikipedia Title: Alizarin
• Color Index Number: 58000

CALCULATED PROPERTIES

• Acid pKa: 7.4990964
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.9572794
• LogD (pH = 7.4): 2.7099679
• Log P: 2.9615755
• Molar Refractivity: 65.1128 cm^3
• Polarizability: 24.523544 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: slightly to sparingly soluble in water
• Apperance: orange-red crystals or powder
• Melting Point: 279-283 °C(lit.); 279–83 °C; 286-290°C; 287-291 °C
• Boiling Point: 430 °C; ca 430°C subl.
• Density: 1.540 g/cm^3
• Absorption Wavelength: λmax 567 nm (2nd); λmax 568 nm; λmax 608 nm (2nd); λmax 609 nm
• pKa: 6.94

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: CB6580000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36; R36 R37 R38
• Safety Statements: 26-60; S26 S36
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319; H319
• GHS Precautionary statements: P280-P264-P305+P351+P338-P337+P313; P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Mechanism of Action: Bonds with calcifying tissues

Product Information

• Purity: 85%; 94%; 95+%; 97%; 98%
• Grade: for microscopy; indicator; indicator (pH 5.8-7.2/pH 11.0-13.0); puriss. p.a.; technical grade
• Salt Data: Free Base
• Compostion: Dye content, 97%
• Ignition Residue: ~2% (as SO4)
• Biological Source: Aglycone from madder root Rubia tinctorum. Also found in Rubia iberica, Rubia cordifolia and in tissue cultures of Galium mollugo, Morinda citrifolia, Cinchona ledgeriana and Cinchona pubescens
• Loss on Drying: ≤3% loss on drying, 105 °C
• Application(s): In clinical practice is used to stain synovial fluid to assess for basic calcium phosphate crystals
• Visual Transition Interval: 10.1 - 12.1, red to violet (alkaline); 5.5 - 6.8, yellow to red (acid)
• abs.: absorption1%/422 nm ≥120 (1 cm; pH 5.8); absorption1%/520 nm ≥230 (1 cm; pH 7.2)
• Empirical Formula (Hill Notation): C14H8O4

DETAILS

MP Biomedicals - 05206455

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02150271

C.I. 58000
Purity: 97%

MP Biomedicals - 05204600

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2526

Research Area

• Description: Metabolic Disease

Biological Activity

• Description: Alizarin strongly inhibits P450 isoform CYP1A1, CYP1A2 and CYP1B1 with IC50 of 6.2 μM, 10.0 μM and 2.7 μM, respectively.
• Targets: CYP1A1; CYP1A2; CYP1B1
• IC50: 6.2 μM; 10.0 μM; 2.7 μM ^[1]
• In Vitro: Alizarin weakly inhibits CYP2A6 and CYP2E1. Alizarin shows competitive inhibition against CYP1B1 with K_i of 0.5 μM. Alizarin deduces the mutagenicity of MeIQx, which induced by each CYP1A2 or CYP1B1, while does not effectively reduce the mutation induced by B[a]P. ^[1] Alizarin exhibits antioxidants against iodophenol-derived phenoxyl radicals, superoxide anion radicals and lipid peroxidation in rat liver microsomes. ^[2]
• In Vivo: Alizarin also reduces the hepatic content of thiobarbituric acid-reactive substances and the serum level of alanine aminotransferase in poisoned animals. ^[2]

Protocol

• Protocol: Kinase Assay ^[1]
• Measurement of enzyme activities of CYPs: Enzyme activities are measured by fluorometric quantification of each metabolite produced by O-deethylation of 7-ethoxycoumarin by CYP1A1 and CYP1B1, O-deethylation of 7-ethoxyresorufin by CYP1A2 and 7-hydroxylation of coumarin by CYP2A6, using Hitachi F-2000 fluorescence spectrophotometer. The fluorescence of metabolite is not influenced by the presence of anthraquinone pigments at the doses tested in these experiments. 7-Ethoxycoumarin is used at 40 μM for CYP1A1 and at 20 μM for CYP1B1. In the cases of CYP2C19, CYP2E1, CYP3A4 and CYP3A5, the amount of each metabolite derived from the catalytic reaction by individual CYPs is determined by HPLC equipped with a UV detector. The activities of CYP2C19 and CYP2E1 are determined by 4′-hydroxylation of (S)-mephenytoin and by 6-hydroxylation of chlorzoxazone, respectively. In the case of CYP3As, their activities are determined by 1′-hydroxylation of midazolam with a modification in which the metabolites are extracted from the incubation mixture before injection to HPLC. Briefly, 1 μM diazepam is added to the reaction mixture as an internal standard with an excess amount of ammonium sulfate and 5 volumes of ethyl acetate immediately after the incubation. After shaking for 10 min, 1′-hydroxymidazolam and diazepam are extracted into the ethyl acetate layer by centrifugation at 2000×g for 10 min, at 4 °C. Then ethyl acetate is removed by evaporation and the residue is used for HPLC after dissolving in methanol. A volume of 20 μM of midazolam is used for the detection of CYP3A4 activity and 7 μM for CYP3A5. To evaluate the K_m value of CYP1B1, the measurement of activity is carried out at substrate doses from 2.5 to 40 μM. K_i value of Alizarin against the activity of CYP1B1 is calculated from the enzyme activities in the presence of 0.2-1.6 μM Alizarin.

References

• References: [1] Takahashi E, et al. Mutat Res, 2002, 508(1-2), 147-156.
• References: [2] Zhang J, et al. J Nutr Environ Med, 1997, 7(2), 79-89.

Sigma Aldrich - 122777

Application
Biological stain
Packaging
100, 500 g in glass bottle

REFERENCES

• Takahashi E, et al. Mutat Res, 2002, 508(1-2), 147-156.
• Zhang J, et al. J Nutr Environ Med, 1997, 7(2), 79-89.
• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 90D, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 86D, (ir)
• Fieser, L.F. et al., J. Chem. Educ., 1930, 7, 2609-2633, (rev)
• Kido, H. et al., Anal. Chim. Acta, 1960, 23, 116-123, (ir)
• Nazarenko, V.A. et al., Zh. Anal. Khim., 1972, 27, 2369-2376; J. Anal. Chem. USSR (Engl. Transl.), 1972, 27, 2151-2157, (detn, Ge)
• Idris, K.A. et al., Egypt. J. Chem., 1973, 67-76, (uv)
• Leistner, G., Phytochemistry, 1973, 12, 1669-1674, (biosynth)
• Leistner, G., Planta Med., suppl., 1975, 214, (biosynth)
• Holzbecher, Z. et al., Handbook of Organic Reagents in Inorganic Analysis, Horwood, Chichester, 1976, (use)
• Sigma-Aldrich Library of Stains, Dyes and Indicators, 75
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DMG800
• Acid-base indicator: pH 5.8 - 7.2, 11.0 - 13.0.