55418-52-5

Usage

Uses

Used in Flavor and Fragrance Industry:
Piperonyl acetone is used as a flavoring agent for its intensely sweet, floral, and slightly woody odor. It is particularly suitable for enhancing the taste and aroma of various food products, beverages, and confectioneries.
Used in Perfumery:
In the perfumery industry, Piperonyl acetone is used as a fixative and fragrance ingredient. Its sweet, floral, and woody scent adds depth and complexity to perfume compositions, making it a valuable addition to the perfumer's palette.
Used in Insecticide Synergists:
Piperonyl acetone is also used as an insecticide synergist, which helps to enhance the effectiveness of certain insecticides by inhibiting the insects' ability to metabolize the chemicals. This application is particularly useful in agriculture and pest control, where it can help reduce the amount of insecticides needed and minimize the environmental impact.
Used in Pharmaceutical Industry:
Due to its unique chemical properties and intense sweet odor, Piperonyl acetone may also find applications in the pharmaceutical industry, potentially as a component in the development of new drugs or as a flavoring agent for medications that require a pleasant taste.

Preparation

By condensation of heliotropin with acetone, followed by hydrogenation in the presence of a palladium catalyst

Metabolism

The oxygen-aromatic carbon link of aromatic ethers is generally biologically stable, and possible metabolites include the p-hydroxy derivative of the ether, the phenol or the p-hydroxyphenol (Williams, 1959). Ketones are not readily metabolized in the body. As a derivative of 2-butanone, piperonyl acetone might be expected to be partially reduced to the secondary alcohol and excreted as the glucuronide (Williams, 1959), since Saneyoshi (1911) isolated the glucuronide of 2-butanol from the urine of rabbits receiving methyl ethyl ketone.

InChI:InChI=1/C21H30FN3O2.C3H6O/c22-18-8-6-17(7-9-18)19(26)5-4-12-24-15-10-21(11-16-24,20(23)27)25-13-2-1-3-14-25;1-3(2)4/h6-9H,1-5,10-16H2,(H2,23,27);1-2H3

Upstream product

• 3160-37-0 4-(benzo[d][1,3]dioxol-5-yl)but-3-en-2-one 
• 22214-31-9 (E)-4-(benzo[d][1,3]dioxol-5-yl)but-3-en-2-one 
• 17975-66-5 (Z)-4-(benzo[d][1,3]dioxol-5-ylmethylene)-3-methylisoxazol-5(4H)-one 
• 62518-51-8 4-(6-Iodo-benzo[1,3]dioxol-5-yl)-butan-2-one 
• 78-94-4 methyl vinyl ketone 
• 109586-40-5 1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate 
• 141-78-6 ethyl acetate 
• 7664-93-9 sulfuric acid 
• 64-17-5 ethanol 
• 186581-53-3 diazomethane 
• 120-57-0 piperonal 
• 60-29-7 diethyl ether 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 495-76-1 piperonol 

Downstream Products

• 108248-08-4 (3-benzo[1,3]dioxol-5-yl-1-methyl-propyl)-methyl-amine 
• 53581-95-6 (E)-4-(3,4-methylenedioxyphenyl)butan-2-one oxime 
• 56290-93-8 methyl 5-<2-<<3-(1,3-benzodioxol-5-yl)-1-methylpropyl>amino>-1-hydroxyethyl>-2-hydroxybenzoate 
• 1155868-94-2 N-[4-(2H-1,3-benzodioxol-5-yl)butan-2-yl]-4-methoxyaniline 
• 1155868-98-6 N-[4-(2H-1,3-benzodioxol-5-yl)butan-2-yl]aniline 
• 1374002-62-6 N-(4-(benzo[d][1,3]dioxol-5-yl)butan-2-yl)-4-bromoaniline 
• 40742-32-3 α-methyl-1,3-benzodioxole-5-propanamine 
• 1021105-18-9 N-(4-(benzo[d][1,3]dioxol-5-yl)butan-2-yl)-4-methoxyaniline 
• 1258964-70-3 N-methyl-N-phenyl-N,α-methyl-1,3-benzodioxole-5-propanamine 
• 1036547-57-5 N-(4-(benzo[d][1,3]dioxol-5-yl)butan-2-yl)-4-bromoaniline 
• 375395-24-7 2-(2-(benzo[d][1,3]-dioxol-5-yl)ethyl)-1,2,3,4-tetrahydroquinoline 
• 608525-33-3 (R)-2-( 3’,4’methylenedioxyphenethyl)-1,2,3,4-tetrahydroquinoline 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 608525-33-3 (S)-2-[2-(3,4-methylenedioxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

Methanol as hydrogen source: Chemoselective transfer hydrogenation of α,β-unsaturated ketones with a rhodacycle

Methanol is a safe, economic and easy-to-handle hydrogen source. It has rarely been used in transfer hydrogenation reactions, however. We herein report that a cyclometalated rhodium complex, rhodacycle, catalyzes highly chemoselective hydrogenation of α,β-unsaturated ketones with methanol as the hydrogen source. A wide variety of chalcones, styryl methyl ketones and vinyl methyl ketones, including sterically demanding ones, were reduced to the saturated ketones in refluxing methanol in a short reaction time, with no need for inter gas protection, and no reduction of the carbonyl moieties was observed. The catalysis described provides a practically easy and operationally safe method for the reduction of olefinic bonds in α,β-unsaturated ketone compounds.

Organic photocatalysis for the radical couplings of boronic acid derivatives in batch and flow

We report an acridium-based organic photocatalyst as an efficient replacement for iridium-based photocatalysts to oxidise boronic acid derivatives by a single electron process. Furthermore, we applied the developed catalytic system to the synthesis of four active pharmaceutical ingredients (APIs). A straightforward scale up approach using continuous flow photoreactors is also reported affording gram an hour throughput.

Simple Synthesis of Phytochemicals by Heterogeneous Pd- and Ir-Catalyzed Hydrogen-Borrowing C–C Bond Formation

Chitin-supported palladium and iridium catalysts (i.e., Pd/chitin, Ir/chitin) successfully promote the hydrogen borrowing C–C bond formation reaction to afford phytochemicals and aroma compounds in excellent yields.

A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters

We report herein the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin-3-ol or 4-dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters. This system enabled a wide range of alkyl boronic esters and aryl or alkyl boronic acids to react with electron-deficient olefins via radical addition to efficiently form C?C coupled products in a redox-neutral fashion. The Lewis base catalyst was shown to form a redox-active complex with either the boronic esters or the trimeric form of the boronic acids (boroxines) in solution.

Novel diarylheptanoids as inhibitors of TNF-α production

Synthesis and anti-inflammatory activity of novel diarylheptanoids [5-hydroxy-1-phenyl-7-(pyridin-3-yl)-heptan-3-ones and 1-phenyl-7-(pyridin-3-yl) hept-4-en-3-ones] as inhibitors of tumor necrosis factor-α (TNF-α) production is described in the present article. The key reactions involve the formation of a β-hydroxyketone by the reaction of substituted 4-phenyl butan-2-ones with pyridine-3-carboxaldehyde in presence of LDA and the subsequent dehydration of the same to obtain the α,β-unsaturated ketones. Compounds 4i, 5b, 5d, and 5g significantly inhibit lipopolysaccharide (LPS)-induced TNF-α production from human peripheral blood mononuclear cells in a dose-dependent manner. Of note, the in vitro TNF-α inhibition potential of 5b and 5d is comparable to that of curcumin (a naturally occurring diarylheptanoid). Most importantly, oral administration of 4i, 5b, 5d, and 5g (each at 100 mg/kg) but not curcumin (at 100 mg/kg) significantly inhibits LPS-induced TNF-α production in BALB/c mice. Collectively, our findings indicate that these compounds may have potential therapeutic implications for TNF-α-mediated auto-immune/inflammatory disorders.

Compounds having protected hydroxy groups

The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.

Compounds having protected hydroxy groups

The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.

Precursors for fragrant ketones and fragrant aldehydes

The present invention refers to fragrance precursors of formula I for a fragrant ketone of formula II and one or more fragrant aldehydes or ketones of formula III and IV, These fragrance precursors are useful in perfumery, especially in the fine and functional perfumery.

Beta-ketoester compounds

The beta-ketoesters of formula I are useful as precursors for organoleptic compounds, especially for flavors, fragrances and masking agents and antimicrobial compounds.

Selectivity in palladium catalyzed arylation: Synthetic application leading to aromatized ionone natural products

The selectivity in aromatic substitution vs conjugate addition during palladium catalyzed reactions has been controlled simply by changing the base. These reaction conditions have been applied to the syntheses of aromatized β-ionone natural products 1 and its dihydroderivatives 7.