Coumarin

Product Name:

Coumarin

Synonyms:

High quality 98% Coumarin with cheap price 91-64-5;Coumarin solution;TIMTEC-BB SBB000094;O-HYDROXYCINNAMIC ACID LACTONE;TONKA BEAN CAMPHOR;5,6-BENZO-2-PYRONE;AKOS 212-75;2H-1-BENZOPYRAN-2-ONE

CAS:

91-64-5

MF:

C9H6O2

MW:

146.14

EINECS:

202-086-7

Mol File:

91-64-5.mol

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)

Fp 

162 °C

storage temp. 

Refrigerator

solubility 

1.7g/l

form 

Crystals or Crystalline Powder

color 

White

PH Range

Non' uorescence (9.5) to light green ' uorescence (10.5)

Water Solubility 

1.7 g/L (20 ºC)

λmax

275nm

Merck 

14,2562

BRN 

383644

InChIKey

ZYGHJZDHTFUPRJ-UHFFFAOYSA-N

CAS DataBase Reference

91-64-5(CAS DataBase Reference)

NIST Chemistry Reference

Coumarin(91-64-5)

EPA Substance Registry System

Coumarin (91-64-5)

Hazard Codes 

Xn

Risk Statements 

22-40-36/37/38-20/21/22-43

Safety Statements 

36-36/37-26

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

1

RTECS 

GN4200000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29322010

Hazardous Substances Data

91-64-5(Hazardous Substances Data)

Toxicity

LD50 orally in rats, guinea pigs: 680, 202 mg/kg (Jenner)

Chemical Properties

Golden crystalline solid (fronds or rhomboid); it is sweet with black beans-like aroma, dried herbs aroma and fennel aroma. After dilution, it smells like dried straw, nuts and tobacco. It is insoluble in cold water but soluble in hot water, ethanol and chloroform, easily soluble in ether and benzene. The solubility in 100ml of water at 25 ℃ is only 0.01g; 13 7g in 100ml of ethanol at 16 ℃; 1g in 50 mL 100℃ hot water. Oral LD50: 680mg / kg for rat.

Chemical Properties

WHITE CRYSTALS OR CRYSTALLINE POWDER

Chemical Properties

Coumarin occurs widely in nature and determines, for example, the odor of woodruff. It forms white crystals (mp 70.6°C) with a hay-like, spicy odor. When treated with dilute alkali, coumarin is hydrolyzed to the corresponding coumarinic acid salt [(Z)-2-hydroxycinnamic acid]. Heating with concentrated alkali or with sodium ethanolate in ethanol results in the formation of o-coumaric acid salts [(E)-2-hydroxycinnamic acid]. 3,4-Dihydrocoumarin is obtained by catalytic hydrogenation, for example, with Raney nickel as a catalyst; octahydrocoumarin is obtained if hydrogenation is carried out at high temperature (200–250°C).

Chemical Properties

Coumarin has a sweet, fresh, hay-like, odor similar to vanilla seeds, and a burning taste with bitter undertone and nutlike flavor on dilution.

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

Definition

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

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.

Definition

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

Aroma threshold values

Detection at 34 to 50 ppb; recognition, 250 ppb

General Description

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

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Coumarin is sensitive to exposure to light. Coumarin is also sensitive to heat. Coumarin is incompatible with strong acids, strong bases and oxidizers. Coumarin is hydrolyzed by hot concentrated alkalis. Coumarin can be halogenated, nitrated and hydrogenated (in the presence of catalysts).

Hazard

Toxic by ingestion; carcinogenic. Use in food products prohibited (FDA). Questionable carcinogen.

Health Hazard

SYMPTOMS: Exposure to Coumarin may cause narcosis. It may also cause irritation and liver damage.

Fire Hazard

Coumarin is combustible.

Contact allergens

Coumarin is an aromatic lactone naturally occurring in Tonka beans and other plants. As a fragrance allergen, it has to be mentioned by name in cosmetics within the EU

Safety Profile

Poison by ingestion, intraperitoneal, and subcutaneous routes. Questionable carcinogen with experimental tumorigenic data. Experimental teratogenic effects. Mutation data reported. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and fumes. See also KETONES and ANHYDRIDES.

Chemical Synthesis

May be extracted from tonka beans; from salicylaldehyde and acetic anhydride in the presence of sodium acetate; also from o-cresol and carbonyl chloride followed by chlorination of the carbonate and fusion with a mixture of alkali acetate, acetic anhydride and a catalyst.

Purification Methods

Coumarin crystallises from ethanol or water and sublimes in vacuo at 43o [Srinivasan & deLevie J Phys Chem 91 2904 1987]. [Beilstein 17/10 V 143.]

Raw materials

Phosphorus oxychloride-->Sodium acetate trihydrate-->Salicylaldehyde-->o-Cresol-->SULPHOSUCCINIC ACID ESTER

Preparation Products

Benzofuran-->Bromadiolone-->N,N-Dimethyl-1,4-phenylenediamine-->COUMARIN 7-->Hydrocoumarin