7-hydroxy-6-methoxy-2H-chromen-2-one

• ChemBase编号: 79856
• 分子式: C10H8O4
• 平均质量: 192.16812
• 单一同位素质量: 192.04225874
• SMILES: o1c2cc(c(cc2ccc1=O)OC)O
• Canonical SMILES: COc1cc2ccc(=O)oc2cc1O
• InChI: InChI=1S/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3
• InChIKey: RODXRVNMMDRFIK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 7-hydroxy-6-methoxy-2H-chromen-2-one
• IUPAC传统名: scopoletin; 7-hydroxy-6-methoxy-2H-chromen-2-one
• 别名: 6-甲氧基伞形酮; 7-羟基-6-甲氧基-2H-1-苯并吡喃-2-酮; 7-羟基-5-甲氧基香豆素; 七叶亭-6-甲醚; 柯阿托酸; 钩吻酸; 东莨菪内酯; 7-Hydroxy-6-methoxy-2H-chromen-2-one; 6-Methoxyumbelliferone; Scopoletin; 7-Hydroxy-6-methoxycoumarin; CHRYSATROPIC ACID; Gelseminic acid; Chrysatropic acid; Scopoletine; 6-Methylesculetin; Murrayetin; Scopoletol; Escopoletin; Methylesculetin; 6-O-Methylesculetin; Esculetin-6-methyl ether; 7-Hydroxy-5-methoxycoumarin; Scopoletin; 7-Hydroxy-6-methoxycoumarin; Aesculetin 6-methyl ether; Gelseminic acid; beta-Methylaesculetin; Buxuletin; Baogongteng B; 7-Hydroxy-6-methoxy-coumarin; 6-Methoxy-umbelliferone; β-Methylesculetin; NSC 405647; 7-Hydroxy-6-methoxy-2H-1-benzopyran-2-one; SCOPOLETIN

登记号

• CAS号: 92-61-5
• EC号: 202-171-9
• MDL号: MFCD00006872
• Beilstein号: 156296
• PubChem SID: 162044619; 24899524; 24888268
• PubChem CID: 5280460
• 维基百科标题: Scopoletin

理论计算性质

• Acid pKa: 8.263752
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 1.3213807
• LogD (pH = 7.4): 1.26684
• Log P: 1.322123
• 摩尔折射率: 49.9927 cm^3
• 极化性: 18.85889 Å^3
• 极化表面积: 55.76 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

• 溶解度: Sparingly Soluble in Chloroform and Methanol
• 外观: Off-Whhite Solid; Powder
• 熔点: 202-205°C; 203-205 °C(lit.); 203-205°C; 204-207 °C

安全信息

• 保存条件: -20°C Freezer; Room Temperature (15-30°C)
• 保存注意事项: Irritant
• RTECS编号: GN6930000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 2
• 危险公开号: 36/37/38; R:36/37/38
• 安全公开号: 26-36; S:20-25-26-37/39
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... ACHE(43)
• 生物活性机理: C (PKC) protein kinase inhibitor

产品相关信息

• 纯度: ≥98.0% (HPLC); ≥98.5% (HPLC); ≥99%; 95%; 98.5
• 级别: analytical standard; purum
• 生物来源: Occurs widely in the plant world, for example, the root of Gelsemium sempervirens, Atropa belladonna, Convolvulus scammonia, Ipomoea orizabensis, Prunus serotina, Fabiana imbricata and also Diospyros spp., Peucedanum spp., Heracleum spp., Skimmia spp. Also occurs in the Chinese crude drug Toki (from Angelica acutiloba )
• 有效期: (limited shelf life, expiry date on the label)
• 应用领域: Antispasmodic; Antitumour agent
• Empirical Formula (Hill Notation): C10H8O4

详细说明

MP Biomedicals - 02156590

Crystalline

MP Biomedicals - 05210164

MP Biomedicals Rare Chemical collection

Sigma Aldrich - S2500

Biochem/physiol Actions
Dye that can be used to detect the release of reactive oxygen species during the oxidative burst; peroxynitrite scavenger; acetylcholinesterase inhibitor.
Scopoletin significantly increases activity of lipoprotein lipase in adipocytes by promoting transcription of the LPL gene. It also partially reverses inhibition of LPL by TNF-α.
包装
1 g in glass bottle
100, 500 mg in glass bottle
50 mg in poly bottle

Sigma Aldrich - 246581

Biochem/physiol Actions
Scopoletin significantly increases activity of lipoprotein lipase in adipocytes by promoting transcription of the LPL gene. It also partially reverses inhibition of LPL by TNF-α.1

Sigma Aldrich - 38332

Biochem/physiol Actions
Scopoletin significantly increases activity of lipoprotein lipase in adipocytes by promoting transcription of the LPL gene. It also partially reverses inhibition of LPL by TNF-α.1

Sigma Aldrich - 84792

Biochem/physiol Actions
Scopoletin significantly increases activity of lipoprotein lipase in adipocytes by promoting transcription of the LPL gene. It also partially reverses inhibition of LPL by TNF-α.1

Toronto Research Chemicals - S200500

The aglucone of Scopolin. Used for cosmetics, topical formulations, and foods.

参考文献

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• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1314B, (nmr)
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• Head, F.G.H. et al., J.C.S., 1931, 1241, (synth)
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• Tanaka, S. et al., Arzneim.-Forsch., 1977, 27, 2039, (isol)
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• Murray, R.D.H. et al., The Natural Coumarins, J. Wiley, 1982, (occur, rev)
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