Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2007-01-23 13:27:56 UTC |
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Update Date | 2023-02-21 17:17:08 UTC |
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HMDB ID | HMDB0005809 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Eugenol |
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Description | Eugenol or 4-allyl-2-methoxyphenol is classified as a phenylpropanoid, formally derived from guaiacol, with an allyl chain positioned para to the hydroxy group. It is soluble in water, alcohol, chloroform, ether and oils. Eugenol is a neutral compound. It is biosynthesized from tyrosine. Eugenol is widely distributed in plants. It is a clear to pale yellow oily liquid extracted from clove oil, nutmeg, cinnamon, basil and bay leaf. It has a pleasant, spicy, clove-like odor with a spicy pungent taste. Eugenol is found in highest concentrations in cloves, allspices, and carrots and in lower concentrations in walnuts, ceylon cinnamons, and wild carrots. Eugenol has also been detected in shea tree, passion fruits, winged beans, fireweeds, and gingers, making it a potential biomarker for the consumption of these foods. Eugenol is used in perfumeries, flavorings and essential oils. It was first used for the manufacture of vanillin (https://doi.org/10.1021/ed054p776), though most vanillin is now produced from petrochemicals or from by-products of paper manufacture. Eugenol is hepatotoxic, meaning it may cause damage to the liver, if consumed in high doses. Eugenol has local antiseptic and anaesthetic properties (PMID:15089054 ; PMID:935250 ) and acts as positive allosteric modulators of the GABA-A receptor. It has high antioxidant, anti-proliferative, and anti-inflammatory activities with potential roles in alleviating and preventing cancer and inflammatory reactions (PMID:27771920 ). |
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Structure | InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3 |
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Synonyms | Value | Source |
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1,3,4-Eugenol | ChEBI | 1-Allyl-3-methoxy-4-hydroxybenzene | ChEBI | 1-Allyl-4-hydroxy-3-methoxybenzene | ChEBI | 1-Hydroxy-2-methoxy-4-allylbenzene | ChEBI | 1-Hydroxy-2-methoxy-4-prop-2-enylbenzene | ChEBI | 1-Hydroxy-2-methoxy-4-propenylbenzene | ChEBI | 2-Hydroxy-5-allylanisole | ChEBI | 2-Methoxy-1-hydroxy-4-allylbenzene | ChEBI | 2-Methoxy-4-(2-propen-1-yl)phenol | ChEBI | 2-Methoxy-4-(2-propenyl)phenol | ChEBI | 2-Methoxy-4-allylphenol | ChEBI | 2-Methoxy-4-prop-2-enyl-phenol | ChEBI | 2-Methoxy-4-prop-2-enylphenol | ChEBI | 4-Allyl-1-hydroxy-2-methoxybenzene | ChEBI | 4-Allyl-2-methoxyphenol | ChEBI | 4-Allylcatechol-2-methyl ether | ChEBI | 4-Allylguaiacol | ChEBI | 4-Hydroxy-3-methoxy-1-allylbenzene | ChEBI | Allylguaiacol | ChEBI | Caryophyllic acid | ChEBI | Eugenic acid | ChEBI | p-Allylguaiacol | ChEBI | p-Eugenol | ChEBI | Caryophyllate | Generator | Eugenate | Generator | 2-Methoxy-4-(3-propenyl)phenol | HMDB | 2-Methoxy-4-(prop-2-en-1-yl)phenol | HMDB | 4-Allyl-2-methoxy-phenol | HMDB | 4-Allylcatechol 2-methyl ether | HMDB | 4-Hydroxy-3-methoxyallylbenzene | HMDB | 5-Allylguaiacol | HMDB | Engenol | HMDB | Eugenol (natural) | HMDB | Synthetic eugenol | HMDB | 2-Methoxy-4-(2'-propenyl)phenol | PhytoBank | 2-Methoxy-4-(2’-propenyl)phenol | PhytoBank | 2-Methoxy-4-[2-allyl]phenol | PhytoBank | 3-(3-Methoxy-4-hydroxyphenyl)propene | PhytoBank | 3-(4-Hydroxy-3-methoxyphenyl)-1-propene | PhytoBank | 4-Allenylguaiacol | PhytoBank |
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Chemical Formula | C10H12O2 |
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Average Molecular Weight | 164.2011 |
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Monoisotopic Molecular Weight | 164.083729628 |
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IUPAC Name | 2-methoxy-4-(prop-2-en-1-yl)phenol |
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Traditional Name | eugenol |
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CAS Registry Number | 97-53-0 |
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SMILES | COC1=CC(CC=C)=CC=C1O |
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InChI Identifier | InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3 |
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InChI Key | RRAFCDWBNXTKKO-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. |
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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 | Methoxyphenols |
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Direct Parent | Methoxyphenols |
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Alternative Parents | |
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Substituents | - Methoxyphenol
- Phenoxy compound
- Methoxybenzene
- Phenol ether
- Anisole
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Monocyclic benzene moiety
- Ether
- 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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Physiological effect | |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Eugenol EI-B (Non-derivatized) | splash10-0ik9-5900000000-3d3a9e4f250074741003 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Eugenol EI-B (Non-derivatized) | splash10-03di-2900000000-395df8510f0db4933abe | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Eugenol EI-B (Non-derivatized) | splash10-03di-6900000000-1afdd3b83f6832b11f70 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Eugenol EI-B (Non-derivatized) | splash10-03di-4900000000-1d96ae8b031e47e13112 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Eugenol EI-B (Non-derivatized) | splash10-0ik9-6900000000-def0c646d72c040b58da | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Eugenol EI-B (Non-derivatized) | splash10-03di-0900000000-dfa64951eb648f5c9df1 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Eugenol EI-B (Non-derivatized) | splash10-0ik9-5900000000-3d3a9e4f250074741003 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Eugenol EI-B (Non-derivatized) | splash10-03di-2900000000-395df8510f0db4933abe | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Eugenol EI-B (Non-derivatized) | splash10-03di-6900000000-1afdd3b83f6832b11f70 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Eugenol EI-B (Non-derivatized) | splash10-03di-4900000000-1d96ae8b031e47e13112 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Eugenol EI-B (Non-derivatized) | splash10-0ik9-6900000000-def0c646d72c040b58da | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Eugenol EI-B (Non-derivatized) | splash10-03di-0900000000-dfa64951eb648f5c9df1 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Eugenol GC-MS (Non-derivatized) - 70eV, Positive | splash10-03ms-1900000000-da27a86009649c155318 | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Eugenol GC-MS (1 TMS) - 70eV, Positive | splash10-00di-8790000000-0d0c6f0e58d7dc3e5620 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Eugenol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Eugenol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0il0-6900000000-ff0dc492bab70317bb2a | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Eugenol LC-ESI-QTOF , positive-QTOF | splash10-014i-0900000000-4541582e8f6395e2fa87 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eugenol LC-ESI-QTOF , positive-QTOF | splash10-00di-0900000000-84f950d2fc0742e324d5 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eugenol LC-ESI-QTOF , positive-QTOF | splash10-0ab9-0900000000-4c037643a10913a70f5e | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eugenol LC-ESI-QTOF , positive-QTOF | splash10-0a4i-0900000000-83f8f32dfd9b94fb1d24 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eugenol LC-ESI-QTOF , positive-QTOF | splash10-0a4i-2900000000-c65a2dab49b8ebb431da | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eugenol Linear Ion Trap , positive-QTOF | splash10-001i-0900000000-65a67ccd1df0d2f1796f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eugenol 40V, Positive-QTOF | splash10-0a4i-0900000000-83f8f32dfd9b94fb1d24 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eugenol 30V, Positive-QTOF | splash10-0ab9-0900000000-4c037643a10913a70f5e | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eugenol 10V, Positive-QTOF | splash10-014i-0900000000-4541582e8f6395e2fa87 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eugenol 20V, Positive-QTOF | splash10-00di-0900000000-84f950d2fc0742e324d5 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eugenol 10V, Positive-QTOF | splash10-014i-0900000000-f5092971e88a27de65e9 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eugenol 50V, Positive-QTOF | splash10-0a4i-2900000000-c65a2dab49b8ebb431da | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Eugenol 40V, Positive-QTOF | splash10-0a4i-0900000000-7beab8e102e0252d1a87 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Eugenol 10V, Positive-QTOF | splash10-014i-0900000000-9d2a857e8a482a061127 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Eugenol 20V, Positive-QTOF | splash10-014i-2900000000-9c846765367542bf4db1 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Eugenol 40V, Positive-QTOF | splash10-0fr6-9500000000-98fcaf3ccca850c34bd3 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Eugenol 10V, Negative-QTOF | splash10-03di-0900000000-835320dc79855273af7f | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Eugenol 20V, Negative-QTOF | splash10-03di-0900000000-3a70eb9601589d9108a1 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Eugenol 40V, Negative-QTOF | splash10-052e-4900000000-1c4834945c53d64bab3b | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Eugenol 10V, Negative-QTOF | splash10-03di-0900000000-8db47caa9667c101bd0f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Eugenol 20V, Negative-QTOF | splash10-03ka-0900000000-ab5855c31f23e61c7f54 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Eugenol 40V, Negative-QTOF | splash10-03k9-3900000000-868b72d9162a6b307829 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Eugenol 10V, Positive-QTOF | splash10-0159-0900000000-63a94aabae02f360ee77 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Eugenol 20V, Positive-QTOF | splash10-05nr-1900000000-ce4d363c5e701cb34dfd | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Eugenol 40V, Positive-QTOF | splash10-004i-9000000000-8e444a7d43baeb4d68f0 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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