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IUPAC name
Other names
78-59-1 YesY
ChemSpider 6296 YesY
EC number 201-126-0
Jmol-3D images Image
KEGG C14743 YesY
PubChem 6544
Molar mass 138.21 g·mol−1
Appearance Colorless to white liquid
Odor Peppermint-like[2]
Density 0.9255 g/cm3
Melting point −8.1 °C (17.4 °F; 265.0 K)
Boiling point 215.32 °C (419.58 °F; 488.47 K)
1.2 g/100 mL
Solubility ether, acetone, hexane, dichloromethane, benzene, toluene, alcohol
Vapor pressure 0.3 mmHg (20°C)[2]
Viscosity 2.62 cP
43.4 kJ/mol
Flash point 84 °C (183 °F; 357 K)
460 °C (860 °F; 733 K)
Explosive limits 0.8%-3.8%[2]
Lethal dose or concentration (LD, LC):
2280 mg/kg (rat, oral)[citation needed]
2330 mg/kg (rat, oral)
2690 mg/kg (mouse, oral)[3]
4600 ppm (guinea pig, 8 hr)[3]
885 ppm (rat, 6 hr)
1840 ppm (rat, 4 hr)[3]
US health exposure limits (NIOSH):
TWA 25 ppm (140 mg/m3)[2]
TWA 4 ppm (23 mg/m3)[2]
200 ppm[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Isophorone is an α,β-unsaturated cyclic ketone, a colorless to yellowish liquid with a characteristic peppermint-like smell. It is used as a solvent and as an intermediate in organic synthesis. Isophorone also occurs naturally in cranberries.[4]


Isophorone can be manufactured by catalyzed self-condensation of acetone.[5] Mesityl oxide is the initial product of the self-aldol condensation of acetone. The mesityl oxide formed can react further with acetone via a Michael reaction and subsequent intramolecular aldol condensation to eventually obtain the six-membered ring of isophorone. This is an example of the Robinson annulation. The yield of the two compounds depends on the reaction conditions.

Isophorone mesityl oxide.png


The use of isophorone as a solvent resulted from the search for ways to dispose of or recycle acetone, which is a waste product of phenol synthesis by the Hock method.[6]


Isophorone is used as a solvent in some printing inks, paints, lacquers, adhesives, copolymers, coatings, finishings and pesticides.[4] It is also used as a chemical intermediate and as an ingredient in wood preservatives and floor sealants.

See also[edit]


  1. ^ Merck Index, 13th Edition, 5215.
  2. ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0355". National Institute for Occupational Safety and Health (NIOSH). 
  3. ^ a b c "Isophorone". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH). 
  4. ^ a b Chronic Toxicity Summary
  5. ^ U.S. Patent 5,849,957
  6. ^ Isophorone history at Degussa