2-Acetylbutyrolactone

2-Acetylbutyrlactone
Names
	Preferred IUPAC name 2--Acetylbutyrolactone
Identifiers
CAS Number	517-23-7 ;
3D model (JSmol)	Interactive image;
UNII	I3D73T5K0Q ;
	InChI InChI=1S/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3 Key: JWUJQDFVADABEY-UHFFFAOYSA-N ; InChI=1S/C6H8O3/c1-4(7)5-2-3-9-6(5)8/h5H,2-3H2,1H3 Key: OMQHDIHZSDEIFH-UHFFFAOYSA-N;
	SMILES CC(=O)C1CCOC1=O;
Properties
Chemical formula	C6H8O3
Molar mass	128.127 g·mol−1
Boiling point	107–108 °C (225–226 °F; 380–381 K)
Solubility in water	310 g/L (20 ºC)
Hazards
Safety data sheet (SDS)	External MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

2-acetylbutyrolactone is the chemical compound, it has played important role in chemical and pharmacy area. As it 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. Hence, it is notable in the Wikipedia because it’s extensive application. In addition, in terms of neutrality, the physical property including molecular weight, structure and isomers, which is the 2-acetylbutyrolactone’s s unique properties. 2-acetylbutyrolactone have many isomers, they thus have different names, like 4, 5-dihydro-3-acetylfuran-2(3H)-one and alpha-acetyl-gamma-butyrolactone. 2-acetylbutyrolactone not only can function as a raw material to synthesize pilocarpine but also can function as 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 a great progress from natural extraction to artificial synthesis. More importantly, 2-acetylbutyrolactone could be 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-acetylbutyrolactone will help people who suffered from narrow and wide glaucoma, which states its notability. 2-acetyl butyrolactone could enhance the spectroscopy, reacting as analytical reagent. In terms of how to sythesize 2-acetylbutyrolactone, it is produced by reacting ethylene oxide with ethyl acetoacetate under alkaline conditions.

Physical Properties^[2]

The molecular weight of 2-acetyl butyrolactone is 128.127g/mol. The molecular formula is C6H8O3. It has many isomers, including alpha-acetyl butyrolactone, 2-acetyl-gamma-butyrolactone and 3- acetyltetrahydro-2-furanone. Water solubility is 1.56M.

Chemical properties

2-acetyl butyrolactone 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. When it combined with metal ions like copper, this type of function could be more obvious.2-acetyl butyrolactone 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 butyrolactone is an intermediate to synthesize santalene with 4-methyl-4-pentenyl side chain. As Chemists used 2-acetyl butyrolactone to obtain the ketone. 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 butyrolactone 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. 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

To determine the amine compounds^[6]

Chemists use 2-acetylbutyrolactone as a fluorogenic reagent for spectrofluorometric to confirm amines. 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. 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.

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

To synthesize pilocarpine^[7]

Pilocarpine is an effective and significant medicine to cure narrow and wide glaucoma. It is first derived from the leaves of Pilocarpus jaborandi. Such type of the tree only grow in tropical area in Brazil and Paraguay. The demands of such type of tree to cure glaucoma almost caused the extinct of this tree. Use acetylbutenolide to synthesis pilocarpine have four stages, one of the key process is to synthesize unsaturated acetylbutyrolactone from 2-acetylbutyrolactone. In this process, 2-acetylbutyrolactone is functioned as an important raw materials.

To be an analytical reagent^[8]

2-acetyl butyrolactone could enhance the spectroscopy. As 2-acetyl butyrolactone has a cyclic β‐keto ester, it can react with arylamines, formed arylhydrazones. 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. 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. 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. This article also considered the concentration effect of 2-acetyl butyrolactone, and find a combination of 0.6%(v/v) 2-acetyl butyrolactone and the 0.6M alkaline solution has a higher reaction efficiency in terms of reaction time and sensitivity.

How to synthesize 2-acetyl butyrolactone^[9]

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. 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. 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. The biggest advantage of this experiment is: does not need metallic sodium and can finish it at the normal laboratory.

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References

^ Cite error: The named reference 517-23-7 was invoked but never defined (see the help page).
^ 2-Acetylbutyrolactone. (2019). Retrieved from https://pubchem.ncbi.nlm.nih.gov/compound/2-Acetylbutyrolactone
^ ^a ^b Taha, A., Adly, O., & Shebl, M. (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. https://doi.org/10.1016/j.saa.2014.11.056
^ Unnikrishnan, P., & Vatakencherry, P. (1992). Syntheses of epi-β-Santalene, β-Santalene and an Isomer of β-Santalene with 4-Methyl-4-pentenyl Side Chain. Synthetic Communications, 22(22), 3159-3168. doi: 10.1080/00397919208021129
^ ^a ^b Asghari, S., & Mohammadi, L. (2006). Reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in the presence of 2-acetylbutyrolactone. Synthesis of functionalized α-methylene-γ-butyrolactones. Tetrahedron Letters, 47(25), 4297–4299. https://doi.org/10.1016/j.tetlet.2006.03.109
^ 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.
^ Horne, D., Fugmann, B., Yakushijin, K., & Buchi, G. (2019). A synthesis of pilocarpine.
^ Sabry, S. M. (2006). Enhanced spectrophotometry of sulfonamides with novel 2‐acetylbutyrolactone derivatives. Analytical letters, 39(13), 2591-2615.
^ Johnson, W. L. (1948). U.S. Patent No. 2,443,827. Washington, DC: U.S. Patent and Trademark Office.

^[1]

^ "517-23-7 | CAS数据库". www.chemicalbook.com. Retrieved 2019-05-17.

[517-23-7-1] Cite error: The named reference 517-23-7 was invoked but never defined (see the help page).

[2] 2-Acetylbutyrolactone. (2019). Retrieved from https://pubchem.ncbi.nlm.nih.gov/compound/2-Acetylbutyrolactone

[:0-3] Taha, A., Adly, O., & Shebl, M. (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. https://doi.org/10.1016/j.saa.2014.11.056

[4] Unnikrishnan, P., & Vatakencherry, P. (1992). Syntheses of epi-β-Santalene, β-Santalene and an Isomer of β-Santalene with 4-Methyl-4-pentenyl Side Chain. Synthetic Communications, 22(22), 3159-3168. doi: 10.1080/00397919208021129

[:1-5] Asghari, S., & Mohammadi, L. (2006). Reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in the presence of 2-acetylbutyrolactone. Synthesis of functionalized α-methylene-γ-butyrolactones. Tetrahedron Letters, 47(25), 4297–4299. https://doi.org/10.1016/j.tetlet.2006.03.109

[6] 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.

[7] Horne, D., Fugmann, B., Yakushijin, K., & Buchi, G. (2019). A synthesis of pilocarpine.

[8] Sabry, S. M. (2006). Enhanced spectrophotometry of sulfonamides with novel 2‐acetylbutyrolactone derivatives. Analytical letters, 39(13), 2591-2615.

[9] Johnson, W. L. (1948). U.S. Patent No. 2,443,827. Washington, DC: U.S. Patent and Trademark Office.

[10] "517-23-7 | CAS数据库". www.chemicalbook.com. Retrieved 2019-05-17.

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2-Acetylbutyrolactone

Physical Properties[2]

Chemical properties

Applications

To determine the amine compounds[6]

To synthesize pilocarpine[7]

To be an analytical reagent[8]

How to synthesize 2-acetyl butyrolactone[9]