55418-52-5 Usage
Description
Piperonyl acetone, also known as 4-(3,4-Methylenedioxyphenyl)-2-butanone, is a synthetic compound with an intensely sweet, floral, and slightly woody odor. It is reminiscent of raspberry, cotton candy, and has a cassie and heliotrope association. Piperonyl acetone is prepared by condensation of heliotropin with acetone, followed by hydrogenation in the presence of a palladium catalyst. It has not been reported to occur naturally and has a distinct taste threshold value with sweet, berry-like, and spicy, jamy nuances at 40 ppm.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 55418-52-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,5,4,1 and 8 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 55418-52:
(7*5)+(6*5)+(5*4)+(4*1)+(3*8)+(2*5)+(1*2)=125
125 % 10 = 5
So 55418-52-5 is a valid CAS Registry Number.
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
55418-52-5Relevant articles and documents
Methanol as hydrogen source: Chemoselective transfer hydrogenation of α,β-unsaturated ketones with a rhodacycle
Aboo, Ahmed H.,Begum, Robina,Zhao, Liangliang,Farooqi, Zahoor H.,Xiao, Jianliang
, p. 1795 - 1799 (2019/11/11)
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.
Simple Synthesis of Phytochemicals by Heterogeneous Pd- and Ir-Catalyzed Hydrogen-Borrowing C–C Bond Formation
Hori, Yoji,Suruga, Chiharu,Akabayashi, Yuta,Ishikawa, Tomoka,Saito, Marina,Myoda, Takao,Toeda, Kazuki,Maeda, Yuna,Yoshida, Yutaka
supporting information, p. 7295 - 7299 (2018/01/02)
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.
Novel diarylheptanoids as inhibitors of TNF-α production
Dhuru, Sameer,Bhedi, Dilip,Gophane, Dnyaneshwar,Hirbhagat, Kiran,Nadar, Vijaya,More, Dattatray,Parikh, Sapna,Dalal, Roda,Fonseca, Lyle C.,Kharas, Firuza,Vadnal, Prashant Y.,Vishwakarma, Ram A.,Sivaramakrishnan
, p. 3784 - 3787 (2011/07/31)
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.