Record Information
Version1.0
Creation date2010-04-08 22:10:02 UTC
Update date2018-05-29 18:27:59 UTC
Primary IDFDB012171
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEugenol
DescriptionEugenol is an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like aroma. Eugenol is an allyl chain-substituted guaiacol, i.e. 2-methoxy-4-(2-propenyl)phenol. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from petrochemicals or from by-products of paper manufacture (Wikipedia). Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anesthetic. It is a key ingredient in Indonesian kretek (clove) cigarettes. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from phenol or from lignin. It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study. Eugenol has a very widespread occurrence in essential oils. Major component of clove oil. Also found in citrus and thyme oils. It is found in foods such as apple, apricot, banana and cherry fruits.
CAS Number97-53-0
Structure
Thumb
Synonyms
SynonymSource
1,3,4-EugenolChEBI
1-Allyl-3-methoxy-4-hydroxybenzeneChEBI
1-Allyl-4-hydroxy-3-methoxybenzeneChEBI
1-Hydroxy-2-methoxy-4-allylbenzeneChEBI
1-Hydroxy-2-methoxy-4-prop-2-enylbenzeneChEBI
1-Hydroxy-2-methoxy-4-propenylbenzeneChEBI
2-Hydroxy-5-allylanisoleChEBI
2-Methoxy-1-hydroxy-4-allylbenzeneChEBI
2-Methoxy-4-(2-propen-1-yl)phenolChEBI
2-Methoxy-4-(2-propenyl)phenolChEBI
2-Methoxy-4-allylphenolChEBI
2-Methoxy-4-prop-2-enylphenolChEBI
4-Allyl-1-hydroxy-2-methoxybenzeneChEBI
4-Allyl-2-methoxyphenolChEBI
4-Allylcatechol-2-methyl etherChEBI
4-AllylguaiacolChEBI
4-Hydroxy-3-methoxy-1-allylbenzeneChEBI
AllylguaiacolChEBI
Caryophyllic acidChEBI
Eugenic acidChEBI
P-AllylguaiacolChEBI
P-EugenolChEBI
CaryophyllateGenerator
EugenateGenerator
2-Methoxy-4-(3-propenyl)phenolHMDB
2-Methoxy-4-(prop-2-en-1-yl)phenolHMDB
4-Allyl-2-methoxy-phenolHMDB
4-Allylcatechol 2-methyl etherHMDB
4-Hydroxy-3-methoxyallylbenzeneHMDB
5-AllylguaiacolHMDB
EngenolHMDB
Eugenol (natural)HMDB
Synthetic eugenolHMDB
1-hydroxy-2-methoxy-4-propenylbenze nebiospider
1-hydroxy-4-allyl-2-methoxybenzenebiospider
2-methoxy-4-(2-propen-1-yl)phenolbiospider
2-Methoxy-4-(2-propenyl)phenylbiospider
2-methoxy-4-(prop-2-en-1-yl)phenolbiospider
2-Methoxy-4-[2-propenyl]phenolbiospider
2-Metoksy-4-allilofenolbiospider
4 -allyl-1-hydroxy-2-methoxybenzenebiospider
4-(2-Propenyl)-2-methoxyphenol (eugenol)biospider
4-Allyl-1-Hydroxy-2-Methoxy Benzenebiospider
4-allyl-2-methoxy-Phenolbiospider
4-allyl-2-methoxyphenol (eugenol)biospider
4-Allyl-2-rnethoxyphenol (eugenol)biospider
4-Allylguaicolbiospider
Caryophyllic ac idbiospider
Eugenolbiospider
Eugenol (2-Methoxy-4-(2-propenyl)phenol)biospider
Eugenol (usp)biospider
Eugenol [usan]biospider
Eugenol specialbiospider
Eugenol, USANdb_source
FEMA 2467db_source
P-allylguaiacolbiospider
P-eugenolbiospider
Phenol, 2-methoxy-4-(2-propen-1-yl)-biospider
Phenol, 2-methoxy-4-(2-propenyl)-biospider
Phenol, 4-allyl-2-methoxy-biospider
Predicted Properties
PropertyValueSource
Water Solubility1.44 g/LALOGPS
logP2.66ALOGPS
logP2.61ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.79 m³·mol⁻¹ChemAxon
Polarizability17.9 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H12O2
IUPAC name2-methoxy-4-(prop-2-en-1-yl)phenol
InChI IdentifierInChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
InChI KeyRRAFCDWBNXTKKO-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(CC=C)=C1
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
Classification
DescriptionThis compound belongs to the class of organic compounds known as methoxyphenols. These 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
  • 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 73.15%; H 7.37%; O 19.49%DFC
Melting PointFp -9°DFC
Boiling PointBp15 128-130°DFC
Experimental Water Solubility2.46 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.27SANGSTER (1993)
Experimental pKapKa1 10.19 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 1.07DFC
Refractive Indexn20D 1.5400DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-5900000000-3d3a9e4f250074741003View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-2900000000-395df8510f0db4933abeView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-6900000000-1afdd3b83f6832b11f70View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-4900000000-1d96ae8b031e47e13112View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-6900000000-def0c646d72c040b58daView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0900000000-dfa64951eb648f5c9df1View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-5900000000-3d3a9e4f250074741003View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-2900000000-395df8510f0db4933abeView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-6900000000-1afdd3b83f6832b11f70View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-4900000000-1d96ae8b031e47e13112View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-6900000000-def0c646d72c040b58daView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0900000000-dfa64951eb648f5c9df1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ms-1900000000-da27a86009649c155318View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8790000000-0d0c6f0e58d7dc3e5620View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-4541582e8f6395e2fa87View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-84f950d2fc0742e324d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ab9-0900000000-4c037643a10913a70f5eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-83f8f32dfd9b94fb1d24View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-2900000000-c65a2dab49b8ebb431daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-65a67ccd1df0d2f1796fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-9d2a857e8a482a061127View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-9c846765367542bf4db1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-9500000000-98fcaf3ccca850c34bd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-835320dc79855273af7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-3a70eb9601589d9108a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-4900000000-1c4834945c53d64bab3bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0il0-6900000000-ff0dc492bab70317bb2aView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID13876103
ChEMBL IDCHEMBL42710
KEGG Compound IDC10453
Pubchem Compound ID3314
Pubchem Substance IDNot Available
ChEBI ID470
Phenol-Explorer ID646
DrugBank IDNot Available
HMDB IDHMDB05809
CRC / DFC (Dictionary of Food Compounds) IDHDW90-Y:HDW90-Y
EAFUS ID1326
Dr. Duke IDEUGENOL
BIGG IDNot Available
KNApSAcK IDC00000619
HET IDEOL
Flavornet ID97-53-0
GoodScent IDrw1004991
SuperScent ID3314
Wikipedia IDEugenol
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
acaricide22153 A substance used to destroy pests of the subclass Acari (mites and ticks).DUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anestheticDUKE
anti aggregantDUKE
anti arachidonate35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti edemicDUKE
anti estrogenic35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti feedantDUKE
anti genotoxic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti keratoticDUKE
anti mitoticDUKE
anti mutagenicDUKE
anti nitrosatingDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
anti radicularDUKE
anti salmonella33282 A substance that kills or slows the growth of bacteria.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti thromboxane35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti TNF35222 A substance that diminishes the rate of a chemical reaction.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
apifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
candidicideDUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
carminativeDUKE
cholereticDUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
cyclooxygenase-1 inhibitor50630 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.DUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
cytochrome-P450 inhibitor50183 An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
dermatitigenicDUKE
enterorelaxantDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
herbicide24527 A substance used to destroy plant pests.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
irritantDUKE
juvabionalDUKE
larvicideDUKE
motor depressantDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
neurotoxic50910 A poison that interferes with the functions of the nervous system.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
prostaglandin synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
termiticideDUKE
trichomonicideDUKE
trichomonistatDUKE
trypsin enhancerDUKE
ulcerogenicDUKE
varroacideDUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
vermifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
Enzymes
NameGene NameUniProt ID
UDP-glucuronosyltransferase 2B28UGT2B28Q9BY64
UDP-glucuronosyltransferase 2B17UGT2B17O75795
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
clove
  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
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  3. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
honey
  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
cinnamon
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
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.
woody
  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).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.