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

• ChemBase编号: 72622
• 分子式: C14H8O4
• 平均质量: 240.21092
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 1,2-dihydroxy-9,10-dihydroanthracene-9,10-dione
• IUPAC传统名: alizarin; 1,2-dihydroxy-9,10-dihydroanthracene-9,10-dione
• 别名: 1,2-二羟基蒽醌; 媒染红 11; 茜素; 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

登记号

• CAS号: 72-48-0
• EC号: 200-782-5
• MDL号: MFCD00001201
• Beilstein号: 1914037
• 默克索引号: 14251
• PubChem SID: 24859562; 24860109; 162037547; 24847507; 24845856
• PubChem CID: 6293
• CHEBI ID: 16866
• CHEMBL: 55814
• Chemspider ID: 6056
• KEGG ID: C01474
• 美国药典/FDA物质标识码: 60MEW57T9G
• 维基百科标题: Alizarin
• Color Index Number: 58000

理论计算性质

• Acid pKa: 7.4990964
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 2.9572794
• LogD (pH = 7.4): 2.7099679
• Log P: 2.9615755
• 摩尔折射率: 65.1128 cm^3
• 极化性: 24.523544 Å^3
• 极化表面积: 74.6 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: slightly to sparingly soluble in water
• 外观: orange-red crystals or powder
• 熔点: 279-283 °C(lit.); 279–83 °C; 286-290°C; 287-291 °C
• 沸点: 430 °C; ca 430°C subl.
• 密度: 1.540 g/cm^3
• 紫外吸收波长: λmax 567 nm (2nd); λmax 568 nm; λmax 608 nm (2nd); λmax 609 nm
• pKa: 6.94

安全信息

• 保存条件: -20°C; Room Temperature (15-30°C)
• RTECS编号: CB6580000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36; R36 R37 R38
• 安全公开号: 26-60; S26 S36
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H319; H319
• GHS警示性声明: P280-P264-P305+P351+P338-P337+P313; P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 生物活性机理: Bonds with calcifying tissues

产品相关信息

• 纯度: 85%; 94%; 95+%; 97%; 98%
• 级别: for microscopy; indicator; indicator (pH 5.8-7.2/pH 11.0-13.0); puriss. p.a.; technical grade
• 成盐信息: Free Base
• 主要成分: Dye content, 97%
• 燃烧残渣: ~2% (as SO4)
• 生物来源: 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
• 干燥失重: ≤3% loss on drying, 105 °C
• 应用领域: In clinical practice is used to stain synovial fluid to assess for basic calcium phosphate crystals
• 变色范围: 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

详细说明

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
包装
100, 500 g in glass bottle

参考文献

• 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.