Coumarin
2H-Chromen-2-one · COUMARINE · 2H-1-BENZOPYRAN-2-ONE · CUMARIN · 1,2-BENZOPYRONE · CHROMEN-2-ONE · Kumarin · coumarin powder
Identifiers & Physical Properties
| CAS No. | 91-64-5 |
|---|---|
| Molecular formula | C9H6O2 |
| Average molar mass | 146.14 g/mol |
| Monoisotopic mass | 146.03677943 g/mol |
| SMILES | O=c1ccc2ccccc2o1 |
| InChIKey | ZYGHJZDHTFUPRJ-UHFFFAOYSA-N |
| PubChem CID | 323 |
| ChEMBL | CHEMBL6466 |
| ChEBI | CHEBI:28794 |
| EC No. | 202-086-7 |
| DTXSID | DTXSID7020348 |
Chemical & Physical Properties
| XLogP | 1.4 |
|---|---|
| Topological polar surface area | 26.3 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 0 |
| Heavy atoms | 11 |
| Formal charge | 0 |
| Complexity | 196 |
| Melting point | 68-73 °C (lit.) |
| Boiling point | 298 °C (lit.) |
| Density | 0.935 |
| Vapor pressure | 0.01 mm Hg ( 47 °C) |
| Refractive index | 1.5100 (estimate) |
| Flash point | 162 °C |
| Storage conditions | Store below +30°C. |
| Solubility | 1.7g/l1.7 g/L (20 ºC) |
| Physical state | Crystals or Crystalline Powder |
| Color | White |
| PH Range | Non' uorescence (9.5) to light green ' uorescence (10.5) |
| Odor | at 10.00 % in dipropylene glycol. sweet hay tonka new mown hay |
| Odor type | tonka |
| Biological source | synthetic |
| λmax | 275nm |
| Merck | 14,2562 |
| BRN | 383644 |
| Henry's law constant | 9.9×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Major applications | color filter, organic electroluminescent devices, liquid crystal displays, field emission displays, inks, nickel plating, detergents, deodorant for shoes, petroleum products, cigarettes, personal care products, cosmetics, sunscreen cream, perfumes, nucleic acid sequencing, antiinflammatory agent, treatment of cancer, neurotransmission disorders, bleeding disorders, cerebrovascular disease, thrombosis, hemorrhoids, rheumatic disease, arthritic disease, epilepsy, vaginitis, painkiller, teeth whitening agent, skin whitening agent, wound healing promoter |
| Cosmetics Ingredients Functions | PERFUMING |
| InChI | 1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H |
| InChIKey | ZYGHJZDHTFUPRJ-UHFFFAOYSA-N |
| SMILES | O=C1Oc2ccccc2C=C1 |
| LogP (partition coefficient) | 1.39 at 25℃ |
| Toxicology and Carcinogenesis | Toxicology and Carcinogenesis Studies of Coumarin (CASRN 91-64-5) in F344/N Rats and B6C3F1 Mice (Gavage Studies) |
| Substances Added to Food (formerly EAFUS) | COUMARIN--PROHIBITED |
| FDA 21 CFR | 189.130 |
| CAS DataBase Reference | 91-64-5(CAS DataBase Reference) |
| EWG's Food Scores | 4-7 |
| NCI Dictionary of Cancer Terms | coumarin |
| FDA UNII | A4VZ22K1WT |
| NCI Drug Dictionary | coumarin |
| IARC | 3 (Vol. Sup 7, 77) 2000 |
| NIST Chemistry Reference | Coumarin(91-64-5) |
| EPA Substance Registry System | Coumarin (91-64-5) |
| UNSPSC Code | 85151701 |
| NACRES | NA.25 |
| GHS pictogram | GHS06 |
| Signal word | Danger |
| GHS hazard statements | H301+H311-H317 |
| GHS precautionary statements | P261-P264-P270-P280-P301+P310-P302+P352+P312 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Faceshields, Gloves |
| Hazard symbols | Xn |
| Risk statements (R) | 22-40-36/37/38-20/21/22-43 |
| Safety statements (S) | 36-36/37-26 |
| UN transport number | UN 2811 6.1/PG 3 |
| Water hazard class (WGK) | 1 |
| RTECS number | GN4200000 |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1Acute Tox. 3 DermalAcute Tox. 3 OralSkin Sens. 1 |
| Packing group | III |
| Customs code | 29322010 |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Hazardous substances data | 91-64-5(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats, guinea pigs: 680, 202 mg/kg (Jenner) |
| REACH registrations | Active |
| Limited quantities | 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Faceshields, Gloves |
|---|---|
| Water hazard class (WGK) | 1 |
| TSCA inventory status | TSCA listed |
| RTECS number | GN4200000 |
| UN transport number | UN 2811 6.1/PG 3 |
| Customs code | 29322010 |
| Toxicity | LD50 orally in rats, guinea pigs: 680, 202 mg/kg (Jenner) |
| Risk statements (R) | 22-40-36/37/38-20/21/22-43 |
| Signal word | Danger |
| GHS pictogram | GHS06 |
| Hazard symbols | Xn |
| Safety statements (S) | 36-36/37-26 |
| Hazard class | 6.1Acute Tox. 3 DermalAcute Tox. 3 OralSkin Sens. 1 |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Packing group | III |
| GHS hazard statements | H301+H311-H317 |
| Limited quantities | 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
| REACH registrations | Active |
| GHS precautionary statements | P261-P264-P270-P280-P301+P310-P302+P352+P312 |
| Hazardous substances data | 91-64-5(Hazardous Substances Data) |
Applications & Uses
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:
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.
Occurrence
Found in many plants and essential oils such as cassia, melilot, orchid, lavender and balsam of Peru (Spth, 1937; Gildemeister & Hoffman, 1966).
Uses
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.
Uses
Pharmaceutic aid (flavor). Found in tonka beans, levender oil, woodruff, sweet clover.
Uses
antineoplastic, antiinflammatory, antihyperglycaemic
General Description
Colorless crystals, flakes or colorless to white powder with a pleasant fragrant vanilla odor and a bitter aromatic burning taste.
Preparation & Synthesis
Preparation
Coumarin is currently produced by Perkin synthesis from salicylaldehyde. In the presence of sodium acetate, salicylaldehyde reacts with acetic anhydride to produce coumarin and acetic acid. The reaction is carried out in the liquid phase at elevated temperature.A process for the production of coumarin from hexahydrocoumarin by dehydrogenation has also been elaborated.Since the odor of coumarin is relatively weak, strong-smelling by-products (e.g., vinylphenol) must be removed. Many purification methods have been reported and patented.