Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:05:30 UTC |
---|
Update date | 2020-09-17 15:35:23 UTC |
---|
Primary ID | FDB002728 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | Isoeugenol |
---|
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. |
---|
CAS Number | 97-54-1 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
Not Available | Not Available |
|
---|
Predicted Properties | |
---|
Chemical Formula | C10H12O2 |
---|
IUPAC name | 2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol |
---|
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+ |
---|
InChI Key | BJIOGJUNALELMI-ONEGZZNKSA-N |
---|
Isomeric SMILES | COC1=CC(\C=C\C)=CC=C1O |
---|
Average Molecular Weight | 164.2011 |
---|
Monoisotopic Molecular Weight | 164.083729628 |
---|
Classification |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Benzenoids |
---|
Class | Phenols |
---|
Sub Class | Methoxyphenols |
---|
Direct Parent | Methoxyphenols |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aromatic homomonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Role | Industrial application: |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Liquid | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 73.15%; H 7.37%; O 19.49% | DFC |
---|
Melting Point | -10 oC | |
---|
Boiling Point | Not Available | |
---|
Experimental Water Solubility | Not Available | |
---|
Experimental logP | 3.04 | GRIFFIN,S ET AL. (1999) |
---|
Experimental pKa | 9.88 | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
EI-MS | Mass Spectrum (Electron Ionization) | splash10-0ik9-7900000000-d378eaa3d6e1b33ea92e | 2014-09-20 | View Spectrum | GC-MS | Isoeugenol, non-derivatized, GC-MS Spectrum | splash10-03di-5900000000-d5e9036e83fd9c1033b0 | Spectrum | GC-MS | Isoeugenol, non-derivatized, GC-MS Spectrum | splash10-03di-4900000000-f0dd30e91dc041336262 | Spectrum | GC-MS | Isoeugenol, non-derivatized, GC-MS Spectrum | splash10-03di-1900000000-1530d67ee6f2740c4978 | Spectrum | GC-MS | Isoeugenol, non-derivatized, GC-MS Spectrum | splash10-03di-5900000000-d5e9036e83fd9c1033b0 | Spectrum | GC-MS | Isoeugenol, non-derivatized, GC-MS Spectrum | splash10-03di-4900000000-f0dd30e91dc041336262 | Spectrum | GC-MS | Isoeugenol, non-derivatized, GC-MS Spectrum | splash10-03di-1900000000-1530d67ee6f2740c4978 | Spectrum | Predicted GC-MS | Isoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03ds-1900000000-54cb7bf6efac012f1f93 | Spectrum | Predicted GC-MS | Isoeugenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-7790000000-39afffdef59235ab22a4 | Spectrum | Predicted GC-MS | Isoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
MS/MS | LC-MS/MS Spectrum - n/a 11V, positive | splash10-0019-0900000000-95d2bb40c1282fcc841b | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 11V, positive | splash10-0a4i-0900000000-66bdcdfc1f3c9d7059ef | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 11V, positive | splash10-0a4i-2900000000-1eef4e3fa8cc372a7bd0 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, positive | splash10-000i-0900000000-568dabede3d6d65eef27 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 4V, positive | splash10-000i-0900000000-704d8c207b799f62a165 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 5V, positive | splash10-0079-1900000000-dc5eb5b27b41f37fff51 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 6V, positive | splash10-00du-6900000000-724fc19b181ae95ed7f0 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 7V, positive | splash10-0006-9400000000-e33fcab9c4877cbfaaa8 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 9V, positive | splash10-00kf-9100000000-7581434dd013744b10fe | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 11V, positive | splash10-014l-9000000000-a332174b204c08062e14 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 14V, positive | splash10-014i-9000000000-eca4e980b9dcfbfa0d88 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9100000000-51b1ddd89b75760804fb | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-59e54fb66a534d3ff6dc | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-92bea35f22ee86583e9f | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0900000000-976746f8642ed9cede8f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-2900000000-aeeef853384070786115 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f6x-9400000000-28c3454817ba3f918700 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-ba4c51d900ead0baa741 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0900000000-b71be30e0aefb9374dd3 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0535-4900000000-dc2d63615991af22ecd9 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0159-0900000000-6f75a3780b4d03c3f78f | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00m3-2900000000-f418214add56c19743ea | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00or-9000000000-95268ee51bd407edd9b8 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-8db47caa9667c101bd0f | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03ds-0900000000-c240e3167c4ef90295d0 | 2021-09-25 | View Spectrum |
|
---|
NMR | Type | Description | | View |
---|
1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum |
|
---|
External Links |
---|
ChemSpider ID | 21106129 |
---|
ChEMBL ID | CHEMBL193598 |
---|
KEGG Compound ID | C10469 |
---|
Pubchem Compound ID | 853433 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | 18224 |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB05802 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | CNH06-V:CNH06-V |
---|
EAFUS ID | 1886 |
---|
Dr. Duke ID | ISOEUGENOL |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | C00000620 |
---|
HET ID | EUG |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | 97-54-1 |
---|
GoodScent ID | rw1006911 |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Isoeugenol |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | |
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Flavor | Citations |
---|
flower |
- 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
| sweet |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| spicy |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| clove |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| woody |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| carnation |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| floral |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
|
|
---|
Files |
---|
MSDS | show |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
|
---|