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Showing Compound Isoeugenol (FDB002728)

Record Information
Version1.0
Creation date2010-04-08 22:05:30 UTC
Update date2020-09-17 15:35:23 UTC
Primary IDFDB002728
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsoeugenol
DescriptionIsoeugenol 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 Number97-54-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(e)-2-Methoxy-4-(prop-1-enyl)phenolChEBI
2-Methoxy-4-[(1E)-1-propenyl]phenolChEBI
2-Methoxy-4-propenylphenolChEBI
3-Methoxy-4-hydroxy-1-propen-1-ylbenzeneChEBI
3-Methoxy-4-hydroxypropenylbenzeneChEBI
4-Hydroxy-3-methoxy-1-propenylbenzeneChEBI
Iso-eugenol 2ChEBI
Isoeugenol (I)ChEBI
Isoeugenol eChEBI
Isoeugenol trans-formChEBI
PropenylgualacolChEBI
trans-2-Methoxy-4-(1-propenyl)phenolChEBI
trans-2-Methoxy-4-propenylphenolChEBI
trans-4-PropenylgualacolChEBI
trans-p-PropenylquaiacolChEBI
2-Methoxy-4-(prop-1-en-1-yl)phenolKegg
(e)-2-Methoxy-4- (1-propenyl)-phenolHMDB
(e)-2-Methoxy-4-(1-propenyl)-phenolHMDB
(e)-2-Methoxy-4-propenyl-phenolHMDB
(E)-IsoeugenolHMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propaneHMDB
1-Hydroxy-2-methoxy-4-propen-1-ylbenzeneHMDB
2-Methoxy-4-(1-propenyl)-phenolHMDB
2-Methoxy-4-(1-propenyl)phenolHMDB
2-Methoxy-4-(1-propenyl)phenol (acd/name 4.0)HMDB
2-Methoxy-4-propenyl-phenolHMDB
2-Methoxy-4-[(1E)-prop-1-en-1-yl]phenolHMDB
4-Hydroxy-3-methoxy-1-propen-1-ylbenzeneHMDB
4-Hydroxy-3-methoxypropenylbenzeneHMDB
trans-IsoeugenolHMDB
Isoeugenol, (e)-isomerMeSH, HMDB
IsoeugenolMeSH
(E)-2-Methoxy-4-(1-propenyl)phenolHMDB
(E)-2-Methoxy-4-(prop-1-en-1-yl)phenolHMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propeneHMDB
2-Methoxy-4(E)-1-propenylphenolHMDB
2-Methoxy-4-(1-propen-1-yl)phenolHMDB
2-Methoxy-4-(1E)-1-propen-1-ylphenolHMDB
2-Methoxy-4-[(E)-1-propenyl]phenolHMDB
3-Methoxy-4-hydroxy-1-propenylbenzeneHMDB
4-(1-Propenyl) GuaiacolHMDB
4-Hydroxy-3-methoxy-beta-methylstyreneHMDB
4-Hydroxy-3-methoxy-β-methylstyreneHMDB
4-PropenylguaiacolHMDB
iso-EugenolHMDB
trans-4-PropenylguaiacolHMDB
trans-p-PropenylguaiacolHMDB
2-Methoxy-4-propenyl phenolbiospider
5-(1-Propenyl)guaiacoldb_source
FEMA 2468db_source
Phenol, 2-methoxy-4-(1-propen-1-yl)-biospider
Phenol, 2-methoxy-4-(1-propenyl)-biospider
Phenol, 2-methoxy-4-propenyl-biospider
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP2.79ALOGPS
logP2.64ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)10.01ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.86 m³·mol⁻¹ChemAxon
Polarizability18.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H12O2
IUPAC name2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol
InChI IdentifierInChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+
InChI KeyBJIOGJUNALELMI-ONEGZZNKSA-N
Isomeric SMILESCOC1=CC(\C=C\C)=CC=C1O
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 73.15%; H 7.37%; O 19.49%DFC
Melting Point-10 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP3.04GRIFFIN,S ET AL. (1999)
Experimental pKa9.88
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0ik9-7900000000-d378eaa3d6e1b33ea92e2014-09-20View Spectrum
GC-MSIsoeugenol, non-derivatized, GC-MS Spectrumsplash10-03di-5900000000-d5e9036e83fd9c1033b0Spectrum
GC-MSIsoeugenol, non-derivatized, GC-MS Spectrumsplash10-03di-4900000000-f0dd30e91dc041336262Spectrum
GC-MSIsoeugenol, non-derivatized, GC-MS Spectrumsplash10-03di-1900000000-1530d67ee6f2740c4978Spectrum
GC-MSIsoeugenol, non-derivatized, GC-MS Spectrumsplash10-03di-5900000000-d5e9036e83fd9c1033b0Spectrum
GC-MSIsoeugenol, non-derivatized, GC-MS Spectrumsplash10-03di-4900000000-f0dd30e91dc041336262Spectrum
GC-MSIsoeugenol, non-derivatized, GC-MS Spectrumsplash10-03di-1900000000-1530d67ee6f2740c4978Spectrum
Predicted GC-MSIsoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03ds-1900000000-54cb7bf6efac012f1f93Spectrum
Predicted GC-MSIsoeugenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-7790000000-39afffdef59235ab22a4Spectrum
Predicted GC-MSIsoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0019-0900000000-95d2bb40c1282fcc841b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0a4i-0900000000-66bdcdfc1f3c9d7059ef2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-0a4i-2900000000-1eef4e3fa8cc372a7bd02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-000i-0900000000-568dabede3d6d65eef272020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000i-0900000000-704d8c207b799f62a1652020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0079-1900000000-dc5eb5b27b41f37fff512020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00du-6900000000-724fc19b181ae95ed7f02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0006-9400000000-e33fcab9c4877cbfaaa82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-00kf-9100000000-7581434dd013744b10fe2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014l-9000000000-a332174b204c08062e142020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-014i-9000000000-eca4e980b9dcfbfa0d882020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-51b1ddd89b75760804fb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-59e54fb66a534d3ff6dc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-92bea35f22ee86583e9f2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-976746f8642ed9cede8f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-aeeef8533840707861152016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9400000000-28c3454817ba3f9187002016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ba4c51d900ead0baa7412016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-b71be30e0aefb9374dd32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0535-4900000000-dc2d63615991af22ecd92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-6f75a3780b4d03c3f78f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m3-2900000000-f418214add56c19743ea2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-9000000000-95268ee51bd407edd9b82021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-8db47caa9667c101bd0f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ds-0900000000-c240e3167c4ef90295d02021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
ChemSpider ID21106129
ChEMBL IDCHEMBL193598
KEGG Compound IDC10469
Pubchem Compound ID853433
Pubchem Substance IDNot Available
ChEBI ID18224
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05802
CRC / DFC (Dictionary of Food Compounds) IDCNH06-V:CNH06-V
EAFUS ID1886
Dr. Duke IDISOEUGENOL
BIGG IDNot Available
KNApSAcK IDC00000620
HET IDEUG
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID97-54-1
GoodScent IDrw1006911
SuperScent IDNot Available
Wikipedia IDIsoeugenol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Allergenic50904 A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.DUKE
Anti-aggregantAn agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti TNF35222 An agent that blocks tumor necrosis factor, a pro-inflammatory cytokine, reducing inflammation and immune responses. Therapeutically used to treat autoimmune diseases, such as rheumatoid arthritis, psoriasis, and Crohn's disease, by mitigating inflammation and tissue damage.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Bacteristat33282 An agent that inhibits bacterial growth, reducing the proliferation of microorganisms without killing them. Therapeutically, bacteristats are used to treat infections, preventing the spread of bacteria and allowing the host's immune system to clear the infection. Key medical uses include treating urinary tract infections, acne, and other bacterial infections where bactericidal agents may not be necessary.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
CandidistatAn antifungal agent that inhibits the growth of Candida species, such as Candida albicans, used to treat fungal infections, particularly candidiasis.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.DUKE
FungistatAn agent that inhibits fungal growth, used to prevent fungal infections, commonly applied in therapeutic applications such as treating skin and nail infections, and managing fungal diseases in immunocompromised patients.DUKE
Motor depressantAn agent that reduces the normal functioning level of motor neurons, mainly in voluntary muscles, used to treat conditions such as muscle spasms, seizures, and anxiety disorders, promoting relaxation and relieving symptoms.DUKE
Motor stimulantAn agent that increases the normal functioning level of motor neurons, enhancing alertness and physical activity. Therapeutically, it treats attention deficit hyperactivity disorder (ADHD), narcolepsy, and fatigue, improving focus, attention, and overall cognitive function.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.DUKE
TrichomonistatAn antiprotozoal agent that inhibits growth of Trichomonas parasites, used to treat trichomoniasis, a sexually transmitted infection caused by Trichomonas vaginalis.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
flower
  1. 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
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
clove
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
carnation
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot 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.