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4-(4-Hy-droxy-phen-yl)butan-2-one. (PDF Download …

4-(4-hydroxyphenyl)butan-2-one - chemical information, properties, structures, articles, patents and more chemical data.

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CAS No. 61844-32-4, 4-(2-hydroxyphenyl)butan-2-one …

Submerged cells of the basidiomycete Nidula niveo-tomentosa, a microbial producer of 4-(4-hydroxyphenyl)-butan-2-one, were supplemented with 13C-labeled -phenylalanines and with [1-13C]glucose. Labeled transformation products were detected by a novel method of analyzing stable isotope-labeled metabolites, gas chromatography (GC) coupled to an atomic emission detector, and by GC-mass spectrometry. A benzoate moiety was side chain elongated according to the poly-β-keto scheme. The presence of an acetyl coenzyme A-carboxylase inhibitor shifted the spectrum of products to benzyl compounds. Hence, the fungal pathway differs from the one established for plant tissues.

61844-32-4| Product 4-(2-hydroxyphenyl)butan-2-one} is NOT available for now

Raspberry ketone is a natural phenolic compound that is the primary aroma compound of red raspberries. The smell of raspberries is due to lots of molecules, but raspberry ketone is the "impact molecule",230 volatile compounds, associated with their particular smell. It also called Frambinone is evidently derived from framboise, the French word for raspberry. name is 4-(4-hydroxyphenyl)butan-2-one. Raspberry ketone occurs in a variety of fruits including raspberries, cranberries and blackberries. It is biosynthesized from coumaroyl-CoA. Extraction of pure raspberry ketone. Raspberry ketone is used in perfumery, in cosmetics, and as a food additive to impart a fruity odor. It is one of the most expensive natural flavor components used in the food industry.

4-(4-hydroxyphenyl)butan-2-one: Traditional Name: ..

The 4-(4-Hydroxyphenylbutan)-2-one,is ..

It can be made in the laboratory by more than one route. One convenient two-step synthesis involves, first, the crossed-aldol condensation of 4-hydroxybenzaldehyde with propanone, forming (4-(4'-hydroxyphenyl)-3-buten-2-one). This double-bond in the side-chain can then be catalytically hydrogenated forming rheosmin.

Another method that has been described involves a Friedel-Crafts alkylation of phenol by 4-hydroxybutan-2-one, using a cation-exchanged montmorillonite catalyst

Since the natural abundance of raspberry ketone is very low, it is prepared industrially by a variety of methods from chemical intermediates. One of the ways this can be done is through a crossed aldol-catalytic hydrogenation. In acetone and sodium hydroxide, 4-hydroxybenzaldehyde can form the α,β-unsaturated ketone. The ,is synthesized from p-coumaryl-coenzyme A and malonyl-coenzyme A in a two-step reaction sequence that is catalyzed by benzalacetone synthase and benzalacetone reductase.

SYNTHESIS EXAMPLE 4 Synthesis of 3-[6(S)-2,2,6 ..

It can be made in the laboratory by more than one route. One convenient two-step synthesis involves, first, the crossed-aldol condensation of 4-hydroxybenzaldehyde with propanone, forming (4-(4'-hydroxyphenyl)-3-buten-2-one). This double-bond in the side-chain can then be catalytically hydrogenated forming it.
Another method that has been described involves a Friedel-Crafts alkylation of phenol by 4-hydroxybutan-2-one, using a cation-exchanged montmorillonite catalyst

Free or glycosidically bound 4-(4-hydroxyphenyl)-butan-2-one (p-HPB) has been found in numerous plant genera, such as Artemisia, Capparis, Dendrobium, Hippophae, Larix, Limonium, Pinus, Prunus, Rheum, Rubus, Saxifraga, Taxus, Vaccinium, Vanilla, and Vitis, and in the glands of the melon fly, Dacus cucurbitae, and of the North American beaver, Castor canadensis (, , , , , , ). Surface cultures of the basidiomycete Nidula niveo-tomentosa were reported as another source as early as 1980 ().

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  • alkylation of phenol by 4-hydroxybutan-2-one, ..

    (4-(4-hydroxyphenyl)butan-2-one ..

  • Biosynthesis of p-hydroxyphenylbutan-2-one in …

    p-hydroxyphenylbutan-2-one, 2-[2-(4-methyl ..

  • decatone, p-hydroxyphenylbutan-2-one, 2-[2-(4 ..

    Sciencemadness Discussion Board » Fundamentals » Organic Chemistry » Synthesis of 4 ..

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Synthesis of 4-hydroxybenzaldehyde from ..

Raspberry ketone is a natural phenolic compoundred raspberries. p-Hydroxyphenylbutan-2-one, the characteristic aroma compound of raspberries (Rubus idaeus L.), is synthesized from p-coumaryl-coenzyme A and malonyl-coenzyme A in a two-step reaction sequence that is catalyzed by benzalacetone synthase and benzalacetone reductase (W. Borejsza-Wysocki and G. Hrazdina [1994] Phytochemistry 35: 623-628). Benzalacetone synthase condenses one malonate with p-coumarate to form the pathway intermediate p-hydroxyphenylbut-3-ene-2-one (p-hydroxybenzalacetone) in a reaction that is similar to those catalyzed by chalcone and stilbene synthases. We have obtained an enzyme preparation from ripe raspberries that was preferentially enriched in benzalacetone synthase (approximately 170-fold) over chalcone synthase (approximately 14-fold) activity. This preparation was used to characterize benzalacetone synthase and to develop polyclonal antibodies in rabbits. Benzalacetone synthase showed similarity in its molecular properties to chalcone synthase but differed distinctly in its substrate specificity, response to 2-mercaptoethanol and ethylene glycol, and induction in cell-suspension cultures. The product of the enzyme, p-hydroxybenzalacetone, inhibited mycelial growth of the raspberry pathogen Phytophthora fragariae var rubi at 250 [mu]M. We do not know whether the dual activity in the benzalacetone synthase preparation is the result of a bifunctional enzyme or is caused by contamination with chalcone synthase that was also present. The rapid induction of the enzyme in cell-suspension cultures upon addition of yeast extract and the toxicity of its product, p-hydroxybenzalacetone, to phytopathogenic fungi also suggest that the pathway may be part of a plant defense response.)

p-Hydroxyphenylbutan-2-one (pHPB), the raspberry ketone, ..

The presence of labeled 4-(4-hydroxyphenyl)-3-buten-2-one is consistent with the general route of polyketide synthesis: reduction of the β-keto function followed by elimination of water would yield just this intermediate. Hydrogenation of the α,β double bond concludes the sequence, delivering a saturated hydrocarbon chain.

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The studies feeding labeled and nonlabeled precursor substrates suggest the fungal provision of a benzyl starter which is then side chain elongated by a twofold condensation to form compounds possessing a phenylbutanoid skeleton, with -glucose acting as an efficient malonyl donor (Fig. ). As was presumed previously (), this pathway is obviously different from the one well established previously for raspberry (, , ) and rhubarb (), where phenylbutanoids were formed via one-step decarboxylative condensation of 4-coumaryl-CoA with malonyl-CoA. While benzalacetone synthase from rhubarb was cloned and sequenced, the respective fungal enzyme was not reported yet. The reductive decarboxylation of a phenylpentanoic moiety with accumulation of phenylbutanoids is a singular step in microbial biochemistry, and no microorganism besides N. niveo-tomentosa is known to be capable of this reaction. The formation of phenylbutanoid compounds may be explained by a premature release of intermediates from a polyketide synthase complex incapable of regularly handling longer-chain intermediates. This deficiency, however, becomes easily observable only in the presence of a large supply of exogenous benzyl precursor leading to pathway overflow: in the absence of added precursor, the total concentration of phenylbutanoids in a submerged culture in standard nutrient medium without complex ingredients is only in the range of 2 to 3 mg/liter (12 days of cultivation).

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