182219-43-8

Basic information

• Product Name: 4-(4’-Hydroxyphenyl)-2-butanone-d5
• Synonyms: 4-(4’-Hydroxyphenyl)-2-butanone-d5;4-(4’-Hydroxyphenyl)-
• CAS NO: 182219-43-8
• Molecular Formula: C10H12O2
• Molecular Weight: 164.20108
• Product Categories: Aromatics;Isotope Labelled Compounds;Aromatics, Isotope Labelled Compounds
• Mol File: 182219-43-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 4-(4’-Hydroxyphenyl)-2-butanone-d5(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4’-Hydroxyphenyl)-2-butanone-d5(182219-43-8)
• EPA Substance Registry System: 4-(4’-Hydroxyphenyl)-2-butanone-d5(182219-43-8)

Safety Data

• Hazardous Substances Data: 182219-43-8(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
4-(4’-Hydroxyphenyl)-2-butanone-d5 is used as a flavoring agent for its natural raspberry aroma, enhancing the taste and smell of food products.
Used in Perfumery:
4-(4’-Hydroxyphenyl)-2-butanone-d5 is used as a fixative in perfume compositions, helping to stabilize and prolong the scent of fragrances.
Used in Cosmetics:
4-(4’-Hydroxyphenyl)-2-butanone-d5 is used as a fragrance ingredient in shampoos, lotions, and other personal care products, providing a pleasant scent and enhancing the overall sensory experience.
Used in Food Industry:
4-(4’-Hydroxyphenyl)-2-butanone-d5 is used as a food additive, imparting a raspberry flavor to various food items such as candies, beverages, and baked goods.
Chemical Properties:
4-(4’-Hydroxyphenyl)-2-butanone-d5 is a white solid with a molecular structure that includes deuterium atoms, which may provide unique properties compared to its non-deuterated counterpart. Its chemical stability and reactivity can be influenced by the presence of these deuterium atoms, making it suitable for specific applications in research and development.

Upstream product

• 5471-51-2 4-(4-hydroxyphenyl)-2-oxobutane 

Relevant articles and documents

Biogeneration and Biodegradation of Raspberry Ketone in the Fungus Beauveria bassiana

In growing cultures of the fungus Beauveria bassiana (ATCC 7159) the incubation of 4-(4′-hydroxyphenyl)but-3-en-2-one (p-hydroxybenzylidenacetone, 3), of 4-(4′-hydroxyphenyl)butan-2-one (raspberry ketone, 1), and of the S and R,S forms of 4-(4′-hydroxyphenyl)butan-2-ol (2) yields 2-(4′-hydroxyphenyl)ethanol (tyrosol, 4) as a final product. The experiments support the view that the actual substrate for the Baeyer-Villiger-type degradation is raspberry ketone (1) and that there is a kinetic preference in the microbial enzymatic system for the oxidation to 1 of the S form of the 4-(4′-hydroxyphenyl)butan-2-ol (2).

An algorithm for the deconvolution of mass spectrosopic patterns in isotope labeling studies. Evaluation for the hydrogen-deuterium exchange reaction in ketones

(Graph Presented) An easy to use computerized algorithm for the determination of the amount of each labeled species differing in the number of incorporated isotope labels based on mass spectroscopic data is described and evaluated. Employing this algorithm, the microwave-assisted synthesis of various α-labeled deuterium ketones via hydrogen-deuterium exchange with deuterium oxide was optimized with respect to time, temperature, and degree of labeling. For thermally stable ketones the exchange of α-protons was achieved at 180°C within 40-200 min. Compared to reflux conditions, the microwave-assisted protocol led to a reduction of the required reaction time from 75-94 h to 40-200 min. The α-labeled deuterium ketones were reduced by biocatalytic hydrogen transfer to the corresponding enantiopure chiral alcohols and the deconvolution algorithm validated by regression analysis of a mixture of labeled and unlabeled ketones/alcohols.

Stereochemistry of the Baeyer-Villiger-type conversion of 4-(4-hydroxyphenyl)butan-2-one (raspberry ketone) into tyrosol mediated by Beauveria bassiana

Feeding experiments in Beauveria bassiana (ATCC 7159) of (2R,3S)-[2,3-2H2]-4-(4-hydroxyphenyl)butan-2-ol (15) and (2R,3R)-[1,3-2H4]-4-(4-hydroxyphenyl)-butan-2-ol (16) afford (1S)- and (1R)-[1-2H]tyrosol (17) and (18), respectively, as indicated by NMR studies on the (+)-MTPA esters 21 and 23 and comparison with an authentic sample of the (S) enantiomer. These results indicate that the C-2, Baeyer-Villiger-type, chain shortening of the C-6-C-4 framework of the intermediate rashberry ketone 1 to give the C-6-C-2 tyrosol (4) occurs with retention of configuration. The asymmetrically labeled substrates 15 and 16 have been obtained by enzymic resolution of derivatives of (2SR,3RS)-6 and (2SR,3SR)-12, pared, in turn, by syn catalytic reduction with deuterium and with hydrogen gas, respectively, of the (Z) enol acetates 5 and 11.