Record Information |
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Version | 1.0 |
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Created at | 2007-01-23 13:27:56 UTC |
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Updated at | 2020-11-24 22:12:06 UTC |
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NP-MRD ID | NP0000011 |
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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, also known as 4-allylguaiacol or 1,3,4-eugenol, 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. Eugenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Eugenol exists in all eukaryotes, ranging from yeast to humans. A phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group. Eugenol is a sweet, cinnamon, and clove tasting compound. Outside of the human body, Eugenol is found, on average, in the highest concentration within a few different foods, such as cloves, allspices, and wild carrots and in a lower concentration in sweet marjorams, turmerics, and bilberries. Eugenol has also been detected, but not quantified in, several different foods, such as kelps, orange mints, pomegranates, soursops, and brassicas. This could make eugenol a potential biomarker for the consumption of these foods. Eugenol is a potentially toxic compound. |
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Structure | |
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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 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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Spectra |
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| | Species of Origin |
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Species | Animalia; Plantae |
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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 | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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