Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:08:03 UTC |
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Update date | 2019-11-26 03:02:34 UTC |
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Primary ID | FDB008393 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 4-Hexyl-gamma-butyrolactone |
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Description | Xi-5-hexyldihydro-2(3h)-furanone, also known as 4-decanolide or gamma-decanolactone, is a member of the class of 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. Xi-5-hexyldihydro-2(3h)-furanone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Xi-5-hexyldihydro-2(3h)-furanone can be found in fruits, which makes xi-5-hexyldihydro-2(3h)-furanone a potential biomarker for the consumption of this food product. |
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CAS Number | 706-14-9 |
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Structure | |
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Synonyms | Synonym | Source |
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4-Decanolide | ChEBI | 4-Hexyl-gamma-butyrolactone | ChEBI | 4-Hydroxydecanoic acid gamma-lactone | ChEBI | 5-Hexyldihydro-2(3H)-furanone | ChEBI | 5-Hexyloxolan-2-one | ChEBI | 5-Hexyltetrahydro-2-furanone | ChEBI | Decan-4-olide | ChEBI | gamma-Decanolactone | ChEBI | gamma-Hexyl-gamma-butyrolactone | ChEBI | gamma-N-Decalactone | ChEBI | gamma-N-Hexyl-gamma-butyrolactone | ChEBI | 4-Hexyl-g-butyrolactone | Generator | 4-Hexyl-γ-butyrolactone | Generator | 4-Hydroxydecanoate g-lactone | Generator | 4-Hydroxydecanoate gamma-lactone | Generator | 4-Hydroxydecanoate γ-lactone | Generator | 4-Hydroxydecanoic acid g-lactone | Generator | 4-Hydroxydecanoic acid γ-lactone | Generator | g-Decanolactone | Generator | Γ-decanolactone | Generator | g-Hexyl-g-butyrolactone | Generator | Γ-hexyl-γ-butyrolactone | Generator | g-N-Decalactone | Generator | Γ-N-decalactone | Generator | g-N-Hexyl-g-butyrolactone | Generator | Γ-N-hexyl-γ-butyrolactone | Generator | 4-Hexyl-4-butanolide | HMDB | gamma-Lactone decanoic acid | HMDB | gamma-Decalactone | HMDB | (±)-4-n-Hexylbutyrolactone | manual | (±)-gamma-Decalactone | manual | (±)-gamma-Decanolactone | manual | (RS)-gamma-Decalactone | manual | 2-Decalactone | manual | 4-Hydroxydecanoic acid lactone, 8CI | db_source | Decanolactone | db_source | g-Decalactone | db_source | g-Hexylbutyrolactone | db_source | gamma-Decanolide | manual | gamma-Hexylbutyrolactone | manual |
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Predicted Properties | |
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Chemical Formula | C10H18O2 |
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IUPAC name | 5-hexyloxolan-2-one |
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InChI Identifier | InChI=1S/C10H18O2/c1-2-3-4-5-6-9-7-8-10(11)12-9/h9H,2-8H2,1H3 |
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InChI Key | IFYYFLINQYPWGJ-UHFFFAOYSA-N |
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Isomeric SMILES | CCCCCCC1CCC(=O)O1 |
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Average Molecular Weight | 170.2487 |
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Monoisotopic Molecular Weight | 170.13067982 |
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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 | Not Available |
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Ontology |
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Disposition | Biological location: Source: |
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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 70.55%; H 10.66%; O 18.80% | DFC |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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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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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-000i-9100000000-5c41e313dc97eb12ddd5 | 2015-03-01 | View Spectrum | GC-MS | 4-Hexyl-gamma-butyrolactone, non-derivatized, GC-MS Spectrum | splash10-000i-9000000000-4b166790a11e7c302d92 | Spectrum | GC-MS | 4-Hexyl-gamma-butyrolactone, non-derivatized, GC-MS Spectrum | splash10-000i-9000000000-4b166790a11e7c302d92 | Spectrum | Predicted GC-MS | 4-Hexyl-gamma-butyrolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0ap3-9100000000-b00c7215590a3d9b2e9d | Spectrum | Predicted GC-MS | 4-Hexyl-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 - LC-ESI-QTOF , positive | splash10-0udr-0900000000-d70fbbe72766763b45e2 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-052s-4900000000-0e9fb29ea39a5db8b46d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-052s-4900000000-ca7c24e9577963b4e53e | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0udr-0900000000-d70fbbe72766763b45e2 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-052s-4900000000-0e9fb29ea39a5db8b46d | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-290b1fa859383e242f93 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dj-9800000000-93589434f6ecccc40d35 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9000000000-d48426fb0e1a4c1a49a7 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-63a514b1d1c53dbcbd66 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-016r-2900000000-d4ee5269c414e9f521f4 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9200000000-9b6a92e807e7ae4e5fd5 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-efbd93a1a83feefc94df | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-1900000000-175297cb580811c14bb1 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9200000000-9db65c438d4cb8beba4f | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05fu-9500000000-c1c23158375af766301b | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4l-9100000000-032097fa4e962fbd8056 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9000000000-15c616405145e21bbc24 | 2021-09-24 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 12813 |
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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 | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | DHQ01-E:DHQ01-E |
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EAFUS ID | 829 |
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Dr. Duke ID | GAMMA-DECALACTONE|GAMMA-DECANOLACTONE |
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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 | 706-14-9 |
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GoodScent ID | rw1012281 |
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SuperScent ID | 12813 |
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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 | |
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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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peach |
- 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
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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- 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
| fresh |
- 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.
| waxy |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| coconut |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| buttery |
- 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.
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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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