Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:09:54 UTC |
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Update date | 2019-11-26 03:05:45 UTC |
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Primary ID | FDB011929 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Apiole |
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Description | Occurs in Sassafras albidum (sassafras) and Anethum graveolens (dill)
Apiol is an organic chemical compound, also known as parsley apiol, apiole or parsley camphor. It is found in celery, parsley seeds, and the essential oil of parsley. Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. In 1855 Joret and Homolle discovered that apiol was an effective treatment of amenorrea or lack of menstruation.; In medicine it has been used, as essential oil or in purified form, for the treatment of menstrual disorders. It is an irritant and in high doses it is toxic and can cause liver and kidney damage. |
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CAS Number | 523-80-8 |
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Structure | |
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Synonyms | Synonym | Source |
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1-Allyl-2,5-dimethoxy-3, 4-(methylenedioxy)benzene | HMDB | 1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)-benzene | HMDB | 1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)benzene | HMDB | 1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene | HMDB, MeSH | 4,7-Dimethoxy-5-(2-propen-1-yl)-1,3-benzodioxole | HMDB, MeSH | 4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole | HMDB | 4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, 9ci | HMDB | 5-Allyl-4,7-dimethoxy-1,3-benzodioxol | HMDB | 5-Allyl-4,7-dimethoxy-1,3-benzodioxole | HMDB | Apiol | HMDB | Apiole (parsley) | HMDB | Apioline | HMDB | Camphre de persil | HMDB | Parsley apiol | HMDB | Parsley apiole | HMDB | Parsley camphor | HMDB | Petersiliencampher | HMDB | 1,3-Benzodioxole, 4, 7-dimethoxy-5-(2-propenyl)- | biospider | 1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propen-1-yl)- | biospider | 1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propenyl)- | biospider | 4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, 9CI | db_source | Benzene, 1-allyl-2,5-dimethoxy-3, 4-(methylenedioxy)- | biospider | Benzene, 1-allyl-2,5-dimethoxy-3,4-(methylenedioxy)- | biospider |
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Predicted Properties | |
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Chemical Formula | C12H14O4 |
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IUPAC name | 4,7-dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole |
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InChI Identifier | InChI=1S/C12H14O4/c1-4-5-8-6-9(13-2)11-12(10(8)14-3)16-7-15-11/h4,6H,1,5,7H2,2-3H3 |
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InChI Key | QQRSPHJOOXUALR-UHFFFAOYSA-N |
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Isomeric SMILES | COC1=C2OCOC2=C(OC)C(CC=C)=C1 |
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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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Role | 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 64.85%; H 6.35%; O 28.80% | DFC |
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Melting Point | Mp 30° | DFC |
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Boiling Point | Bp33 179° | 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 | [neutral] lmax 280 () (no solvent reported) | DFC |
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Density | d204 1.02 | DFC |
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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) | splash10-00di-5890000000-b5cf6efedda43e9d694c | 2015-03-01 | View Spectrum | Predicted GC-MS | Apiole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052f-2920000000-1cc8f418618578cdd948 | Spectrum | Predicted GC-MS | Apiole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Apiole, 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-0190000000-2a13687cd8d861844f6a | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-2390000000-527ad08f36c5b6d7fc09 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-3900000000-54ca6ec7708d663c0eec | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0090000000-2497b3799235c68f1f37 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0690000000-e9c82cedbafb1cfbb38d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0aos-3900000000-4c9e9c13ad062d6f79d3 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0090000000-e696c56af8179794e7ad | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00dl-0980000000-013e17a78d3735e96600 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-2900000000-d0e703a0356e829446de | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0090000000-b55ce853fd840758bfab | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-0290000000-9af70ca3804ef5b209f9 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01bc-6940000000-4f291648385a3987c36e | 2021-09-24 | View Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 21106259 |
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ChEMBL ID | CHEMBL1560118 |
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KEGG Compound ID | C10429 |
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Pubchem Compound ID | 10659 |
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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 | HMDB33776 |
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CRC / DFC (Dictionary of Food Compounds) ID | HBW16-S:HBW16-S |
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EAFUS ID | Not Available |
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Dr. Duke ID | APIOLE|APIOL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002714 |
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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 | rw1011001 |
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SuperScent ID | Not Available |
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Wikipedia ID | Apiole |
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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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abortifacient | 50691 | A chemical substance that interrupts pregnancy after implantation. | DUKE | anti dysmenorrheic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti malarial | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti neuralgic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti pyretic | 35493 | A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever. | DUKE | anti reproductive | | | DUKE | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | calcium antagonist | 48706 | Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. | DUKE | central nervous system stimulant | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | diuretic | 35498 | An agent that promotes the excretion of urine through its effects on kidney function. | DUKE | emmenagogue | | | DUKE | hepatotoxic | 50908 | A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals. | 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 | intoxicant | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | irritant | | | 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 | secretolytic | | | DUKE | synergist | | | DUKE | utero tonic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | vasodilator | 35620 | A drug used to cause dilation of the blood vessels. | 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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parsley |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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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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