1-Benzopyran-2-on

Coumarin

HCID 323CAS 91-64-5

Grundinformationen

Standard-SMILES
O=c1ccc2ccccc2o1
InChIKey
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
Summenformel
C9H6O2
Durchschnittliche Molmasse
146,14 g/mol
Monoisotopische Masse
146,03677943

Namen und Bezeichner

Bevorzugter Name
Coumarin
IUPAC
chromen-2-one
Lokaler Name
1-Benzopyran-2-on
Englischer Name
Coumarin
Summenformel
C9H6O2
Molmasse
146.14

Namen und Synonyme

coumarin91-64-52H-Chromen-2-one2H-1-Benzopyran-2-onecumarin1,2-Benzopyronechromen-2-oneTonka bean camphorRattexCoumarinic anhydrideCoumarinecis-o-Coumarinic acid lactone
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,4
Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
0
Schwere Atome
11

Physikochemische Eigenschaften

Schmelzpunkt
68 · 68-73 °C (lit.)
Siedepunkt
298 °C · 298 °C (lit.)
Dichte
0.935 · 0.935
Dampfdruck
0.01 mm · 0.01 mm Hg ( 47 °C)
Brechungsindex
1.51 · 1.5100 (estimate)
Flammpunkt
162 °C · 162 °C

Sicherheit und Regulatorisches

Sicherheitsdaten

wgk
1
tsca
TSCA listed
ridadr
UN 2811 6.1/PG 3
hs_code
29322010
RTECS-Nr.
GN4200000
risk_code
22-40-36/37/38-20/21/22-43

Chemie und Industrie

Anwendungen · 3 Einträge

BeschreibungCoumarin 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).

Verwendencoumarin 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.

Darstellung · 1 Eintrag

synthetischeCoumarin 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.

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Ergänzende Hinweise

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

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