5,7-dihydroxy-2-phenyl-4H-chromen-4-one

• ChemBase编号: 59746
• 分子式: C15H10O4
• 平均质量: 254.2375
• 单一同位素质量: 254.0579088
• SMILES: c12c(=O)cc(oc1cc(cc2O)O)c1ccccc1
• Canonical SMILES: Oc1cc(O)c2c(c1)oc(cc2=O)c1ccccc1
• InChI: InChI=1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H
• InChIKey: RTIXKCRFFJGDFG-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5,7-dihydroxy-2-phenyl-4H-chromen-4-one
• IUPAC传统名: chrysin; 5,7-dihydroxy-2-phenyl-4H-chromen-4-one
• 别名: 5,7-二羟黄酮; 柯因; 5,7-二羟基黄酮; NP-005901; Galangin flavanone; CHRYSINE; Chrysin; Chrysin; Chrysin; 5,7-Dihydroxyflavone; 5,7-Dihydroxy-2-phenyl-4H-chromen-4-one; 5,7-Dihydroxyflavone; 5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one; 5,7-Dihydroxy-2-phenylchromen-4-one; Crysin; NSC 407436; Chrysinic acid

登记号

• CAS号: 480-40-0
• EC号: 207-549-7
• MDL号: MFCD00006834
• Beilstein号: 233276
• 默克索引号: 142256
• PubChem SID: 24893009; 162064509; 24856455
• PubChem CID: 5281607
• CHEMBL: 117
• Chemspider ID: 4444926
• KEGG ID: C10028
• 美国药典/FDA物质标识码: 3CN01F5ZJ5
• 维基百科标题: Chrysin

理论计算性质

• Acid pKa: 6.577777
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 2.9755785
• LogD (pH = 7.4): 2.0891845
• Log P: 3.0102544
• 摩尔折射率: 70.933 cm^3
• 极化性: 26.480106 Å^3
• 极化表面积: 66.76 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: Yellow powder
• 熔点: 284-286 °C; 284-286 °C(lit.); 284-289°C
• 紫外吸收波长: λmax 348 nm

安全信息

• 保存条件: -20°C; Room Temperature (15-30°C)
• 保存注意事项: IRRITANT
• RTECS编号: LK8329050
• 德国WGK号: 3
• TSCA收录: false; 否
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... CDC2(983), CDK5(1020), CDK6(1021), CYP19A1(1588), CYP1A2(1544), GSK3A(2931)mouse ... Hexa(15211), Ptgs2(19225)rat ... Gabra2(29706)
• 生物活性机理: Lipid peroxidation inhibitor in rat liver microsomes

产品相关信息

• 纯度: ≥96.0% (HPLC); ≥98% (HPLC); 97%; 98%
• 级别: analytical standard
• 成盐信息: Free Base
• 生物来源: Isol. from Ulmus sieboldiana, Flourensia resinosa, Oroxylum indicum (bark), Pinus and Scutellaria spp. and others
• 有效期: (limited shelf life, expiry date on the label)
• 应用领域: Shows antifungal activity
• Empirical Formula (Hill Notation): C15H10O4

详细说明

MP Biomedicals - 05210927

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02154985

(5,7-Dihydroxyflavone) Crystalline

Selleck Chemicals - S2281

Research Area: Inflammation
Biological Activity:
Chrysin is a naturally occurring flavone chemically extracted from the blue passion flower (Passiflora caerulea). [1] It has been shown to induce an anti-inflammatory effect, most likely by inhibition of COX-2 expression and via IL-6 signaling.[2] In rodent in vivo studies, chrysin was found anxiolytic. However asbestos was not known to cause cancer because it did not cause cancer in non-human animals

Sigma Aldrich - C80105

包装
25 g in glass bottle

Toronto Research Chemicals - C432730

Chrysin is a flavanoid with anti-inflammatory effect and potential protective effects against cancer and cardiovascular disease. Studies show that Chrysin is central benzodiazepine receptor ligand with possible anxiolytic effects. Chrysin was initially be

参考文献

• Woo KJ et al. FEBS Lett. 2005 Jan 31;579(3):705-11.
• O’Leary, K.A. et al.: Mutat. Res., 551, 245 (2004)
• Wolfman, C. et al.: Pharmacol. Biochem. Behav., 47, 1 (2004)
• Saarinen, N. et al.: J. Steroid Biochem. Mol. Biol., 78, 231 (2004)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 95C, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 918C, (nmr)
• Nadkarni, D.R. et al., J.C.S., 1938, 1320, (synth)
• Marsh, C.A., Biochem. J., 1955, 59, 58, (isol, deriv)
• Katyal, M. et al., Proc. - Indian Acad. Sci., Sect. A, 1962, 56, 125; CA, 58, 3884c, (detn, Th)
• Dev, B. et al., Fresenius' Z. Anal. Chem., 1963, 196, 178, (synth, use, deriv)
• Batterham, T.J. et al., Aust. J. Chem., 1964, 17, 428, (pmr)
• Katyal, M. et al., Talanta, 1968, 15, 95, (detn, U)
• Bowie, J.H. et al., J.C.S.(B), 1969, 89, (ms)
• Asakawa, Y., Bull. Chem. Soc. Jpn., 1971, 44, 2761, (isol)
• Nevskaya, E.M. et al., Zh. Anal. Khim., 1972, 27, 1699, (reactions)
• Kingston, D.G.I. et al., Tetrahedron, 1973, 29, 4083, (ms)
• Wagner, H. et al., Tet. Lett., 1976, 1799, (cmr)
• Gaydon, E.M. et al., Bull. Soc. Chim. Fr., Part II, 1978, 43, (synth, uv, cmr)
• Davoust, D. et al., Org. Magn. Reson., 1978, 11, 547, (pmr)
• Jaipetch, T. et al., Phytochemistry, 1983, 22, 625, (isol)
• Agrawal, P.K. et al., Tet. Lett., 1983, 177, (cmr)
• Wollenweber, E. et al., Planta Med., 1985, 50, 459, (isol)
• Saxena, S. et al., Synthesis, 1985, 697, (synth)
• Le Floc'h, Y. et al., Tet. Lett., 1986, 27, 5503, (synth)
• The Flavonoids: Advances in Research since 1980, (Ed. Harborne, J.B.), Chapman and Hall, London, 1988
• Jung, J.H. et al., Phytochemistry, 1990, 29, 1271, (pmr, cmr)
• Shen, C.-C. et al., Phytochemistry, 1993, 34, 843, (pmr, cmr)
• Litkei, G. et al., Annalen, 1995, 1711, (synth, pmr)
• Hounghton, P.J. et al., Pharm. Pharmacol. Lett., 1997, 7, 96-98, (activity)
• Rashad, M.A. et al., Phytomedicine, 1998, 5, 375-381, (isol, activity)
• Lee, J.-M. et al., Synthesis, 2001, 2247-2254, (synth, pmr, cmr)