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Coumarin structure
Coumarin structure

Coumarin

Iupac Name:chromen-2-one
CAS No.:91-64-5
Molecular Weight:146.14274
Introduction: Colorless crystals, flakes or colorless to white powder with a pleasant fragrant vanilla odor and a bitter aromatic burning taste. View more+
1. Names and Identifiers
1.1 Name
Coumarin
1.2 Synonyms

1,2-BENZOPYRONE 2H-1-BENZOPYAN-2-ONE 2H-1-BENZOPYRAN-2-ONE 5,6-BENZO-2-PYRONE AKOS 212-75 chromen-2-one COUMARINE CUMARIN EINECS 202-086-7 Kumarin MFCD00006850 O-HYDROXYCINNAMIC ACID LACTONE Rattex TIMTEC-BB SBB000094 TONKA BEAN CAMPHOR

1.3 CAS No.
91-64-5
1.4 CID
323
1.5 EINECS(EC#)
202-086-7
1.6 Molecular Formula
C9H6O2 (isomer)
1.7 Inchi
InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
1.8 InChkey
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
1.9 Canonical Smiles
C1=CC=C2C(=C1)C=CC(=O)O2
1.10 Isomers Smiles
C1=CC=C2C(=C1)C=CC(=O)O2
2. Properties
3.1 Density
0.935
3.1 Melting point
68-71℃
3.1 Boiling point
298℃
3.1 Refractive index
1.594
3.1 Flash Point
162℃
3.1 Vapour pressure
0.01 mm Hg ( 47 °C)
3.1 Precise Quality
146.03700
3.1 PSA
30.21000
3.1 logP
1.79300
3.1 Solubility
1.7g/l
3.2 Λmax
275nm
3.3 Appearance
white crystalline solid
3.4 Color/Form
Powder
3.5 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
3.6 Decomposition
When heated to decomposition it emits acrid smoke and fumes.
3.7 Odor
Pleasant, fragrant odor resembling that of vanilla beans.
3.8 Water Solubility
1.7 g/L (20 oC)
3.9 Spectral Properties
MAX ABSORPTION (ALCOHOL): 274.5 NM (LOG E= 4.20); 312 NM (LOG E= 3.91)
IR: 270 (Sadtler Research Laboratories IR Grating Collection)
UV: 492 (Sadtler Research Laboratories Spectral Collection)
NMR: 225 (Varian Associates NMR Spectra Catalogue)
RAMAN: 130 (Sadtler Research Laboratories IR Grating collection)
13C NMR: 33 (Johnson and Jankowski, Carbon13 NMR Spectra, John Wiley & Sons, New York)
MASS: 71714 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 99 (Aldermaston Eight Peak Index of Mass Spectra UK)
3.10 Stability
Converted to a dimer on long exposure to light.
3.11 StorageTemp
Store below +30°C.
3. Use and Manufacturing
4.1 Definition
ChEBI: A chromenone having the keto group located at the 2-position.
4.2 Fire Hazard
Coumarin is combustible.
4.3 General Description
Colorless crystals, flakes or colorless to white powder with a pleasant fragrant vanilla odor and a bitter aromatic burning taste.
4.4 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.] Coumarin Preparation Products And Raw materials Raw materials
4.5 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.
4.6 Storage
Ambient temperatures.
4.7 Usage
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:
4. Safety and Handling
5.1 Symbol
GHS06
5.1 Hazard Codes
Xn
5.1 Signal Word
Danger
5.1 Risk Statements
R20/21/22;R36/37/38;R40
5.1 Safety Statements
S26;S36/37
5.1 Exposure Standards and Regulations
(a) Coumarin is the chemical 1,2-benzopyrone, C9H6O2. It is found in tonka beans and extract of tonka beans, among other natural sources, and is also synthesized. It has been used as a flavoring agent. (b) Food containing any added coumarin as such or as a constituent of tonka beans or tonka extract is deemed to be adulterated under the act, based upon an order published in the Federal Register of March 5, 1954 (19 FR 1239).
5.2 Packing Group
III
5.2 Octanol/Water Partition Coefficient
log Kow = 1.39
5.3 Other Preventative Measures
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
...Substitution of less irritating substances, ...redesign of operations...prevent contact, provision of a physical barrier against contact, proper washing facilities, work clothing and storage facilities, protective clothing, and barrier creams. Medical control... .
5.4 Hazard Class
6.1
5.4 Hazard Declaration
H301
5.4 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Incineration: Coumarin should be combined with paper or other flammable material. An alternate procedure is to dissolve the solid in a flammable solvent and spray the soln into the fire chamber.
5.5 RIDADR
50kg
5.5 FirePotential
SLIGHT, WHEN EXPOSED TO HEAT OR FLAME.
5.6 Caution Statement
P301 + P310
5.6 WGK Germany
1
5.6 RTECS
GN4200000
5.6 Safety
Hazard Codes:Xn
Risk Statements:22-40-36/37/38-20/21/22-43
22:Harmful if swallowed
40:Limited evidence of a carcinogenic effect
36/37/38:Irritating to eyes, respiratory system and skin
20/21/22:Harmful by inhalation, in contact with skin and if swallowed
43:May cause sensitization by skin contact
Safety Statements:36-36/37-26
36:Wear suitable protective clothing
36/37:Wear suitable protective clothing and gloves
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
RIDADR:UN 2811 6.1/PG 3
WGK Germany:1
HazardClass:6.1
PackingGroup:III
5.7 Specification

WHITE CRYSTALS OR CRYSTALLINE POWDER
usageEng:Pharmaceutic aid (flavor). Found in tonka beans, levender oil, woodruff, sweet clover.
Safety Statements:36-36/37-26
36:Wear suitable protective clothing
36/37:Wear suitable protective clothing and gloves
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
5.8 Toxicity
SYMPTOMS: Exposure to Coumarin may cause narcosis. It may also cause irritation and liver damage.
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Acute toxicity - Dermal, Category 3

Skin sensitization, Category 1

Acute toxicity - Inhalation, Category 3

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H301 Toxic if swallowed

H311 Toxic in contact with skin

H317 May cause an allergic skin reaction

H331 Toxic if inhaled

H411 Toxic to aquatic life with long lasting effects

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P271 Use only outdoors or in a well-ventilated area.

P273 Avoid release to the environment.

Response

P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

P361+P364 Take off immediately all contaminated clothing and wash it before reuse.

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P311 Call a POISON CENTER/doctor/\u2026

P391 Collect spillage.

Storage

P405 Store locked up.

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Merck
14,2562
9.1 BRN
383644
9.2 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.
9.3 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.
9.4 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:
9.5 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.
9.6 Chemical Properties
WHITE CRYSTALS OR CRYSTALLINE POWDER
9.7 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).
9.8 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.
9.9 Occurrence
Found in many plants and essential oils such as cassia, melilot, orchid, lavender and balsam of Peru (Sp?th, 1937; Gildemeister & Hoffman, 1966).
9.10 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.
9.11 Uses
Pharmaceutic aid (flavor). Found in tonka beans, levender oil, woodruff, sweet clover.
9.12 Uses
antineoplastic, antiinflammatory, antihyperglycaemic
9.13 Definition
ChEBI: A chromenone having the keto group located at the 2-position.
9.14 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.
9.15 Definition
A colorless crystalline compound with a pleasant odor, used in making perfumes. On hydrolysis with sodium hydroxide it forms coumarinic acid.
9.16 Aroma threshold values
Detection at 34 to 50 ppb; recognition, 250 ppb
9.17 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
9.18 General Description
Colorless crystals, flakes or colorless to white powder with a pleasant fragrant vanilla odor and a bitter aromatic burning taste.
9.19 Air & Water Reactions
Insoluble in water.
9.20 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).
9.21 Hazard
Toxic by ingestion; carcinogenic. Use in food products prohibited (FDA). Questionable carcinogen.
9.22 Health Hazard
SYMPTOMS: Exposure to Coumarin may cause narcosis. It may also cause irritation and liver damage.
9.23 Fire Hazard
Coumarin is combustible.
9.24 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.
9.25 Usage
Coumarin is an anticoagulant found in medicinal plants and used in phytomedicine for the treatment of venous diseases. This compound is found to have anti-tumor activities in several human cells lines.
9.26 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
9.27 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.
9.28 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.
9.29 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.
9.30 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.]
9.31 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.
10. Computational chemical data
  • Molecular Weight:146.14274g/mol
  • Molecular Formula:C9H6O2
  • Compound Is Canonicalized:True
  • XLogP3-AA:
  • Exact Mass:146.036779430
  • Monoisotopic Mass:146.036779430
  • Complexity:196
  • Rotatable Bond Count:0
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:2
  • Topological Polar Surface Area:26.3
  • Heavy Atom Count:11
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
11. Question & Answer
  • By applying the logic that phenol exists in enol form rather than keto form as it attains aromatic character, why is it not the case in coumarin?
  • I'm trying to figure out how to get the following reaction: (coumarin from eugenol) My immediate thoughts are O H " style="position: relative;" tabindex="0" id="MathJax-Element-2-Frame" class="MathJax" O H O H and O C H X 3 " style="position: relative;" tabindex="0" id="MathJax-Element-3-Frame" cla...
  • I came across this problem.. I thought that the Grignard reagent, PhMgBr, would cleave the lactone and then subsequently add to the ketone formed, giving an allylic tertiary alcohol after aqueous workup. Treatment with acid would then lead to intramolecular etherification, giving 2,2-diphenyl-2? H ...
  • 1. Introduction Phytochemicals are chemical compounds that occur naturally in the plant kingdom. Some are responsible for the organoleptic properties of the natural sources in which they are present. The term is generally used to refer to those chemicals that may have biological significance, for e...
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