35241-55-5

Usage

Uses

Used in Pharmaceutical Industry:
1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropan-1-one is used as a pharmaceutical compound for its potential therapeutic properties. 1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropan-1-one's unique structure allows it to interact with various biological targets, making it a promising candidate for the development of new drugs. Its hydroxy and methoxy groups enable it to form hydrogen bonds and other interactions with proteins and other macromolecules, which can be exploited for targeted drug delivery and enhanced bioavailability.
Used in Cosmetic Industry:
In the cosmetic industry, 1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropan-1-one is used as an active ingredient for its antioxidant and anti-inflammatory properties. Its ability to scavenge free radicals and reduce inflammation can help protect the skin from environmental stressors and promote a healthier, more youthful appearance. Additionally, its potential to modulate cellular signaling pathways may contribute to anti-aging effects and improved skin health.
Used in Food Industry:
1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropan-1-one can be utilized in the food industry as a natural additive due to its antioxidant properties. It can help extend the shelf life of perishable products by neutralizing harmful free radicals and preventing oxidation, which can lead to spoilage and degradation of food quality. Furthermore, its potential health benefits may add value to functional foods and beverages, contributing to a growing market for health-conscious consumers.
Used in Agricultural Industry:
In agriculture, 1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropan-1-one may be employed as a natural pesticide or growth regulator. Its ability to modulate cellular signaling pathways could potentially be harnessed to control the growth of unwanted plants or deter pests, reducing the need for synthetic chemicals and promoting more sustainable agricultural practices.
Overall, 1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropan-1-one is a versatile compound with a wide range of potential applications across various industries. Its unique structure and biological activities make it an attractive candidate for further research and development, with the potential to contribute to advancements in healthcare, cosmetics, food preservation, and sustainable agriculture.

InChI:InChI=1/C16H16O4/c1-20-12-9-14(18)16(15(19)10-12)13(17)8-7-11-5-3-2-4-6-11/h2-6,9-10,18-19H,7-8H2,1H3

Upstream product

• 75291-74-6 pinostrobin 
• 77-78-1 dimethyl sulfate 
• 520-28-5 tectochrysine 
• 21392-57-4 Dimethyl-chrysin 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 77129-49-8 1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenyl-2-propen-1-one 
• 2174-64-3 5-methoxyresorcinol 
• 645-45-4 hydrocinnamic acid chloride 
• 501-52-0 3-Phenylpropionic acid 
• 108-73-6 3,5-dihydroxyphenol 

Downstream Products

• 2174-64-3 5-methoxyresorcinol 
• 501-52-0 3-Phenylpropionic acid 
• 108-73-6 3,5-dihydroxyphenol 
• 74-88-4 methyl iodide 
• 155023-56-6 piperaduncin C 
• 943896-07-9 (+)-hostmanin A 

Relevant academic research and scientific papers

Total syntheses of (+)-adunctins C and D: Assignment of their absolute configurations

The first total synthesis of (+)-adunctin C (ent-1) and (+)-adunctin D (2), two monoterpene-substitued dihydrochalcones isolated from Piper aduncum (Piperaceae), was achieved. A regioselective oxidative [3 + 2] cycloaddition of acylphloroglucinol with (-)-β-phellandrene was developed to construct their unique spirobenzofuran skeleton. The absolute configurations of natural adunctins 1 and 2 were thus assigned through these endeavors. This journal is

Chemical Modification of Pinostrobin and Tectochrysin

Results from chemical modification of the flavonoids pinostrobin and tectochrysin are reported. Atoms C-3, C-6, C-8, HO–, and CO– in these molecules were determined to be the reactive sites. Pinostrobin and tectochrysin are polyfunctional compounds that underwent aminomethylation, complexation, nucleophilic addition at the carbonyl, and electrophilic substitution to synthesize seven new compounds.

Preparation method of spirobenzofuran compounds

The invention discloses a preparation method of spirobenzofuran compounds. The method comprises the steps: taking commercially available phloroglucinol and 4-isopropyl cyclohexanone as raw materials;dihydrochalcone and beta-phellandrene with an extracyclic double bond are respectively synthesized through a Friedel-Crafts reaction and a Wittig reaction; after two fragment compounds of the hydrochalcone and the beta-phellandrene are obtained, with oxidized cycloaddition reactions, connecting the two fragment compounds, constructing a spirobenzofuran core skeleton, and thus preparing natural products adunctin C and adunctin D. According to the invention, an organic chemical synthesis means is adopted, synthesis of the target natural products adunctin C and adunctin D is used as guidance, anda new method for constructing the structural units is developed; meanwhile, the method is applied to synthesis and preparation of the natural products adunctin C and D with important physiological and pharmacological activities, the preparation yield is high, the cost is low, and the limitation of sources of the natural products is greatly broken through.

Total Synthesis of Adunctin B

Total synthesis of (±)-adunctin B, a natural product isolated from Piper aduncum (Piperaceae), has been achieved using two different strategies, in seven and three steps. The efficient approach features highly atom economical and diastereoselective Friedel-Crafts acylation, alkylation reaction and palladium catalyzed Wacker type oxidative cyclization.

Enantioselective Total Syntheses of (+)-Hostmanin A, (-)-Linderol A, (+)-Methyllinderatin and Structural Reassignment of Adunctin E

A one-step protocol has been developed for the enantioselective synthesis of hexahydrodibenzofuran derivatives using a modified Friedel-Crafts reaction. The developed method was applied to the synthesis of a series of natural products including (+)-hostmanin A, (+)-methyllinderatin, and (-)-linderol A. The synthetic and spectroscopic data investigations led to the structural reassignment of natural product adunctin E, which was further confirmed by single-crystal X-ray analysis. (Chemical Presented).

Facile formation of methylenebis(chalcone)s through unprecedented methylenation reaction. Application to antiparasitic and natural product synthesis

The formation of methylenebis(chalcone)s has been discovered during deprotection with methoxymethyl groups from trihydroxychalcones. Studies on this methylenation reaction led to a mechanism hypothesis that was extended to other chalcones and to dihydrochalcone, acetophenone, benzophenone and flavone derivatives. This new method was applied to the rapid synthesis of natural product piperanduncin C. These original methylenebis compounds were also evaluated for their antiparasitic activity. Copyright

Synthesis, structure-activity relationship analysis and kinetics study of reductive derivatives of flavonoids as Helicobacter pylori urease inhibitors

In a continuing study for discovering urease inhibitors based on flavonoids, nineteen reductive derivatives of flavonoids were synthesized and evaluated against Helicobacter pylori urease. Analysis of structure-activity relationship disclosed that 4-deoxy analogues are more potent than other reductive products. Out of them, 4′,7,8-trihydroxyl-2-isoflavene (13) was found to be the most active with IC50 of 0.85 μM, being over 20-fold more potent than the commercial available urease inhibitor, acetohydroxamic acid (AHA). Kinetics study revealed that 13 is a competitive inhibitor of H. pylori urease with a Ki value of 0.641 μM, which is well matched with the results of molecular docking. Biological evaluation and mechanism study of 13 suggest that it is a good candidate for discovering novel anti-gastritis and anti-gastric ulcer agent.

Cytotoxicity against KB and NCI-H187 cell lines of modified flavonoids from Kaempferia parviflora

Flavones 1-4 isolated from Kaempferia parviflora were used for structural modification. Sixteen flavonoid derivatives, including four new derivatives, were synthesized and evaluated for cytotoxicity against KB and NCI-H187 cell lines. Flavanones 2a-4a demonstrated higher cytotoxic activity than the parent compounds. Cytotoxicity against KB cell line of oxime 1c was about 7 times higher than the ellipticine standard. Interestingly, oximes 1c and 2c exhibited highly potent cytotoxicity against NCI-H187 cell line with IC50 values of 0.014 and 0.23 μM, respectively. Oximes 4c and 5c showed strong cytotoxicity against NCI-H187 cell line with IC50 values of 4.04 and 2.32 μM, respectively.

PHENYLPROPENE, BENZOIC ACID AND FLAVONOID DERIVATIVES FROM FRUITS OF JAMAICAN PIPER SPECIES

1-Allyl-2,3-(methylenedioxy)-4,5-dimethoxybenzene, 4-methoxy-3,5-bis(3'-methyl-2'-butenyl)-benzoic acid, and the known compounds 5-hydroxy-7-methoxyflavanone and 2,6-dihydroxy-4-methoxydihydrochalcone have been isolated from the fruits of Jamaican Piper aduncum and Piper hispidum. Key Word Index - Piper aduncum; P. hispidum; Piperaceae; fruits; pseudo-dillapiole; 4-methoxy-3,5-bis(3'-methyl-2'-butenyl)-benzoic acid; flavonoids.