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2-Acetylbutyrolactone

Description Reference
Product Name
2-Acetylbutyrolactone
CAS No.
517-23-7
Chemical Name
2-Acetylbutyrolactone
Synonyms
ABL;3-acetyldihydrofuran-2(3H)-one;ABL1;ACETYLBUTYROLACTONE;2-Acetylbutyrolacton;-Acetyl-hydroxybutyricacid;2-Oxo-3-acetyltetrahydrofuran;JTK7;p190;CHDSKM
CBNumber
CB8101532
Molecular Formula
C6H8O3
Formula Weight
128.13
MOL File
517-23-7.mol
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2-Acetylbutyrolactone Property

Melting point:
<25 °C
Boiling point:
107-108 °C5 mm Hg(lit.)
Density 
1.19 g/mL at 25 °C(lit.)
vapor pressure 
0.131Pa at 20℃
refractive index 
n20/D 1.459(lit.)
Flash point:
>230 °F
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
200g/l
pka
12.00±0.20(Predicted)
form 
Liquid
color 
Clear
biological source
human
Water Solubility 
310 g/L (20 ºC)
Merck 
14,83
Specific Activity
717-971nmol/min·mg
BRN 
112676
Stability:
Stable. Incompatible with strong oxidizing agents, strong bases.
LogP
-0.43 at 22℃
CAS DataBase Reference
517-23-7(CAS DataBase Reference)
NIST Chemistry Reference
2(3H)-Furanone, 3-acetyldihydro-(517-23-7)
EPA Substance Registry System
2(3H)-Furanone, 3-acetyldihydro- (517-23-7)
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Safety

Hazard Codes 
Xi,T
Risk Statements 
36/37/38-61
Safety Statements 
26-36-37/39-45-53
WGK Germany 
1
RTECS 
LU3456000
TSCA 
Yes
HS Code 
29322980
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A13409
Product name
α-Acetylbutyrolactone
Purity
≥99%
Packaging
100g
Price
$42.4
Updated
2025/07/31
Sigma-Aldrich
Product number
A13409
Product name
α-Acetylbutyrolactone
Purity
≥99%
Packaging
500g
Price
$46.8
Updated
2025/07/31
Sigma-Aldrich
Product number
SRP5279
Product name
ABL1, active, His tagged human
Purity
PRECISIO<SUP>&#174;</SUP>, recombinant, expressed in baculovirus infected <I>Sf</I>9 cells, &#8805;7
Packaging
10 μg
Price
$456
Updated
2025/07/31
Sigma-Aldrich
Product number
A0608
Product name
ABL1 (27-end), active, His-tagged from mouse
Purity
PRECISIO? Kinase, recombinant, expressed in baculovirus infected Sf9 cells, ≥70% (SDS-PAGE), buffered aqueous glycerol solution
Packaging
10μG
Price
$457
Updated
2025/07/31
Sigma-Aldrich
Product number
SRP5279
Product name
ABL1, active, His tagged human
Purity
PRECISIO?, recombinant, expressed in baculovirus infected Sf9 cells, ≥70% (SDS-PAGE), buffered aqueous glycerol solution
Packaging
10μG
Price
$498
Updated
2023/06/20
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2-Acetylbutyrolactone Chemical Properties,Usage,Production

Description

It is an important intermediate involved in the synthesis of chemical and pharmaceutical products such as vitamin B, 3,4-substituted pyridine, 5-(2-Hydroxyethyl)-4-methylthiazole. In presence of 2-acetylbutyrolactone, reaction of tert-butyl isocyanide with dialkyl acetylenedicarboxylates leads to the formation of dialkyl (E)-2-{(tert-butylamino)[2-oxo-4,5-dihydro-3(2H)-furanylidene]methyl}-2-butenedioates.1 Moreover, reaction of 2-acetylbutyrolactone with thiosemicarbazide and 3-(2-bromo-acetyl)-chromen-2-one in anhydrous ethanol produced 3-{2-[5-hydroxyl-4-(2-hydroxyl-ethyl)-3-methyl-pyrazol-1-yl]-thiazol-4-yl}-chromen-2-one in good yields.2 In addition, 2-acetylbutyrolactone can also function as the raw material for synthesizing pilocarpine that is a leading therapeutic agent for the treatment of narrow and wide angle glaucoma.3 Besides, this chemical can also act as a fluorogenic reagent in the quantitative spectrofluorometric determination of primary amines, which has been demonstrated to be equally accurate and precise as the officially or other reported methods.4

Reference

  1. Asghari, S.; Mohammadi, L., Reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in the presence of 2-acetylbutyrolactone. Synthesis of functionalized alpha-methylene-gamma-butyrolactones. Tetrahedron Lett. 2006, 47, 4297-4299.
  2. Rao, V. R.; Kumar, P. V., Facile one-pot synthesis of 3-{25-hydroxy-4-(2-hydroxy-ethyl)-3-methyl-pyrazol-1-yl -thiazol-4-yl} -chromen-2-ones via a three-component reaction. Synth. Commun. 2006, 36, 2157-2161.
  3. Horne, D. A.; Fugmann, B.; Yakushijin, K.; Buchi, G., A SYNTHESIS OF PILOCARPINE. J. Org. Chem. 1993, 58, 62-64.
  4. Sabry, S. M., Application of 2-acetylbutyrolactone to spectrofluorinietry: Fluorescence properties of Schiff bases derived from 2-acetylbutyrolactone and spectrofluorimetric determination of primary amine-containing compounds. J. Pharm. Biomed. Anal. 2006, 40, 1057-1067.

Chemical Properties

Colorless to light yellow liqui

Uses

An intermediate in the synthesis of 2,4-disubstituted pyridines. A fluorogenic reagent for the spectrofluorimetric determination of primary amines.

Uses

In synthesis of 3,4-disubstituted pyridines; of 5-(b-hydroxethyl)-4-methylthiazole.

Definition

ChEBI: 3-Acetyldihydro-2(3H)-furanone is a gamma-lactone.

Flammability and Explosibility

Not classified

Biological Activity

ABL1 protooncogene encodes a cytoplasmic and nuclear protein tyrosine kinase th at has been implicated in processes of cell differentiation, cell division, cell adhesion, and stress response. Activity of ABL protein is negatively regulated by its SH3 domain and deletion of the SH3 domain turns ABL1 into an oncogene. Translocation and head-to-tail fusion of the BCR and ABL1 genes is present in many cases of chronic myelogeneous leukemia. The DNA-binding activity of the ubiquitously expressed ABL1 tyrosine kinase is regulated by CDK1-mediated phosphorylation, suggesting a cell cycle function for ABL1.

Synthesis

75-21-8

105-45-3

517-23-7

Example 2: Ethylene oxide (EO, 25.0 g, 1.4 eq.) was slowly added to a methanol (MeOH, 144.0 g) solution of methyl acetoacetate (MAA, 46.9 g, 0.40 mol) followed by triethylamine (TEA, 40.7 g, 1.0 eq.) at 5°C. The reaction mixture was warmed up to 60 °C within 0.5 h and maintained at this temperature for 2.5 h. The reaction mixture was then heated up to 60 °C within 0.5 h and maintained at this temperature for 2.5 h. Quantitative GC analysis showed 50.8% conversion of MAA and 72.9% selectivity of α-acetyl-γ-butyrolactone (ABL). Example 4: Ethylene oxide (EO, 35.3 g, 2.0 eq.) was slowly added to a methanol (MeOH, 144 g) solution of methyl acetoacetate (MAA, 47.0 g, 0.40 mol) at 5 °C, followed by triethylamine (TEA, 42.4 g, 1.0 eq.). The reaction mixture was warmed up to 60 °C within 0.5 h and maintained at this temperature for 4.5 h. The reaction mixture was then heated up to 60 °C within 0.5 h and maintained at this temperature for 4.5 h. Quantitative GC analysis showed 67.7% conversion of MAA and 75.0% selectivity of α-acetyl-γ-butyrolactone (ABL). Examples 7-27: The reaction was carried out according to the method of Example 1 by adjusting the amount of ethylene oxide (EO), the optional addition of the catalysts and additives specified in Table 1, and the reaction times specified in Table 1. Table 1 details the reaction conditions, conversion and selectivity data for Examples 7-27. All reactions of Examples 7-26 were carried out at 60°C using 11 equivalents of methanol as solvent and 0.40 equivalents of MAA. Examples 27 and 28, on the other hand, used 0.10 eq. of MAA and 1 eq. of EO at 60 °C, using 11 eq. of methanol as solvent. Example of Example 28: Example of optimal reaction conditions using triethylamine (TEA) as a catalyst: 37 g of methanol was added to a 250 mL autoclave, pressurized with 2-3 bar nitrogen and heated to 65 °C. Subsequently, a solution of MAA (39.9 g, 0.34 mol, 1 eq.) and triethylamine (TEA, 34.4 g, 0.34 mol, 1 eq.) in methanol (27 g) with ethylene oxide (EO, 30.1 g, 0.68 mol, 2 eq.) was added simultaneously via two pumps over 11 min. After 2 h of reaction, analysis by GC showed a selectivity of 77% for ABL and a yield of 52.3% based on the added MAA. The conditions for this series of reactions ranged from 65 to 95 °C, addition times from 9 to 13 min, concentrations of MAA in the solvent from 1.3 to 2.1 mol/L, TEA/MAA molar ratios from 0.7 to 1.3, and EO/MAA molar ratios from 1.7 to 2.2.The results of this series of reactions showed MAA conversions ranging from 65.6 to 85.0%, ABL selectivities of 47.5-77.4% and the yield of ABL based on MAA was 40.4-52.3%.

References

[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 2585 - 2598
[2] Patent: EP1911752, 2008, A1. Location in patent: Page/Page column 6; 7; 7-8; 8
[3] Patent: EP1911752, 2008, A1. Location in patent: Page/Page column 6; 7; 8; 8-9
[4] Patent: EP1911752, 2008, A1. Location in patent: Page/Page column 7; 8; 9
[5] Patent: EP1911752, 2008, A1. Location in patent: Page/Page column 7; 8

2-Acetylbutyrolactone Preparation Products And Raw materials

Raw materials

Ethyl acetoacetate Acetyl ketene ETHYLENE OXIDE Methyl acetoacetate Vinyl acetate Sodium hydroxide METHANE Gamma Butyrolactone

Preparation Products

Thiamine chloride 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Fursultiamine
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View Lastest Price from 2-Acetylbutyrolactone manufacturers

Shandong Vital Biotechnology Co., Ltd.
Product
2-Acetylbutyrolactone 517-23-7
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
100tons
Release date
2025-11-20
Jinan Finer Chemical Co., Ltd
Product
2-Acetylbutyrolactone 517-23-7
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000mt
Release date
2022-02-17
Qingdao RENAS Polymer Material Co., Ltd.
Product
2-Acetylbutyrolactone 517-23-7
Price
US $0.00/kg
Min. Order
20kg
Purity
99%
Supply Ability
20 tons
Release date
2025-03-24

517-23-7, 2-AcetylbutyrolactoneRelated Search:

N-ACETYL-L-TYROSINE ETHYL ESTER Acetyl coenzyme A sodium salt Dihydromyrcenol Acetylacetone Acetyl chloride tributyl acetocitrate Gamma Butyrolactone ALPHA-ACETYL-ALPHA-METHYL-GAMMA-BUTYROLACTONE ABL PROTEIN TYROSINE KINASE,ABL PROTEIN TYROSINE KINASE, RECOMBINANT, E COLI ABL-21 Acid Blue 9 butalactin OXO-(2-OXO-TETRAHYDRO-FURAN-3-YL)-ACETIC ACID ETHYL ESTER Dihydro-3-(3-pyridoyl)-2-(3H)-furanone okilactomycin SETOSUSIN 2-CHLOROACETYL BUTYROLACTONE RK-682

  • -(-2-Hydroxyethyl)acetoaceticacid-lactone
  • 2-Acetyl-4-hydroxybutyric acid gamma-lactone
  • 2-Acetylbutyrolacton
  • 2-Oxo-3-acetyltetrahydrofuran
  • -Acetyl-hydroxybutyricacid
  • alpha-(2-Hydroxyethyl)acetoacetic acid gamma-lactone
  • alpha-Acetobutyrolactone
  • alpha-Acetylbutyrolactone
  • alpha-Acetyl-gamma-hydroxybutyric acid gamma-lactone
  • 2-ACETYL-GAMA-BUTYROLACTONE
  • 2-ACETYL-GAMMA-BUTYROLACTONE
  • 2-ACETYLBUTYROLACTONE
  • 2-ACETYL-4-BUTANOLIDE
  • 2-ACETOBUTANOATE-4-LACTONE
  • AKOS BBS-00004292
  • AKOS NCG-0049
  • ALPHA-ACETYL-GAMMA-BUTYROLACTONE
  • ALPHA-ACETYL-GAMMA-HYDROXYBUTYRIC ACID LACTONE
  • ABL
  • ACETYLBUTYROLACTONE
  • 3-Acetyloxolane-2-one
  • 3-acetyl-dihydro-2(3h)-furanone
  • 3-ACETYL-DIHYDRO-FURAN-2-ONE
  • OMEGA-ACETYL-GAMMA-BUTYROLACTONE
  • 2-acetyl-4-butyrolactone
  • 2-Acetyl-gaMMa-butyrolactone for synthesis
  • 3-Acetotetrahydrofuranone-2
  • NSC 2019
  • α-Acetyl-γ-hydroxybutyric Acid γ-Lactone
  • 2-AcetylbutyrolaCLone
  • 2-ACETYL-G-BUTYROLACTONE FOR SYNTHESIS
  • The2- acetyl-butyrolactone
  • α-Acetylbutyrolactone, 98%+
  • Anti-Abl-interactor protein 1
  • Anti-eps8 binding
  • Anti-interactor protein AblBP4
  • Anti-Nap1 binding protein NAP1BP
  • Anti-spectrin SH3 domain binding protein 1 SSH3BP1
  • ABL1, active, His tagged human
  • bcr/abl
  • ABL1 (27-end), active, His-tagged from mouse
  • ANTI-C ABL (ABL1)(C-TERMINAL) antibody produced in rabbit
  • Anti-eps8 binding protein
  • Abelson murine leukemia viral oncogene homolog 1
  • ABL1
  • ANTI-PHOSPHO-ABL(Y204) antibody produced in rabbit
  • JTK7
  • Monoclonal Anti-ABL1 antibody produced in mouse
  • ANTI-PHOSPHO-ABL(Y412) antibody produced in rabbit
  • Anti-Abelson interactor 1
  • 3-acetyldihydrofuran-2(3H)-one
  • butyroL
  • Alpha - acetyl - -butyllactone
  • 3-Acetyl-2-(3H)-4,-5-dihydrofuranone
  • 3-Acetyl-2(3H)-4,5-dihydrofuranone
  • 3-acetyldihydro-2(3h)-furanon
  • 3-Acetyltetrahydro-2-furanone
  • -Acetobutyrolacton