Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 10:22:01 -0600 |
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Update Date | 2015-09-13 12:56:06 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | Gluconolactone |
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Description | Gluconolactone is a lactone or oxidized derivative of glucose. Gluconolactone is a polyhydroxy acid (PHA) that is capable of chelating metals and may also function by scavenging free radicals. When dissolved in water, it is partially hydrolysed to gluconic acid, with the balance between the lactone form and the acid form established as a chemical equilibrium. The rate of hydrolysis of gluconolactone is increased by heat and high pH. It is an intermediate in glucose and glucose-1-phosphate degradation. |
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Structure | |
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Synonyms: | - δ-gluconolactone
- 1,5-D-Gluconolactone
- 1,5-delta-Gluconolactone
- 1,5-Gluconolactone
- 1,5-δ-Gluconolactone
- 3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-one
- 3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one
- b-glucono-1,5-Lactone
- Beta-Glucono-1,5-Lactone
- D(+)-Gluconate g-lactone
- D(+)-Gluconate gamma-lactone
- D(+)-Gluconate γ-lactone
- D(+)-Gluconic acid g-lactone
- D(+)-Gluconic acid gamma-lactone
- D(+)-Gluconic acid γ-lactone
- D-(+)-Gluconate D-lactone
- D-(+)-Gluconate-delta lactone
- D-(+)-Gluconate-δ lactone
- D-(+)-Gluconic acid D-lactone
- D-(+)-Gluconic acid-delta lactone
- D-(+)-Gluconic acid-δ lactone
- D-Aldonolactone
- D-delta-Gluconolactone
- D-Gluconate 1,5-lactone
- D-Gluconate D-lactone
- D-Gluconate delta-lactone
- D-Gluconate lactone
- D-Gluconate δ-lactone
- D-Gluconate-1,5-lactone
- D-Gluconate-delta-lactone
- D-Gluconate-δ-lactone
- D-Gluconic acid 1,5-lactone
- D-Gluconic acid D-lactone
- D-Gluconic acid delta-lactone
- D-Gluconic acid lactone
- D-Gluconic acid δ-lactone
- D-Gluconic acid-1,5-lactone
- D-Gluconic acid-delta-lactone
- D-Gluconic acid-δ-lactone
- D-Gluconic delta-lactone
- D-Gluconic δ-lactone
- D-glucono-δ-lactone
- D-Glucono-1,5-lactone
- D-Glucono-D-lactone
- D-Glucono-delta-lactone
- D-glucono-δ-Lactone
- D-Gluconolactone
- D-δ-Gluconolactone
- Delta-(+)-Gluconate D-lactone
- Delta-(+)-Gluconate-delta lactone
- Delta-(+)-Gluconic acid D-lactone
- Delta-(+)-Gluconic acid-delta lactone
- Delta-Aldonolactone
- Delta-D-Gluconolactone
- Delta-delta-Gluconolactone
- Delta-Gluconate 1,5-lactone
- Delta-Gluconate D-lactone
- Delta-Gluconate delta-lactone
- Delta-Gluconate lactone
- Delta-Gluconate-1,5-lactone
- delta-Gluconate-delta-lactone
- Delta-Gluconic acid 1,5-lactone
- Delta-Gluconic acid D-lactone
- Delta-Gluconic acid delta-lactone
- Delta-Gluconic acid lactone
- Delta-Gluconic acid-1,5-lactone
- Delta-Gluconic acid-delta-lactone
- Delta-Gluconic delta-lactone
- Delta-Glucono-1,5-lactone
- Delta-Glucono-delta-lactone
- Delta-Gluconolactone
- Fujiglucon
- g-Gluconolactone
- Gamma-Gluconolactone
- Glucarolactone
- Gluconate lactone
- Gluconate, lactone
- Gluconic acid lactone
- Gluconic acid, lactone
- Gluconic delta-lactone
- Gluconic lactone
- Gluconic δ-lactone
- Glucono 1,5-lactone
- Glucono delta lactone
- Glucono delta-lactone
- glucono g-Lactone
- Glucono gamma-lactone
- glucono γ-Lactone
- glucono δ Lactone
- glucono δ-Lactone
- Glucono-δ-lactone
- Glucono-1,5-lactone
- Glucono-delta-lactone
- glucono-δ-Lactone
- Gluconolactone
- β-glucono-1,5-Lactone
- γ-Gluconolactone
- δ-(+)-Gluconate D-lactone
- δ-(+)-Gluconate-δ lactone
- δ-(+)-Gluconic acid D-lactone
- δ-(+)-Gluconic acid-δ lactone
- δ-Aldonolactone
- δ-D-Gluconolactone
- δ-Gluconate 1,5-lactone
- δ-Gluconate D-lactone
- δ-Gluconate lactone
- δ-Gluconate δ-lactone
- δ-Gluconate-1,5-lactone
- δ-Gluconate-δ-lactone
- δ-Gluconic acid 1,5-lactone
- δ-Gluconic acid D-lactone
- δ-Gluconic acid lactone
- δ-Gluconic acid δ-lactone
- δ-Gluconic acid-1,5-lactone
- δ-Gluconic acid-δ-lactone
- δ-Gluconic δ-lactone
- δ-glucono-1,5-Lactone
- δ-glucono-δ-Lactone
- δ-Gluconolactone
- δ-δ-Gluconolactone
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Chemical Formula: | C6H10O6 |
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Weight: | Average: 178.14 Monoisotopic: 178.047738052 |
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InChI Key: | PHOQVHQSTUBQQK-SQOUGZDYSA-N |
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InChI: | 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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CAS number: | 90-80-2 |
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IUPAC Name: | (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one |
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Traditional IUPAC Name: | gluconolactone |
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SMILES: | OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O |
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Chemical Taxonomy |
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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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Physical Properties |
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State: | Solid |
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Charge: | 0 |
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Melting point: | 151-155 °C |
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Experimental Properties: | Property | Value | Source |
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Water Solubility: | 590.0 mg/mL [MERCK INDEX (1996)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | - Microbial metabolism in diverse environments ec01120
- Pentose phosphate pathway ec00030
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EcoCyc Pathways: | |
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Concentrations |
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| Concentration | Strain | Media | Growth Status | Growth System | Temperature | Details |
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1040± 0 uM | K12 NCM3722 | Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose | Mid-Log Phase | Shake flask and filter culture | 37 oC | PMID: 19561621 |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0002-0932000000-0b9d34fd1930d30adac9 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-005a-0920000000-48470ef74f46934597a0 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-014j-0950000000-483acf515b56ae5dc886 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-0fvi-1952000000-f92fb779cdb5daa45f09 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0fvi-1952000000-f92fb779cdb5daa45f09 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-11bi-9500000000-59fc28b889280c7c2a5c | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-0kki-7239300000-aa269ca53fc88c5847e7 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-001i-5900000000-443ab6dcdad04641cb49 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-0avl-9000000000-5aba2e27767b74e7e315 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-052f-9000000000-081648ead7bc8b21d941 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-054t-9200000000-f80b44237ec36658430a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 28V, Negative | splash10-004i-9800000000-3c2752fe8b35c2f72850 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0ab9-9000000000-05bc27806ac72dbcec47 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9000000000-1f7ea9822812efafd66e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0002-9000000000-32e4789569e5ebdb0a57 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-5c93d1197ecefd3faca0 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0avj-9000000000-56d207c80751c4bc3c09 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-06ei-9300000000-b4b9842c0062ae80b789 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01t9-0900000000-7a99fa6e5ac000ab06f1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03fu-3900000000-7f96bedb201e601e238e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006x-9200000000-c51e82de843b7755c5b6 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-3900000000-b80e81f6d02c1d0116a2 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0adi-6900000000-590a75b51bd97402a88d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9000000000-ea7b9a23b7a07d266c68 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01tc-0900000000-061a17370d3f9bfa1c13 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01tl-9500000000-549c20b0fb39634d8731 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-08mm-9100000000-44352cf8b9847abddc99 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-4498d74e012d572e6493 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a6r-6900000000-2d15c7e5cc6967914c93 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0abc-9000000000-1f0b910b13e645939f4c | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
- Friedrich T, Strohdeicher M, Hofhaus G, Preis D, Sahm H, Weiss H: The same domain motif for ubiquinone reduction in mitochondrial or chloroplast NADH dehydrogenase and bacterial glucose dehydrogenase. FEBS Lett. 1990 Jun 4;265(1-2):37-40. Pubmed: 2142103
- Harkness RA, Purkiss P, Duffy S, Chalmers RA, Jones M: The effects of fetal energy depletion on amniotic fluid concentrations of amino acids, organic acids and related metabolites. J Inherit Metab Dis. 1988;11(1):103-13. Pubmed: 3128683
- Hunt MJ, Barnetson RS: A comparative study of gluconolactone versus benzoyl peroxide in the treatment of acne. Australas J Dermatol. 1992;33(3):131-4. Pubmed: 1303072
- Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
- MacNeil ML, Steinberg KK, Yeager PR, Smith SJ: A semiautomated procedure for urinary D-glucaric acid using a centrifugal analyzer. J Anal Toxicol. 1986 Jan-Feb;10(1):15-7. Pubmed: 3951202
- Puri RN, Zhou FX, Colman RF, Colman RW: Plasmin-induced platelet aggregation is accompanied by cleavage of aggregin and indirectly mediated by calpain. Am J Physiol. 1990 Dec;259(6 Pt 1):C862-8. Pubmed: 2148055
- Rakotomanga S, Baillet A, Pellerin F, Baylocq-Ferrier D: Simultaneous determination of gluconolactone, galactonolactone and galactitol in urine by reversed-phase liquid chromatography: application to galactosemia. J Chromatogr. 1991 Oct 4;570(2):277-84. Pubmed: 1797843
- Steinberg KK, Needham LL: A comparison of two methods for quantifying D-glucaric acid. J Anal Toxicol. 1986 Jul-Aug;10(4):139-41. Pubmed: 3747452
- van Weely S, Brandsma M, Strijland A, Tager JM, Aerts JM: Demonstration of the existence of a second, non-lysosomal glucocerebrosidase that is not deficient in Gaucher disease. Biochim Biophys Acta. 1993 Mar 24;1181(1):55-62. Pubmed: 8457606
- Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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Synthesis Reference: | Chu, Lijia. Technology for industrial production of d-gluconolactone. Shipin Kexue (Beijing, China) (1985), 66 13-14. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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