Brief Introduction Chemical Properties Uses
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Coumarin

Brief Introduction Chemical Properties Uses
Product Name
Coumarin
CAS No.
91-64-5
Chemical Name
Coumarin
Synonyms
2H-Chromen-2-one;COUMARINE;2H-1-BENZOPYRAN-2-ONE;CUMARIN;CHROMEN-2-ONE;1,2-BENZOPYRONE;Kumarin;coumarin powder;1-BENZOPYRAN-2-ONE;Rattex
CBNumber
CB3112168
Molecular Formula
C9H6O2
Formula Weight
146.14
MOL File
91-64-5.mol
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Coumarin Property

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 temp. 
Store below +30°C.
solubility 
1.7g/l
form 
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
Water Solubility 
1.7 g/L (20 ºC)
λmax
275nm
Merck 
14,2562
BRN 
383644
Major Application
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
InChIKey
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
LogP
1.39 at 25℃
CAS DataBase Reference
91-64-5(CAS DataBase Reference)
NIST Chemistry Reference
Coumarin(91-64-5)
IARC
3 (Vol. Sup 7, 77) 2000
EPA Substance Registry System
Coumarin (91-64-5)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H317May cause an allergic skin reaction

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.22316
Product name
Coumarin
Purity
for synthesis
Packaging
250g
Price
$78.6
Updated
2024/03/01
Sigma-Aldrich
Product number
8.22316
Product name
Coumarin
Purity
for synthesis
Packaging
1kg
Price
$245
Updated
2024/03/01
Sigma-Aldrich
Product number
72609
Product name
Coumarin
Purity
certified reference material, TraceCERT
Packaging
100mg
Price
$115
Updated
2024/03/01
Sigma-Aldrich
Product number
01260595
Product name
Coumarin
Purity
primary reference standard
Packaging
50mg
Price
$308
Updated
2024/03/01
Sigma-Aldrich
Product number
CRM40381
Product name
Coumarin solution
Purity
certified reference material, 2000?μg/mL in methanol, ampule of 1?mL
Packaging
1mL
Price
$192
Updated
2022/05/15
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Coumarin Chemical Properties,Usage,Production

Brief Introduction

It is also known as 1, 2-benzopyrone, cis ortho-caberillin, o-hydroxy cinnamon lactone and coumarin. It is contained in many natural plants in the form of glycosides and esters as vanillin instead of free-form. Coumarin will come out when certain plants are fermented and processed. Coumarin is found in the seeds of Dayton beans (Riccinechoides) in 1820 and is widely distributed in the plant kingdom, especially in plant species including Umbelliferae, Soybean, Rutaceae and Calyx. Seeds contain about 1.5% of the coumarin. In addition, coumarin is also contained in lavender oil, cinnamon oil and Peru balsam. Coumarin is spicy with sweet and lemongrass aroma. The aroma is emitted from the pink gum in the leaves of the fragrant beans, and the gum is made from the breakdown of the coumarin glycosides in the leaves. The aroma emitted by Sweet alfalfa is actually from the release of coumarin due to fermentation and decomposition during the stacking process. Precipitate from the ether appears as orthorhombic white pyramid or oblique sheet-like crystals with Lemongrass-type smell. It can subject to sublimation.

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.

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.

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.

Occurrence

Found in many plants and essential oils such as cassia, melilot, orchid, lavender and balsam of Peru (Sp?th, 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

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

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 4704, 1962 DOI: 10.1021/jo01059a541
Tetrahedron Letters, 27, p. 3911, 1986 DOI: 10.1016/S0040-4039(00)83914-3

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.

Flammability and Explosibility

Non flammable

Biological Activity

Oral anticoagulants can be prepared from compounds with coumarin as a base. Coumarin has been known for well over a century and, in addition to its use pharmaceutically, it is also an excellent odor-enhancing agent. However, because of its toxicity, it is not permitted in food products in the United States (Food and Drug Administration). One commercial drug is 3-(alpha-acetonyl-4-nitrobenzyl)- 4-hydroxycoumarin. This drug reduces the concentration of prothrombin in the blood and increases the prothrombin time by inhibiting the formation of prothrombin in the liver. The drug also interferes with the production of factors VII, IX, and X, so that their concentration in the blood is lowered during therapy. The inhibition of prothrombin involves interference with the action of vitamin K, and it has been postulated that the drug competes with vitamin K for an enzyme essential for prothrombin synthesis. Another commercial drug is bis-hydroxy-coumarin, C19H12O6. The actions of this drug are similar to those just described.

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.

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.

Environmental Fate

Coumarin toxicity is a function of blood and target tissue levels of coumarin relative to the metabolic capacity of the target organ. Cellular toxicity results when the formation of the toxic moieties exceeds the capacity of the cell to detoxify. This can have significant impact when comparing dosing by gavage to dietary exposure.

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.]

Toxicity evaluation

Coumarin is readily biodegradable. Coumarin is unlikely to bind to soil. Coumarin does not bioaccumulate; the bioconcentration factor has been determined to be <10–40. Various environmental fate studies have shown that coumarin in the environment would biodegrade and be lost to volatilization. Losses resulting from photolysis may also occur.

Coumarin Preparation Products And Raw materials

Raw materials

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

Preparation Products

COUMARIN 7 Bromadiolone Dihydrocoumarin Benzofuran N,N-Dimethyl-1,4-phenylenediamine
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Americas 1 Argentina 1 Australia 1 Belgium 2 Brazil 4 Canada 4 China 528 Czech 2 Czech Republic 1 Egypt 1 Europe 4 France 6 Germany 11 India 73 Italy 2 Japan 9 Mexico 2 Norway 1 Poland 1 Russia 1 Singapore 1 Slovakia 1 South Africa 1 South Korea 2 Spain 4 Sweden 1 Switzerland 5 The Netherlands 1 Ukraine 2 United Kingdom 28 United States 76 USA 1 Vietnam 1 Global 779
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View Lastest Price from Coumarin manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Coumarin 91-64-5
Price
US $120.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-27
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Coumarin 91-64-5
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-01-16
Changsha Staherb Natural Ingredients Co., Ltd.
Product
Coumarin 91-64-5
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
≥98% HPLC
Supply Ability
1000kg
Release date
2022-10-19

91-64-5, CoumarinRelated Search:

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  • 2H-1-Benzopyran, 2-oxo-
  • 2h-benzo(b)pyran-2-one
  • 2H-Benzo[b]pyran-2-one
  • 2H-Chromen-2-one
  • 2-Oxo-1,2-benzopyran
  • 2-oxo-2h-1-benzopyra
  • 2-Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactone
  • 2-propenoicacid,3-(2-hydroxyphenyl)-delta-lactone
  • 3-(2-hydroxyphenyl)-2-propenoicacidelta-lactone
  • 5,6-benzo-alpha-pyrone
  • Benzo-alpha-pyrone
  • Cinnamic acid, o-hydroxy-, delta-lactone
  • cis-o-coumaricacidanhydride
  • coumariniclactone
  • Kumarin
  • NCI C07103
  • ncic07103
  • o-coumaricacidlactone
  • o-Hydroxycinnamic lactone
  • o-hydroxy-cinnamicacidelta-lactone
  • o-hydroxycinnamiclactone
  • o-Hydroxyzimtsaure-lacton
  • Rattex
  • cis-O-Coumarinic acid lactoneCoumarinic acid lactone Tonka bean camphor
  • COUMARINE
  • CUMARIN
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  • COUMARIN JAPAN
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