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MCA is a derivative of coumarin, used for fluorescent detection of platelet-activating factor in high-performance liquid chromatography and as a tool for protease activity analysis.

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Quality Control of MCA Purity: 98% SDS Specification

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Product Details of MCA

CAS No. :	62935-72-2
Formula :	C₁₂H₁₀O₅
M.W :	234.20
SMILES Code :	O=C(O)CC(C1=C(O2)C=C(OC)C=C1)=CC2=O
English Name :	2-(7-Methoxy-2-oxo-2H-chromen-4-yl)acetic acid
MDL No. :	MFCD00009774
InChI Key :	ZEKAXIFHLIITGV-UHFFFAOYSA-N
Pubchem ID :	342221

Safety of MCA

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Application In Synthesis of MCA

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 62935-72-2 ]

[ 62935-72-2 ] Synthesis Path-Downstream 1~14

1
[ 150-19-6 ]
[ 77-92-9 ]
[ 62935-72-2 ]

Yield	Reaction Conditions	Operation in experiment
33%	With sulfuric acid at 0℃; for 16h; Inert atmosphere;
6.1%	Stage #1: citric acid With sulfuric acid at 20 - 70℃; for 1.58333h; Stage #2: O-methylresorcine at 0 - 10℃;	3.1.3. General Procedure for the Synthesis of Coumarin-4-Acetic acid Derivatives IIa,b General procedure: Route A: A mixture of citric acid monohydrate (4.2 g, 20 mmol) and concentrated H2SO4 (5.6 mL)was stirred at room temperature for 60 min, then slowly heated (rate of heating governed by foaming)to 70 C. After 35 min at this temperature, with stirring throughout, the evolution of carbon monoxidehad slackened, and the clear solution was rapidly cooled to 0 C. Then the appropriate methoxyphenol(2 g, 16.1 mmol) and concentrated H2SO4 (2.24 mL) were added, each in three equal portions, to thestirred solution at such a rate that the internal temperature did not exceed 10 C. The resulting reactionmixture was stored at 0 C for 16 h, poured into ice cold water (40 mL), and the resulting crystallineprecipitate filtered o and washed thoroughly with H2O. The collected solid was dissolved understirring in 1N Na2CO3 solution (20 mL), heated for 15 min at 65 C, and the insoluble matter was filtered o and washed with water (2 10 mL). The combined filtrate and washings were acidifiedwith concentrated HCl to give the respective coumarin-4-acetic acid derivatives IIa,b [32].
	With sulfuric acid

With sulfuric acid

References: [1]Lizzul-Jurse, Antoine; Bailly, Laetitia; Hubert-Roux, Marie; Afonso, Carlos; Renard, Pierre-Yves; Sabot, Cyrille [Organic and Biomolecular Chemistry, 2016, vol. 14, # 32, p. 7777 - 7791].
[2]Almutairi, Maha S.; Al Suwayyid, Areej N.; Aldarwesh, Amal; Aboulwafa, Omaima M.; Attia, Mohamed I. [Molecules, 2020, vol. 25, # 7].
[3]Laskowski; Clinton [Journal of the American Chemical Society, 1950, vol. 72, p. 3987,3989].
[4]Pujar, Kiran K.; Kulkarni, Manohar V.; Alawandi, Ganesh N.; Anilkumar; Basanagouda, Mahantesha [Synthetic Communications, 2015, vol. 45, # 17, p. 2043 - 2052].

2
[ 62935-72-2 ]
[ 1761-61-1 ]
[ 855774-18-4 ]

Yield	Reaction Conditions	Operation in experiment
79%	With sodium hydride In acetic anhydride	Method 2 General procedure: The coumarin-4-acetic acids (0.01mol) and salicylaldehydes (0.01 mol) were taken in a round-bottomed flask containing NaH (1.5eq) and acetic anhydride (3mL). The flask was fitted with guard tube and stirred for 1-1.5 h. The progress of reaction was monitored by TLC, and the solid separated was filtered off and washed with ether and 5% NaHCO3 to remove unreacted coumarins-4-acetic acids. Then the remaining residue was dried and recrystallized from DMF.
58%	With potassium acetate In acetic anhydride at 130 - 140℃; for 3h;

References: [1]Pujar, Kiran K.; Kulkarni, Manohar V.; Alawandi, Ganesh N.; Anilkumar; Basanagouda, Mahantesha [Synthetic Communications, 2015, vol. 45, # 17, p. 2043 - 2052].
[2]Dubovik; Garazd; Khilya [Chemistry of Natural Compounds, 2004, vol. 40, # 5, p. 434 - 443].

3
[ 62935-72-2 ]
[ 24313-88-0 ]
[ 908562-48-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h;	1 To a solution of 7-methoxycoumarin-4-acetic acid (0.10 g, 0.4 mmol) in 2 mL of CH2Cl2 was added EDCI (0.11 g, 0.6 mmol) and 3,4,5-trimethoxyaniline (0.078 g, 0.4 mmol). The mixture was stirred at room temperature for 16 h. The reaction mixture was partitioned between CH2Cl2 and brine. The aqueous layer was extracted with EPO CH2Cl2 and the combined organic extracts were washed with brine and dried overMgSO4.The crude product was purified by silica chromatography (1-10% MeOH/ CH2Cl2) to afford the desired product. Calc'd for C21H21NO7: 399.4, [M+H]+ = 400.

References: [1]Current Patent Assignee: SIRTRIS PHARMACEUTICALS - WO2006/94237, 2006, A2 Location in patent: Page/Page column 140-141.

4
[ 613-84-3 ]
[ 62935-72-2 ]
[ 1801743-82-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium hydride In acetic anhydride	Method 2 General procedure: The coumarin-4-acetic acids (0.01mol) and salicylaldehydes (0.01 mol) were taken in a round-bottomed flask containing NaH (1.5eq) and acetic anhydride (3mL). The flask was fitted with guard tube and stirred for 1-1.5 h. The progress of reaction was monitored by TLC, and the solid separated was filtered off and washed with ether and 5% NaHCO3 to remove unreacted coumarins-4-acetic acids. Then the remaining residue was dried and recrystallized from DMF.

References: [1]Pujar, Kiran K.; Kulkarni, Manohar V.; Alawandi, Ganesh N.; Anilkumar; Basanagouda, Mahantesha [Synthetic Communications, 2015, vol. 45, # 17, p. 2043 - 2052].

5
[ 62935-72-2 ]
[ 635-93-8 ]
[ 869079-30-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium hydride In acetic anhydride	Method 2 General procedure: The coumarin-4-acetic acids (0.01mol) and salicylaldehydes (0.01 mol) were taken in a round-bottomed flask containing NaH (1.5eq) and acetic anhydride (3mL). The flask was fitted with guard tube and stirred for 1-1.5 h. The progress of reaction was monitored by TLC, and the solid separated was filtered off and washed with ether and 5% NaHCO3 to remove unreacted coumarins-4-acetic acids. Then the remaining residue was dried and recrystallized from DMF.

References: [1]Pujar, Kiran K.; Kulkarni, Manohar V.; Alawandi, Ganesh N.; Anilkumar; Basanagouda, Mahantesha [Synthetic Communications, 2015, vol. 45, # 17, p. 2043 - 2052].

6
[ 62935-72-2 ]
[ 90-02-8 ]
[ 855774-16-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydride In acetic anhydride	Method 2 General procedure: The coumarin-4-acetic acids (0.01mol) and salicylaldehydes (0.01 mol) were taken in a round-bottomed flask containing NaH (1.5eq) and acetic anhydride (3mL). The flask was fitted with guard tube and stirred for 1-1.5 h. The progress of reaction was monitored by TLC, and the solid separated was filtered off and washed with ether and 5% NaHCO3 to remove unreacted coumarins-4-acetic acids. Then the remaining residue was dried and recrystallized from DMF.

References: [1]Pujar, Kiran K.; Kulkarni, Manohar V.; Alawandi, Ganesh N.; Anilkumar; Basanagouda, Mahantesha [Synthetic Communications, 2015, vol. 45, # 17, p. 2043 - 2052].

7
[ 492-88-6 ]
[ 62935-72-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydride In acetic anhydride	Method 2 General procedure: The coumarin-4-acetic acids (0.01mol) and salicylaldehydes (0.01 mol) were taken in a round-bottomed flask containing NaH (1.5eq) and acetic anhydride (3mL). The flask was fitted with guard tube and stirred for 1-1.5 h. The progress of reaction was monitored by TLC, and the solid separated was filtered off and washed with ether and 5% NaHCO3 to remove unreacted coumarins-4-acetic acids. Then the remaining residue was dried and recrystallized from DMF.

References: [1]Pujar, Kiran K.; Kulkarni, Manohar V.; Alawandi, Ganesh N.; Anilkumar; Basanagouda, Mahantesha [Synthetic Communications, 2015, vol. 45, # 17, p. 2043 - 2052].

8
[ 62935-72-2 ]
[ 2123565-50-2 ]
[ 2123565-72-8 ]

Yield	Reaction Conditions	Operation in experiment
64%	With diethyl cyanophosphonate; triethylamine In tetrahydrofuran for 20h; Cooling with ice; Reflux;	4.2 Typical procedure for syntheses of 3a-d General procedure: To a solution of 1 (0.52 g, 2.20 mmol) and l-glutamic acid derivative (n=4) (0.54 g, 2.10 mmol) together with triethylamine (0.9 mL, 6.50 mmol) in THF (100 mL) in an ice bath was added a solution of diethyl cyanophosphonate (DECP) (0.40 mL, 2.67 mmol) in THF (10 mL). After the reaction mixture was refluxed for 20 h, aqueous K2CO3 solution was added to this mixture, followed by additional stirring for 1h. The resulting precipitate was filtered and washed by water and 10 % HCl solution repeatedly to give a white solid. Further purification was carried out by recrystallization with CH2Cl2 and hexane to afford 3a as a white powder (0.79 g, 80 %).