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19040-71-2

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19040-71-2 Usage

Uses

4-(Chloromethyl)-7,8-dihydroxy-2H-chromen-2-one is used to prepare daphnetin derivatives as potent antioxidant agents.

Check Digit Verification of cas no

The CAS Registry Mumber 19040-71-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,0,4 and 0 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 19040-71:
(7*1)+(6*9)+(5*0)+(4*4)+(3*0)+(2*7)+(1*1)=92
92 % 10 = 2
So 19040-71-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H7ClO4/c11-4-5-3-8(13)15-10-6(5)1-2-7(12)9(10)14/h1-3,12,14H,4H2

19040-71-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(chloromethyl)-7,8-dihydroxychromen-2-one

1.2 Other means of identification

Product number -
Other names 4-(chloromethyl)-5,7-dihydroxy-2H-chromen-2-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:19040-71-2 SDS

19040-71-2Relevant articles and documents

Expeditious Pechmann condensation by using biodegradable cellulose sulfuric acid as a solid acid catalyst

Kuarm, B. Suresh,Madhav, J. Venu,Laxmi, S. Vijaya,Rajitha,Reddy, Y. Thirupathi,Reddy, P. Narsimha,Crooks, Peter A.

, p. 3358 - 3364 (2010)

A facile synthesis of coumarins was performed in excellent yields via Pechmann condensation by using different type of phenols and ethylacetoacetates under solvent-free media using both conventional method and microwave irradiation in short reaction times is described. The reaction workup is very simple, and the catalyst can be easily separated from the reaction mixture and reused several times in subsequent reactions. Copyright

Dipyridine cobalt chloride: A novel catalyst for the synthesis of coumarins via Pechmann condensation

Madhav, Janganati Venu,Kuarm, Bowroju Suresh,Someshwar, Pola,Rajitha, Bavanthula,Reddy, Yerram,Reddy, Thirupathi,Crooks, Peter A.

, p. 232 - 234 (2008)

Dipyridine cobalt chloride is a novel catalyst for the Pechmann condensation involving different phenols and ethylacetoacetate under solvent-free conditions using both conventional methods and microwave irradiation. It gives the corresponding coumarins in excellent yields with high purity. The catalyst is thermally stable, inexpensive and recyclable. A faster reaction and higher yields compared to the conventional method and no side products were identified using microwave irradiation. In this reaction, electron releasing groups on the phenol ring shown more reactivity and gave high yields than simple phenol. These products were identified by 1H NMR, 13C NMR, MS, IR and elemental analysis.

Sulfated zirconia, a mild alternative to mineral acids in the synthesis of hydroxycoumarins

Rodríguez-Domínguez, Juan Carlos,Kirsch, Gilbert

, p. 3279 - 3281 (2006)

Sulfated zirconia (1%) was employed as Pechmann's catalyst without solvent or in some cases using a small amount of ethanol to obtain coumarins in moderate to good yields. With this procedure, no significant acidic waste was obtained and an environmental friendly alternative to obtain coumarins is provided.

Synthesis and structure-activity relationship of coumarins as potent Mcl-1 inhibitors for cancer treatment

Xia, Yang-Liu,Wang, Jing-Jing,Li, Shi-Yang,Liu, Yong,Gonzalez, Frank J.,Wang, Ping,Ge, Guang-Bo

, (2020/11/25)

Myeloid cell leukemia-1 (Mcl-1) is a validated and attractive target for cancer therapy. Over-expression of Mcl-1 in many cancers allows cancer cells to evade apoptosis and contributes to their resistance to current chemotherapeutics. In this study, more than thirty coumarin derivatives with different substituents were designed and synthesized, and their Mcl-1 inhibitory activities evaluated using a fluorescence polarization-based binding assay. The results showed that the catechol group was a key constituent for Mcl-1 inhibitory activity of the coumarins, and methylation of the catechol group led to decreased inhibitory activity. The introduction of a hydrophobic electron-withdrawing group at the C-4 position of 6,7-dihydroxycoumarin, enhanced Mcl-1 inhibitory capacity, and a hydrophilic group in this position was unbeneficial to the inhibitory potency. In addition, the introduction of a nitrogen-containing group to the C-5 or C-8 position, which allowed an intramolecular hydrogen bond, was also unfavorable for Mcl-1 inhibition. Among all coumarins tested, 4-trifluoromethyl-6,7-dihydroxycoumarin (Cpd 4) displayed the most potent inhibitory activity towards Mcl-1 (Ki = 0.21 ± 0.02 μM, IC50 = 1.21 ± 0.56 μM, respectively), for which the beneficial effect on taxol resistance was also validated in A549 cells. A strong interaction between Cpd 4 and Mcl-1 in docking simulations further supported the observed potent Mcl-1 inhibition ability of Cpd 4. 3D-QSAR analysis of all tested coumarin derivatives further provides new insights into the relationships linking the inhibitory effects on Mcl-1 and the steric-electrostatic properties of coumarins. These findings could be of great value for medicinal chemists for the design and development of more potent Mcl-1 inhibitors for biomedical applications.

Synthesis and structure-activity relationship of daphnetin derivatives as potent antioxidant agents

Xia, Yangliu,Chen, Chen,Liu, Yong,Ge, Guangbo,Dou, Tongyi,Wang, Ping

, (2018/10/05)

In this study, daphnetin 1 was chosen as the lead compound, and C-3 or C-4-substituted daphnetins were designed and synthesized to explore the potential relationship between the antioxidant activities and the chemical structures of daphnetin derivatives. The antioxidant activities of the generated compounds were evaluated utilizing the free radical scavenging effect on 2,2-diphenyl-1-picrylhydrazyl, 2,2-azinobis-(3-ethylbenzthiazoline-6-sulfonate) cation, and the ferric reducing power assays, and were then compared with those of the standard antioxidant Trolox. The results showed that the catechol group was the key pharmacophore for the antioxidant activity of the daphnetins. The introduction of an electron-withdrawing hydrophilic group at the C-4 position of daphnetin enhanced the antioxidative capacity, but this trend was not observed for C-3 substitution. In addition, introduction of a a hydrophobic phenyl group exerted negative effects on the antioxidant activity in both the C-3 and C-4 substitutions. Among all of the derivatives tested, the most powerful antioxidant was 4-carboxymethyl daphnetin (compound 9), for which the strongest antioxidant activity was observed in all of the assays. In addition, compound 9 also displayed strong pharmaceutical properties in the form of metabolic stability. To summarize, compound 9 holds great potential to be developed as an antioxidant agent with excellent antioxidant activity and proper pharmacokinetic behavior.

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