Isoeugenol (5932-68-3, 97-54-1)

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  25 g
  $23.00

  100 g
  $39.00

  500 g
  $132.00

Most-cited Publications

• Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester (Proceedings of the National Academy of Sciences of the United States of America, 2006)
• Insecticidal properties of eugenol, isoeugenol and methyleugenol and their effects on nutrition of Sitophilus zeamais Motsch. (Coleoptera: Curculionidae) and Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae) (Journal of Stored Products Research, 2002)
• Dehydrozingerone and isoeugenol as inhibitors of lipid peroxidation and as free radical scavengers (Biochemical Pharmacology, 1993)
• Characterization of a petunia acetyltransferase involved in the biosynthesis of the floral volatile isoeugenol (Plant Journal, 2007)
• The Time-Dose-Response Relationship for Elicitation of Contact Dermatitis in Isoeugenol Allergic Individuals (Toxicology and Applied Pharmacology, 2001)
• Skin sensitization to eugenol and isoeugenol in mice: possible metabolic pathways involving ortho-quinone and quinone methide intermediates. (Chemical Research in Toxicology, 1997)

Areas of Application

Safety

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  Predict GHS Hazards for Any Chemical in silico.
  Including Acute Oral Tox, Skin Sensitization, Eye Irritation, Aquatic Tox, & more.
• H302: Harmful if swallowed
  Warning Acute toxicity, oral - Category 4
• H315: Causes skin irritation
  Warning Skin corrosion/irritation - Category 2
• H319: Causes serious eye irritation
  Warning Serious eye damage/eye irritation - Category 2A
• H373: Causes damage to organs through prolonged or repeated exposure
  Warning Specific target organ toxicity, repeated exposure - Category 2

Trends

Alternate Names

• 2-methoxy-4-propenylphenol
• isoeugenol, (E)-isomer
• isoeugenol, sodium salt
• isoeugenol, (Z)-isomer
• SMILES
  CC=CC1=CC(=C(C=C1)O)OC
• InChIKey
  BJIOGJUNALELMI-UHFFFAOYSA-N

External Links

• Pubchem - Isoeugenol
• Wikipedia - Isoeugenol
  Isoeugenol is a phenylpropene, a propenyl-substituted guaiacol. A phenylpropanoid, it occurs in the essential oils of plants such as ylang-ylang (Cananga odorata). It can be synthesized from eugenol and has been used in the manufacture of vanillin.

Synthesis

PROPYLENE  +  4-Chloro-2-methoxyphenol (Heck terminal vinyl)

1-Propenyl bromide  +  4-Chloro-2-methoxyphenol (Stille)

Reactant  +  Methyl hydroperoxide (Dakin oxidation)

Reactant  +  1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (Nicolaou IBX dehydrogenation)

acetaldehyde  +  Reactant (Wittig)

Synthesis of Isoeugenol ›

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Isoeugenol

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