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1214-47-7

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1214-47-7 Usage

Chemical Properties

Yellow needle-like crystals (ethanol). Melting point 88-89°C.

Uses

2'-Hydroxychalcone can be used as intermediates in drug synthesis, such as the preparation of flavonol compounds. Flavonols are widely distributed in nature as secondary metabolites in living organisms, and they have a wide variety of physiological activities, mainly in the cardiovascular system, antiviral, anti-inflammatory and antitumor effects.

Definition

ChEBI: 2'-hydroxychalcone is a member of the class of chalcones that is trans-chalcone substituted by a hydroxy group at position 2'. It has a role as an anti-inflammatory agent. It is a member of phenols and a member of chalcones. It derives from a trans-chalcone.

Preparation

Synthesis of 2'-hydroxychalcone: add 30 ml of 20% (V/V) ethanol and (11.06 mmol) sodium hydroxide in a 50 mL single mouth flask, stir for 0.5 h at room temperature and then add substituted 2-Hydroxyacetophenone (1.66 mmol) and benzaldehyde (1.66 mmol), stir for 18 h at room temperature, TLC monitoring until the new point produces raw material point no longer changes, stop the reaction Then the reaction was poured into water, stirred while adjusting the pH value to acidic with 6 mol/L hydrochloric acid, the reaction was filtered, the filter cake was obtained, rinsed twice with pure water, and 2'-hydroxychalcone was obtained by silica gel column chromatography [V(petroleum ether):V(ethyl acetate) = 5:1] in 85% yield.

Check Digit Verification of cas no

The CAS Registry Mumber 1214-47-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,1 and 4 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1214-47:
(6*1)+(5*2)+(4*1)+(3*4)+(2*4)+(1*7)=47
47 % 10 = 7
So 1214-47-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H12O2/c16-14-9-5-4-8-13(14)15(17)11-10-12-6-2-1-3-7-12/h1-11,16H/b11-10+

1214-47-7 Well-known Company Product Price

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  • TCI America

  • (H0385)  2'-Hydroxychalcone  >98.0%(HPLC)

  • 1214-47-7

  • 25g

  • 690.00CNY

  • Detail
  • TCI America

  • (H0385)  2'-Hydroxychalcone  >98.0%(HPLC)

  • 1214-47-7

  • 500g

  • 5,990.00CNY

  • Detail
  • Alfa Aesar

  • (L13937)  2'-Hydroxychalcone, 98+%   

  • 1214-47-7

  • 5g

  • 274.0CNY

  • Detail
  • Alfa Aesar

  • (L13937)  2'-Hydroxychalcone, 98+%   

  • 1214-47-7

  • 25g

  • 853.0CNY

  • Detail

1214-47-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2'-Hydroxychalcone

1.2 Other means of identification

Product number -
Other names 1-(2-Hydroxyphenyl)-3-phenylprop-2-en-1-one

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:1214-47-7 SDS

1214-47-7Relevant articles and documents

Low DNA and high BSA binding affinity of cationic ruthenium(II) organometallic featuring pyridine and 2’-hydroxychalcone ligands

Zahirovi?, Adnan,Roca, Sun?ica,Kahrovi?, Emira,Vi?njevac, Aleksandar

, (2021)

The chiral-at-metal, piano-stool ruthenium(II) racemic organometallic [Ru(cymene)(chalconato)(pyridine)]PF6 was prepared by a multistep solution synthesis and its molecular and crystal structure was determined by single crystal X-ray diffractio

Exploring the anti-breast cancer potential of flavonoid analogs

Thakor, Vanrajsinh,Poddar, Mayur,Dey, Sumit,Manjula,Madhunapantula, Subbarao V.,Pawara, Rahul,Patel, Harun M.,Noolvi, Malleshappa N.

, p. 79166 - 79179 (2016)

In the course of our search for new antitumor agents for breast cancer, novel flavone derivatives were synthesized, characterized and examined for their antitumor activities against breast cancer cell lines. In initial screening, analogs 7a [3-(5-amino-1,3,4-thiadiazol-2-yl)methoxy-2-phenyl-4H-chromen-4-one] and 7b [3-(5-amino-1,3,4-thiadiazol-2-yl)methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one] were found to be effective against the estrogen receptor negative cell line (MDA-MB 453), which was followed by their evaluation in five dose assays. In addition, mechanistic studies of 7a and 7b were performed by cytometric analysis and electrophoretic studies and it was observed that apoptosis is a mechanism of cell death, confirmed morphologically by acridine orange/ethidium bromide double staining and TUNEL analysis. Further in vivo evaluation of the anti-tumor activity of compound 7a and 7b by Ehrlich Ascites Carcinoma (EAC) model and related studies confirms the anti-breast cancer potential of flavonoid analogs.

Synthesis of Hierarchically Porous Zeolite Composites with Enhanced Catalytic Activity: Effect of Different Long-Chain Structure Directing Agents

Ding, He,Zhang, Yixiao,Xiao, Zixing,Zhang, Jingshuang,Bai, Peng,Li, Najun,Guo, Xianghai

, p. 1730 - 1737 (2018)

A two-section temperature strategy was employed to achieve micromesoporous composites with five kinds of long-chain alkyl quaternary ammonium salts as single template. Zeolites with an ordered two-dimensional hexagonal mesopore and crystallized MFI domain were successfully obtained. Gemini quaternary ammonium salt surfactants C18N2 and C22N2 are effective in directing the structure of MCM-41 than CTAB at 100 °C and will transform to lamellar MFI structures at 150 °C gradually. While single quaternary ammonium salts C18N and C22N direct lamellar M41s at 100 °C and transform to mesoporous structure at a higher temperature of 150 °C, it is possible to get a composite of microporous and mesoporous material with a surface area as high as 1046 m2 g-1. Catalytic performance of typical hierarchical zeolites was evaluated by Claisen-Schmidt condensation of bulky reactants. The excellent conversion suggested the synergy effects of improved large molecule diffusion in mesopores and highly separated MFI domains as catalytic centers in the hierarchical zeolites, which can be explained by an apple-tree model.

Primary, secondary, and tertiary silanamine sites formed on nitrided SBA-15 for base catalytic C–C bond formation reactions

Moteki, Takahiko,Koga, Yuuki,Ogura, Masaru

, p. 131 - 139 (2019)

The relationship between catalyst preparation conditions and resulting their catalytic properties on silica substituted nitrogen site, silanamine site, has been discussed for a long time. In this study, the contribution of each silanamine site for several

Synthesis of flavanones using nanocrystalline MgO

Choudary,Ranganath,Yadav, Jagajit,Lakshmi Kantam

, p. 1369 - 1371 (2005)

The design and development of a truly nano heterogeneous catalyst for the Claisen-Schmidt condensation (CSC) of benzaldehydes with 2-hydroxyacetophenone to yield substituted chalcones followed by isomerization to afford flavanones with excellent yields and selectivity is described.

Synthesis of nanocrystalline MFI-zeolites with intracrystal mesopores and their application in fine chemical synthesis involving large molecules

Srivastava, Rajendra,Iwasa, Nobuhiro,Fujita, Shin-Ichiro,Arai, Masahiko

, p. 9507 - 9511 (2008)

Synthesis of nanocrystalline MFI-zeolite with intracrystal mesopores, to be used to control the size of the zeolite crystals, particle morphology, and mesoporodity, and their application in fine chemical synthesis involving large molecules, was determined. An increase in the amount of PrTES to 5.0 mol% led to spherical macroporous zeolite particles of 300 nm diameter. The mesopores show a pore size distribution in the range of 3-8 nm, while Al and Si MAS MR show that all the samples contain only tetrahedral aluminum sites. It is also proposed that the mesoporous-zeolite crystallization is mediated by the nanoscale segregation of organic-rich and organic-lean domains on the growing zeolite particles. The high catalytic activity of MFI-10PrTES is due to the formation of smaller zeolite crystallites and the presence of intracrystal mesopores.

Hierarchical mesoporous zeolites: Direct self-assembly synthesis in a conventional surfactant solution by kinetic control over the zeolite seed formation

Zhu, Yan,Hua, Zile,Zhou, Jian,Wang, Lijun,Zhao, Jinjin,Gong, Yun,Wu, Wei,Ruan, Meiling,Shi, Jianlin

, p. 14618 - 14627 (2011)

By kinetic control over the zeolite seed formation, we report the direct fabrication of hierarchical mesoporous zeolites using hexadecyl trimethyl ammonium bromide (CTAB) as the soft template in a conventional solution route. Nanometer-sized, subnanocrystal-type zeolite seeds with a high degree of polymerization are essential to prevent the formation of a separate amorphous mesoporous phase and the phase separation between the mesophase and zeolite crystals in the presence of CTAB and a certain amount of ethanol. The mechanisms for the formation of hierarchically porous zeolites in the solution process, including the effect of mother liquid aging, formation of subnanocrystal zeolite seeds and their self-assembly effect with CTAB, and the role of ethanol are proposed and discussed in detail. The prepared mesoporous ZSM-5 zeolite showed much higher catalytic activity than conventional counterparts for aldol condensations involving large molecules, especially in the synthesis of vesidryl.

Synthesis and catalytic activity of amino-functionalized SBA-15 materials with controllable channel lengths and amino loadings

Chen, Shih-Yuan,Huang, Ching-Ya,Yokoi, Toshiyuki,Tang, Chih-Yuan,Huang, Shing-Jong,Lee, Jey-Jau,Chan, Jerry C. C.,Tatsumi, Takashi,Cheng, Soofin

, p. 2233 - 2243 (2012)

Aminopropyl-functionalized SBA-15 mesoporous materials (NH 2-SBA-15) with different lengths of channeling pores and aminopropyl loadings up to 2.6 mmol g-1 were synthesized by one-pot co-condensation of tetraethyl orthosilicate (TEOS

A new pyrazoline-based fluorescent sensor for Al3+ in aqueous solution

Hu, Shengli,Song, Jingjing,Wu, Gongying,Cheng, Cuixia,Gao, Qing

, p. 1188 - 1194 (2015)

A new pyrazoline-based fluorescent sensor was synthesized and the structure was confirmed by single crystal X-ray diffraction. The sensor responds to Al3+ with high selectivity among a series of cations in aqueous methanol. This sensor forms a

A simple route to synthesize mesoporous ZSM-5 templated by ammonium-modified chitosan

Jin, Junjiang,Zhang, Xingdi,Li, Yongsheng,Li, Hua,Wu, Wei,Cui, Yunlong,Chen, Qian,Li, Liang,Gu, Jinlou,Zhao, Wenru,Shi, Jianlin

, p. 16549 - 16555 (2012)

Uniform mesoporous zeolite ZSM-5 crystals have been successfully fabricated through a simple hydrothermal synthetic method by utilizing ammonium-modified chitosan and tetrapropylammonium hydroxide (TPAOH) as the meso- and microscale template, respectively. It was revealed that mesopores with diameters of 5-20nm coexisted with microporous network within mesoporous ZSM-5 crystals. Ammonium-modified chitosan was demonstrated to serve as a mesoporogen, self-assembling with the zeolite precursor through strong static interactions. As expected, the prepared mesoporous ZSM-5 exhibited greatly enhanced catalytic activities compared with conventional ZSM-5 and Al-MCM-41 in reactions involving bulky molecules, such as the Claisen-Schmidt condensation of 2-hydroxyacetophenone with benzaldehyde and the esterification reaction of dodecanoic acid and 2-ethylhexanol. Mesoporous zeolite: Ammonium-modified chitosan served as a mesoporogen in the hydrothermal synthesis of mesoporous zeolite Socony Mobil (ZSM)-5, self-assembling with the zeolite precursor through strong static interactions (see figure; TPA=tetrapropylammonium, HTCC=N-(2-hydroxy)propyl-3-trimethylammonium chitosan chloride).

Water stable fluorescent organotin(iv) compounds: aggregation induced emission enhancement and recognition of lead ions in an aqueous system

Capalash, Neena,Kaur, Kulwinder,Kaur, Varinder,Singh, Raghubir

, p. 148 - 161 (2021/12/31)

Herein, synthesis, spectroscopic studies, single-crystal X-ray diffraction, aggregation-induced emission enhancement (AIEE) and sensing application of water-stable organotin(iv) compounds (4a-6aand4b-6b) obtained from 3-hydroxy-4H-chromen-4-one ligands are reported. All the synthesized organotin(iv) compounds were characterized using elemental analysis, FT-IR spectroscopy, multi-nuclei NMR (1H,13C, and119Sn) spectroscopy, UV-VIS, fluorescence spectroscopy, mass spectrometry, and single-crystal X-ray diffraction. The119Sn NMR signal of compounds in the range ofδ?144.92 to ?190.68 ppm indicated the formation of hexacoordinated organotin species. The spectroscopic and single-crystal X-ray diffraction studies confirmed the formation of [L2SnR2] type compounds (where L is the bidentate ligand and R is an alkyl group) with a ‘skew-trapezoidal bipyramidal’ geometry. Furthermore, DFT calculations of compound4bbased on the DGDZVP basis set fully supported the stability of the structure where two short bonds Sn-O(C-O)acquire thecisposition rather than thetransposition. Single-crystal X-ray diffraction analysis of the crystals grown in the presence of water confirmed the stability of4ain water. Moreover, the water stability of a test compound4awas established by119Sn NMR data and spectrofluorimetric data. The spectrofluorimetric scan at different time intervals revealed the stability and constant emission response up to 24 h. The compounds were found to be fluorescent and exhibited aggregation-induced emission enhancement in MeOH/H2O mixtures, which was confirmed by HRTEM analysis. The test compound4ashowed selective spectrofluorimetric recognition of Pb2+ions in an aqueous medium by displaying an enhanced emission signal at 478 nm and enabled detection up to 22.66 μM. A mechanism of interaction is also proposed by spectroscopic experiments, spectrofluorimetric experiments and computational studies.

Stereoselective reduction of flavanones by marine-derived fungi

Birolli, Willian G.,Nitschke, Marcia,Porto, André Luiz M.,Santos, Darlisson de A.,de Matos, Iara L.

, (2021/08/13)

Biotransformation is an alternative with great potential to modify the structures of natural and synthetic flavonoids. Therefore, the bioreduction of synthetic halogenated flavanones employing marine-derived fungi was described, aiming the synthesis of flavan-4-ols 3a-g with high enantiomeric excesses (ee) of both cis- and trans-diastereoisomers (up to >99% ee). Ten strains were screened for reduction of flavanone 2a in liquid medium and in phosphate buffer solution. The most selective strains Cladosporium sp. CBMAI 1237 and Acremonium sp. CBMAI1676 were employed for reduction of flavanones 2a-g. The fungus Cladosporium sp. CBMAI 1237 presented yields of 72–87% with 0–64% ee cis and 0–30% ee trans with diastereoisomeric ratio (dr) from 52:48 to 64:36 (cis:trans). Whereas Acremonium sp. CBMAI 1676 resulted in 31% yield with 77–99% ee of the cis and 95–99% ee of the trans-diastereoisomers 3a-g with a dr from 54:46 to 96:4 (cis:trans). To our knowledge, this is the first report of the brominated flavon-4-ols 3e and 3f. The use of fungi, with emphasis for these marine-derived strains, is an interesting approach for enantioselective reduction of halogenated flavanones. Therefore, this strategy can be explored to obtain enantioenriched compounds with biological activities.

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