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Human Metabolome Database Version 3.5

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Showing metabocard for Isoeugenol (HMDB05802)

Record Information
Version 3.5
Creation Date 2007-01-22 15:53:28 -0700
Update Date 2013-02-08 17:14:20 -0700
HMDB ID HMDB05802
Secondary Accession Numbers None
Metabolite Identification
Common Name Isoeugenol
Description Isoeugenol is is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil and cinnamon. It is very slightly soluble in water and soluble in organic solvents. It has a spicy odor and taste of clove. Isoeugenol is prepared from eugenol by heating. Eugenol is used in perfumeries, flavorings, essential oils and in medicine (local antiseptic and analgesic). It is used in the production of isoeugenol for the manufacture of vanillin. Eugenol derivatives or methoxyphenol derivatives in wider classification are used in perfumery and flavoring. They are used in formulating insect attractants and UV absorbers, analgesics, biocides and antiseptics. They are also used in manufacturing stabilizers and antioxidants for plastics and rubbers. Isoeugenol is used in manufacturing perfumeries, flavorings, essential oils (odor description: Clove, spicy, sweet, woody) and in medicine (local antiseptic and analgesic) as well as vanillin. (PMID: 15964168 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (E)-2-methoxy-4- (1-propenyl)-Phenol
  2. (E)-2-methoxy-4-(1-propenyl)-Phenol
  3. (E)-2-Methoxy-4-(prop-1-enyl)phenol
  4. (E)-2-methoxy-4-propenyl-Phenol
  5. (e)-isoeugenol
  6. 1-(3-Methoxy-4-hydroxyphenyl)-1-propane
  7. 1-Hydroxy-2-methoxy-4-propen-1-ylbenzene
  8. 2-Methoxy-4-(1-propenyl)-Phenol
  9. 2-Methoxy-4-(1-propenyl)phenol
  10. 2-Methoxy-4-(1-propenyl)phenol (ACD/Name 4.0)
  11. 2-Methoxy-4-propenyl-Phenol
  12. 2-Methoxy-4-propenylphenol
  13. 2-Methoxy-4-propenylphenol (isoeugenol)
  14. 2-Methoxy-4-[(1E)-1-propenyl]phenol
  15. 2-Methoxy-4-[(1E)-prop-1-en-1-yl]phenol
  16. 3-Methoxy-4-hydroxy-1-propen-1-ylbenzene
  17. 3-Methoxy-4-hydroxypropenylbenzene
  18. 4-Hydroxy-3-methoxy-1-propen-1-ylbenzene
  19. 4-Hydroxy-3-methoxy-1-propenylbenzene
  20. 4-Hydroxy-3-methoxypropenylbenzene
  21. Isoeugenol
  22. Isoeugenol (I)
  23. Isoeugenol trans-form
  24. Propenylgualacol
  25. trans-2-Methoxy-4-propenylphenol
  26. trans-4-Propenylgualacol
  27. Trans-isoeugenol
  28. Trans-p-propenylquaiacol
Chemical Formula C10H12O2
Average Molecular Weight 164.2011
Monoisotopic Molecular Weight 164.083729628
IUPAC Name 2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol
Traditional IUPAC Name trans-isoeugenol
CAS Registry Number 97-54-1
SMILES COC1=CC(\C=C\C)=CC=C1O
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
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class Methoxyphenols and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Phenylpropenes
  • isoeugenol(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Styrene
Direct Parent Methoxyphenols and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Cosmetic
  • Drug
Biofunction Not Available
Application
  • Scent and flavoring agent
  • Used in manufacture of vanillin
Cellular locations Not Available
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point -10 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 3.04 GRIFFIN,S ET AL. (1999)
Predicted Properties
Property Value Source
Water Solubility 1.36 g/L ALOGPS
LogP 2.79 ALOGPS
LogP 2.64 ChemAxon
LogS -2.08 ALOGPS
pKa (strongest acidic) 10.01 ChemAxon
pKa (strongest basic) -4.9 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 29.46 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 49.86 ChemAxon
Polarizability 18.3 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB002728
KNApSAcK ID C00000620 Link_out
Chemspider ID 21106129 Link_out
KEGG Compound ID C10469 Link_out
BioCyc ID ISOEUGENOL Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB05802 Link_out
Metagene Link HMDB05802 Link_out
METLIN ID Not Available
PubChem Compound 853433 Link_out
PDB ID EUG Link_out
ChEBI ID 50545 Link_out
References
Synthesis Reference Mannich, C.; Schmitt, Frida. Synthesis of amino alcohols from isosafrole, isoeugenol and anethole. Arch. Pharm. (1928), 266 73-84. CAN 22:39242 AN 1928:39242
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available