| Record Information |
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| Version | 2.0 |
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| Created at | 2007-01-23 13:27:56 UTC |
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| Updated at | 2024-09-15 14:01:27 UTC |
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| NP-MRD ID | NP0000011 |
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| Natural Product DOI | https://doi.org/10.57994/0475 |
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| Secondary Accession Numbers | None |
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| Natural Product 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-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 Mass | 164.2011 Da |
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| Monoisotopic Mass | 164.08373 Da |
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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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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-06 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-06 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-06 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, CDCl3, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-06 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-06 | View Spectrum | | 1D_DEPT NMR | 13C NMR Spectrum (1D, 126 MHz, CDCl3, experimental) | shaolidong@ynutcm.edu.cn | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D_DEPT NMR | 13C NMR Spectrum (1D, 126 MHz, CDCl3, experimental) | shaolidong@ynutcm.edu.cn | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, CDCl3, experimental) | shaolidong@ynutcm.edu.cn | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | shaolidong@ynutcm.edu.cn | Not Available | Not Available | 2024-05-11 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 600, CDCl3, simulated) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-06 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500.33, CDCl3, simulated) | Not Available | Not Available | Not Available | 2024-05-11 | View Spectrum |
| | Species |
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| Species of Origin | |
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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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| Physical Properties |
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| State | Solid |
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| Experimental Properties | |
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| Predicted Properties | |
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| General References | - Jadhav BK, Khandelwal KR, Ketkar AR, Pisal SS: Formulation and evaluation of mucoadhesive tablets containing eugenol for the treatment of periodontal diseases. Drug Dev Ind Pharm. 2004 Feb;30(2):195-203. doi: 10.1081/ddc-120028715. [PubMed:15089054 ]
- Sell AB, Carlini EA: Anesthetic action of methyleugenol and other eugenol derivatives. Pharmacology. 1976;14(4):367-77. doi: 10.1159/000136617. [PubMed:935250 ]
- Fujisawa S, Murakami Y: Eugenol and Its Role in Chronic Diseases. Adv Exp Med Biol. 2016;929:45-66. doi: 10.1007/978-3-319-41342-6_3. [PubMed:27771920 ]
- Guironnet G, Dalbiez-Gauthier C, Rousset F, Schmitt D, Peguet-Navarro J: In vitro human T cell sensitization to haptens by monocyte-derived dendritic cells. Toxicol In Vitro. 2000 Dec;14(6):517-22. doi: 10.1016/s0887-2333(00)00043-6. [PubMed:11033063 ]
- Fujisawa S, Okada N, Muraoka E: Comparative effects of eugenol to bis-eugenol on oral mucous membranes. Dent Mater J. 2001 Sep;20(3):237-42. doi: 10.4012/dmj.20.237. [PubMed:11806158 ]
- Xiao WW, Zhang HL, Wang CF, Chen Y, Zhan R, Li D, Shao LD: Chemical Synthesis Enables the Configurational Determination of Myristriol, a Highly Oxygenated Phenylpropanoid from Myristica fragrans Houtt. Chem Biodivers. 2023 Mar;20(3):e202201075. doi: 10.1002/cbdv.202201075. Epub 2023 Feb 20. [PubMed:36762483 ]
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