579-07-7 Usage
Description
1-Phenyl-1,2-propanedione, also known as Pyruvophenone, is an alpha-diketone that consists of 1-phenylpropane bearing keto substituents at positions 1 and 2. It is a volatile flavor compound found in various natural sources such as khat leaves, cambará honey, coffee, and baked potato. This clear yellow liquid has a pungent, plastic odor and is characterized by its creamy, buttery, fatty, slightly vanilla-like, walnut nutty, almond, and marzipan-like aroma with a woody styrax-like nuance and a slightly sour yeasty and fermented nuance.
Uses
1. Used in Pharmaceutical Industry:
1-Phenyl-1,2-propanedione is used as a synthetic intermediate for the production of opioid receptor agonists, which are essential in treating gastrointestinal disorders. The enantioselective hydrogenation of Pyruvophenone over Pt colloids has also been studied for its potential applications in the pharmaceutical field.
2. Used in Flavor and Fragrance Industry:
1-Phenyl-1,2-propanedione is used as a flavoring agent for its unique creamy, buttery, and slightly vanilla-like taste. It is particularly useful in the food and beverage industry to enhance the taste of various products.
3. Used in Coffee Industry:
As a constituent found in coffee, 1-Phenyl-1,2-propanedione contributes to the overall flavor profile of the beverage, providing a creamy, dairy-like, and slightly astringent taste with a hint of spicy caraway/cumin nuance.
4. Used in Food Industry:
In the food industry, 1-Phenyl-1,2-propanedione is used as an additive to impart a rich, creamy, and slightly nutty flavor to various products, such as baked goods, snacks, and dairy products.
5. Used in Research and Development:
1-Phenyl-1,2-propanedione serves as a valuable compound for researchers in the field of organic chemistry, particularly in the study of alpha-diketone chemistry and its applications in various chemical reactions and processes.
Synthesis Reference(s)
The Journal of Organic Chemistry, 36, p. 3553, 1971 DOI: 10.1021/jo00822a019
Synthesis
By oxidation of propiophenone or benzyl methyl ketone with selenium dioxide; by the acid hydrolysis of oximonopropiophenone
or other synthetic routes.
Check Digit Verification of cas no
The CAS Registry Mumber 579-07-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,7 and 9 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 579-07:
(5*5)+(4*7)+(3*9)+(2*0)+(1*7)=87
87 % 10 = 7
So 579-07-7 is a valid CAS Registry Number.
InChI:InChI=1/C9H8O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6H,1H3
579-07-7Relevant articles and documents
Catalyst-Free and Transition-Metal-Free Approach to 1,2-Diketones via Aerobic Alkyne Oxidation
Shen, Duyi,Wang, Hongyan,Zheng, Yanan,Zhu, Xinjing,Gong, Peiwei,Wang, Bin,You, Jinmao,Zhao, Yulei,Chao, Mianran
, p. 5354 - 5361 (2021/05/05)
A catalyst-free and transition-metal-free method for the synthesis of 1,2-diketones from aerobic alkyne oxidation was reported. The oxidation of various internal alkynes, especially more challenging aryl-alkyl acetylenes, proceeded smoothly with inexpensive, easily handled, and commercially available potassium persulfate and an ambient air balloon, achieving the corresponding 1,2-diketones with up to 85% yields. Meanwhile, mechanistic studies indicated a radical process, and the two oxygen atoms in the 1,2-diketons were most likely from persulfate salts and molecular oxygen, respectively, rather than water.
Ozonolysis of Alkynes - A Flexible Route to Alpha-Diketones: Synthesis of AI-2
Alterman, Joshua L.,Halverson, Larry J.,Kraus, George A.,Stroud, Marissa Roghair,Vang, Dua X.
supporting information, p. 7424 - 7426 (2020/10/05)
A mild procedure for the low-temperature conversion of alkynes to diketones has been developed and employed in the synthesis of AI-2.
Copper(I)-catalyzed aerobic oxidation of α-diazoesters
Xu, Changming,Bai, Lei,Wang, Yongchang
, p. 12579 - 12584 (2020/11/09)
A practical Cu-catalyzed oxidation of α-diazoesters to α-ketoesters using molecular oxygen as an oxidant has been developed. Both electron-poor and electron-rich aryl α-diazoesters are suitable substrates and provide the α-ketoesters in good yields. In this oxidative system, α-diazo-β-ketoesters are also compatible as substrates but unexpectedly furnish α-ketoesters via C-C bond cleavage, rather than the vicinal tricarbonyl products.