| Description | 4-Heptanone is an organic ketone containing seven carbon atoms. It can be found in urine samples of human being. It arises from in vivo beta-oxidation of 2-ethylhexanoic acid (EHA) from plasticisers, which is similar to the formation of 3-heptanone from valproic acid. It is mainly used as the solvents of nitrocellulose, nitrocellulose paint and synthetic resin and as the raw materials of organic synthesis. It can also be used as a internal standard of gas chromatography-mass spectrometry for the analysis of 3-monochloro-1, 2-propane diol which is a potential carcinogen found in soy sauce. It can be synthesized during the reaction of 1-butanol over base catalysts such as MgO.
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| References | Walker V, and Mills GA. "Urine 4-heptanone: a beta-oxidation product of 2-ethylhexanoic acid from plasticisers. " Clinica Chimica Acta306.2(2001):51-61.
Dayrit, F. M., and M. R. Niñonuevo. "Development of an analytical method for 3-monochloropropane-1,2-diol in soy sauce using 4-heptanone as derivatizing agent." Food Additives & Contaminants 21.3(2004):204-9.
Plint, Neville, et al. "Catalysed synthesis of 4-heptanone from 1-butanol."Catalysis Today 49.1–3(1999):71-77.
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| Description | 4-Heptanone has a penetrating odor and burning taste. It is prepared by passing butyric acid over a wood coal at 425°C and then
over cerium oxide at 500°C or over thorium oxide; also over
manganese oxide at 400 - 425°C. |
| Chemical Properties | 4-Heptanone has a penetrating odor and burning taste. |
| Chemical Properties | colourless liquid |
| Occurrence | Reported found in apple juice, papaya, pear, cabbage, baked potato, roasted peanut, chicken fat, coffee, bachang (Mangifera foetida L ) and rooibus tea (Aspalathius linearis) |
| Uses | Solvent for nitrocellulose, oils, resins,
and polymers and in flavorings |
| Uses | Dipropyl ketone (DPK) is used as a solventin oils, resins, nitrocellulose, and polymers;and as a flavoring compound. |
| Uses | 4-Heptanone is used as a solvent for nitrocellulose as well as in organic synthesis. It is involved in the preparation of flavorings. It is used as an intermediate in the synthesis of active pharmaceutical ingredients. Further, it is used in paints and coatings. |
| Preparation | By passing butyric acid over wood coal at 425°C and then over cerium oxide at 500°C or over thorium oxide; also over manganese oxide at 400 to 425°C. |
| Definition | ChEBI: 4-heptanone is a dialkyl ketone that is heptane in which the two methylene protons at position 4 have been replaced by an oxo group. It has a role as a biomarker, a human xenobiotic metabolite, a human urinary metabolite and a rat metabolite. It derives from a hydride of a heptane. |
| Aroma threshold values | Detection: 8.2 to 41 ppb; aroma characteristics at 1.0%: sweet ethereal, banana fruity, pungent, green apple with cheese nuances. |
| Taste threshold values | Taste characteristics at 5 ppm: fruity, banana, green apple, blue cheese with nut-like nuances. |
| Synthesis Reference(s) | The Journal of Organic Chemistry, 59, p. 245, 1994 DOI: 10.1021/jo00080a042 |
| General Description | A colorless liquid with a pleasant odor. Insoluble in water and less dense than water. Flash point 120°F. Toxic by inhalation. A skin irritant. Used to make flavorings and as a solvent. |
| Air & Water Reactions | Flammable. Insoluble in water. |
| Reactivity Profile | 4-Heptanone is incompatible with the following: Oxidizers . |
| Health Hazard | Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. |
| Health Hazard | Inhalation of DPK vapors can cause narcosisand irritation of the eyes and respiratory tract.Exposure to 4000 ppm for 4 hours was fatalto rats. This compound exhibited low to verylow oral toxicity in test animals.
LD50 value, oral (rats): 3730 mg/kg. |
| Fire Hazard | Combustible liquid; flash point (closed cup)
49°C (120°F); vapor density 3.9 (air = 1);
vapor pressure 5.2 torr at 20°C (68°F); fireextinguishing agent: “alcohol” foam or water
spray. DPK forms explosive mixtures with
air; LEL and UEL values have not been
reported. It is incompatible with strong acids,
alkalies, and oxidizers.
. |
| Biochem/physiol Actions | Taste at 5 ppm |
| Safety Profile | and skin contact. A
skin and eye irritant. Flammable liquid when
exposed to heat or flame; can react with
oxidizing materials. To fight fire, use CO2,
dry chemical, alcohol foam, fog, and mist.
When heated to decomposition it emitsacrid smoke and fumes. See also
KETONES. |
| Metabolism | When 950 mg methyl amyl ketone/kg body weight was administered orally to rabbits, 40% was excreted as heptyl-2-glucuronide, and traces of the unchanged ketone were also found in the urine (Kamil, Smith & Williams, 1953). 2-Heptanone (methyl amyl ketone) was identified as being among the approximately 300 compounds present in the volatile constituents of urine from male and female subjects (Zlatkis & Liebich, 1971). |
| Purification Methods | Dry 4-pentanone with CaSO4, then distil it from P2O5 under nitrogen. [Beilstein 1 IV 3323.] |
| Waste Disposal | DPK is burned in a chemical incineratorequipped with an afterburner and scrubber. |
