EOL

2-methoxy-4-(prop-2-en-1-yl)phenol

Created: 2011-05-17
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count24
Chiral Atom Count0
Bond Count24
Aromatic Bond Count6
2D diagram of EOL

Chemical Component Summary

Name2-methoxy-4-(prop-2-en-1-yl)phenol
Synonymseugenol
Systematic Name (OpenEye OEToolkits)2-methoxy-4-prop-2-enyl-phenol
FormulaC10 H12 O2
Molecular Weight164.201
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01Oc1ccc(cc1OC)C\C=C
SMILESCACTVS3.370COc1cc(CC=C)ccc1O
SMILESOpenEye OEToolkits1.7.2COc1cc(ccc1O)CC=C
Canonical SMILESCACTVS3.370 COc1cc(CC=C)ccc1O
Canonical SMILESOpenEye OEToolkits1.7.2 COc1cc(ccc1O)CC=C
InChIInChI1.03 InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
InChIKeyInChI1.03 RRAFCDWBNXTKKO-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB09086 
NameEugenol
Groups approved
DescriptionEugenol is a naturally occurring phenolic molecule found in several plants such as cinnamon, clove, and bay leaves. It has been used as a topical antiseptic as a counter-irritant and in dental preparations with zinc oxide for root canal sealing and pain control. Although not currently available in any FDA-approved products (including OTC), eugenol has been found to have anti-inflammatory, neuroprotective, antipyretic, antioxidant, antifungal and analgesic properties. Its exact mechanism of action is unknown, however, it has been shown to interfere with action potential conduction. There are a number of unapproved OTC products available containing eugenol that advertise its use for the treatment of toothache.
SynonymsEugenol
Brand Names
  • DenTek Eugenol
  • TotalArthritis
  • AnaDent Childrens Kanka Gel
  • Jiffy Toothache Drops
  • Walgreens Natural Eugenol/Toothache Medication with cotton pellets and tweezers
IndicationEugenol is not currently available in any FDA-approved drug products. There are a number of unapproved OTC products that advertise it for the use of toothache. Eugenol is is also commonly used in combination with zinc oxide in dental procedures for the cementation of temporary prostheses and the temporary restoration of teeth and cavities.
Categories
  • Acids, Carbocyclic
  • Alkenes
  • Allyl Compounds
  • Allylbenzene Derivatives
  • Anti-Infective Agents
CAS number97-53-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Amine oxidase [flavin-containing] BMSNKCDVVVVGGGISGMAAAKLLHDSGLNVVVLEARDRVGGRTYTLRNQK...unknowninhibitor
Estrogen receptorMTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPA...unknown
Estrogen receptor betaMDIKNSPSSLNSPSSYNCSQSILPLEHGSIYIPSSYVDSHHEYPAMTFYS...unknown
Androgen receptorMEVQLGLGRVYPRPPSKTYRGAFQNLFQSVREVIQNPGPRHPEAASAAPP...unknownantagonist
Transient receptor potential cation channel subfamily V member 3MKAHPKEMVPLMGKRVAAPSGNPAILPEKRPAEITPTKKSAHFFLEIEGF...unknown
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 3314
ChEMBL CHEMBL42710
ChEBI CHEBI:4917
CCDC/CSD WUTFEZ, WUTDOH