Acetylpropionyl, also known as acetyl propionyl or 2,3-pentanedione, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

, specifically a

diketone In organic chemistry, a dicarbonyl is a molecule containing two carbonyl () groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls ...

.Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. Uses for acetylpropionyl include as a: *

Solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

for cellulose acetate,

paint Paint is a material or mixture that, when applied to a solid material and allowed to dry, adds a film-like layer. As art, this is used to create an image or images known as a painting. Paint can be made in many colors and types. Most paints are ...

ink Ink is a gel, sol, or solution that contains at least one colorant, such as a dye or pigment, and is used to color a surface to produce an image, text, or design. Ink is used for drawing or writing with a pen, brush, reed pen, or quill. ...

s, and

lacquer Lacquer is a type of hard and usually shiny coating or finish applied to materials such as wood or metal. It is most often made from resin extracted from trees and waxes and has been in use since antiquity. Asian lacquerware, which may be c ...

s * Starting material for

dye Juan de Guillebon, better known by his stage name DyE, is a French musician. He is known for the music video of the single "Fantasy Fantasy is a genre of speculative fiction that involves supernatural or Magic (supernatural), magical ele ...

pesticide Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for approximately 50% of all p ...

s, and

drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...

s * Flavor, with an odor described as "buttery, cheesy, sweet, nutty, fruity, creamy, caramel" Food production facilities use acetylpropionyl in foods such as cookies, coffee, cereal, and chocolate. It is also found in nicotine containing liquids for vaping, and in flavored cigarettes. It is often used as a flavoring substitute for

diacetyl Diacetyl ( ; IUPAC systematic name: butanedione or butane-2,3-dione) is an organic compound with the chemical formula (CH3CO)2. It is a yellow liquid with an intensely buttery flavor. It is a vicinal diketone (two C=O groups, side-by-side). Di ...

, but may share similar human pulmonary toxicity.

Safety

As a flavoring agent, it is an ingredient in some

e-liquid An electronic cigarette is a handheld battery-powered vaporizer that simulates smoking, but without tobacco combustion. E-cigarette components include a mouthpiece (drip tip), a cartridge (liquid storage area), a heating element/ atomizer, a m ...

products for use with

electronic cigarette An electronic cigarette (e-cigarette), or vape, is a device that simulates smoking. It consists of an atomizer, a power source such as a battery, and a container such as a cartridge or tank. Instead of smoke, the user inhales vapor. As such ...

s to give a buttery or caramel flavor. There is substantial evidence of the pulmonary toxicity of acetylpropionyl in animals. Rats exposed to acetylpropionyl develop both

fibrosis Fibrosis, also known as fibrotic scarring, is the development of fibrous connective tissue in response to an injury. Fibrosis can be a normal connective tissue deposition or excessive tissue deposition caused by a disease. Repeated injuries, ch ...

and

necrosis Necrosis () is a form of cell injury which results in the premature death of cells in living tissue by autolysis. The term "necrosis" came about in the mid-19th century and is commonly attributed to German pathologist Rudolf Virchow, who i ...

of the respiratory tract. Mice exposed to acetylpropionyl demonstrate more

bronchial A bronchus ( ; : bronchi, ) is a passage or airway in the lower respiratory tract that conducts Atmosphere of Earth, air into the lungs. The first or primary bronchi to branch from the trachea at the Carina of trachea, carina are the right main b ...

constriction in response to methacholine challenge. It is also known to cause genetic changes in animal brains. Acetylpropionyl has been used as a substitute for the toxic flavoring chemical

. However, in one flavoring manufacturing facility that substituted

for acetylpropionyl, abnormal lung function values were associated with total time spent in production areas. An investigation by

NIOSH The National Institute for Occupational Safety and Health (NIOSH, ) is the United States federal agency responsible for conducting research and making recommendations for the prevention of work-related injury, illness, disability, and death. It ...

in 2009 at a facility that used buttermilk flavoring containing acetylpropionyl demonstrated that workers had higher than average reports of shortness of breath,

asthma Asthma is a common long-term inflammatory disease of the airways of the lungs. It is characterized by variable and recurring symptoms, reversible airflow obstruction, and easily triggered bronchospasms. Symptoms include episodes of wh ...

, and restrictive type

spirometry Spirometry (meaning ''the measuring of breath'') is the most common of the pulmonary function tests (PFTs). It measures lung function, specifically the amount (volume) and/or speed (flow) of air that can be inhaled and exhaled. Spirometry is h ...

defects. Another investigation by

in 2013 at a flavoring manufacturer that used acetylpropionyl revealed that those workers who spent the most time working with flavoring chemicals, including acetylpropionyl, were more likely to have abnormal lung function as detected by pulmonary function tests.

References

{{reflist, 40em Diketones Flavors

Safety

See also

References