Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:21 UTC |
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Update date | 2019-11-26 03:10:21 UTC |
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Primary ID | FDB014575 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Lactucin |
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Description | Lactucin 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. Lactucin has been detected, but not quantified in, several different foods, such as robusta coffees (Coffea canephora), green vegetables, coffee and coffee products, arabica coffees (Coffea arabica), and herbs and spices. This could make lactucin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Lactucin. |
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CAS Number | 1891-29-8 |
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Structure | |
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Synonyms | Synonym | Source |
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11beta,13-Dihydrolactucin | HMDB | Lactucin | MeSH |
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Predicted Properties | |
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Chemical Formula | C15H16O5 |
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IUPAC name | 4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione |
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InChI Identifier | InChI=1S/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3 |
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InChI Key | VJQAFLAZRVKAKM-UHFFFAOYSA-N |
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Isomeric SMILES | CC1=C2C(C3OC(=O)C(=C)C3C(O)C1)C(CO)=CC2=O |
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Average Molecular Weight | 276.288 |
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Monoisotopic Molecular Weight | 276.099773615 |
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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
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Carboxylic acid ester
- Ketone
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Oxacycle
- Carbonyl group
- Primary alcohol
- Organooxygen compound
- Organic oxygen compound
- Alcohol
- Organic oxide
- Hydrocarbon derivative
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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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 65.21%; H 5.84%; O 28.95% | DFC |
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Melting Point | Mp 224-228° | DFC |
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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 | [a]D +49 (c, 0.9 in MeOH) | DFC |
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Spectroscopic UV Data | [neutral] lmax 257 (e 14000) (EtOH) (Berdy) | DFC |
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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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Predicted GC-MS | Lactucin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052b-5790000000-b95d08ba5457bf6b2069 | Spectrum | Predicted GC-MS | Lactucin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0ab9-2139000000-fe4b945f22fd4dcc8988 | Spectrum | Predicted GC-MS | Lactucin, 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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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a6r-0090000000-adba28495fd27a848006 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052u-0490000000-fb65751d00ebf7cfc048 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f76-5950000000-cc2ba0ae124168adaaa1 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-aa9e3a2cce7827efdc3a | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057i-0090000000-48ae893a3deee473fadb | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00dl-2910000000-9062473d504431458708 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0090000000-5eee9e278d85992a4bc3 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a6u-0090000000-a5e6ac486e245f455cda | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00bd-0960000000-d62be5c7a1ff74131be2 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-aa99d0f367d18fe63c0c | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a6r-0090000000-9caf2622ff8214727496 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004r-0290000000-3d238649ddfe7d1c32b0 | Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 2985716 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C09489 |
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Pubchem Compound ID | 3756497 |
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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 | HMDB35814 |
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CRC / DFC (Dictionary of Food Compounds) ID | JFR52-Z:JSS68-A |
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EAFUS ID | Not Available |
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Dr. Duke ID | LACTUCIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00003311 |
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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 | Lactucin |
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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 | Descriptor | ID | Definition | Reference |
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antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | bitter | | | DUKE | central nervous system depressant | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | sedative | 35717 | A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. | DUKE | tonic | | | DUKE |
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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 | 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 | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — 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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