| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-05-25 18:37:19 UTC |
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| Update Date | 2016-11-09 01:17:31 UTC |
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| Accession Number | CHEM022490 |
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| Identification |
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| Common Name | Solerol |
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| Class | Small Molecule |
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| Description | Solerol, also known as 4,5-dihydroxyhexanoic acid lactone, is a volatile component originally identified in extracts of grape wines and numerous fruits, with aroma being among the most important factors in determining wine character and quality (PMID: 11052736 ). Solerol (4,5-dihydroxyhexanoic acid lactone) also appears to be a marker for Succinic semialdehyde dehydrogenase (SSADH) deficiency and probably arises from the reaction of succinic semialdehyde with an intermediate in the pyruvate dehydrogenase pathway (PMID: 3126356 ). SSADH is a disorder that arises from a defect in gamma-aminobutyric acid catabolism, resulting in the accumulation of gamma-hydroxybutyric acid (GHB), 2,4-dihydroxybutyric acid, adipic acid as well as elevated levels of 4,5-dihydroxyhexanoic acid, and 4,5-dihydroxyhexanoic acid lactone and causing neurological and cognitive disorders of varying severity (PMID: 3126356 ). Children with SSADH deficiency usually manifest with developmental delay, behavioral symptoms, language dysfunction, seizures, hypotonia, extrapyramidal symptoms, and ataxia (PMID: 32055132). |
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| Contaminant Sources | - FooDB Chemicals
- HMDB Contaminants - Urine
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| Contaminant Type | Not Available |
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| Solerole | HMDB | | 4,5-Dihydroxyhexanoic acid-γ-lactone | HMDB | | 4,5-Dihydroxyhexanoic acid lactone | HMDB | | 4,5-Dihydroxyhexanoic acid-g-lactone | HMDB | | 4,5-Dihydroxyhexanoic acid-gamma-lactone | HMDB | | dihydro-5-(1-Hydroxyethyl)-2(3H)-furanone | HMDB |
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| Chemical Formula | C6H10O4 |
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| Average Molecular Mass | 146.141 g/mol |
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| Monoisotopic Mass | 146.058 g/mol |
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| CAS Registry Number | 27610-27-1 |
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| IUPAC Name | 5,6-dihydroxyoxepan-2-one |
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| Traditional Name | solerole |
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| SMILES | OC1CCC(=O)OCC1O |
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| InChI Identifier | InChI=1S/C6H10O4/c7-4-1-2-6(9)10-3-5(4)8/h4-5,7-8H,1-3H2 |
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| InChI Key | QFCPIZSGDXQFDK-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. |
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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 | Not Available |
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| Direct Parent | Lactones |
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| Alternative Parents | |
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| Substituents | - Caprolactone
- Oxepane
- 1,2-diol
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Carboxylic acid derivative
- Oxacycle
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Alcohol
- Organooxygen compound
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Not Available |
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| Cellular Locations | Not Available |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-9200000000-4c970f40f73e58f9971e | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0gk9-5690000000-02dfab8d541737d5816f | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002b-1900000000-f0da1cd33e0a89590303 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002b-4900000000-4ee8f2053b2708df1351 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ap0-9100000000-905eb8b9c2fa3f5bd816 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-1900000000-e73f6fc151da3a771b0c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-002b-3900000000-d8df955390befe22fbde | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-e66e7f28804f18fb65c1 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-06rb-9800000000-1689bfe8ea052b9a30da | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-9300000000-f2e635a0beec9e7988b2 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-4ab08fecdbc70f7d2a29 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-2900000000-37fd96e4bae9be6114ea | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-056s-9700000000-e46015afa96bc6c36704 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9000000000-ebe5150e09325866136b | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | Not Available |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB0002173 |
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| FooDB ID | FDB022885 |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | 6526 |
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| PDB ID | Not Available |
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| Wikipedia Link | Not Available |
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| Chemspider ID | 13628309 |
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| ChEBI ID | 89760 |
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| PubChem Compound ID | 21252275 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | | 1. Hoekman, Mark J.; Fagan, Gian L.; Webb, A. Dinsmoor; Kepner, Richard E. Synthesis of homologs of 4,5-dihydroxy- and 4-hydroxy-5-oxohexanoic acid g-lactones. Journal of Agricultural and Food Chemistry (1982), 30(5), 920-4. | | 2. Rocha S, Coutinho P, Barros A, Coimbra MA, Delgadillo I, Dias Cardoso A: Aroma potential of two bairrada white grape varieties: Maria Gomes and Bical. J Agric Food Chem. 2000 Oct;48(10):4802-7. | | 3. Brown GK, Cromby CH, Manning NJ, Pollitt RJ: Urinary organic acids in succinic semialdehyde dehydrogenase deficiency: evidence of alpha-oxidation of 4-hydroxybutyric acid, interaction of succinic semialdehyde with pyruvate dehydrogenase and possible secondary inhibition of mitochondrial beta-oxidation. J Inherit Metab Dis. 1987;10(4):367-75. | | 4. Yoganathan S, Arunachal G, Kratz L, Varman M, Thomas M, Sudhakar SV, Oommen SP, Danda S: Metabolic Stroke: A Novel Presentation in a Child with Succinic Semialdehyde Dehydrogenase Deficiency. Ann Indian Acad Neurol. 2020 Jan-Feb;23(1):113-117. doi: 10.4103/aian.AIAN_213_18. |
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