| Identification |
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| YMDB ID | YMDB01418 |
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| Name | gamma-butyrolactone |
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| Species | Saccharomyces cerevisiae |
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| Strain | Brewer's yeast |
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| Description | gamma-Butyrolactone, also known as 1,4-butanolide or 4-hydroxy-butanoate, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, gamma-butyrolactone is considered to be a fatty ester. gamma-Butyrolactone exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on gamma-Butyrolactone. |
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| Structure | |
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| Synonyms | - -lactone
- 1-Oxacyclopentan-2-one
- 1,2-Butanolide
- 1,4-Butanolide
- 1,4-Butyrolactone
- 1,4-Lactone
- 2-Dihydrofuranone
- 2-Oxolanone
- 2-Oxotetrahydrofuran
- 2,3,4,5-Tetrahydro-2-furanone
- 2(3H)-Dihydrofuranone
- 2(3H)-Furanone, dihydro-
- 3-Hydroxybutyric acid lactone
- 4-Butanolide
- 4-Butyrolactone
- 4-Deoxytetronate
- 4-Deoxytetronic acid
- 4-hydroxy-Butanoate
- 4-hydroxy-Butanoic acid
- 4-hydroxy-Butanoic acid g-lactone
- 4-Hydroxybutanoate
- 4-Hydroxybutanoic acid
- 4-Hydroxybutanoic acid lactone
- 4-Hydroxybutanoic acid, «
- 4-Hydroxybutyric acid lactone
- 4-Hydroxybutyric acid, «
- 4,5-Dihydro-2(3H)-furanone
- alpha-Butyrolactone
- BLO
- BLON
- Butyric acid lactone
- Butyric acid, 4-hydroxy-, gamma-lactone
- Butyrolactone
- Butyryl lactone
- Butyrylactone
- Dehydro-2(3H)-furanone
- dihydro-(3 H)-furan-2-one
- Dihydro-2-furanone
- Dihydro-2(3H)-furanone
- Dihydro-2(3H)-furanone (-butyrolactone)
- dihydrofuran-2(3h)-one
- g-Butalactone
- g-Butyrolactone
- g-Butyryllactone
- g-Hydroxybutyric acid lactone
- gamma-Butalactone
- gamma-butanolactone
- GAMMA-BUTYROLACTONE
- gamma-Butyryllactone
- gamma-Hydroxybutyric acid lactone
- gamma-hydroxybutyrolactone
- GBL
- Paint Clean G
- Tetrahydro-2-furanone
- Tetrahydrofuran-2-one
- 4-Hydroxybutyrate lactone
- g-Butanolactone
- Γ-butanolactone
- g-Hydroxybutyrate lactone
- gamma-Hydroxybutyrate lactone
- Γ-hydroxybutyrate lactone
- Γ-hydroxybutyric acid lactone
- g-Hydroxybutyrolactone
- Γ-hydroxybutyrolactone
- Γ-butyrolactone
- 4 Butyrolactone
- gamma Butyrolactone
- Furanone, tetrahydro 2
- 1,4 Butanolide
- 4 Hydroxybutyric acid lactone
- Lactone, 4-hydroxybutyric acid
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| CAS number | 187997-16-6 |
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| Weight | Average: 86.0892
Monoisotopic: 86.036779436 |
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| InChI Key | YEJRWHAVMIAJKC-UHFFFAOYSA-N |
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| InChI | InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2 |
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| IUPAC Name | oxolan-2-one |
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| Traditional IUPAC Name | butyrolactone |
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| Chemical Formula | C4H6O2 |
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| SMILES | O=C1CCCO1 |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Lactones |
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| Sub Class | Gamma butyrolactones |
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| Direct Parent | Gamma butyrolactones |
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| Alternative Parents | |
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| Substituents | - Gamma butyrolactone
- Tetrahydrofuran
- Carboxylic acid ester
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Liquid |
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| Charge | 0 |
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| Melting point | -45 |
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| Experimental Properties | | Property | Value | Reference |
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| Water Solubility | 1000 mg/mL [WEAST,RC (1972)] | PhysProp | | LogP | -0.64 [HANSCH,C ET AL. (1995)] | PhysProp |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations | |
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| Organoleptic Properties | |
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| SMPDB Pathways | Not Available |
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| KEGG Pathways | Not Available |
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| SMPDB Reactions | Not Available |
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| KEGG Reactions | Not Available |
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| Concentrations |
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| Intracellular Concentrations | | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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| 105 ± 12 µM | Must from Vitis vinifera, cv. Pedro Ximrnez (Sherry Wine) | anaerobic | Brewer's yeast | Zea, L., Moreno, J., Ortega, J. M., Mauricio, J. C., Medina, M. (1995) "Comparative study of the _-butyrolactone and pantolactone contents in cells and musts during vinification by three Saccharomyces cerevisiae races." Biotechnology Letters. Volume 17, Number 12, 1351-1356 | | Conversion Details Here |
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| Extracellular Concentrations | | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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| 174 ± 35 µM | Must from Vitis vinifera, cv. Pedro Ximrnez (Sherry Wine) | anaerobic | Brewer's yeast | Zea, L., Moreno, J., Ortega, J. M., Mauricio, J. C., Medina, M. (1995) "Comparative study of the _-butyrolactone and pantolactone contents in cells and musts during vinification by three Saccharomyces cerevisiae races." Biotechnology Letters. Volume 17, Number 12, 1351-1356 | | Conversion Details Here |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-004l-9000000000-500445dc73cb69119e6b | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-002f-9000000000-d3df175d3315ed446e14 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-004l-9000000000-500445dc73cb69119e6b | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-002f-9000000000-d3df175d3315ed446e14 | JSpectraViewer | MoNA | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-002f-9000000000-bd4b413f20907d13a107 | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-9000000000-4a6de93563809aa51a33 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000i-9000000000-4a6de93563809aa51a33 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000i-9000000000-b5163f6eb1e8004e61a9 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-004l-9000000000-1066d349a6023c66dd64 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive | splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-002f-9000000000-d3df175d3315ed446e14 | JSpectraViewer | MoNA | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-fb7c9ada825a0c62979f | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000l-9000000000-95fda8a898d02f7e71ff | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000l-9000000000-c8282365f175b61ca8c0 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-ec20127c74818b1f634d | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052r-9000000000-86d21b481322417edf81 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-4f454124d6cece18a212 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-9000000000-507998514018a44c4cf0 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000l-9000000000-d4ec4947321dfb11fab4 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-b2a1436205f5365513b0 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-9000000000-709821dd006aa045c8b0 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9000000000-ffe2d9473d85a58305c1 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-a4219a074939d10a0f5f | JSpectraViewer | | MS | Mass Spectrum (Electron Ionization) | splash10-004l-9000000000-2fc3f4165b5808b41e93 | JSpectraViewer | MoNA | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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| References |
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| References: | - Antonelli, A., Castellari, L., Zambonelli, C., Carnacini, A. (1999). "Yeast influence on volatile composition of wines." J Agric Food Chem 47:1139-1144.10552428
- Zea, L., Moreno, J., Ortega, J. M., Mauricio, J. C., Medina, M. (1995) "Comparative study of the _-butyrolactone and pantolactone contents in cells and musts during vinification by three Saccharomyces cerevisiae races." Biotechnology Letters. Volume 17, Number 12, 1351-1356
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| Synthesis Reference: | Zhu, Yulei; Li, Yongwang; Xiang, Hongwei; Su, Hualian; Wu, Jiaxiang. Process for preparation of g-butyrolactone with high yield and selectivity. Faming Zhuanli Shenqing Gongkai Shuomingshu (2001), 13 pp. |
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| External Links: | |
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