Names | |
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Preferred IUPAC name Pentane-2,3-dione | |
Other names 2,3-Pentanedione | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.009.078 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C5H8O2 | |
Molar mass | 100.117 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Acetylpropionyl, also known as acetyl propionyl or 2,3-pentanedione, [1] is an organic compound, specifically a diketone. [2]
Uses for acetylpropionyl include as a:
Food production facilities use acetylpropionyl in foods such as cookies, coffee, cereal, and chocolate. [4] It is also found in nicotine containing liquids for vaping, and in flavored cigarettes. [4] It is often used as a flavoring substitute for diacetyl, but may share similar human pulmonary toxicity. [5] [6]
As a flavoring agent, it is an ingredient in some e-liquid products for use with electronic cigarettes to give a buttery or caramel flavor. [7] There is substantial evidence of the pulmonary toxicity of acetylpropionyl in animals. [4] Rats exposed to acetylpropionyl develop both fibrosis and necrosis of the respiratory tract. [4] Mice exposed to acetylpropionyl demonstrate more bronchial constriction in response to methacholine challenge. [4] It is also known to cause genetic changes in animal brains. [5]
Acetylpropionyl has been used as a substitute for the toxic flavoring chemical diacetyl. [4] However, in one flavoring manufacturing facility that substituted diacetyl for acetylpropionyl, abnormal lung function values were associated with total time spent in production areas. [4] An investigation by NIOSH in 2009 at a facility that used buttermilk flavoring containing acetylpropionyl demonstrated that workers had higher than average reports of shortness of breath, asthma, and restrictive type spirometry defects. [8] Another investigation by NIOSH 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. [9]
Tobacco smoke is a sooty aerosol produced by the incomplete combustion of tobacco during the smoking of cigarettes and other tobacco products. Temperatures in burning cigarettes range from about 400 °C between puffs to about 900 °C during a puff. During the burning of the cigarette tobacco, thousands of chemical substances are generated by combustion, distillation, pyrolysis and pyrosynthesis. Tobacco smoke is used as a fumigant and inhalant.
Nitrogen dioxide is a chemical compound with the formula NO
2. It is one of several nitrogen oxides. NO
2 is an intermediate in the industrial synthesis of nitric acid, millions of tons of which are produced each year for use primarily in the production of fertilizers. At higher temperatures it is a reddish-brown gas. It can be fatal if inhaled in large quantities. Nitrogen dioxide is a paramagnetic, bent molecule with C2v point group symmetry.
The Maillard reaction is a chemical reaction between amino acids and reducing sugars that gives browned food its distinctive flavor. Seared steaks, fried dumplings, cookies and other kinds of biscuits, breads, toasted marshmallows, and many other foods undergo this reaction. It is named after French chemist Louis Camille Maillard, who first described it in 1912 while attempting to reproduce biological protein synthesis. The reaction is a form of non-enzymatic browning which typically proceeds rapidly from around 140 to 165 °C. Many recipes call for an oven temperature high enough to ensure that a Maillard reaction occurs. At higher temperatures, caramelization and subsequently pyrolysis become more pronounced.
Diacetyl ( dy-yuh-SEE-tuhl) (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). Diacetyl occurs naturally in alcoholic beverages and is added as a flavoring to some foods to impart its buttery flavor.
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 are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical or unsymmetrical.
Bromoform (CHBr3) is a brominated organic solvent, colorless liquid at room temperature, with a high refractive index, very high density, and sweet odor is similar to that of chloroform. It is one of the four haloforms, the others being fluoroform, chloroform, and iodoform. Currently its main use is as a laboratory reagent. It is soluble in about 800 parts water and is miscible with alcohol, benzene, chloroform, ether, petroleum ether, acetone and oils.
Acetoin, also known as 3-hydroxybutanone or acetyl methyl carbinol, is an organic compound with the formula CH3CH(OH)C(O)CH3. It is a colorless liquid with a pleasant, buttery odor. It is chiral. The form produced by bacteria is (R)-acetoin.
Bronchiolitis obliterans (BO), also known as obliterative bronchiolitis, constrictive bronchiolitis and popcorn lung, is a disease that results in obstruction of the smallest airways of the lungs (bronchioles) due to inflammation. Symptoms include a dry cough, shortness of breath, wheezing and feeling tired. These symptoms generally get worse over weeks to months. It is not related to cryptogenic organizing pneumonia, previously known as bronchiolitis obliterans organizing pneumonia.
Occupational lung diseases are work-related, lung conditions that have been caused or made worse by the materials a person is exposed to within the workplace. It includes a broad group of diseases, including occupational asthma, industrial bronchitis, chronic obstructive pulmonary disease (COPD), bronchiolitis obliterans, inhalation injury, interstitial lung diseases, infections, lung cancer and mesothelioma. These diseases can be caused directly or due to immunological response to an exposure to a variety of dusts, chemicals, proteins or organisms.
Flavored tobacco products — tobacco products with added flavorings — include types of cigarettes, cigarillos and cigars, hookahs and hookah tobacco, various types of smokeless tobacco, and more recently electronic cigarettes. Flavored tobacco products are especially popular with youth and have therefore become targets of regulation in several countries.
In organic chemistry, ethenone is the formal name for ketene, an organic compound with formula C2H2O or H2C=C=O. It is the simplest member of the ketene class. It is an important reagent for acetylations.
α-Naphthylthiourea (ANTU) is an organosulfur compound with the formula C10H7NHC(S)NH2. This a white, crystalline powder although commercial samples may be off-white. It is used as a rodenticide and as such is fairly toxic. Naphthylthiourea is available as 10% active baits in suitable protein- or carbohydrate-rich materials and as a 20% tracking powder.
Perchloromethyl mercaptan is the organosulfur compound with the formula CCl3SCl. It is mainly used as an intermediate for the synthesis of dyes and fungicides (captan, folpet). It is a colorless oil, although commercial samples are yellowish. It is insoluble in water but soluble in organic solvents. It has a foul, unbearable, acrid odor. Perchloromethyl mercaptan is the original name. The systematic name is trichloromethanesulfenyl chloride, because the compound is a sulfenyl chloride, not a mercaptan.
Artificial butter flavoring is a flavoring used to give a food the taste and smell of butter. It may contain diacetyl, acetylpropionyl, or acetoin, three natural compounds in butter that contribute to its characteristic taste and smell. Manufacturers of margarines or similar oil-based products typically add it to make the final product butter-flavored, because it would otherwise be relatively tasteless.
The use of electronic cigarettes (vaping) carries health risks. The risk depends on the fluid and varies according to design and user behavior. In the United Kingdom, vaping is considered by some to be around 95% less harmful than tobacco after a controversial landmark review by Public Health England.
Indium lung is a rare occupational lung disease caused by exposure to respirable indium in the form of indium tin oxide. It is classified as an interstitial lung disease.
The chemical composition of the electronic cigarette aerosol varies across and within manufacturers. Limited data exists regarding their chemistry. However, researchers at Johns Hopkins University analyzed the vape clouds of popular brands such as Juul and Vuse, and found "nearly 2,000 chemicals, the vast majority of which are unidentified."
An outbreak of e-cigarette, or vaping, product use-associated lung injury (EVALI) started in 2019 among users of illegal, unregulated cannabis vaping products, almost exclusively in the United States. The first cases of this particular outbreak were identified in Illinois and Wisconsin in April 2019; as of 18 February 2020, a total of 2,807 hospitalized cases, including 68 deaths, have been confirmed. According to the U.S Centers for Disease Control (CDC), "Vitamin E acetate is strongly linked to the EVALI outbreak...Evidence is not sufficient to rule out the contribution of other chemicals of concern, including chemicals in either THC or non-THC products, in some of the reported EVALI cases".
Vaping-associated pulmonary injury (VAPI), also known as vaping-associated lung injury (VALI) or e-cigarette, or vaping, product use associated lung injury (E/VALI), is an umbrella term, used to describe lung diseases associated with the use of vaping products that can be severe and life-threatening. Symptoms can initially mimic common pulmonary diagnoses, such as pneumonia, but sufferers typically do not respond to antibiotic therapy. Differential diagnoses have overlapping features with VAPI, including COVID-19. According to an article in the Radiological Society of North America news published in March 2022, EVALI cases continue to be diagnosed. “EVALI has by no means disappeared,” Dr. Kligerman said. “We continue to see numerous cases, even during the pandemic, many of which are initially misdiagnosed as COVID-19.”
A hydrofluoric acid burn is a chemical burn from hydrofluoric acid. Where it contacts the skin it results in significant pain, swelling, redness, and skin breakdown. If the fumes are breathed in swelling of the upper airway and bleeding may occur. Complications can include electrolyte, heart, lung, kidney, and neurological problems.