Coumarin

HCID 323CAS 91-64-5

Basic information

Standard SMILES
O=c1ccc2ccccc2o1
InChIKey
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
Molecular formula
C9H6O2
Average molar mass
146.14 g/mol
Monoisotopic mass
146.03677943

Names & identifiers

Preferred name
Coumarin
IUPAC
chromen-2-one
English name
Coumarin
Molecular formula
C9H6O2
Molecular weight
146.14

Names & synonyms

coumarin91-64-52H-Chromen-2-one2H-1-Benzopyran-2-onecumarin1,2-Benzopyronechromen-2-oneTonka bean camphorRattexCoumarinic anhydrideCoumarinecis-o-Coumarinic acid lactone
Show more names
coumarin powder1-BENZOPYRAN-2-ONE
Coumarinic lactoneo-Hydroxycinnamic acid lactoneBenzo-alpha-pyrone5,6-Benzo-2-pyroneo-Hydroxycinnamic lactone2-Oxo-1,2-benzopyranKumarin2H-Benzo(b)pyran-2-one

Database identifiers

CAS
91-64-5
PubChem CID
323
DTXSID
DTXSID7020348
ChEMBL
CHEMBL6466
ChEBI
CHEBI:28794
UNII
A4VZ22K1WT
EC Number
202-086-7
Nikkaji
J3.218B

Properties

Computed structural properties

XLogP
1.4
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
11

Physicochemical properties

Melting point
68 · 68-73 °C (lit.)
Boiling point
298 °C · 298 °C (lit.)
Density
0.935 · 0.935
vapor pressure
0.01 mm · 0.01 mm Hg ( 47 °C)
refractive index
1.51 · 1.5100 (estimate)
Flash point
162 °C · 162 °C

Safety & regulation

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
1
tsca
TSCA listed
rtecs
GN4200000
ridadr
UN 2811 6.1/PG 3
hs_code
29322010

Chemistry & industry

Applications · 7 items

Usesused 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:

DescriptionCoumarin 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.

OccurrenceFound in many plants and essential oils such as cassia, melilot, orchid, lavender and balsam of Peru (Spth, 1937; Gildemeister & Hoffman, 1966).

Usescoumarin 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.

UsesPharmaceutic aid (flavor). Found in tonka beans, levender oil, woodruff, sweet clover.

Usesantineoplastic, antiinflammatory, antihyperglycaemic

General DescriptionColorless crystals, flakes or colorless to white powder with a pleasant fragrant vanilla odor and a bitter aromatic burning taste.

Preparation methods · 1 item

PreparationCoumarin 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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

Additional notes

DefinitionChEBI: A chromenone having the keto group located at the 2-position.

DefinitionA colorless crystalline compound with a pleasant odor, used in making perfumes. On hydrolysis with sodium hydroxide it forms coumarinic acid.

Related reactions

72 records

Linked notes

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