2-Acetylpyrrole
(Synonyms: 2-乙酰吡咯) 目录号 : GC61710
2-Acetylpyrrole是模型褐变系统的产物，可作为许多食品的主要风味成分。2-Acetylpyrrole已用于2-acetyl-1-pyrroline的合成。
Cas No.:1072-83-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2-Acetylpyrrole is a product of model browning systems, and has been isolated as a major flavour component of many foods[1]. 2-Acetylpyrrole has been used in the synthesis of 2-acetyl-1-pyrroline[2].
[1]. C J Wang, et al. Mutagenicity and cytotoxicity of nitropyrrole compounds derived from the reaction of 2-acetyl pyrrole with nitrite. Food Chem Toxicol. 1994 Sep;32(9):839-44. [2]. Ron G. Buttery, et al. Cooked rice aroma and 2-acetyl-1-pyrroline. J. Agric. FoodChem. 1983, 31, 4, 823-826
| Cas No. | 1072-83-9 | SDF | |
| 别名 | 2-乙酰吡咯 | ||
| Canonical SMILES | CC(=O)C1=CC=CN1 | ||
| 分子式 | C6H7NO | 分子量 | 109.13 |
| 溶解度 | DMSO : 100 mg/mL (916.34 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 9.1634 mL | 45.8169 mL | 91.6338 mL |
| 5 mM | 1.8327 mL | 9.1634 mL | 18.3268 mL |
| 10 mM | 0.9163 mL | 4.5817 mL | 9.1634 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Mutagen formation in the reaction of Maillard browning products, 2-Acetylpyrrole and its analogues, with nitrite
Food Chem Toxicol 1986 Dec;24(12):1303-8.PMID:3542764DOI:10.1016/0278-6915(86)90062-1.
Three 2-substituted pyrroles (2-Acetylpyrrole, pyrrole-2-carboxaldehyde and pyrrole-2-carboxylic acid), which are products of the Maillard browning reaction, were reacted with nitrite in buffer solution (pH 3) at 50 degrees C for 24 hr. The reaction mixtures were extracted with methylene chloride and the extracts were tested for mutagenicity using Salmonella typhimurium strains TA97, TA98, TA100, TA102 and TA104, with and without S-9 metabolic activation. The methylene chloride extract of the 2-acetylpyrrole-nitrite reaction mixture showed strong mutagenicity to all the tester strains, both in the presence and absence of S-9 mix. The reaction product of pyrrole-2-carboxaldehyde with nitrite only gave a weak mutagenic response with strain TA100, while the pyrrole-2-carboxylic acid-nitrite reaction product did not produce a mutagenic response in any of the tester strains. Two mutagenically active fractions, separated by thin-layer chromatography, were found in the reaction of 2-Acetylpyrrole with nitrite. The formation of mutagenic products in the latter reaction was found to vary with reaction pH, time and temperature, with nitrite level and with 2-Acetylpyrrole concentration.
A critical evaluation of the s-cis-trans isomerism of 2-Acetylpyrrole and its N-methyl derivative through infrared and NMR spectroscopies and theoretical calculations
Spectrochim Acta A Mol Biomol Spectrosc 2013 Dec;116:196-203.PMID:23933556DOI:10.1016/j.saa.2013.07.024.
Literature data are controversial regarding the conformational equilibria of 2-Acetylpyrrole (AP) and its N-methyl derivative (AMP). Now, a detailed study through infrared spectroscopy and theoretical calculations has shown that previous data were erroneously interpreted, since only a N,O-cis conformer is present in solution and that it is the stable conformer in the isolated state (ΔE(trans-cis) = 5.05 kcal mol(-1), for AP; ΔE(trans-cis) = 7.14 kcal mol(-1), for AMP). Carbonyl and NH absorption data in different solvents, supported by theoretical results taking into account the solvent effects [at IEFPCM-B3LYP/6-311++G(3df,3p) level of theory] clearly demonstrated that only the N,O-cis conformer is present in solution. However, a doublet was observed for AP, in CCl4, which can be attributed to this conformer and the lowest wavenumber component to the cis dimer form, stabilized through intermolecular hydrogen bonds (NH · · · OC). The overall preference for the N,O-cis conformer, in AP and AMP, as interpreted by the NBO analysis, indicated that the hyperconjugative effect is the main contribution to stabilize this rotamer, overcoming the possible steric repulsion. (13)C NMR experiments at low temperature in two different solvents (CS2/CDCl2 and acetone-d6) confirmed the occurrence of a single conformer since no separated signals were observed.
Fractionation and identification of minor and aroma-active constituents in Kangra orthodox black tea
Food Chem 2015 Jan 15;167:290-8.PMID:25148991DOI:10.1016/j.foodchem.2014.06.112.
The aroma constituents of Kangra orthodox black tea were isolated by simultaneous distillation extraction (SDE), supercritical fluid extraction and beverage method. The aroma-active compounds were identified using gas chromatography-olfactometry-mass spectrometry. Geraniol, linalool, (Z/E)-linalool oxides, (E)-2-hexenal, phytol, β-ionone, hotrienol, methylpyrazine and methyl salicylate were major volatile constituents in all the extracts. Minor volatile compounds in all the extracts were 2-ethyl-5-methylpyrazine, ethylpyrazine, 2-6,10,14-trimethyl-2-pentadecanone, acetylfuran, hexanoic acid, dihydroactinidiolide and (E/Z)-2,6-nonadienal. The concentrated SDE extract was fractionated into acidic, basic, water-soluble and neutral fractions. The neutral fraction was further chromatographed on a packed silica gel column eluted with pentane and diethyl ether to separate minor compounds. The aroma-active compounds identified using gas chromatography-olfactometry-mass spectrometry were 2-amylfuran, (E/Z)-2,6-nonadienal, 1-pentanol, epoxylinalool, (Z)-jasmone, 2-Acetylpyrrole, farnesyl acetone, geranyl acetone, cadinol, cubenol and dihydroactinidiolide. AEDA studies showed 2-hexenal, 3-hexenol, ethylpyrazine, (Z/E)-linalool oxides, linalool, (E/Z)-2,6-nonadienal, geraniol, phenylethanol, β-ionone, hotrienol and dihydroactinidiolide to be odour active components.
Mutagenicity and cytotoxicity of nitropyrrole compounds derived from the reaction of 2-acetyl pyrrole with nitrite
Food Chem Toxicol 1994 Sep;32(9):839-44.PMID:7927082DOI:10.1016/0278-6915(94)90161-9.
2-Acetylpyrrole (AP) is a product of model browning systems, and has been isolated as a major flavour component of many foods. Reaction of AP with nitrite produces two N-nitropyrrole compounds, 1-nitro-2-acetyl-pyrrole (NAP) and 1,3,5-trinitro-2-acetylpyrrole (TNAP), the chemical structures of which have been confirmed by spectral studies, including UV mass, nuclear magnetic resonance, infra-red and elemental analysis (EA). NAP and TNAP are moderately mutagenic to the Salmonella strains TA98 and TA100 in the absence of a mammalian activation system and are markedly cytotoxic to mouse C3H10T1/2 cells. These results suggest that the formation of direct-acting mutagens of nitro-derivatives may take place in nitrite-containing food or in vivo by nitrosation following ingestion of AP.
Microwave Irradiation Syntheses and Crystal Structures of Two Series of Novel Fivemembered Heterocyclic Mono-Imine Compounds
Curr Org Synth 2019;16(3):444-448.PMID:31984907DOI:10.2174/1570179416666181207125604.
Aim and objective: The late transition metal complexes with five-membered heterocyclic mono-imine ligands have attracted much attention because of their potential application in olefin polymerization catalysis. In order to increase the coordination ability of heteroatom N and S to center metals, CH3 group was introduced into the side arm of pyrrole imine and thiophene imine respectively, to get two series of novel five-membered heterocyclic imine compounds, mono(imino)pyrroles and mono(imino)thiophenes. Materials and methods: Two series of novel five-membered heterocyclic compounds with the mono-imine group were synthesized from the p-toluene sulfonic acid catalyzed Schiff base condensation of aromatic amines and 2-Acetylpyrrole/ 2-acetylthiophene respectively, using CH3 group to substitute the common H atom on the side arm of pyrrole imine/ thiophene imine. Results: All the heterocyclic mono-imine compounds were characterized adequately by means of 1H NMR, 13C NMR, FT-IR, elementary analysis, as well as X-ray crystallographic diffraction. The reactivity differences between two precursor 2-Acetylpyrrole and 2-acetylthiophene with aromatic amines were compared and discussed in detail. Conclusion: Compared to traditional heating methods, the solvent-free microwave irradiation seemed more efficient to prepare these series of five-membered heterocyclic mono-imine compounds, which resulted in a higher yield and cleaner product.