Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:28 UTC |
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Update date | 2019-11-26 02:57:45 UTC |
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Primary ID | FDB002649 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Dillapiol |
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Description | Dillapiol belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Dillapiol is a spice and wood tasting compound. Dillapiol is found, on average, in the highest concentration within dills (Anethum graveolens) and cumins (Cuminum cyminum). Dillapiol has also been detected, but not quantified in, several different foods, such as corianders (Coriandrum sativum), fennels (Foeniculum vulgare), herbs and spices, and parsleys (Petroselinum crispum). This could make dillapiol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dillapiol. |
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CAS Number | 484-31-1 |
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Structure | |
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Synonyms | Synonym | Source |
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5-Allyl 6,7-dimethoxy 1,3-benzodioxole | MeSH | 1-Allyl-2,3-dimethoxy-4,5-(methylenedioxy)benzene | MeSH | 2-Methyl-5-(1-methylethenyl)-1,3-benzodioxole | MeSH | 1,3-Benzodioxole, 4,5-dimethoxy-6-(2-propenyl)- (9ci) | HMDB | 1-Allyl-2,3-dimethoxy-4,5-(methylenedioxy)-benzene | HMDB | 1-Allyl-2,3-dimethoxy-4,5-methylenedioxybenzene | HMDB | 4,5-Dimethoxy-6-(2-propenyl)-1,3-benzodioxole | HMDB | 4,5-Dimethoxy-6-(2-propenyl)-1,3-benzodioxole, 9ci | HMDB | 6-Allyl-4,5-dimethoxy-1,3-benzodioxole | HMDB | Apiole (dill) | HMDB | Dill apiol | HMDB | Dill apiole | HMDB | Dillapiole | HMDB | Dillapiol | KEGG | 1,3-Benzodioxole, 4,5-dimethoxy-6-(2-propenyl)- | biospider | 1,3-Benzodioxole, 4,5-dimethoxy-6-(2-propenyl)- (9CI) | biospider | 4,5-Dimethoxy-6-(2-propenyl)-1,3-benzodioxole, 9CI | db_source | Benzene, 1-allyl-2,3-dimethoxy-4,5-(methylenedioxy)- | biospider |
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Predicted Properties | |
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Chemical Formula | C12H14O4 |
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IUPAC name | 4,5-dimethoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole |
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InChI Identifier | InChI=1S/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3 |
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InChI Key | LIKYNOPXHGPMIH-UHFFFAOYSA-N |
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Isomeric SMILES | COC1=C(OC)C(CC=C)=CC2=C1OCO2 |
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Average Molecular Weight | 222.2372 |
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Monoisotopic Molecular Weight | 222.089208936 |
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Classification |
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Description | Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzodioxoles |
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Sub Class | Not Available |
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Direct Parent | Benzodioxoles |
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Alternative Parents | |
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Substituents | - Benzodioxole
- Anisole
- Alkyl aryl ether
- Benzenoid
- Oxacycle
- Ether
- Acetal
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- 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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Disposition | Route of exposure: Source: Biological location: |
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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 | C 64.85%; H 6.35%; O 28.80% | DFC |
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Melting Point | Mp 29.5° | DFC |
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Boiling Point | Bp0.8 100° | DFC |
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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 | n25D 1.5278 | DFC |
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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) | splash10-00di-9660000000-7cd909d21ca4a4c8bb1e | 2015-03-01 | View Spectrum | Predicted GC-MS | Dillapiol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052f-1930000000-759fd9f5828da82064eb | Spectrum | Predicted GC-MS | Dillapiol, 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 | splash10-00di-0190000000-65afe20a9d6ea8212ae4 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dl-2490000000-a585b5b3566814b251fc | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03g3-6900000000-e4d0d60144cac96a91bb | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0090000000-a993c42f8477ed292846 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0690000000-969d0f40c3543ae56108 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0040-7900000000-72a37bef985f024191df | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0090000000-434847f7ec0085e24b80 | 2021-09-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-0390000000-7be09d177fcf76fa1e71 | 2021-09-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ldi-9520000000-f36f591d0e5c5b2747dd | 2021-09-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0090000000-e696c56af8179794e7ad | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0970000000-d9ab44e0dc7f91b8576e | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03fr-9700000000-dc4990fb9e6601280905 | 2021-09-25 | View Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 9814 |
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ChEMBL ID | CHEMBL470874 |
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KEGG Compound ID | C10449 |
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Pubchem Compound ID | 10231 |
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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 | HMDB30725 |
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CRC / DFC (Dictionary of Food Compounds) ID | CMX09-T:CMX09-T |
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EAFUS ID | Not Available |
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Dr. Duke ID | DILLAPIOLE|DILLAPIOL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002737 |
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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 | 484-31-1 |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Dillapiol |
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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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anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | insecticide | 24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | DUKE | molluscicide | 33904 | A substance used to destroy pests of the phylum Mollusca. | 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 | sedative | 35717 | A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. | 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 | Flavor | Citations |
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wood |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
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- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
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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). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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