3-acetyl-7-hydroxy-2H-chromen-2-one

Base Information

• Chemical Name: 3-acetyl-7-hydroxy-2H-chromen-2-one
• CAS No.: 10441-27-7
• Molecular Formula: C11H8O4
• Molecular Weight: 204.182
• Hs Code.: 29339900
• European Community (EC) Number: 635-172-1
• UNII: BLX779DF5D
• DSSTox Substance ID: DTXSID20419817
• Nikkaji Number: J785.250I
• Wikidata: Q82231020
• ChEMBL ID: CHEMBL153064
• Mol file: 10441-27-7.mol

Synonyms:3-acetyl-7-hydroxy-2H-chromen-2-one;10441-27-7;3-acetyl-7-hydroxychromen-2-one;3-Acetyl-umbelliferone;3-Acetyl-7-hydroxy-chromen-2-one;3-acetylumbelliferone;CHEMBL153064;MFCD00037379;2H-1-Benzopyran-2-one, 3-acetyl-7-hydroxy-;D09BVA;CBDivE_005922;MLS000777662;SCHEMBL592707;cid_5392139;DTXSID20419817;BBL005231;BDBM50096008;STK365153;AKOS000275988;AS-62496;PD181224;SMR000414056;CS-0312609;EU-0017123;FT-0660659;D96021;AB00073948-01;J-511501;F0110-0011

Chemical Property of 3-acetyl-7-hydroxy-2H-chromen-2-one

Chemical Property:

• Vapor Pressure: 1.42E-09mmHg at 25°C
• Melting Point: 234 °C(lit.)
• Refractive Index: 1.619
• Boiling Point: 473.1°C at 760 mmHg
• Flash Point: 195.2°C
• PSA: 67.51000
• Density: 1.41g/cm³
• LogP: 1.70120
• Storage Temp.: 2-8°C
• Solubility.: DMF: soluble
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 204.04225873
• Heavy Atom Count: 15
• Complexity: 332

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Acetyl-7-hydroxy-2H-chromen-2-one ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC2=C(C=C(C=C2)O)OC1=O
• Uses: These lipoid indicators are also probes for phase transitions in lipid membranes and may register the detailed chemical structure of the polar head-group region or the packing density in lamellar lipid layers.

Technology Process of 3-acetyl-7-hydroxy-2H-chromen-2-one

There total 10 articles about 3-acetyl-7-hydroxy-2H-chromen-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

ethyl acetoacetate (141-97-9) + 2,4-Dihydroxybenzaldehyde (95-01-2) → 3-acetyl-7-hydroxy-chromen-2-one (10441-27-7)

Guidance literature:

With piperidine; In ethanol; Inert atmosphere; Reflux;

DOI:10.1016/j.molliq.2019.111920

Reference yield: 85.0%

2,5-Dihydroxybenzaldehyde (1194-98-5) + acetoacetic acid methyl ester (105-45-3) → 3-acetyl-7-hydroxy-chromen-2-one (10441-27-7)

Guidance literature:

With thiourea S,S-dioxide; at 80 ℃; for 4h;

DOI:10.1039/c1ob05818e

Reference yield: 84.0%

2,5-Dihydroxybenzaldehyde (1194-98-5) + ethyl acetoacetate (141-97-9) → 3-acetyl-7-hydroxy-chromen-2-one (10441-27-7)

Guidance literature:

With thiourea S,S-dioxide; at 80 ℃; for 4h;

DOI:10.1039/c1ob05818e

upstream raw materials:

ethyl acetoacetate

2,4-Dihydroxybenzaldehyde

2-ethoxymethylene-3-oxobutanoic acid ethyl ester

recorcinol

Downstream raw materials:

3-acetyl-7-phenyl-2H-chromen-2-one

3-acetyl-7-p-tolyl-2H-chromen-2-one

3-acetyl-7-(4-methoxyphenyl)-2H-chromen-2-one

3-acetyl-7-(4-hydroxyphenyl)-2H-chromen-2-one

Refernces

• 1、 Er?at?r, Mehmet,Giray, Elife Sultan,Y?ld?r?m, Metin,Yal?n, Serap. "Synthesis and antiproliferative evaluation of novel biheterocycles based on coumarin and 2-aminoselenophene-3-carbonitrile unit". . p. 625 - 636. Retrieved 2020.
• 2、 Zerangnasrabad, Sara,Jabbari, Atena,Khavari Moghadam, Elahe,Sadeghian, Hamid,Seyedi, Seyed Mohammad. "Design, synthesis, and structure–activity relationship study of O-prenylated 3-acetylcoumarins as potent inhibitors of soybean 15-lipoxygenase". . p. 826 - 834. Retrieved 2021.
• 3、 Yang, Xiaopeng,Liu, Wenya,Tang, Jun,Li, Ping,Weng, Haibo,Ye, Yong,Xian, Ming,Tang, Bo,Zhao, Yufen. "A multi-signal mitochondria-targeted fluorescent probe for real-time visualization of cysteine metabolism in living cells and animals". . p. 11387 - 11390. Retrieved 2018.
• 4、 Wu, Wei-hui,Wang, Xin,Zong, Liang,Li, Dan,Xiao, Yan-hua,Sui, Shao-hui,Li, Jian,Liu, Meng,Chen, Gao-yun,Luo, Teng,Liu, Min,Wang, Xin-ming,Jiang, Zhi-gang. "A Fluorogenic and Chromogenic Probe Distinguishes Fluoride Anions and Thiols: Implications for Discrimination of Fluoride-Containing G Series and Sulfur-Containing V Series Nerve Agents". . p. 141 - 149. Retrieved 2021.
• 5、 Bassyouni, Fatma A.,Abu-Baker, Sherifa M.,Mahmoud, Khaled,Moharam, Maysa,El-Nakkady, Sally S.,Abdel-Rehim, Mohamed. "Synthesis and biological evaluation of some new triazolo[1,5-a]quinoline derivatives as anticancer and antimicrobial agents". . p. 24131 - 24141. Retrieved 2014.
• 6、 Hamlin, Trevor A.,Leadbeater, Nicholas E.. "Raman spectroscopy as a tool for monitoring mesoscale continuous-flow organic synthesis: Equipment interface and assessment in four medicinally-relevant reactions". . p. 1843 - 1852. Retrieved 2013.
• 7、 Cao, Duxia,Feng, Fei,Ma, Shuyue,Pan, Qiling,Wang, Kang-Nan,Xing, Miaomiao. "A coumarin-boronic ester derivative as fluorescent chemosensor for detecting H2O2 in living cells". . . Retrieved 2021.
• 8、 ?ubari?, Domagoj,Agi?, Dejan,Be?lo, Drago,Kara?i?, Zrinka,Karna?, Maja,Lisjak, Miroslav,Lon?ari?, Melita,Molnar, Maja,Popovi?, Boris M.,Rastija, Vesna,Tomi?, Sanja. "Coumarin derivatives act as novel inhibitors of human dipeptidyl peptidase III: Combined in vitro and in silico study". . . Retrieved 2021.
• 9、 KhanYusufzai, Samina,Osman, Hasnah,Khan, Mohammad Shaheen,Mohamad, Suriyati,Sulaiman, Othman,Parumasivam, Thaigarajan,Gansau, Jualang Azlan,Johansah, Norhaniza,Noviany. "Design, characterization, in vitro antibacterial, antitubercular evaluation and structure–activity relationships of new hydrazinyl thiazolyl coumarin derivatives". . p. 1139 - 1148. Retrieved 2017.
• 10、 Yang, Qiaomei,Zhou, Liyi,Peng, Longpeng,Yuan, Gangqiang,Ding, Haiyuan,Tan, Libin,Zhou, Yizhuang. "A smart mitochondria-targeting TP-NIR fluorescent probe for the selective and sensitive sensing of H2S in living cells and mice". . p. 7315 - 7320. Retrieved 2021.