| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:06:50 UTC |
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| Update date | 2019-11-26 03:00:45 UTC |
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| Primary ID | FDB005766 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Citrinin |
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| Description | Citrinin is practically insoluble (in water) and an extremely strong acidic compound (based on its pKa). Citrinin can be found in barley and common wheat, which makes citrinin a potential biomarker for the consumption of these food products. Citrinin is a mycotoxin which is often found in food. It is a secondary metabolite produced by fungi that contaminate long-stored food and it causes different toxic effects, like nephrotoxic, hepatotoxic and cytotoxic effects. Citrinin is mainly found in stored grains, but sometimes also in fruits and other plant products . |
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| CAS Number | 642-15-9 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C13H14O5 |
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| IUPAC name | (3S,4R)-7-(dihydroxymethylidene)-3,4,5-trimethyl-4,6,7,8-tetrahydro-3H-2-benzopyran-6,8-dione |
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| InChI Identifier | InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,16-17H,1-3H3/t5-,7-/m0/s1 |
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| InChI Key | JLWQFKMKUKQXMW-FSPLSTOPSA-N |
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| Isomeric SMILES | C[C@@H]1OC=C2C(=O)C(=C(O)O)C(=O)C(C)=C2[C@H]1C |
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| Average Molecular Weight | 250.2473 |
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| Monoisotopic Molecular Weight | 250.084123558 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Benzopyrans |
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| Sub Class | Not Available |
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| Direct Parent | Benzopyrans |
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| Alternative Parents | |
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| Substituents | - Benzopyran
- O-quinomethane
- Quinomethane
- Cyclohexenone
- Vinylogous acid
- Vinylogous ester
- Ketene acetal or derivatives
- Ketone
- Cyclic ketone
- Oxacycle
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- 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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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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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 | Not Available | |
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| Melting Point | 178.5 oC | |
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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 | Not Available | |
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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 | Not Available |
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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 | splash10-0ue9-0090000000-2c1fe13db983b1f6c99f | 2019-02-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0kai-0490000000-bde2f788648a9c305069 | 2019-02-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uxr-9610000000-2f7d75f4059482aaf75b | 2019-02-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4j-0090000000-e603034317e276018345 | 2019-02-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0zfr-0390000000-c7d684f9c3624209613f | 2019-02-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-002o-4910000000-f674c2dc0f9332acc237 | 2019-02-23 | View Spectrum |
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| NMR | Not Available |
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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 | C16765 |
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| Pubchem Compound ID | 219203 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 48708 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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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 | CITRININ |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00029979 |
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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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| 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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| aldose reductase inhibitor | 48550 | An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). | DUKE | | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | 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 | — 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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