(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

• ChemBase编号: 72970
• 分子式: C17H19NO3
• 平均质量: 285.33766
• 单一同位素质量: 285.13649347
• SMILES: C1CN(CCC1)C(=O)/C=C/C=C/c1cc2c(cc1)OCO2
• Canonical SMILES: O=C(N1CCCCC1)/C=C/C=C/c1ccc2c(c1)OCO2
• InChI: InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+
• InChIKey: MXXWOMGUGJBKIW-YPCIICBESA-N

名称和登记号

名称

• IUPAC标准名: (2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one; 5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
• IUPAC传统名: bioperine; (2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one; 5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
• 别名: 1-胡椒酰哌啶; 胡椒碱; 1-Piperoylpiperidine; Piperin; Piperine; 5-(3,4-methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidine; piperoylpiperidine; Piperine; (E,E)-5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoylpiperidide; (2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-(1-piperidinyl)-2,4-pentadien-1-one; (E,E)-1-[5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]piperidine; Bioperine; NSC 21727; Piperin; (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

登记号

• CAS号: 94-62-2495-91-0; 94-62-2
• EC号: 202-348-0
• MDL号: MFCD00005839
• Beilstein号: 90741
• 默克索引号: 147472
• PubChem SID: 162037890; 24901388; 24887584; 24898568
• PubChem CID: 638024
• CHEMBL: 43185
• Chemspider ID: 553590
• FEMA编号: 2909
• 美国药典/FDA物质标识码: U71XL721QK
• 维基百科标题: Piperine
• 欧洲委员会编号: 492
• Flavis Number: 14.003

理论计算性质

• 里宾斯基五规则: true
• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 2.7773101
• LogD (pH = 7.4): 2.777311
• Log P: 2.777311
• 摩尔折射率: 82.903 cm^3
• 极化性: 31.274258 Å^3
• 极化表面积: 38.77 Å^2
• 可自由旋转的化学键: 3

分子性质

理化性质

• 溶解度: Methanol
• 外观: Off-White Solid
• 熔点: 101-103°C; 128-131°C; 128-132 °C; 128-133°C; 130°C; 131-135 °C(lit.)
• 沸点: decomposes
• 密度: 1.193 g/cm^3
• 感官: pepper; animal

安全信息

• 保存条件: -20°C; Refrigerator
• 保存注意事项: Irritant
• RTECS编号: TN2321500
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22; 22-62
• 安全公开号: 22-24/25; 36/37
• TSCA收录: 是
• GHS危险品标识: GHS06; GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H301-H361; H302
• GHS警示性声明: P281-P301+P310-P321-P308+P313-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002; FDA 21 CFR (172.515)

药理学性质

• 相关基因信息: human ... CYP3A4(1576)
• 过敏源: no known allergens
• 生物活性机理: Activator of the heat and acidity sensing TRPV ion channel TRPV1 on nociceptors (pain sensing nerve cells).

产品相关信息

• 纯度: ≥97%; ≥98.0% (TLC); 97%; 98%
• 级别: FG; Halal; Kosher; NI; purum
• 成盐信息: Free Base
• 生物来源: Constit. of pepper (Piper nigrum) and many other Piper spp. (Piperaceae)
• 应用领域: Analeptic; Bactericidal agent
• Empirical Formula (Hill Notation): C17H19NO3

详细说明

MP Biomedicals - 05217593

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02156273

Purity: 98%

Selleck Chemicals - S2344

Research Area: Neurological Disease
Biological Activity:
Piperine(1-Piperoylpiperidine) is the alkaloid responsible for the pungency of black pepper and long pepper, along with chavicine (an isomer of piperine). It has also been used in some forms of traditional medicine and as an insecticide. [1]

Toronto Research Chemicals - P483000

The alkaloid which gives pepper its spiciness, and has been used as an organic insecticide.

Sigma Aldrich - W290904

Biochem/physiol Actions
Piperine, a major component of black pepper extracts, shown to have potential for inhibiting fat cell formation.1

Sigma Aldrich - P49007

包装
1, 5 g in glass bottle
Application
Reactant for synthesis of:
• Dimeric amide alkaloids1
• Piperoyl-amino acid conjugates used for antileishmanial activity2
• Piperine derived amides with TRPV1 activity3
• Piperine analogues as S. aureus NorA efflux pump inhibitors4
• Bioactive conjugates of curcumin with antimicrobial and antiproliferative properties5
• Piperine derivatives for use as trypanocidal agents6

参考文献

• http://en.wikipedia.org/wiki/Piperine
• Trivedi, A., et al.: J. Adv. Pharm. Technol. Res., 1, 190 (2010)
• Kakarala, M., et al.: J. Agric. Food Chem., 58, 6594 (2010)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 362C, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1379B, (nmr)
• Rgheimer, L., Ber., 1882, 15, 1390, (synth, Piperine)
• Grewe, R. et al., Chem. Ber., 1970, 103, 3752, (isol, uv, ir, pmr, synth)
• Wenkert, E. et al., J.A.C.S., 1971, 93, 6271, (pmr, cmr, Piperine)
• Grynpas, M. et al., Acta Cryst. B, 1975, 31, 2663, (cryst struct, Piperine)
• DeCleyn, R. et al., Chromatographia, 1975, 8, 342, (isol, uv)
• Tsuboi, S. et al., Tet. Lett., 1979, 1043, (synth, Piperine, Isochavicine)
• Schulze, A. et al., Annalen, 1981, 1725, (synth)
• Kaga, H. et al., Synlett, 1994, 607, (synth, Piperine)
• De Araujo-Junior, J.X. et al., Phytochemistry, 1997, 44, 559, (pmr, cmr, Piperine)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PIV600