Coumarin

Base Information

• Chemical Name: Coumarin
• CAS No.: 91-64-5
• Molecular Formula: C9H6O2
• Molecular Weight: 146.145
• Hs Code.: 2932.21
• European Community (EC) Number: 202-086-7
• ICSC Number: 1105
• NSC Number: 755852,8774
• UN Number: 2811
• UNII: A4VZ22K1WT
• DSSTox Substance ID: DTXSID7020348
• Nikkaji Number: J3.218B
• Wikipedia: Coumarin
• Wikidata: Q111812
• NCI Thesaurus Code: C397
• RXCUI: 2898
• Pharos Ligand ID: KV9F3XPABNSJ
• Metabolomics Workbench ID: 37669
• ChEMBL ID: CHEMBL6466
• Mol file: 91-64-5.mol

Synonyms:1,2-benzopyrone;5,6-benzo-alpha-pyrone;coumarin

Chemical Property of Coumarin

Chemical Property:

• Appearance/Colour: white crystals or crystalline powder
• Vapor Pressure: 0.01 mm Hg ( 47 °C)
• Melting Point: 68-73 °C(lit.)
• Refractive Index: 1.594
• Boiling Point: 297.999 °C at 760 mmHg
• Flash Point: 118.268 °C
• PSA: 30.21000
• Density: 1.248 g/cm³
• LogP: 1.79300
• Storage Temp.: Refrigerator
• Solubility.: 1.7g/l
• Water Solubility.: 1.7 g/L (20 ºC)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 146.036779430
• Heavy Atom Count: 11
• Complexity: 196
• Transport DOT Label: Poison

Purity/Quality:

99%, ^*data from raw suppliers

Coumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn
• Statements: 22-40-36/37/38-20/21/22-43
• Safety Statements: 36-36/37-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: C1=CC=C2C(=C1)C=CC(=O)O2
• Inhalation Risk: Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly.
• Effects of Short Term Exposure: The substance is irritating to the skin.
• Effects of Long Term Exposure: This substance is possibly carcinogenic to humans.
• Uses: used as a spice for the preparation of floral fragrances such as lavender, rosemary and rosemary, used in perfumes, cosmetics, soaps and detergents; used as flavoring agents for blending fragrances to make the aroma be lasting and unchanged; used as an electroplating additive to prevent the occurrence of pores in coating and can increase the brightness; as the flavor enhancer of printing ink and plastic; formerly used as spices and cigarettes spices, banned from 197; Since then, China had also prohibited it application in food; used as pharmaceutical raw materials. Coumarin, as a laser dye, has an output laser range be within the blue-green region (420 ~ 570nm), has high fluorescence quantum efficiency, such as 7-ethylamino-6-methyl-4-trifluoromethyl coumarin Lactone 307), the structure is as follows: coumarin is considered a blood thinner, it can also increase blood flow. Some sources cite anti-oxidant capacities, as well. It is a specific plant constituent and is what creates the fragrance of freshly mowed hay. Coumarin is found in such plants as cherries, lavender, licorice, and sweet clover. Pharmaceutic aid (flavor). Found in tonka beans, levender oil, woodruff, sweet clover. antineoplastic, antiinflammatory, antihyperglycaemic
• Description: Coumarin is a naturally occurring Benzopyrone compound. It is found in a large number of plants belonging to many different families including tonka beans, woodruff, lavender oil, cassia, melilot (sweet clover), and other plants. It is found in edible plants such as strawberries, cinnamon, peppermint, green tea, carrots, and celery, as well as in partially fermented tea, red wine, beer, and other foodstuffs. Concentrations range from 87 000 ppm in cassia and 40 000 ppm in cinnamon to 20 ppm in peppermint and 5 ppb in tangerines.

Technology Process of Coumarin

There total 297 articles about Coumarin 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: 100.0%

2-thiocoumarin (3986-98-9) → coumarin (91-64-5)

Guidance literature:

With sodium hydroxide; copper(l) chloride; In water; acetonitrile; at 25 ℃; for 0.25h;

DOI:10.1016/S0040-4039(00)83914-3

Reference yield: 95.0%

2-oxo-2H-chromene-3-carboxylic acid (531-81-7) → coumarin (91-64-5)

Guidance literature:

With pyridine; for 5h; Heating;

Reference yield: 94.0%

(E)-ethyl 2-hydroxycinnamate (3943-94-0,17041-46-2,6236-62-0) → coumarin (91-64-5)

Guidance literature:

With tris[2-phenylpyridinato-C₂,N]iridium(III); In acetonitrile; at 20 ℃; for 24h; Sealed tube; Inert atmosphere; Irradiation;

upstream raw materials:

methanol

o-Coumaric acid

methyl 2-hydroxycinnamate

4-chloro-2H-1-benzopyran-2-one

Downstream raw materials:

(E)-2-(3-hydroxy-3-methylbut-1-en-1-yl)phenol

4-methyl-2H-chromen-2-one

3-(2-hydroxyphenyl)propionic acid

3,4-dihydro-4-phenyl-2H-1-benzopyran-2-one

Refernces

• 1、 Song, Dan,Wang, Chao-Ming,Ye, Zhi-Peng,Xia, Peng-Ju,Deng, Zhi-Xiong,Xiao, Jun-An,Xiang, Hao-Yue,Yang, Hua. "Visible-light-driven, photoredox-catalyzed cascade of ortho-hydroxycinnamic esters to access 3-fluoroalkylated coumarins". . p. 7480 - 7487. Retrieved 2019.
• 2、 Rychlik, Michael. "Quantification of free coumarin and its liberation from glucosylated precursors by stable isotope dilution assays based on liquid chromatography-tandem mass spectrometry detection". . p. 796 - 801. Retrieved 2008.
• 3、 Hartman, Tomá?,Reisnerová, Martina,Chudoba, Josef,Svobodová, Eva,Archipowa, Nataliya,Kutta, Roger Jan,Cibulka, Radek. "Photocatalytic Oxidative [2+2] Cycloelimination Reactions with Flavinium Salts: Mechanistic Study and Influence of the Catalyst Structure". . p. 373 - 386. Retrieved 2021/02/01.
• 4、 Cervi, Aymeric,Vo, Yen,Chai, Christina L. L.,Banwell, Martin G.,Lan, Ping,Willis, Anthony C.. "Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes". . p. 178 - 198. Retrieved 2020/12/22.