Related Searches: Coumarin, methyl coumarin, coumarin 47, Coumarin-3-carboxylic acid

Coumarin(CAS No. 91-64-5)

Coumarin C9H6O2 (cas 91-64-5) Molecular Structure

91-64-5 Structure

Identification and Related Records

【Name】
Coumarin
【Iupac name】
chromen-2-one
【CAS Registry number】
91-64-5
【Synonyms】
2H-1-Benzopyran-2-one
COUMARINE
1-Benzopyran-2-one
1,2-Benzopyrone
Chromen-2-one
O-Oxy-Cinnamic Lactone
【EINECS(EC#)】
202-086-7
【Molecular Formula】
C9H6O2 (Products with the same molecular formula)
【Molecular Weight】
146.14
【Inchi】
InChI=1/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
【InChIKey】
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
【Canonical SMILES】
C1=CC=C2C(=C1)C=CC(=O)O2
【MOL File】
91-64-5.mol

Chemical and Physical Properties

【Appearance】
white crystalline solid
【Density】
0.935
【Melting Point】
68-71℃
【Boiling Point】
298℃
【Vapour】
0.01 mm Hg ( 47 °C)
【Refractive Index】
1.594
【Flash Point】
162℃
【Water】
1.7 g/L (20℃)
【Solubilities】
Slightly soluble AUTOI
【Color/Form】
Orthorhombic, rectangular plates
Colorless, crystals, flakes, or powder
White crystals
【Storage temp】
Refrigerator
【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)
【Computed Properties】
Molecular Weight:146.14274 [g/mol]
Molecular Formula:C9H6O2
XLogP3:1.4
H-Bond Donor:0
H-Bond Acceptor:2
Rotatable Bond Count:0
Exact Mass:146.036779
MonoIsotopic Mass:146.036779
Topological Polar Surface Area:26.3
Heavy Atom Count:11
Formal Charge:0
Complexity:196
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Ring Count:2
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R20/21/22;R36/37/38;R40
【Safety Statements 】
S26;S36/37
【HazardClass】
6.1
【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
【PackingGroup 】
III
【Transport】
50kg
【Fire Potential】
SLIGHT, WHEN EXPOSED TO HEAT OR FLAME.
【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).
【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... .
【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
【Octanol/Water Partition Coefficient】
log Kow = 1.39
【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

...Made synthetically by heating salicylic aldehyde, sodium acetate, and acetic acid anhydride.
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.
Synthesis from salicyladehyde by the Perkin reaction. 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 temperatures.
Synthesis from o-cresol by the Raschig process. The hydroxyl group of o-cresol is protected by a carbonate or phosphate group, and the ester can be converted into the corresponding benzal chloride derivative by chlorination of the methyl group. Reaction of this intermediate with acetic anhydride yields o-acetylsalicylaldehyde and acetyl chloride. Ring closure of the aldehyde with acetic anhydride gives coumarin.
U.S. Production

(1990) >500 tons
【Usage】
Pharmaceutic aid (flavor). Found in tonka beans, levender oil, woodruff, sweet clover.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents that prevent clotting.
【Therapeutic Uses】
Pharmaceutic aid (flavor). Found in tonka beans, levender oil, woodruff, sweet clover.
【Biomedical Effects and Toxicity】
A species difference has been reported for the excretion of an oral dose of (14)C-coumarin. Within 4 days rats excreted 47% of the label in the urine and 39% in the feces, whereas rabbits excreted 92% in the urine and negligible amount in the feces.
Female rabbits dosed orally with 50 mg/kg of 3-14C-coumarin excreted over 80% of the label in the urine in 24 hours. No label was found in the expired air and only a small amount in the feces.
The reason for the considerable fecal excretion of (14)C /after oral administration of (14)C-coumarin/ in rat... may represent unabsorbed material.
Twenty-four hr after an IP dose to rats of... (14)C-coumarin, 38% had been excreted in the urine, 13% in the feces, 30% was excreted in the air as (14)C-carbon dioxide and 9% of the remainder was mainly present in the cecum.
Toxicokinetic studies in humans have demonstrated that coumarin is rapidly absorbed from the gastrointestinal tract after oral administration and extensively metabolized by the liver in the first pass, with only 2-6% reaching the systemic circulation intact.
... /Orally administered 3-(14)C-coumarin/ was rapidly absorbed in rats and widely distributed in serum, liver and kidney within 5 min, serum levels reaching maximum after about 30 min.
In man, 68-92% of an oral dose of coumarin was excreted in urine as 7-hydroxy coumarin and 1-6% as 2-hydroxyphenylacetic acid.
IV and oral administration revealed that all of coumarin is absorbed, however, only approximately 2-6% reaches systemic circulation in intact form. Fraction of unchanged drug reaching systemic circulation varied between 0 and 38% assuming liver blood flow rate of 1.53 L/min. [Ritschel WA et al; Int J Clin Pharmacol Biopharm 17 (3): 99 (1979)] PubMed Abstract
In blood, brain, heart, lung, muscle, and spleen, peak concentrations were observed 2.5 min after retroorbital injection of (14)C-labeled coumarin. Liver and kidney showed greatest accumulation with peak concentration being reached after 10 min. Blood and brain concentrations were equal.
Unmetabolized coumarin was found in all organs studied; 7-hydroxycoumarin (7-HC) was found in all organs but brain, and 7-HC glucuronide was found in all organs but brain and spleen. Apparently, coumarin crosses blood brain barrier but the metabolites do not.
The chicken excretes (14)C-labeled coumarin similar to man and suggests that this species is most appropriate model for coumarin pharmacodynamic studies applicable to humans. Analysis of urine from infused and control side kidneys indicate negative coumarin tubular secretion. [Cacini W et al; Arch Int Pharmacodyn Ther 243 (2): 197 (1980)] PubMed Abstract
The current studies were designed to determine the impact of oral gavage vs dietary administration on the pharmacokinetics and metabolism of coumarin in CD-1 and B6C3F1 mice and F344 rats. Following the administration of 200 mg/kg 14C-coumarin via oral gavage, lung C(max) values (total 14C-associated radioactivity) were five- and 37-fold greater than those resulting from a 50 mg/kg oral gavage dose or 1000 ppm in diet, respectively.
(14)C Coumarin (ca. 0.5 microCi per cell) absorption in skin was measured by using two vehicles: ethanol (15 microliters cm-2) and an oil-in-water emulsion (3 mg cm-2). Absorption was determined for 24 h by using flow-through diffusion cells (0.64 cm2, exposed skin) with a receptor fluid consisting of HEPES-buffered Hank's balanced salt solution (pH 7.4). Coumarin metabolism was determined by high-performance liquid chromatography methodology. In rat skin (n = 3), the percentages of applied dose absorbed after 24 h were 54.9 +/- 0.63 (mean +/- SEM) and 86.8 +/- 5.4 for the ethanol and emulsion vehicles, respectively, with ca. 5% remaining in skin. In human skin (n = 2), the percentages of applied dose absorbed after 24 h were 64.4 +/- 0.29 and 98.0 +/- 5.3 for the ethanol and emulsion vehicles, respectively, with ca. 1% remaining in skin. The extent of skin absorption was greater from the emulsion vehicle than from the ethanol vehicle in both human and rat skin. Coumarin rapidly penetrated both rat and human skin with > 75% and > 95%, respectively, of the absorbed dose found in the receptor fluid within 6 h. No evidence of coumarin metabolism was found in either skin or receptor fluid fractions. These studies indicate that coumarin absorption is significant in skin. Systemic coumarin absorption must be expected after dermal contact with coumarin-containing products.
The in vitro percutaneous absorption and skin metabolism of coumarin (1,2-benzopyrone) was studied in metabolically viable human, rat (F344), and mouse (CD1 and DBA/2) skin. Following application of (14C)coumarin (3.7 g/sq cm; 0.02% in ethanol) to unoccluded skin in flow-through diffusion cells of a skin absorption model (SAM), the absorption through the skin into the receptor fluid at 72 hr was rapid and extensive in all species, reaching (mean + or - SD) 50.4 + or - 9.1% of the applied dose in human, 51.3 + or - 7.3% in rat, and 44.9 + or - 13.5% in mouse. When the skin was occluded immediately after exposure, the extent of absorption at 72 hr was enhanced in all species. At 72 hr, substantial amounts of (14C)coumarin were found in unoccluded mouse skin (31.7 + or - 13.6%), with less in human (10.2 + or - 6.5%) and rat (12.7 + or - 5.0%) tissue. When occluded, the skin residues at 72 hr were 10.4 + or - 11.7% (mouse), 8.5 + or - 3.9% (human), and 11.9 + or - 7.5% (rat). The absorption of coumarin through rat skin into the receptor fluid over 72 hr was linearly related to the applied dose (r2= 0.998 unoccluded skin;r2= 0.999 occluded skin) over the dose range 3.7 to 378.7 g/sq cm. ... [Senam A.J. Beckley-Kartey, et al; Toxicology and Applied Pharmacology 145 (1): 34-42 (1997)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 140(SRC), determined from a log Kow of 1.39(2) and a regression-derived equation(3), indicates that coumarin is expected to have high mobility in soil(SRC). Volatilization of coumarin from moist soil surfaces is not expected to be an important fate process(SRC) based upon a Henry's Law constant of 9.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 9.8X10-4 mm Hg(4), and water solubility, 1,900 mg/l(5). Coumarin is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.8X10-4 mm Hg(4). Coumarin is confirmed to be biodegradable according to the standard test of the Japanese Ministry of Industry and Trade (MITI) that employs a mixed inoculum obtained from freshwater, soil, and sludge(6). Therefore, biodegradation may be an important environmental fate process in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 140(SRC), determined from a log Kow of 1.39(2) and a regression-derived equation(3), indicates that coumarin is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 9.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 9.8X10-4 mm Hg(3), and water solubility, 1,900 mg/l(4). According to a classification scheme(5), a BCF
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), coumarin, which has a vapor pressure of 9.8X10-4 mm Hg at 25 deg C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase coumarin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 29 hrs(SRC), calculated from its rate constant of 1.3X10-11 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Particulate-phase coumarin may be removed from the air by wet and dry deposition(SRC). 59.2% of the initial concn of coumarin was mineralized to CO2 when exposed to UV radiation >290 nm for 17 hr(4).

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