Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:47 UTC |
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Update date | 2019-11-26 02:59:09 UTC |
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Primary ID | FDB003392 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | gamma-Butyrolactone |
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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. gamma-Butyrolactone is a sweet, caramel, and creamy tasting compound. gamma-Butyrolactone is found, on average, in the highest concentration within red wine. gamma-Butyrolactone has also been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), blackberries (Rubus), peppers (Capsicum annuum), pineapples (Ananas comosus), and yellow bell peppers (Capsicum annuum). This could make gamma-butyrolactone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on gamma-Butyrolactone. |
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CAS Number | 96-48-0 |
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Structure | |
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Synonyms | Synonym | Source |
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1,2-Butanolide | ChEBI | 1,4-Butanolide | ChEBI | 1,4-Lactone | ChEBI | 4-Butyrolactone | ChEBI | 4-Deoxytetronic acid | ChEBI | 4-Hydroxybutyric acid lactone | ChEBI | Butyrolactone | ChEBI | Dihydro-2(3H)-furanone | ChEBI | gamma-Butanolactone | ChEBI | gamma-Hydroxybutyric acid lactone | ChEBI | gamma-Hydroxybutyrolactone | ChEBI | Tetrahydrofuran-2-one | ChEBI | 4-Deoxytetronate | Generator | 4-Hydroxybutyrate lactone | Generator | g-Butanolactone | Generator | Γ-butanolactone | Generator | g-Hydroxybutyrate lactone | Generator | g-Hydroxybutyric acid lactone | Generator | gamma-Hydroxybutyrate lactone | Generator | Γ-hydroxybutyrate lactone | Generator | Γ-hydroxybutyric acid lactone | Generator | g-Hydroxybutyrolactone | Generator | Γ-hydroxybutyrolactone | Generator | g-Butyrolactone | Generator | Γ-butyrolactone | Generator | 1-Oxacyclopentan-2-one | HMDB | 2,3,4,5-Tetrahydro-2-furanone | HMDB | 2-Oxolanone | HMDB | 2-Oxotetrahydrofuran | HMDB | 4,5-Dihydro-2(3H)-furanone | HMDB | 4-Butanolide | HMDB | 4-Hydroxy-butanoate | HMDB | 4-Hydroxy-butanoic acid | HMDB | 4-Hydroxy-butanoic acid g-lactone | HMDB | 4-Hydroxybutanoate | HMDB | 4-Hydroxybutanoic acid | HMDB | 4-Hydroxybutanoic acid lactone | HMDB | Butyric acid lactone | HMDB | g-Butalactone | HMDB | g-Butyryllactone | HMDB | gamma-Butalactone | HMDB | gamma-Butyryllactone | HMDB | GBL | HMDB | Paint clean g | HMDB | Tetrahydro-2-furanone | HMDB | 4 Butyrolactone | HMDB | gamma Butyrolactone | HMDB | Furanone, tetrahydro 2 | HMDB | 1,4 Butanolide | HMDB | 4 Hydroxybutyric acid lactone | HMDB | Lactone, 4-hydroxybutyric acid | HMDB | gamma-Butyrolactone | MeSH | 1-Oxacyclopentane-2-one | biospider | 1,4-Butyrolactone | biospider | 2-Dihydrofuranone | biospider | 2(3H)-dihydrofuranone | biospider | 3-Hydroxybutyric acid lactone | biospider | 4-Hydroxy-Butanoic acid g-lactone | biospider | 4-Hydroxybutanoic acid, «gamma»-lactone | biospider | 4-Hydroxybutyric acid, «gamma»-lactone | biospider | Butyryl lactone | biospider | Butyrylactone | biospider | Dihydro-2-furanone | biospider | Dihydrofuran-2(3H)-one | biospider | Dihyro-2-furanone | biospider | FEMA 3291 | db_source | gamma-Hydroxybutyric acid cyclic ester | biospider | gamma-Lactone 4-hydroxy-butanoic acid | biospider | gamma-Lactone 4-hydroxy-butyric acid | biospider | gamma-Lactone 4-hydroxybutanoic acid | biospider | gamma-Lactone 4-hydroxybutyric acid | biospider | Hydroxybutanoic acid lactone | biospider | γ-butanolactone | Generator | γ-butyrolactone | Generator | γ-hydroxybutyrate lactone | Generator | γ-hydroxybutyric acid lactone | Generator | γ-hydroxybutyrolactone | Generator |
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Predicted Properties | |
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Chemical Formula | C4H6O2 |
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IUPAC name | oxolan-2-one |
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InChI Identifier | InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2 |
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InChI Key | YEJRWHAVMIAJKC-UHFFFAOYSA-N |
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Isomeric SMILES | O=C1CCCO1 |
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Average Molecular Weight | 86.0892 |
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Monoisotopic Molecular Weight | 86.036779436 |
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Classification |
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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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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Indirect biological role: Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 55.81%; H 7.02%; O 37.17% | DFC |
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Melting Point | -45 | |
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Boiling Point | Bp12 89° | DFC |
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Experimental Water Solubility | 1000 mg/mL | WEAST,RC (1972) |
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Experimental logP | -0.64 | HANSCH,C ET AL. (1995) |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | d0 1.44 | DFC |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-004l-9000000000-2fc3f4165b5808b41e93 | Spectrum | GC-MS | gamma-Butyrolactone, non-derivatized, GC-MS Spectrum | splash10-004l-9000000000-500445dc73cb69119e6b | Spectrum | GC-MS | gamma-Butyrolactone, non-derivatized, GC-MS Spectrum | splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1 | Spectrum | GC-MS | gamma-Butyrolactone, non-derivatized, GC-MS Spectrum | splash10-002f-9000000000-d3df175d3315ed446e14 | Spectrum | GC-MS | gamma-Butyrolactone, non-derivatized, GC-MS Spectrum | splash10-004l-9000000000-500445dc73cb69119e6b | Spectrum | GC-MS | gamma-Butyrolactone, non-derivatized, GC-MS Spectrum | splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1 | Spectrum | GC-MS | gamma-Butyrolactone, non-derivatized, GC-MS Spectrum | splash10-002f-9000000000-d3df175d3315ed446e14 | Spectrum | Predicted GC-MS | gamma-Butyrolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-002f-9000000000-bd4b413f20907d13a107 | Spectrum | Predicted GC-MS | gamma-Butyrolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-9000000000-4a6de93563809aa51a33 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000i-9000000000-4a6de93563809aa51a33 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000i-9000000000-b5163f6eb1e8004e61a9 | Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive | splash10-004l-9000000000-1066d349a6023c66dd64 | Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive | splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1 | Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive | splash10-002f-9000000000-d3df175d3315ed446e14 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-fb7c9ada825a0c62979f | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000l-9000000000-95fda8a898d02f7e71ff | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000l-9000000000-c8282365f175b61ca8c0 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-ec20127c74818b1f634d | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052r-9000000000-86d21b481322417edf81 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-4f454124d6cece18a212 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-9000000000-507998514018a44c4cf0 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000l-9000000000-d4ec4947321dfb11fab4 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-b2a1436205f5365513b0 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-9000000000-709821dd006aa045c8b0 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9000000000-ffe2d9473d85a58305c1 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-a4219a074939d10a0f5f | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 7029 |
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ChEMBL ID | CHEMBL95681 |
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KEGG Compound ID | C01770 |
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Pubchem Compound ID | 7302 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 42639 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB04699 |
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HMDB ID | HMDB00549 |
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CRC / DFC (Dictionary of Food Compounds) ID | CXH55-B:CXH55-B |
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EAFUS ID | 1728 |
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Dr. Duke ID | GAMMA-BUTYROLACTONE |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | GBL |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | 96-48-0 |
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GoodScent ID | rw1028441 |
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SuperScent ID | Not Available |
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Wikipedia ID | 4-Hydroxybutyric acid lactone |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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neurotoxic | 50910 | A poison that interferes with the functions of the nervous system. | CHEBI |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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caramel |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| sweet |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
| creamy |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| oily |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| fatty |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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