Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:25:49 UTC |
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Update date | 2015-07-21 06:57:34 UTC |
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Primary ID | FDB023179 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | L-Gulonolactone |
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Description | L-Gulonolactone (also known as reduced ascorbic acid, RAA) is the substrate of the enzyme L-gulono-1,4-lactone oxidoreductase (EC 1.1.3.8), which catalyzes the last step of the biosynthesis of L-ascorbic acid (vitamin C) in plants and animals. The enzyme L-Gulono-1,4-lactone oxidase is missing in scurvy-prone, vitamin C-deficient animals, such as humans. L-Gulonolactone is present in human blood and has been used as one of the markers to compare changes in exercise-induced oxidative stress. (PMID: 16956367, 16494601) [HMDB] |
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CAS Number | 1128-23-0 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C6H10O6 |
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IUPAC name | (3S,4R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one |
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InChI Identifier | InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m0/s1 |
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InChI Key | SXZYCXMUPBBULW-SKNVOMKLSA-N |
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Isomeric SMILES | [H][C@@]1(OC(=O)[C@@H](O)[C@H]1O)[C@@H](O)CO |
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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 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
- Secondary alcohol
- Carboxylic acid ester
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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 | Biological location: Source: |
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Process | Naturally occurring process: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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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 | L-Gulonolactone, 4 TMS, GC-MS Spectrum | splash10-0gc0-2961000000-10e3ffe56d1491c35d8a | Spectrum | GC-MS | L-Gulonolactone, non-derivatized, GC-MS Spectrum | splash10-0gc0-2961000000-10e3ffe56d1491c35d8a | Spectrum | GC-MS | L-Gulonolactone, non-derivatized, GC-MS Spectrum | splash10-0fr2-0930000000-725e277ca1152a7fbc98 | Spectrum | Predicted GC-MS | L-Gulonolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-08fr-9400000000-615dd94b06b3e5e78526 | Spectrum | Predicted GC-MS | L-Gulonolactone, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0pk9-5359600000-e93f868058ca84374468 | Spectrum | Predicted GC-MS | L-Gulonolactone, 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 - 40V, Negative | splash10-0a4i-9000000000-ec8c949182af76945e86 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-9000000000-7a0472476f07853a992b | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a70-9300000000-74777b41198e9cd46262 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-06ds-9000000000-2d40464867d71e6c1135 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-01b9-9400000000-d5de17e2c0c42a02efc0 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9000000000-0435329cc0eb001898fa | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01t9-1900000000-f47818211aa007edc5f4 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-5900000000-c7c9eb2eaa1f91ac9951 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9100000000-072c615a4ace0aca930a | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00or-3900000000-5f8e27814cf4a835d41a | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ar0-6900000000-9a9aef2bcc37f743beab | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0596-9100000000-4892df7d8d2a53c17d7f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-9300000000-cd9f8103b846d70baac0 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4l-9000000000-650b3c2ec9303d9b2a96 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-232c502ee9a5b93d5a17 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03fu-1900000000-a9b5237063a8327d87cd | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0296-9500000000-aadb547d81673dce1915 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-08mm-9100000000-0a3f8e5a08a10aa888eb | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 388493 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C01040 |
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Pubchem Compound ID | 439373 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17587 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB03466 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 36677 |
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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 | Not Available |
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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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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 | Not Available |
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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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