Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:05 UTC |
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Update date | 2019-11-27 17:26:13 UTC |
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Primary ID | FDB014100 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 4-Butyl-gamma-butyrolactone |
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Description | 4-Butyl-gamma-butyrolactone, also known as 5-butyldihydro-2(3H)-furanone or 4-hydroxyoctanoic acid lactone, 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, 4-butyl-gamma-butyrolactone is considered to be a fatty ester lipid molecule. 4-Butyl-gamma-butyrolactone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Butyl-gamma-butyrolactone is a sweet, coconut, and creamy tasting compound. 4-Butyl-gamma-butyrolactone is found, on average, in the highest concentration in pineapples and bilberries. 4-Butyl-gamma-butyrolactone has also been detected, but not quantified in, a few different foods, such as fruits, papaya, and peachs. This could make 4-butyl-gamma-butyrolactone a potential biomarker for the consumption of these foods. |
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CAS Number | 104-50-7 |
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Structure | |
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Synonyms | Synonym | Source |
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4-Butyl-g-butyrolactone | Generator | 4-Butyl-γ-butyrolactone | Generator | 4-Butyl-4-hydroxybutyric acid lactone | HMDB | 4-Hydroxyoctanoic acid lactone | HMDB | 4-Octanolide | HMDB | 5-Butyl-tetrahydro-furan-2-one | HMDB | 5-Butyldihydro-2(3H)-furanone | HMDB | 5-Butyldihydrofuran-2(3H)-one | HMDB | 5-Butylhydro-2(3H)-furanone | HMDB | 5-Butyltetrahydro-2-furanone | HMDB | 8-oxo-5-Octanolide | HMDB | FEMA 2796 | HMDB | gamma-Butyl-gamma-butyrolactone | HMDB | gamma-N-Butyl-gamma-butyrolactone | HMDB | gamma-Octalactone | HMDB | gamma-Octanoic lactone | HMDB | gamma-Octanolactone | HMDB | Octan-4-olide | HMDB | Octano-1,4-lactone | HMDB | Octanoic acid, gamma lactone | HMDB | Octanolide-1,4 | HMDB | g-Octanolide | Generator | Γ-octanolide | Generator | (R)-4-Octanolide | MeSH | 4-Butyl-gamma-butyrolactone | biospider | 8-Oxo-5-octanolide | biospider |
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Predicted Properties | |
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Chemical Formula | C8H14O2 |
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IUPAC name | 5-butyloxolan-2-one |
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InChI Identifier | InChI=1S/C8H14O2/c1-2-3-4-7-5-6-8(9)10-7/h7H,2-6H2,1H3 |
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InChI Key | IPBFYZQJXZJBFQ-UHFFFAOYSA-N |
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Isomeric SMILES | CCCCC1CCC(=O)O1 |
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Average Molecular Weight | 142.1956 |
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Monoisotopic Molecular Weight | 142.099379692 |
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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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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: Biological role: |
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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 | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 67.57%; H 9.92%; O 22.50% | DFC |
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Melting Point | Not Available | |
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Boiling Point | Bp5.5 102-105° | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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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 | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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External Links |
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ChemSpider ID | 7418 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 7704 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB35422 |
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CRC / DFC (Dictionary of Food Compounds) ID | JJR08-S:JNW32-W |
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EAFUS ID | 2746 |
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Dr. Duke ID | GAMMA-OCTALACTONE |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | 104-50-7 |
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GoodScent ID | rw1006541 |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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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 | Not Available |
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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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coconut |
- 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 |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| waxy |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| creamy |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| tonka |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| dairy |
- 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 | Not Available |
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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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