Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:53 UTC |
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Update date | 2018-05-29 00:32:37 UTC |
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Primary ID | FDB001245 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Fujiglucon |
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Description | Gluconolactone, also known as fujiglucon or GDL (gluconate), belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group. Gluconolactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Gluconolactone exists in all living organisms, ranging from bacteria to humans. Gluconolactone is an odorless tasting compound. |
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CAS Number | 90-80-2 |
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Structure | |
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Synonyms | Synonym | Source |
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(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one | ChEBI | 1,5-D-Gluconolactone | ChEBI | 1,5-Gluconolactone | ChEBI | D-Aldonolactone | ChEBI | D-Gluconic acid delta-lactone | ChEBI | D-Gluconic acid lactone | ChEBI | D-Gluconolactone | ChEBI | D-threo-aldono-1,5-Lactone | ChEBI | delta-D-Gluconolactone | ChEBI | delta-Gluconolactone | ChEBI | Glucarolactone | ChEBI | Gluconic acid lactone | ChEBI | Gluconic delta-lactone | ChEBI | Gluconic lactone | ChEBI | D-Gluconate delta-lactone | Generator | D-Gluconate δ-lactone | Generator | D-Gluconic acid δ-lactone | Generator | D-Gluconate lactone | Generator | δ-D-gluconolactone | Generator | δ-Gluconolactone | Generator | Gluconate lactone | Generator | Gluconic δ-lactone | Generator | 1,5-delta-Gluconolactone | HMDB | 3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one | HMDB | D-(+)-Gluconic acid D-lactone | HMDB | D-(+)-Gluconic acid-delta lactone | HMDB | D-delta-Gluconolactone | HMDB | D-Gluconic acid 1,5-lactone | HMDB | D-Gluconic acid D-lactone | HMDB | D-Gluconic acid-1,5-lactone | HMDB | D-Gluconic acid-delta-lactone | HMDB | D-Gluconic delta-lactone | HMDB | D-Glucono-1,5-lactone | HMDB | D-glucono-D-Lactone | HMDB | delta-(+)-Gluconic acid D-lactone | HMDB | delta-Aldonolactone | HMDB | delta-Gluconic acid 1,5-lactone | HMDB | delta-Gluconic acid D-lactone | HMDB | delta-Gluconic acid lactone | HMDB | delta-Gluconic acid-1,5-lactone | HMDB | delta-Glucono-1,5-lactone | HMDB | Fujiglucon | HMDB | Gluconate, lactone | HMDB | Glucono 1,5-lactone | HMDB | Glucono delta lactone | HMDB | Glucono delta-lactone | HMDB | GDL (Gluconate) | MeSH, HMDB | Glucono-delta-lactone | MeSH | (3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-one | HMDB | D-(+)-Gluconic acid delta-lactone | HMDB | D-(+)-Gluconic acid δ-lactone | HMDB | D-(+)-Glucono-1,5-lactone | HMDB | D-(+)-Glucono-delta-lactone | HMDB | D-(+)-Glucono-δ-lactone | HMDB | D-(+)-Glucose delta-lactone | HMDB | D-(+)-Glucose δ-lactone | HMDB | D-Glucono-delta-lactone | HMDB | D-Glucono-δ-lactone | HMDB | Glucono-δ-lactone | HMDB | Gluconolactone | HMDB | Lysactone | HMDB | d-(+)-Glucono-1,5-lactone | biospider | E575 | manual | GDL | manual |
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Predicted Properties | |
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Chemical Formula | C6H10O6 |
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IUPAC name | (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one |
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InChI Identifier | InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1 |
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InChI Key | PHOQVHQSTUBQQK-SQOUGZDYSA-N |
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Isomeric SMILES | OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O |
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Average Molecular Weight | 178.14 |
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Monoisotopic Molecular Weight | 178.047738052 |
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Classification |
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Description | Belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Gluconolactones |
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Alternative Parents | |
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Substituents | - Gluconolactone
- Delta valerolactone
- Delta_valerolactone
- Oxane
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Oxacycle
- Carboxylic acid derivative
- Polyol
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Primary alcohol
- 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 | Source: Biological location: |
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Process | Naturally occurring process: |
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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 | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 40.45%; H 5.66%; O 53.89% | DFC |
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Melting Point | Mp 150-152° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 590 mg/mL at 25 oC | MERCK INDEX (1996) |
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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 | [a]20D +66 -> +9 (1 d) (c, 5.0 in H2O) | DFC |
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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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GC-MS | Fujiglucon, non-derivatized, GC-MS Spectrum | splash10-0002-0932000000-0b9d34fd1930d30adac9 | Spectrum | GC-MS | Fujiglucon, non-derivatized, GC-MS Spectrum | splash10-005a-0920000000-48470ef74f46934597a0 | Spectrum | GC-MS | Fujiglucon, non-derivatized, GC-MS Spectrum | splash10-014j-0950000000-483acf515b56ae5dc886 | Spectrum | GC-MS | Fujiglucon, 4 TMS, GC-MS Spectrum | splash10-0fvi-1952000000-f92fb779cdb5daa45f09 | Spectrum | GC-MS | Fujiglucon, non-derivatized, GC-MS Spectrum | splash10-0fvi-1952000000-f92fb779cdb5daa45f09 | Spectrum | Predicted GC-MS | Fujiglucon, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-11bi-9500000000-59fc28b889280c7c2a5c | Spectrum | Predicted GC-MS | Fujiglucon, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0kki-7239300000-aa269ca53fc88c5847e7 | Spectrum | Predicted GC-MS | Fujiglucon, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Fujiglucon, TBDMS_1_2, 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, N/A (Annotated) | splash10-001i-5900000000-443ab6dcdad04641cb49 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-0avl-9000000000-5aba2e27767b74e7e315 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-052f-9000000000-081648ead7bc8b21d941 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-054t-9200000000-f80b44237ec36658430a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 28V, Negative | splash10-004i-9800000000-3c2752fe8b35c2f72850 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0ab9-9000000000-05bc27806ac72dbcec47 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9000000000-1f7ea9822812efafd66e | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0002-9000000000-32e4789569e5ebdb0a57 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-5c93d1197ecefd3faca0 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0avj-9000000000-56d207c80751c4bc3c09 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-06ei-9300000000-b4b9842c0062ae80b789 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01t9-0900000000-7a99fa6e5ac000ab06f1 | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03fu-3900000000-7f96bedb201e601e238e | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006x-9200000000-c51e82de843b7755c5b6 | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-3900000000-b80e81f6d02c1d0116a2 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0adi-6900000000-590a75b51bd97402a88d | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9000000000-ea7b9a23b7a07d266c68 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01tc-0900000000-061a17370d3f9bfa1c13 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01tl-9500000000-549c20b0fb39634d8731 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-08mm-9100000000-44352cf8b9847abddc99 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-4498d74e012d572e6493 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a6r-6900000000-2d15c7e5cc6967914c93 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0abc-9000000000-1f0b910b13e645939f4c | 2021-09-24 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | 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 | Not Available |
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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 | HMDB00150 |
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CRC / DFC (Dictionary of Food Compounds) ID | BWZ16-K:BWZ17-L |
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EAFUS ID | 1492 |
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Dr. Duke ID | Not Available |
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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 | Not Available |
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GoodScent ID | rw1234591 |
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SuperScent ID | Not Available |
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Wikipedia ID | Glucono_delta-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 | 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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odorless |
- 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 | |
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