Eugenol
Eugenol-UP.gif

Eugenol is the main component of clove oil. Eugenol also occurs in human and rat urine as a very minor metabolite of the oral ingestion of safrole.[3] It's also a metabolite of methyl eugenol.

Eugenol is responsible for the therapeutic actions of clove oil. It's commonly used as a local analgesic and antiseptic.

Eugenol also acts as a potent anti-platelet medicine. One test showed it inhibited platelet aggregation more potently than aspirin.[7] In another test its anti-platelet activity was found to be equal to that of aspirin.[8]

Eugenol is an allylbenzene and can form alkaloids in vivo under certain situations.[6] This is also proven for elemicin, safrole, myristicin and other closely related allylbenzenes (see the article on Oilahuasca Activation for more details).

Non-Alkaloid Metabolites

The metabolism of eugenol was investigated in male and female healthy volunteers. Eugenol was rapidly absorbed and metabolized after oral administration and was almost completely excreted in the urine within 24 hours. Unmetabolized eugenol excreted in urine amounted to less than 0.1% of the dose used.[4]

The following metabolites were detected in man after oral use:

  • 3'-Hydroxyeugenol (needs further verification) [4]
  • Vanillactic Acid (needs further verification) [4]
  • 4-hydroxy-3-methoxyphenyl-propane [4]
  • cis-isoeugenol [4]
  • trans-isoeugenol [4]
  • 3-(4-hydroxy-3-methoxyphenyl)-propylene-1,2-oxide [4]
  • 3-(4-hydroxy-3-methoxyphenyl)-propane-1,2-diol [4]
  • 3-(4-hydroxy-3-methoxyphenyl)-propionic acid [4]

Hydroxychavicol has been found to occur in vitro by the action of CYP2D6 on eugenol.[5]

Chemical Properties

PubChem Compound ID: 3314
Molecular Weight: 164.20108 [g/mol]
Molecular Formula: C10H12O2
Boiling Point: 253.2 deg C at 760 mm Hg[1]
Melting Point: -9.2 to -9.1 deg C[2]
Solubility: Soluble in glacial acetic acid, 1 mL in 2 mL 70% alcohol, aqueous fixed alkali hydroxide solutions; miscible with alcohol, chloroform, ether, oils[2]
XLogP3: 2
IUPAC Name: 2-methoxy-4-prop-2-enylphenol
InChI: InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
InChIKey: RRAFCDWBNXTKKO-UHFFFAOYSA-N
Canonical SMILES: COC1=C(C=CC(=C1)CC=C)O

Bibliography
1. Lide, DR (ed.). CRC Handbook of Chemistry and Physics. 81st Edition. CRC Press LLC, Boca Raton: FL 2000, p. 3-257
2. O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 630
3. Toxicology. 1977 Feb;7(1):69-83.
Absorption, metabolism and excretion of safrole in the rat and man. Benedetti MS, Malno├ź A, Broillet AL; PubMed PMID: 14422
4. Fischer IU, von Unruh GE, Dengler HJ.; The metabolism of eugenol in man; Medizinische Universit├Ątsklinik Bonn, FRG; Xenobiotica. 1990 Feb;20(2):209-22.; PubMed PMID: 2333717
5. Copper-mediated oxidative DNA damage induced by eugenol: possible involvement of O-demethylation.
Sakano K, Inagaki Y, Oikawa S, Hiraku Y, Kawanishi S. PubMed PMID: 15576237
6. Urinary excretion of tertiary amino methoxy methylenedioxy propiophenones as metabolites of myristicin in the rat and guinea pig.
Oswald EO, Fishbein L, Corbett BJ, Walker MP. PubMed PMID: 5125615
7. Platelet anti-aggregation activities of compounds from Cinnamomum cassia.
Kim SY, Koo YK, Koo JY, Ngoc TM, Kang SS, Bae K, Kim YS, Yun-Choi HS. PubMed PMID: 20828311
8. Isolation of bioactive compounds that relate to the anti-platelet activity of Cymbopogon ambiguus.
Grice ID, Rogers KL, Griffiths LR. PubMed PMID: 20047890
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