Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:08 UTC |
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Update date | 2019-11-26 03:06:39 UTC |
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Primary ID | FDB012373 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Chavicol |
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Description | Chavicol, also known as 4-allylphenol, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Chavicol is a medicinal and phenolic tasting compound. Chavicol is found, on average, in the highest concentration within a few different foods, such as cloves (Syzygium aromaticum), sweet marjorams (Origanum majorana), and sweet basils (Ocimum basilicum) and in a lower concentration in pineapples (Ananas comosus). Chavicol has also been detected, but not quantified in, several different foods, such as allspices (Pimenta dioica), chinese cinnamons (Cinnamomum aromaticum), fats and oils, and gingers (Zingiber officinale). This could make chavicol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Chavicol. |
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CAS Number | 501-92-8 |
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Structure | |
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Synonyms | Synonym | Source |
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4-(2-Propenyl)phenol | ChEBI | 4-(Prop-2-enyl)-phenol | ChEBI | 4-Allylphenol | ChEBI | gamma-(p-Hydroxyphenyl)-alpha-propylene | ChEBI | p-Allylphenol | ChEBI | p-Chavicol | ChEBI | p-Hydroxyallylbenzene | ChEBI | g-(p-Hydroxyphenyl)-a-propylene | Generator | Γ-(p-hydroxyphenyl)-α-propylene | Generator | 3-(P-Hydroxyphenyl)-1-propene | HMDB | 4-(2-Propenyl)-phenol | HMDB | alpha -Propylene | HMDB | laquo gammaraquo -(P-Hydroxyphenyl)-alpha -propylene | HMDB | P-Allyl-phenol | HMDB | P-Hydroxyallylpropene | HMDB | Phenol, 4-(2-propenyl)- (9ci) | HMDB | Phenol, P-allyl- (8ci) | HMDB | α-propylene | biospider | «gamma»-(p-hydroxyphenyl)-α-propylene | biospider | 3-(p-Hydroxyphenyl)-1-propene | db_source | Chavicol | db_source | g-(P-Hydroxyphenyl)-a-propylene | Generator | Gamma-(p-hydroxyphenyl)-alpha-propylene | biospider | Laquo gammaraquo -(P-hydroxyphenyl)-alpha -propylene | HMDB | P-chavicol | biospider | p-Hydroxyallylpropene | biospider | Phenol, 4-(2-propenyl)- | biospider | Phenol, 4-(2-propenyl)- (9CI) | biospider | Phenol, p-allyl- | biospider | Phenol, p-allyl- (8CI) | biospider | γ-(P-hydroxyphenyl)-α-propylene | Generator |
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Predicted Properties | |
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Chemical Formula | C9H10O |
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IUPAC name | 4-(prop-2-en-1-yl)phenol |
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InChI Identifier | InChI=1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2 |
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InChI Key | RGIBXDHONMXTLI-UHFFFAOYSA-N |
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Isomeric SMILES | OC1=CC=C(CC=C)C=C1 |
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Average Molecular Weight | 134.1751 |
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Monoisotopic Molecular Weight | 134.073164942 |
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Classification |
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Description | Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenols |
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Sub Class | 1-hydroxy-2-unsubstituted benzenoids |
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Direct Parent | 1-hydroxy-2-unsubstituted benzenoids |
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Alternative Parents | |
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Substituents | - 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 80.56%; H 7.51%; O 11.92% | DFC |
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Melting Point | Mp 16° | DFC |
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Boiling Point | Bp17 120° | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | pKa1 10.23 (25°) | DFC |
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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 | Type | Description | Splash Key | View |
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Predicted GC-MS | Chavicol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a7i-5900000000-11cee9744d22eb93e167 | Spectrum | Predicted GC-MS | Chavicol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05c6-5910000000-7900910b5dbf1db02b3a | Spectrum | Predicted GC-MS | Chavicol, 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 | splash10-000i-0900000000-a1d20c3e3cabaf3d7046 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-2900000000-e73bf4d314fb93006997 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014l-9400000000-40119cbfc7560de6be63 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-617b61173e6f36fe521e | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0900000000-8e1744ff0d8d0e413886 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fsl-6900000000-c8e8472546321e19a5b5 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-2900000000-01e30c58a3acf046cc60 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a6u-9600000000-b0af3d932f868d71af42 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004l-9000000000-0c47676acacbc005f602 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-b646282963ddd573b4f4 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-1900000000-a985243dae14c1d86bf8 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-01t9-9000000000-9768124ac2659e800cc1 | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 21105856 |
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ChEMBL ID | CHEMBL108862 |
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KEGG Compound ID | C16930 |
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Pubchem Compound ID | 68148 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 50158 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB34107 |
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CRC / DFC (Dictionary of Food Compounds) ID | HGQ74-N:HGQ74-N |
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EAFUS ID | 118 |
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Dr. Duke ID | 4-ALLYL-PHENOL|CHAVICOL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000621 |
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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 | 501-92-8 |
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GoodScent ID | rw1015241 |
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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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fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | nematicide | 25491 | A substance used to destroy pests of the phylum Nematoda (roundworms). | 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 |
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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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medicine |
- 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
| phenol |
- 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
| phenolic |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| medicinal |
- 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).
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