2-Nonanone

Description

2-Nonanone has a characteristic rue odor and a rose and teα-like flavor. May be prepared by dry distillation of barium caprylate and barium acetate at 0.5 - 2 mmHg; or by oxidation of methyl heptyl carbinol at room temperature using chromic acid; it can be isolated also from natural products by fractional distillation.

Chemical properties

Clear slightly yellow liquid

Chemical properties

2-Nonanone has a characteristic rue odor. It has a rose and tea-like flavor.

Occurrence

Reported found in the essential oil of rue (Ruta angustifolia Pers., R. bracteosa, R. Montana L. and R. gravelolens); also identified in the oil of carnation, in coconut oil and in the distillate from leaves of a variety of Boronia ledifolia; reported found in mixture with methyl nonyl ketone in the essential oil of Ruta chalepensis. Also reported found in banana, lemon peel oil, guava, grapes, raisin, melon, raspberry, strawberry fruit and jam, asparagus, leek, onion, cooked potato, tomato, clove, ginger, wheat bread, many cheeses, butter, yogurt, milk, cream, caviar, fatty fish, meats, hop oil, beer, rum, malt whiskey, grape wines, cognac, cocoa, coffee, tea, roasted filberts and peanuts, pecans, potato chips, soybean, coconut products, olive, passion fruit, trassi, Brazil nut, rice, quince, jackfruit, buckwheat, sweet corn, corn oil, wort, dried bonito, krill, cherimoya, Bourbon vanilla, shrimp, clams, scallop, crayfish, maté and mastic gum leaf and fruit oil

The Uses of 2-Nonanone

2-Nonanone is used as a component of several food sources and can be used as a flavoring agent.

Definition

ChEBI: A methyl ketone that is nonane in which the methylene hydrogens at position 2 are replaced by an oxo group.

Preparation

By dry distillation of barium caprylate and barium acetate at 0.5 to 2 mmHg; by oxidation of methylheptyl carbinol at room temperature using chromic acid; it can be isolated also from natural products by fractional distillation

Aroma threshold values

Detection: 5 to 200 ppb

Taste threshold values

Taste characteristics at 20 ppm: cheesy, green, fruity, dairy, dirty, and buttery

Synthesis Reference(s)

Journal of the American Chemical Society, 90, p. 5936, 1968 DOI: 10.1021/ja01023a070
Tetrahedron Letters, 29, p. 2885, 1988 DOI: 10.1016/0040-4039(88)85238-9
The Journal of Organic Chemistry, 58, p. 5003, 1993 DOI: 10.1021/jo00070a044

General Description

Colorless liquid.

Air & Water Reactions

Highly flammable. Water insoluble.

Reactivity Profile

Ketones, such as 2-Nonanone, are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Health Hazard

May be harmful by inhalation, ingestion, or skin absorption. May cause eye and skin irritation.

Flammability and Explosibility

Non flammable

Safety Profile

Moderately toxic by ingestion.Combustible when exposed to heat or flame; can reactwith oxidizing materials. To fight fire, use foam, CO2, drychemical. When heated to decomposition it emits acridsmoke and irritating fumes.