Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:24 UTC |
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Update date | 2019-11-26 02:57:33 UTC |
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Primary ID | FDB002515 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Osthol |
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Description | Osthol, also known as 7-methoxy-8-(3-methylpent-2-enyl)coumarin, belongs to coumarins and derivatives class of compounds. Those are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Osthol is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Osthol can be found in a number of food items such as wild celery, lemon, parsley, and wild carrot, which makes osthol a potential biomarker for the consumption of these food products. Osthol is an O-methylated coumarin. It is a calcium channel blocker, found in plants such as Cnidium monnieri, Angelica archangelica and Angelica pubescens . |
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CAS Number | 484-12-8 |
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Structure | |
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Synonyms | Synonym | Source |
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7-Methoxy-8-(3-methylpent-2-enyl)coumarin | MeSH | Osthol | MeSH | 2H-1-Benzopyran-2-one, 7-methoxy-8-(3-methyl-2-butenyl)- | biospider | 7-Methoxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one | db_source | 7-Methoxy-8-(3-methyl-2-butenyl)-2H-chromen-2-one | biospider | 7-Methoxy-8-(3-methyl-2-butenyl)-coumarin | biospider | 7-Methoxy-8-(3-methyl-but-2-enyl)-chromen-2-one | biospider | 7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one | biospider | 7-Methoxy-8-isopentenylcoumarin | biospider | 7-Methoxy-8-prenylcoumarin | db_source | 8-(3-Methyl-2-butenyl)herniarin | biospider | Coumarin, 7-methoxy-8-(3-methyl-2-butenyl)- | biospider | Coumarin, 7-methoxy-8-(3-mmtenyl)- | biospider | Osthole | biospider | Ostol | biospider | Ostole | biospider |
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Predicted Properties | |
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Chemical Formula | C15H16O3 |
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IUPAC name | 7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one |
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InChI Identifier | InChI=1S/C15H16O3/c1-10(2)4-7-12-13(17-3)8-5-11-6-9-14(16)18-15(11)12/h4-6,8-9H,7H2,1-3H3 |
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InChI Key | MBRLOUHOWLUMFF-UHFFFAOYSA-N |
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Isomeric SMILES | COC1=CC=C2C=CC(=O)OC2=C1CC=C(C)C |
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Average Molecular Weight | 244.2857 |
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Monoisotopic Molecular Weight | 244.109944378 |
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Classification |
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Description | Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Coumarins and derivatives |
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Sub Class | Not Available |
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Direct Parent | Coumarins and derivatives |
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Alternative Parents | |
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Substituents | - Coumarin
- Benzopyran
- 1-benzopyran
- Anisole
- Alkyl aryl ether
- Pyranone
- Pyran
- Benzenoid
- Heteroaromatic compound
- Lactone
- Oxacycle
- Ether
- Organoheterocyclic compound
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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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 73.75%; H 6.60%; O 19.65% | DFC |
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Melting Point | Mp 85° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 0.012 mg/mL at 30 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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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 | 322 (e 18221) (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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0f9l-3970000000-4f98b2489c4119cf70b6 | 2015-03-01 | View 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 | splash10-0002-0090000000-2fc5799b180de518e4ef | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kb-3190000000-257f4ccd908ffa56c6c1 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gb9-9820000000-11f5c9b9fcef5d41d09d | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0190000000-a4fb35683e1aa8dd5101 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0490000000-81e15af3a3d9a535f2e7 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-1920000000-570d40b95f6d7db0366f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000j-0970000000-56ccbf122c5f7c9f4d8a | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0910000000-9884c3353133eaaf2dd0 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fi3-9620000000-5f4ce0cf72069169ff7d | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0090000000-204ca24ee8ee58d6cd7a | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01r6-0390000000-1cad35d7e2037c07eb0c | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00e9-0900000000-8b8323aa5449829b6278 | 2021-10-21 | View Spectrum |
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NMR | |
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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 | C09280 |
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Pubchem Compound ID | 10228 |
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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 | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | HGS93-C:CMF77-A |
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EAFUS ID | Not Available |
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Dr. Duke ID | OSTHOL|OSTHOLE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002488 |
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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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5-lipoxygenase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | analgesic | 35480 | An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. | DUKE | anti allergic | 50857 | A drug used to treat allergic reactions. | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | anti malarial | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti mitotic | | | DUKE | anti mutagenic | | | DUKE | calcium antagonist | 48706 | Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | immunosuppressant | 35705 | An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. | DUKE | juvabional | | | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | xanthine oxidase inhibitor | 35634 | An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2). | 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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