2-Acetylbutyrolactone
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| Preferred IUPAC name
2--Acetylbutyrolactone | |
| Identifiers | |
3D model (JSmol)
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CompTox Dashboard (EPA)
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| Properties | |
| C6H8O3 | |
| Molar mass | 128.127 g·mol−1 |
| Boiling point | 107–108 °C (225–226 °F; 380–381 K) |
| 310 g/L (20 ºC) | |
| Hazards | |
| Safety data sheet | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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2-acetylbutyrolactone is a chemical compound with many isomers that has a role in chemistry and pharmacy area. Itt not only can act as the material to synthesize medicine to curing narrow and wide glaucoma but also can be used to determine amine compounds. . 2-acetylbutyrolactone can function as a raw material to synthesize pilocarpine and as an intermediate to synthesize chemical and pharmacy products. Use 2-acetylbutyrolactone to synthesize pilocarpine have far-reaching significance in history. As human-derived it from the leaves of Pilocarpus jaborandi in the past, it is great progress from natural extraction to artificial synthesis. More importantly, 2-acetylbutyrolactone could function as a fluorogenic reagent for the determination of amine compounds. Therefore, I have chosen this topic, as its great effect on chemical and pharmacy. The synthesis of 2-acetyl butyrolactone will help people who suffered from narrow and wide glaucoma.2-acetyl butyrolactone could enhance the spectroscopy, reacting as an analytical reagent. In terms of how to synthesize 2-acetylbutyrolactone, it is produced by reacting ethylene oxide with ethyl acetoacetate under alkaline conditions.
Physical Properties
The molecular weight of 2-acetyl butylrolactone is 128.127g/mol.[1] The molecular formula is C6H8O3. It has many isomers, including alpha-acetyl butylrolactone, 2-acetyl-gamma-butylrolactone and 3- acetyltetrahydro-2-furanone. Water solubility is 1.56M.[1] The GHS classification for 2-acetylbutyrlactone, the pictogram is irritant.[1] Signal is warming.The GHS hazard statement for 2-acetylbutyrlactone; [1]when the concentration is 97.63% , it will cause skin irritation and corrosion; when the concentration of 2-acetylbutyrlactone is 99.41%, it serious eye irritation and serious eye damage/ eye irritation.[1] when the concentration of 2-acetylbutyrlactone is 93.49%, it may cause respiratory irritation, and organ toxicity.[1]
Acetylbutyrolactone has many isomers, like 2-acetylbutyrlactone and alpha gamma butyrolactone. The boiling point is 107~108 degree Celsius at 5 mm pressure.[2] The specific gravity is 20/20 of 1.185-1.189.[2]
Chemical properties
2-acetyl butylrolactone is an important intermediate, used in the chemical and biological area. As many experiments need it for further study. Firstly, for some medical treatment, most of them are the greatest healer for curing rheumatoid arthritis and incendiary illness.[3]Furthermore, it posses high selectivity and neoplastic activity, which could improve the function of medicine, accelerate the speed of curing. [3]When it combined with metal ions like copper, this type of function could be more obvious.2-acetyl butylrolactone is thus used as an intermediate to enhance the effect of medical treatment. Besides, 2-acetyl butyrolactone could be used to synthesize Solvatochromism. it is an important chemical compound for studying biological macro system and polarity.[3]
Furthermore, 2-acetyl butylrolactone is an intermediate to synthesize santalene with 4-methyl-4-pentenyl side chain.[4] As Chemists used 2-acetyl butyrolactone to obtain the ketone.[4] The yield is about 90 percent. And further, convert to ketal, the main method to convert ketone to ketal is by reacting with sodium hydrogen carbonate. Then distilled it, obtained the ketal, to synthesize 4-methyl-4-pentenyl side chain.[4] In addition, use 2-acetyl butylrolactone as intermediates to synthesize another intermediate, called α-methylene-γ-butyrolactones, which is widely used in biological research or to be antotumour, phytotoxic and antibacterial. Besides, many intermediates are usingα-methylene-γ-butyrolactones to synthesize.[5] In this article, it mainly introduced how to use 2-acetyl butyrolactone reacted isonitrile and acetylene diesters to synthesize α-methylene-γ-butyrolactones. The mole ration of the reactants is 1:1:1.[5] During the reaction process, ter-butyl isocyanide reacts with acetylenic diesters through addition reaction, followed by enolized keto ester.[5] Then, the positive charged species will react with enolate anion followed by loose water. it also could react with water to form acetic acid replaced by acetyl group, formed alpha methylene-gamma-butyrlactones. [5]Accorfing to the NMR spectrum analysis, it has determined the product is α-methylene-γ-butyrolactone. One benefit of this article is worth to mention is the reactants and the reagents could mix together, and the procedure is easy to apply.[5]
Applications
Application of 2-acetylbutyrolactone to spectrofluorimetry.
Aniline including primary amino group reacted with 2-acetylbutyrlactone . [6]The product is 2-ethyl-gamma-butyrolactone. In addition, 2-acetylbutyractone react with 4-fluorolactone forming enamine. Some of these reactions are reacted in acid conditions, the results states that the acid conditions benefit the formation of carbonium ion.[6]
The fluorescence is also reacted like primary amine, it reacted in different organic solvents, including acid solutions,DMF, and Britton Robinson buffer solution. [6]According to the spectroscopy data, we know
2-acetylbutyrlactone does not favor the DMF conditions.[6] As the basic property can active alpha carbon to form
carbonion ion. Acidic solution does not favor either, because proton will active alpha carbon to form carbanion ion. [6]Meanwhile, the wavelength of 2-acetylbutyrlactone in DMF or DMF in alkaline are the same, which illustrated that the formation of carbanion and enol form is favored in DMF conditions.[6]
Use SMX as a model of arylamine drug, pilot experiment find the fluorescence intensity is about 14 times higher than the enamine.[6] Hence, 2-acetylbutyrlactone with primary amine is favored in acid aolutions. DMF is also one of the choice for people who are concerned in amine group.[6]
2-acetylbutyrlactone is a fluorogenic reagent.[6] When 2-acetylbutyrlactone is reacted with amino drugs in acidic conditions, it shows analytical sensetivity, although the absorbance is not strong. Compared with amantadine and trimethoprim, it has strong sensetivity.[6] As the concentration of trimethoprim up to 10ug/ml still can not be detected. Specifically, chemists use 2-acetylbutyrolactone as a fluorogenic reagent for spectrofluorometric to confirm amines.[6] If the compounds include amines, like RNH2 and ArNH2, it will react with 2-acetylbutyrolactone to form fluorescent Schiff base in acid solutions or in dimethylformamide (DMF). Sulfamethoxazole (SMX), and ampicillin sodium (AMP Na) are models for aryl and aliphatic amines.[6] The reaction' s mechanism is the alpha acetyl of 2-acetylbutyrlactone will react with aldehyde and ketone to form imine by nucleophilic addition. Two possible reaction pathways were included;
First: Specifically, 2-acetylbutyrolactone reacted with SMX to form 2-[1-(4-substituted pheylimino) ethyl]-r-butyrolactone. Initially, it is the Schiff base and then become yellow fluorescent compound.[6]
Second: 2-acetylbutyrolactone reacted with ampicillin sodium. Ampicillin sodium's α-amino group of the chain reacted with 2-acetylbutyrolactone's reactive carbon group, forming Schiff base.[6]
In these reactions, many variables will affect it. Firstly, it must has serious time controlling. when 2-acetylbutyrlactone reacted with DMF and heated to 100 degree Celsius, it must has suitable interval time and then mixed with distilled water.[6]The results shows fluorescence values is about 30 mins.Secondly, the concentration of 2-acetylbutyrlactone is 8-12% gives the maximum fluorescene intensity.[6]
To synthesize pilocarpine
Pilocarpine is an effective and significant medicine to cure narrow and wide glaucoma.[7]It is first derived from the leaves of Pilocarpus jaborandi. Such type of the tree only grow in tropical area in Brazil and Paraguay.[7]The demands of such type of tree to cure glaucoma almost caused the extinct of this tree.[7]Use acetylbutenolide to synthesis pilocarpine have four stages, one of the key process is to synthesize unsaturated acetylbutyrolactone from 2-acetylbutyrolactone.[7] In this process, 2-acetylbutyrolactone is functioned as an important raw materials.The following are the specific experimental method. 2-acetylbutyrlactone reacted with sodium hydride, and kept the temperature at 0 degree Celsius. [7]Keeping stir it for 30 minutes at 0 degree Celsius. And then this solution mixed with phenylselenenyl chloride. Stir it for 5 minutes at 0 degree Celsius. Dilute it by 300ml Et2O, washed it with suturated sodium hydrocarbonate, water and brine, dried it by magnesium sulfate.[7] During this process, it first form 3-acetyl-furanone, 3-furanone, Dehydrohomopilopic Aldehyde, Homopilopic Aldehyde and Pilocarpine.[7]
To be an analytical reagent
2-acetyl butylrolactone could enhance the spectroscopy. [8]As 2-acetyl butylrolactone has a cyclic β‐keto ester, it can react with arylamines, formed arylhydrazones. [8] Measure its spectroscopy under the alkaline and acidic solutions, it is obvious. Compared arylamines reacted with ethyl acetoacetate, it does not work in acidic solutions. Although ethyl acetoacetate in alkaline has better sensitivity.[8] The main difference is that the reactive functional group. 2-acetyl butyrolactone has a cyclic β‐keto ester, but acetoacetate has the acyclic β‐keto ester. This article uses experiments to illustrates the analytical reagent function by determining the sulfa compounds, including sulfadiazine (SD), sulfamethoxazole (SMX), sulfamoxole (SMO), and sulfametrole (SMR) with other drugs. One thing need to mention is that SMX and SMO were analysed by the computerized compensation spectrophotometric method.[8] The final results are analysed by one way analysis of variance.[8] when2-acetyl butyrolactone reacted with the mixture, it will active methylene compound. Remove the acetyl functional group by the base, formed α‐arylhydrazone‐γ‐butyrolactone.[8] This article also considered the concentration effect of 2-acetyl butylrolactone, and find a combination of 0.6%(v/v) 2-acetyl butylrolactone and the 0.6M alkaline solution has a higher reaction efficiency in terms of reaction time and sensitivity.[8] Specifically, for coupling with 2-acetylbutyrlactone, 0.6% v/v 2-acetylbutyrlactone in 0.6m sodium hydroxide was miaxed with cold diazonium salt solution, and left it for 20 minutes.[8] After 20 minutes, dilute with water until the PH is 2. Recorded the spectrophotometric measurements vs thereagent; For coupling with ethyl acetoacetate, diazonium salt was diluted by EAA solution, the ration is 1.6%(v/v), let it for 25 minutes, then recorded the spectrophotometric measurements vs reagent.[8] When 2-acetylbutyrlactone reacted with analog and EAA, it acted as a promising coupling carbanion.[8]
This article illustrate that 2-acetylbutyrlactone is an novel reagent when analytical potential in UV visible spectroscopy, because 2-acetylbutyrlactone has active methylene group.[8] when it reacted with diazotized substrates, it forms alpha-arylhydrazono- gamma butyrlactones, followed by the analysis in acidic solutions. [8]2-acetylbutyrlactone has the same sensetivity and reactivity, compared with other coupling reagents.[8] Howeverm, 2-acetylbutyelactone is difficult to control it as analytical reagents because of two reactive centers, including carbonyl group and methylene group.[8]
How to synthesize 2-acetyl butylrolactone
The main method to synthesize acetyl butyrolactone is by reacting ethylene oxide with ethyl acetoacetate. And the reaction proceeds under alkaline conditions. However, the procedures are complicated and has high laboratory requirements. These procedures included neutralizations, extractions, and fractionation. Specifically, Dissolve 200mg sodium hydroxide in 1350cc water and cooling it to 20 degrees Celsius. Added 450cc ethyl oxide and 650 grams ethyl acetoacetate.[2] and cooling it to 0 degrees Celsius. The temperature needs to keep 0 degrees Celsius for 2 days. The temperature is important for this experiment. [2]As no matter the temperature higher or lower than that range, it will reduce the yield. And even cause the product is not purified. At the end of the experiment, use 300 grams of acetic acid to neutralize the mixture, extracting it with benzol three times.Finally, removing the benzol by lower pressure. [2]The biggest advantage of this experiment is: does not need metallic sodium and can finish it at the normal laboratory.
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 Pubchem (2019-05-11). "2-Acetylbutyrolactone". National Center for Biotechnology Information.
- ↑ 2.0 2.1 2.2 2.3 2.4 Johnson, William (1945). "preparation of acetylbutyrlacton6" (PDF). United States Patent Office. 28: 43–82 – via patentimages.
- ↑ 3.0 3.1 3.2 A, Taha (5 April 2015). "Reactivity and molecular modeling of new solvatochromic mixed-ligand copper(II) chelates of 2-acetylbutyrolactone and dinitrogen bases". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 140: 74–84. Bibcode:2015AcSpA.140...74T. doi:10.1016/j.saa.2014.11.056. PMID 25589389.
- ↑ 4.0 4.1 4.2 Unnikrishnan, P,A (1992). "Syntheses of epi-β-Santalene, β-Santalene and an Isomer of β-Santalene with 4-Methyl-4-pentenyl Side Chain". An International Journal for Rapid Communication of Synthetic Organic Chemistry. 22 (22): 3159–3168. doi:10.1080/00397919208021129.
- ↑ 5.0 5.1 5.2 5.3 5.4 Aghari, S (2006). "Reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in the presence of 2-acetylbutyrolactone. Synthesis of functionalized α-methylene-γ-butyrolactones". Tetrahedron. 47 (25): 4297–4299. doi:10.1016/j.tetlet.2006.03.109.
- ↑ 6.00 6.01 6.02 6.03 6.04 6.05 6.06 6.07 6.08 6.09 6.10 6.11 6.12 6.13 6.14 6.15 Sabry, S M (2006). "Application of 2-acetylbutyrolactone to spectrofluorimetry: Fluorescence properties of Schiff bases derived from 2-acetylbutyrolactone and spectrofluorimetric determination of primary amine-containing compounds". Journal of Pharmaceutical and Biomedical Analysis. 40 (5): 1057–1067. doi:10.1016/j.jpba.2005.08.036. PMID 16256289.
- ↑ 7.0 7.1 7.2 7.3 7.4 7.5 7.6 Horne, D A (1993). "A Synthesis of Pilocarpine". The Journal of Organic Chemistry. 58: 62–64. doi:10.1021/jo00053a016.
- ↑ 8.00 8.01 8.02 8.03 8.04 8.05 8.06 8.07 8.08 8.09 8.10 8.11 8.12 8.13 Sabry, S M (2006). "Enhanced Spectrophotometry of Sulfonamides with Novel 2‐Acetylbutyrolactone Derivatives". Analytical Letters. 39 (13): 2591–2615. doi:10.1080/00032710600824748.
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