Eugenol

Eugenol
Skeletal formula of eugenol
Ball-and-stick model of the eugenol molecule
Names
Preferred IUPAC name
2-Methoxy-4-(prop-2-en-1-yl)phenol
Other names
  • 4-Allyl-2-methoxyphenol
  • 2-Methoxy-4-(2-propenyl)phenol
  • Eugenic acid
  • Caryophyllic acid
  • 1-Allyl-3-methoxy-4-hydroxybenzene
  • Allylguaiacol
  • 2-Methoxy-4-allylphenol
  • 4-Allylcatechol-2-methyl ether
Identifiers
3D model (JSmol)
1366759
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.355 Edit this at Wikidata
EC Number
  • 202-589-1
KEGG
UNII
  • InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3 checkY
    Key: RRAFCDWBNXTKKO-UHFFFAOYSA-N checkY
  • InChI=1/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
    Key: RRAFCDWBNXTKKO-UHFFFAOYAJ
  • Oc1ccc(cc1OC)CC=C
Properties
C10H12O2
Molar mass 164.204 g·mol−1
Density 1.06 g/cm3
Melting point −7.5 °C (18.5 °F; 265.6 K)
Boiling point 254 °C (489 °F; 527 K)
Acidity (pKa) 10.19 at 25 °C
−1.021×10−4 cm3/mol
Viscosity
  • 9.12 mPa·s at 20 °C
  • 5.99 mPa·s at 30 °C[1]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 104 °C (219 °F; 377 K)
Related compounds
Related compounds
 2-Phenethyl propionate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Eugenol /ˈjuːdʒɪnɒl/ is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds.[2] It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove, nutmeg, cinnamon, basil and bay leaf.[3][4][5][6] It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil.[7] Eugenol has a pleasant, spicy, clove-like scent.[8] The name is derived from Eugenia caryophyllata, the former Linnean nomenclature term for cloves. The currently accepted name is Syzygium aromaticum.[9]

  1. ^ Bingham EC, Spooner LW (1932). "The Fluidity Method for the Determination of Association. I". Journal of Rheology. 3 (2): 221–244. Bibcode:1932JRheo...3..221B. doi:10.1122/1.2116455. ISSN 0097-0360.
  2. ^ Cite error: The named reference pubchem was invoked but never defined (see the help page).
  3. ^ "Constituents of the essential oil from leaves and buds of clove (Syzigium caryophyllatum L.) Alston" (PDF). Bangladesh Council of Scientific and Industrial Research BCSIR Laboratories. 4: 451–454.
  4. ^ Mallavarapu GR, Ramesh S, Chandrasekhara RS, Rajeswara Rao BR, Kaul PN, Bhattacharya AK (1995). "Investigation of the essential oil of cinnamon leaf grown at Bangalore and Hyderabad". Flavour and Fragrance Journal. 10 (4): 239–242. doi:10.1002/ffj.2730100403.
  5. ^ Yield and Oil Composition of 38 Basil (Ocimum basilicum L.) Accessions Grown in Mississippi Archived 15 October 2010 at the Wayback Machine
  6. ^ "Typical G.C. for bay leaf oil". Thegoodscentscompany.com. Archived from the original on 17 March 2014. Retrieved 27 April 2014.
  7. ^ Barnes J, Anderson LA, Phillipson JS (2007) [1996]. Herbal Medicines (PDF) (3rd ed.). London: Pharmaceutical Press. ISBN 978-0-85369-623-0. Archived from the original (PDF) on 1 July 2018. Retrieved 27 April 2015.
  8. ^ Wishart, David S.; Guo, An Chi; Oler, Eponine; et al. "Showing metabocard for Eugenol (HMDB0005809)". Human Metabolome Database, HMDB. 5.0.
  9. ^ Cortés Rojas DF, de Souza CR, Oliveira WP (February 2014). "Clove (Syzygium aromaticum): a precious spice". Asian Pacific Journal of Tropical Biomedicine. 4 (2): 90–6. doi:10.1016/S2221-1691(14)60215-X. PMC 3819475. PMID 25182278.