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(2E)-3-(3-hydroxyphenyl)-1-phenylprop-2-en-1-one, commonly known as chalcone, is a naturally occurring flavonoid found in plants such as licorice, Anogeissus leiocarpa, and the seed coat of soybeans. It is characterized by its yellow color and is widely used in the pharmaceutical and cosmetic industries. Chalcone has been studied for its potential antioxidant, anti-inflammatory, and anticancer properties, and has shown promise in inhibiting the growth of certain cancer cell lines. Additionally, it has been investigated for its potential in the treatment of various other diseases, including diabetes, cardiovascular diseases, and Alzheimer's disease. Chalcone is also used as a precursor in the synthesis of numerous natural and synthetic compounds with diverse biological activities.

81226-95-1

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81226-95-1 Usage

Uses

Used in Pharmaceutical Industry:
(2E)-3-(3-hydroxyphenyl)-1-phenylprop-2-en-1-one is used as a pharmaceutical compound for its potential antioxidant, anti-inflammatory, and anticancer properties. It has shown promise in inhibiting the growth of certain cancer cell lines and has been investigated for its potential in the treatment of various other diseases, including diabetes, cardiovascular diseases, and Alzheimer's disease.
Used in Cosmetic Industry:
(2E)-3-(3-hydroxyphenyl)-1-phenylprop-2-en-1-one is used as a cosmetic ingredient for its yellow color and potential antioxidant properties, which can help protect the skin from oxidative stress and damage.
Used in Synthesis of Natural and Synthetic Compounds:
(2E)-3-(3-hydroxyphenyl)-1-phenylprop-2-en-1-one is used as a precursor in the synthesis of numerous natural and synthetic compounds with diverse biological activities, contributing to the development of new drugs and therapeutic agents.

Check Digit Verification of cas no

The CAS Registry Mumber 81226-95-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,1,2,2 and 6 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 81226-95:
(7*8)+(6*1)+(5*2)+(4*2)+(3*6)+(2*9)+(1*5)=121
121 % 10 = 1
So 81226-95-1 is a valid CAS Registry Number.

81226-95-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (E)-3-(3-hydroxyphenyl)-1-phenylprop-2-en-1-one

1.2 Other means of identification

Product number -
Other names 3-Hydroxychalcone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:81226-95-1 SDS

81226-95-1Relevant academic research and scientific papers

Synthesis and Antimicrobial Evaluations of New 5-aryl Linked Bispyrazolines

Yusuf, Mohamad,Kaur, Manvinder

, p. 735 - 742 (2017)

Syntheses of new bispyrazolines 4a, 4b, 4c, 4d, 4e, 4f, 4g built around the aliphatic linkers of varying lengths have been described. The intermediate bischalcones and final bishetrocyclics were also evaluated for their antimicrobial activities.

Carbamate substituted 2-amino-4,6-diphenylpyrimidines as adenosine receptor antagonists

Robinson, Sarel J.,Petzer, Jacobus P.,Rousseau, Amanda L.,Terre'Blanche, Gisella,Petzer, Anél,Lourens, Anna C.U.

, p. 734 - 738 (2016)

A novel series of carbamate substituted 2-amino-4,6-diphenylpyrimidines was evaluated as potential dual adenosine A1and A2Areceptor antagonists. The majority of the synthesised compounds exhibited promising dual affinities, with Asu

A new method for the synthesis of chalcone derivatives promoted by PPh3/I2under non-alkaline conditions

Xue, Kangsheng,Sun, Guoxiang,Zhang, Yanzhi,Chen, Xubing,Zhou, Yang,Hou, Jinjun,Long, Huali,Zhang, Zijia,Lei, Min,Wu, Wanying

supporting information, p. 625 - 634 (2020/11/23)

A straightforward and general method has been developed for the synthesis of chalcone derivatives by a Claisen-Schmidt reaction in the presence of PPh3/I2 in 1,4-dioxane under reflux temperatures. With the condensation of the aromatic ketone and aldehyde occurring at non-strongly alkaline conditions, our proposed method significantly expands the range of applicable substrates, especially for groups that are unstable under alkaline conditions.

C3 amino-substituted chalcone derivative with selective adenosine rA1 receptor affinity in the micromolar range

Janse van Rensburg, Helena D.,Legoabe, Lesetja J.,Terre’Blanche, Gisella

, p. 1581 - 1605 (2020/11/20)

Abstract: To identify novel adenosine receptor (AR) ligands based on the chalcone scaffold, herein the synthesis, characterization and in vitro and in silico evaluation of 33 chalcones (15–36 and 37–41) and structurally related compounds (42–47) are reported. These compounds were characterized by radioligand binding and GTP shift assays to determine the degree and type of binding affinity, respectively, against rat (r) A1 and A2A ARs. The chalcone derivatives 24, 29, 37 and 38 possessed selective A1 affinity below 10?μM, and thus, are the most active compounds of the present series; compound 38 was the most potent selective A1 AR antagonist (Ki (r) = 1.6?μM). The structure–affinity relationships (SAR) revealed that the NH2-group at position C3 of ring A of the chalcone scaffold played a key role in affinity, and also, the Br-atom at position C3′ on benzylidene ring B. Upon in vitro and in silico evaluation, the novel C3 amino-substituted chalcone derivative 38—that contains an α,?-unsaturated carbonyl system and easily allows structural modification—may possibly be a synthon in future drug discovery. Graphic abstract: C3 amino-substituted chalcone derivative (38) with C3′ Br substitution on benzylidene ring B possesses selective adenosine rA1 receptor affinity in micromolar range.[Figure not available: see fulltext.]

COMPOUNDS AND METHODS FOR TREATING OR PREVENTING HEART FAILURE

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Page/Page column 104; 148-149, (2020/07/25)

The present invention relates to the discovery of novel compounds that can be used to treat and/or prevent heart failure in a subject. In certain embodiments, the compounds of the invention are sulfide: quinone oxidoreductase (SQOR) inhibitors. In other e

Chiral pincer-like compound and palladium or nickel complex and synthesis method thereof

-

Paragraph 0061-0062, (2021/01/15)

The invention relates to a chiral pincer-like compound and a palladium or nickel complex and a synthetic method thereof in the field of catalysts, the chemical formulas of the chiral pincer-like compound and the palladium or nickel complex are shown as (I

Natural product-based design, synthesis and biological evaluation of 2′,3,4,4′-tetrahydrochalcone analogues as antivitiligo agents

Zhong, Hui,Zhou, Jia,An, Xiao-Hong,Hua, Ying-Rong,Lai, Yi-Fan,Zhang, Rui,Ahmad, Owais,Zhang, Ye,Shang, Jing

, p. 523 - 533 (2019/04/01)

A bioactive component, 2′,3,4,4′-tetrahydrochalcone (RY3-a) was first isolated from Vernohia anthelmintica (L.) willd seeds, and a set of its analogs, RY3-a-1–RY3-a-15 and RY3-c were designed and synthesized. Biological activity assays showed that RY3-c exhibited better melanogenesis and antioxidant activity and lower toxicity in comparison with RY3-a and butin. Further study tests showed that RY3-c exhibited better melanogenesis activity compared with the positive control 8-methoxypsoralan (8-MOP) in a vitiligo mouse model, suggesting that RY3-c is a good candidate antivitiligo agent. Mechanistic studies showed that RY3-c could repair cell damage induced by excessive oxidative stress and may exert melanin synthesis activity in the mouse melanoma B16F10 cell line by activating the mitogen-activated protein kinase (MAPK) pathway and the upregulation of c-kit.

Structure-activity relationship with pyrazoline-based aromatic sulfamates as carbonic anhydrase isoforms I, II, IX and XII inhibitors: Synthesis and biological evaluation

Moi, Davide,Nocentini, Alessio,Deplano, Alessandro,Balboni, Gianfranco,Supuran, Claudiu T.,Onnis, Valentina

, (2019/08/30)

Four new series of aromatic sulfamates were synthesized and investigated for the inhibition of four human (h) isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), hCA I, II, IX, and XII. The reported derivatives, obtained by a sulfamoylation reaction of the corresponding phenolic precursors, bear 3,5-diarylpyrazoline moieties as spacers between the benzenesulfamate fragment which binds the zinc ion from the active site, and the tail of the inhibitor. Pyrazolines are biologically privileged scaffolds, endowed with versatile biological activity, such as an anti-proliferative action. The derivatives were tested for the inhibition of the cytosolic, hCA I and II (off target isoforms) and the trans-membrane, tumor-associated hCA IX and XII enzymes (anticancer drug targets). Generally, hCA I was not effectively inhibited, whereas many low nanomolar inhibitors were evidenced against hCA II (KIs in the range of 0.42–90.1 nM), IX (KIs in the range of 0.72–63.6 nM), and XII (KIs in the range of 0.88–85.2 nM). The best substitution fragments at the pyrazoline ring included for CA II a 4-sulfamic group on the 3-aryl and halogens on the 5-aryl or a methoxy group on the 3-aryl and a 4-sulfamate group on the 5-aryl; for CA IX and CA XII they included the sulfamic group on the 3- or 4-position of the 5-aryl and an electronwithdrawing group on the 4-postion of the 3-aryl ring.

Chalcones and their pyrazine analogs: synthesis, inhibition of aldose reductase, antioxidant activity, and molecular docking study

Kucerova-Chlupacova, Marta,Dosedel, Martin,Kunes, Jiri,Soltesova-Prnova, Marta,Majekova, Magdalena,Stefek, Milan

, p. 921 - 929 (2018/02/26)

Abstract: Chalcones and their pyrazine analogs synthesized by Claisen–Schmidt condensation were tested for inhibition of aldose reductase, which is the key enzyme in the development of secondary diabetic complications. The most active compounds exerted IC50 values within the micromolar scale, and their interactions with the enzyme were described in a molecular docking study. Antioxidant activity of several representative compounds was explored in DPPH (2,2-diphenyl-1-picrylhydrazyl) assay, revealing significant scavenging for 4-hydroxy-substituted derivatives endowed with electron-donating methoxy substituent in position 3 of the ring B. To conclude, the novel chalcones hydroxylated and methoxylated in the B-ring and their pyrazine analogs exhibited significant aldose reductase inhibition activity, albeit lower in comparison with the reference epalrestat. Medium antioxidant activity (not exceeding the antioxidant efficacy of the standard Trolox) was shown by the representative compounds tested.

Synthesis and Bioactivity of Reduced Chalcones Containing Sulfonamide Side Chains

Noreljaleel, Anwar E. M.,Wilhelm,Bonnet,Van Der Westhuizen

, p. 41 - 48 (2018/02/07)

The effect on the bioactivity of antibacterial sulfonamide drugs against malaria and tuberculosis via an increase of the lipid solubility groups by condensation with a reduced chalcone was investigated. Sulfonamide derivatives (8a-8d) were obtained via a

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