23130-26-9

Usage

Uses

Used in Pharmaceutical Synthesis:
2',4'-DIHYDROXY-3-(P-HYDROXYPHENYL)-PROPIOPHENONE is used as an intermediate in the synthesis of pharmaceutical drugs. Its unique chemical structure allows it to be a key component in the development of new medications.
Used in Antioxidant Research:
2',4'-DIHYDROXY-3-(P-HYDROXYPHENYL)-PROPIOPHENONE is used as a subject of study for its potential antioxidant properties. Its ability to neutralize free radicals and protect cells from oxidative damage makes it a promising candidate for further research in this area.
Used in Neurotransmitter Metabolism Research:
2',4'-DIHYDROXY-3-(P-HYDROXYPHENYL)-PROPIOPHENONE is used as a subject of study for its potential ability to inhibit the enzyme monoamine oxidase, which plays a role in the metabolism of neurotransmitters in the brain. This research could lead to new treatments for neurological disorders.
Used in Skincare and Cosmetic Products:
2',4'-DIHYDROXY-3-(P-HYDROXYPHENYL)-PROPIOPHENONE is used as an ingredient in skincare and cosmetic products due to its antioxidant and anti-inflammatory properties. Its potential to protect and rejuvenate the skin makes it a valuable component in these products.

InChI:InChI=1/C15H14O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-2,4-7,9,16-17,19H,3,8H2

Upstream product

• 13745-20-5 2',4,4'-trihydroxychalcone 
• 21562-22-1 4'-β-O-D-glucopyranosyl-4,2',4'-trihydroxydihydrochalcone 
• 961-29-5 isoliquirtigenin 
• 123-08-0 4-hydroxy-benzaldehyde 
• 20034-62-2 2'-Hydroxy-4'-(aethoxy-methoxy)-acetophenon 
• 128837-26-3 4-(ethyloxymethoxy)benzaldehyde 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 108-46-3 recorcinol 

Downstream Products

• 224644-18-2 7-hydroxy-3-[(4-hydroxyphenyl)methyl]-4H-chromen-4-one 
• 23140-78-5 4,4'-dihydroxy-dihydrochalcone-2'-O-β-D-glucopyranoside 
• 21562-22-1 4'-β-O-D-glucopyranosyl-4,2',4'-trihydroxydihydrochalcone 
• 1093945-46-0 schoepfin A 

Relevant academic research and scientific papers

Antispasmodic and antioxidant activities of fractions and bioactive constituent davidigenin isolated from Mascarenhasia arborescens

Ethnopharmacological relevance: Mascarenhasia arborescens A. DC. (Apocynaceae) is used in traditional medicine in the North of Madagascar to treat intestinal disorders, intestinal spasms and diarrhoea. Aim of the study: The main objective of this work was

Chemical Constituents of Anneslea fragrans and Their Antiausterity Activity against the PANC-1 Human Pancreatic Cancer Cell Line

An ethanolic extract of Anneslea fragrans leaves showed potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells under a nutrient-deprived condition, with a PC50 value of 9.6 μg/mL. Phytochemical investigation of this active extract led to the isolation of two new secondary metabolites, fragranones A (1) and B (2), along with 15 previously reported compounds. The structure elucidation of the new compounds was achieved by HRFABMS, acid hydrolysis, NMR, and ECD spectroscopic analysis. Fragranone A (1) is the first example of a rare natural product bearing an acetonide glucose moiety. Fragranone B (2) is representative of a rare class of natural products with a threonolactone unit linked to a chalcone through an ether linkage. The isolated compounds exhibited antiausterity activity against PANC-1 cells under nutrient-deprived conditions, and betulin (14) was found to be the most potent compound tested, with a PC50 value of 8.4 μM. In addition, fragranone A (1) was found to suppress PANC-1 cancer cell migration in real time.

COMPOSITIONS AND METHODS OF TREATING UPS-ASSOCIATED DISEASES

The present invention relates to methods for treating a disease characterized by aberrations in the ubiquitin/proteasome system (UPS).

Chemoselective transfer hydrogenation of Α,Β-unsaturated carbonyls catalyzed by a reusable supported Pd nanoparticles on biomass-derived carbon

We herein report highly chemoselective transfer hydrogenation of α,β-unsaturated carbonyl compounds to saturated carbonyls with formic acid as a hydrogen donor over a stable and recyclable heterogeneous Pd nanoparticles (NPs) on N,O-dual doped hierarchical porous biomass-derived carbon. The synergistic effect between Pd NPs and incorporated heteroatoms on carbon plays a critical role on promoting the reaction efficiency. A series of α,β-aromatic and aliphatic unsaturated carbonyl compounds was selectively reduced to their corresponding saturated carbonyls in up to 97% isolated yields with good tolerance of various functional groups. In addition, the catalyst can be successively reused for at least 6 times without significant loss in reaction efficiency.

Chemoselective Hydrogenation of α,β-Unsaturated Carbonyls Catalyzed by Biomass-Derived Cobalt Nanoparticles in Water

Herein, we report highly chemoselective hydrogenation of α,β-unsaturated carbonyls to saturated carbonyls catalyzed by cobalt nanoparticles supported on the biomass-derived carbon from bamboo shoots with molecular hydrogen in water, which is the first prototype using a heterogeneous non-noble metal catalyst for such organic transformation as far as we know. The optimal cobalt nanocatalyst, CoOx@NC-800, manifested remarkable activity and selectivity for hydrogenation of C=C in α,β-unsaturated carbonyls under mild conditions. A broad set of α,β-aromatic and aliphatic unsaturated carbonyls were selectively reduced to their corresponding saturated carbonyls in up to 99 % yields with good tolerance of various functional groups. Meanwhile, a new straightforward one-pot cascade synthesis of saturated carbonyls was realized with high activity and selectivity via the cross-aldol condensation of ketones with aldehydes followed by selective hydrogenation. More importantly, this one-pot strategy is applicable for the expedient synthesis of Loureirin A, a versatile bioactive and medicinal molecule, from readily available starting materials, further highlighting the practical utility of the catalyst. In addition, the catalyst can be easily separated for successive reuses without significant loss in both activity and selectivity.

Anti-aging agent and for preventing aging of the skin (by machine translation)

PROBLEM TO BE SOLVED: To provide a fibroblast proliferation promoter, an MMP-1(matrix metalloprotease-1) activity inhibitor, an elastase activity inhibitor, a profilaggrin production-promoting activity, a filaggrin production promoter or an antiaging agent, based on having found a substance as an active ingredient for the agents, which has excellent fibroblast proliferation-promoting effect, MMP-1 activity inhibitory effect, elastase activity inhibitory effect, profilaggrin production-promoting effect, filaggrin production-promoting effect or antiaging effect.SOLUTION: The fibroblast proliferation promoter, the MMP-1(matrix metalloprotease-1) activity inhibitor, the elastase activity inhibitor, the profilaggrin production promoter, the filaggrin production promoter or the antiaging agent are each included with davidigenin as the active ingredient for the respective agents. Also, a skin care preparation for external use for antiaging is compounded with davidigenin.

Synthesis and detailed spectroscopic characterization of various hydroxy-functionalized fluorescent chalcones: A combined experimental and theoretical study

Abstract Four different bright yellow to orange hydroxy-substituted chalcones (i.e., 2′,4-di-hydroxy (1), 2′,3′,4-trihydroxy (2), 2′,3′,4′-trihydroxy (3), and 2′-hydroxy-4-methoxy (4) chalcones) were synthesized and characterized by LC-MS, FT-IR, FT-Raman

Towards the synthesis of glycosylated dihydrochalcone natural products using glycosyltransferase-catalysed cascade reactions

Regioselective O-β-D-glucosylation of flavonoid core structures is used in plants to create diverse natural products. Their prospective application as functional food and pharmaceutical ingredients makes flavonoid glucosides interesting targets for chemical synthesis, but selective instalment of a glucosyl group requires elaborate synthetic procedures. We report glycosyltransferase-catalysed cascade reactions for single-step highly efficient O-β-D-glucosylation of two major dihydrochalcones (phloretin, davidigenin) and demonstrate their use for the preparation of phlorizin (phloretin 2′-O-β-d-glucoside) and two first-time synthesised natural products, davidioside and confusoside, obtained through selective 2′- and 4′-O-β-d-glucosylation of the dihydroxyphenyl moiety in davidigenin, respectively. Parallel biocatalytic cascades were established by coupling uridine 5′-diphosphate (UDP)-glucose dependent synthetic glucosylations catalysed by herein identified dedicated O-glycosyltransferases (OGTs) to UDP dependent conversion of sucrose by sucrose synthase (SuSy; from soybean). The SuSy reaction served not only to regenerate the UDP-glucose donor substrate for OGT (up to 9 times), but also to overcome thermodynamic restrictions on dihydrochalcone β-d-glucoside formation (up to 20% conversion and yield enhancement). Using conditions optimised for overall coupled enzyme activity, target 2′-O- or 4′-O-β-d-glucoside was obtained in ≥88% yield from reactions consisting of 5 mM dihydrochalcone acceptor, 100 mM sucrose, and 0.5 mM UDP. Davidioside and confusoside were isolated and their proposed chemical structures confirmed by NMR. OGT-SuSy cascade transformations present a green chemistry approach for efficient glucosylation in natural products synthesis. the Partner Organisations 2014.

Synthesis and insight into the structure-activity relationships of chalcones as antimalarial agents

Licochalcone A (I), isolated from the roots of Chinese licorice, is the most promising antimalarial compound reported so far. In continuation of our drug discovery program, we isolated two similar chalcones, medicagenin (II) and munchiwarin (III), from Crotalaria medicagenia, which exhibited antimalarial activity against Plasmodium falciparum. A library of 88 chalcones were synthesized and evaluated for their in vitro antimalarial activity. Among these, 67, 68, 74, 77, and 78 exhibited good in vitro antimalarial activity against P. falciparum strains 3D7 and K1 with low cytotoxicity. These chalcones also showed reduction in parasitemia and increased survival time of Swiss mice infected with Plasmodium yoelii (strain N-67). Pharmacokinetic studies indicated that low oral bioavailability due to poor ADME properties. Molecular docking studies revealed the binding orientation of these inhibitors in active sites of falcipain-2 (FP-2) enzyme. Compounds 67, 68, and 78 showed modest inhibitory activity against the major hemoglobin degrading cysteine protease FP-2.

AROMA COMPOSITIONS OF ALKAMIDES WITH HESPERETIN AND/OR 4-HYDROXYDIHYDROCHALCONES AND SALTS THEREOF FOR ENHANCING SWEET SENSORY IMPRESSIONS

The invention primarily relates to aroma compositions of (i) certain saliva-stimulating alkamides having a tingling, pungent and/or hot flavor (such as for example pellitorines, spilanthol) with (ii) hesperetin (5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-chroman-4-one) or the enantiomers and/or salts thereof and/or (iii) 4-hydroxydihydrochalcones (3-(4-hydroxyphenyl)-1-phenylpropan-1-ones) and/or the salts thereof, the use thereof to enhance the sweet flavor of sweet-tasting substances or the sweet odor impression of aroma substances which give rise to a sweet odor impression, but in particular to enhance the sweet initial flavor or odor (initial sweetness). The invention thus relates to the use of said aroma compositions as general sweetness enhancers and enhancers of initial sweetness. The invention further relates to certain preparations which contain an effective amount of said aroma compositions of (i) alkamides (such as in particular pellitorines, spilanthol) with (ii) hesperetin or the enantiomers and/or salts thereof and/or (iii) 4-hydroxydihydrochalcones and/or the salts thereof and methods for enhancing the sweet flavor or initial sweetness of a sweet-tasting substance or the sweet odor impression or initial sweetness of an aroma substance which gives rise to a sweet odor impression. The invention also relates to the use of certain alkamides (i) to enhance the initial sweetness of a preparation comprising (ii) hesperetin or the enantiomers and/or salts thereof and/or (iii) 4-hydroxydihydrochalcones and/or the salts thereof and (b) sweet-tasting substances and/or (c) aroma substances which give rise to a sweet odor impression.