| Record Information |
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| Version | 1.0 |
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| Created at | 2007-01-22 22:53:28 UTC |
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| Updated at | 2024-09-03 04:22:20 UTC |
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| NP-MRD ID | NP0000257 |
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| DOI | https://doi.org/10.57994/2823 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Isoeugenol |
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| Description | Isoeugenol is an isomer of eugenol, wherein the double bond on the alkyl chain is shifted by one carbon. It also known as propenylgualacol, 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. Isoeugenol is also classified as a phenylpropene, a propenyl-substituted guaiacol. Isoeugenol may occur as either the cis (Z) or trans (E) isomer. Trans (E) isoeugenol is crystalline while cis (Z) isoeugenol is a pale, yellow liquid. Isoeugenol is very slightly soluble in water and soluble in organic solvents. It has a spicy, sweet, carnation-like odour and tastes of sweet spice and clove. Isoeugenol is a widely used food flavoring agent and a perfuming agent. As a food flavoring agent, it is responsible for the flavor of nutmeg (in pumpkin pies), As a fragrance, it is extensively used as a scent agent in consumer products such as soaps, shampoos, perfumes, detergents and bath tissues (often labeled as “Fragrance” rather than isoeugenol). However, some individuals can develop allergies to isoeugenol as it appears to be a strong contact allergen (PMID:10554062 ). Isoeugenol can be prepared from eugenol by heating. In addition to its industrial production via eugenol, isoeugenol can also be extracted from certain essential oils especially from clove oil and cinnamon. It is found naturally in a wide number of foods, spices and plants including allspice, basil, blueberries, cinnamon, cloves, coffee, dill, ginber, nutmeg, thyme and turmeric. Isoeugenol is also a component of wood smoke and liquid smoke. It is one of several phenolic compounds responsible for the mold-inhibiting effect of smoke on meats and cheeses. Isoeugenol (specifically the acetate ester) has also been used in the production of vanillin. Isoeugenol is one of several non-cannabinoid phenols found in cannabis plants (PMID:6991645 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| (e)-2-Methoxy-4-(prop-1-enyl)phenol | ChEBI | | 2-Methoxy-4-[(1E)-1-propenyl]phenol | ChEBI | | 2-Methoxy-4-propenylphenol | ChEBI | | 3-Methoxy-4-hydroxy-1-propen-1-ylbenzene | ChEBI | | 3-Methoxy-4-hydroxypropenylbenzene | ChEBI | | 4-Hydroxy-3-methoxy-1-propenylbenzene | ChEBI | | iso-Eugenol 2 | ChEBI | | Isoeugenol (I) | ChEBI | | Isoeugenol e | ChEBI | | Isoeugenol trans-form | ChEBI | | Propenylgualacol | ChEBI | | trans-2-Methoxy-4-(1-propenyl)phenol | ChEBI | | trans-2-Methoxy-4-propenylphenol | ChEBI | | trans-4-Propenylgualacol | ChEBI | | trans-P-Propenylquaiacol | ChEBI | | (e)-2-Methoxy-4- (1-propenyl)-phenol | HMDB | | (e)-2-Methoxy-4-(1-propenyl)-phenol | HMDB | | (e)-2-Methoxy-4-propenyl-phenol | HMDB | | (E)-Isoeugenol | HMDB | | 1-(3-Methoxy-4-hydroxyphenyl)-1-propane | HMDB | | 1-Hydroxy-2-methoxy-4-propen-1-ylbenzene | HMDB | | 2-Methoxy-4-(1-propenyl)-phenol | HMDB | | 2-Methoxy-4-(1-propenyl)phenol | HMDB | | 2-Methoxy-4-(1-propenyl)phenol (acd/name 4.0) | HMDB | | 2-Methoxy-4-propenyl-phenol | HMDB | | 2-Methoxy-4-[(1E)-prop-1-en-1-yl]phenol | HMDB | | 4-Hydroxy-3-methoxy-1-propen-1-ylbenzene | HMDB | | 4-Hydroxy-3-methoxypropenylbenzene | HMDB | | trans-Isoeugenol | HMDB | | Isoeugenol, (e)-isomer | MeSH, HMDB | | Isoeugenol | MeSH | | 2-Methoxy-4-(prop-1-en-1-yl)phenol | KEGG | | (E)-2-Methoxy-4-(1-propenyl)phenol | HMDB | | (E)-2-Methoxy-4-(prop-1-en-1-yl)phenol | HMDB | | 1-(3-Methoxy-4-hydroxyphenyl)-1-propene | HMDB | | 2-Methoxy-4(E)-1-propenylphenol | HMDB | | 2-Methoxy-4-(1-propen-1-yl)phenol | HMDB | | 2-Methoxy-4-(1E)-1-propen-1-ylphenol | HMDB | | 2-Methoxy-4-[(E)-1-propenyl]phenol | HMDB | | 3-Methoxy-4-hydroxy-1-propenylbenzene | HMDB | | 4-(1-Propenyl) Guaiacol | HMDB | | 4-Hydroxy-3-methoxy-beta-methylstyrene | HMDB | | 4-Hydroxy-3-methoxy-β-methylstyrene | HMDB | | 4-Propenylguaiacol | HMDB | | iso-Eugenol | HMDB | | trans-4-Propenylguaiacol | HMDB | | trans-p-Propenylguaiacol | HMDB |
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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 | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | 97-54-1 |
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| SMILES | Not Available |
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| InChI Identifier | InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+ |
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| InChI Key | BJIOGJUNALELMI-ONEGZZNKSA-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, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-14 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-14 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-14 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-14 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-14 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | 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, CD3OD, simulated) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-14 | 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
- Styrene
- 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 | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | -10 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | 3.04 | Griffin, S., Wyllie, S. G., & Markham, J. (1999). Determination of octanol-water partition coefficient for terpenoids using reversed-phase high-performance liquid chromatography. Journal of Chromatography A, 864(2), 221-228. |
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| Predicted Properties | Not Available |
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| General References | - Atsumi T, Fujisawa S, Tonosaki K: A comparative study of the antioxidant/prooxidant activities of eugenol and isoeugenol with various concentrations and oxidation conditions. Toxicol In Vitro. 2005 Dec;19(8):1025-33. Epub 2005 Jun 17. [PubMed:15964168 ]
- White IR, Johansen JD, Arnau EG, Lepoittevin JP, Rastogi S, Bruze M, Andersen KE, Frosch PJ, Goossens A, Menne T: Isoeugenol is an important contact allergen: can it be safely replaced with isoeugenyl acetate? Contact Dermatitis. 1999 Nov;41(5):272-5. doi: 10.1111/j.1600-0536.1999.tb06160.x. [PubMed:10554062 ]
- Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
- de Lacy Costello B, Amann A, Al-Kateb H, Flynn C, Filipiak W, Khalid T, Osborne D, Ratcliffe NM: A review of the volatiles from the healthy human body. J Breath Res. 2014 Mar;8(1):014001. doi: 10.1088/1752-7155/8/1/014001. Epub 2014 Jan 13. [PubMed:24421258 ]
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