COUMARIN

PRODUCT IDENTIFICATION

CAS NO. 91-64-5

COUMARIN

EINECS NO. 202-086-7
FORMULA C9H6O2
MOL WT. 146.15
H.S. CODE 2932.20.0500
TOXICITY Oral rat LD50: 293 mg/kg
SYNONYMS 1,2-Benzopyrone; 2-Oxo-1,2-benzopyran;
3-(2-Hydroxyphenyl)-delta-lactone-2-propenoic acid; Tonka bean camphor; Coumaric acid; cis-o-Coumaric acid lactone; 2H-1-Benzopyran-2-one; 2-Oxo-2H-1-benzopyran; cis-o-Coumarinic acid lactone; Benzo-alpha-pyrone; o-Hydroxycinnamic acid deltalactone; Coumarinic anhydride; o-Hydroxycinnamic acid lactone; o-Hydroxycinnamic lactone; Coumarinac lactone; 2H-Benzopyran-2-one; Benzo-2-pyrone; Benzopyran-2-one; 3-(2-Hydroxyphenyl)propenoic acid delta-lactone; Cumarin (German); Cumarina (Spanish); Coumarine (French);
SMILES c12c(ccc(o1)=O)cccc2

CLASSIFICATION

Anticoagulant,

EXTRA NOTES

Overall Carcinogenic Evaluation: Group 3

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white crystalline solid
MELTING POINT 69 - 73 C
BOILING POINT 298 C
SPECIFIC GRAVITY 0.935
SOLUBILITY IN WATER 1.7 g/l at 20 C
SOLVENT SOLUBILITY Soluble in ethanol, ether, chloroform
AUTOIGNITION  
pH  
VAPOR DENSITY 5.04
log P 1.39 (Octanol-water)
HENRY LAW CONSTANT 6.95E-06 (atm-m3/mole at 25 C)
OH RATE CONSTANT 1.32E-11 (cm3/molecule-sec at 25 C Atmospheric )
NFPA RATINGS Health: 2; Flammability: 0; Reactivity: 0 
FLASH POINT

150 C

STABILITY Stable under ordinary conditions

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking

Google Scholar Search

Drug Information Portal (U.S. National Library of Medicine) - Coumarin

PubChem Compound Summary - Coumarin

IPCS INCHEM -  Coumarin

Drug Bank -  Coumarin

KEGG (Kyoto Encyclopedia of Genes and Genomes) -  Coumarin

http://www.ebi.ac.uk/chebi/ -  Coumarin

http://www.ncbi.nlm.nih.gov/ -  Coumarin

Human Metabolome Database - Coumarin

Material Safety Data Sheet

http://doria17-kk.lib.helsinki.fi/
Coumarins owe their class name to ’coumarou’, the vernacular name of the tonka bean (Dipteryxodorata Willd., Fabaceae), from which coumarin itself was isolated in 1820 (BRUNETON, 1999). Coumarins belong to a group compounds known as the benzopyrones, all of which consist of a benzene ring joined to a pyrone. Coumarin and the other members of the coumarin family are benzo-α-pyrones, while the other main members of the benzopyrone group – the flavonoids –contain the γ-pyrone group (KEATING and O’KENNEDY, 1997). Coumarins may also be found in nature in combination with sugars, as glycosides. The coumarins can be roughly categorised as follows (MURRAY et al., 1982; see Fig. 1 for coumarins used in this study):·simple – these are the hydroxylated, alkoxylated and alkylated derivatives of the parent compound, coumarin, along with their glycosides. · furanocoumarins – these compounds consist of a five-membered furan ring attached to the coumarin nucleus, divided to linear and angular types with substituents at one or both of the remaining benzenoid positions. · pyranocoumarins – members of this group are analogous to the furanocoumarins, but contain a six-membered ring· coumarins substituted in the pyrone ring.

http://www.leffingwell.com/
Coumarin (2H-1-benzopyran-2-one) CAS No 91-64-5, is a crystalline white solid when seen pure, with a hay-like, sweet aromatic creamy odour with certain nutty shadings, much used in synthetic form as a fragrance chemical for perfumes and for fragranced soaps and detergents. Coumarin has a widespread occurrence in natural products too (see separate section below), and is a representative of the lactones (where a lactone is an ester group integrated into a carbon ring system).

http://arxiv.org/
Coumarin Dyes for Dye-Sensitized Solar Cells – A Long-Range-Corrected Density Functional Study

http://www.people.vcu.edu/
Biochemical Mechanism of Action: Coumarins are competitive inhibitors of vitamin K in the biosynthesis of prothrombin. The coagulation cascade relies on the conversion of prothrombin to thrombin in a very important step. However, this conversion depends on the presence of 10 g-carboxyglutamic acid (GLA) residues in the N-terminus of prothrombin. The multiple Gla residues form a binding site for Ca+2. Under normal circumstances 10 glutamic acid (Glu) residues of prothrombin are converted to Gla residues in a  post-translational modification. This post-translation modification is catalyzed by an enzymes vitamin K reductase and vitamin K epoxide reductase. Vitamin K is a co-factor in this conversion reaction. Thus it cycles between a reduced form and an epoxide form. Because of their structural similarity with vitamin K coumarins are thought to bind the enzymes, vitamin K reductase and vitamin K epoxide reductase, without facilitating the conversion of Glu residues of prothrombin to Gla. Thus prothrombin cannot be acted upon by factor Xa.

Local:
Coumarin (anhydride of o-coumaric acid) is white, crystalline lactone, obtainable naturally from several plants, such as tonka bean, lavender, sweet clover grass, strawberries, and cinnamon, or produced synthetically from an amino acid, phenylalanine. It is the principle of dicumarol which inhibits the hepatic synthesis of the vitamin K–dependent coagulation factors. Coumarin derivatives are used widely as anticoagulants (such as warfarin, -OH group is attached at 4 position) for the treatment of disorders in which there is excessive or undesirable clotting, such as thrombophlebitis, pulmonary embolism, and certain cardiac conditions. Coumarin derivatives are also used as rodenticides due to the property of causing fatal hemorrhaging. Coumarin has the characteristic odour like that of vanilla beans. It is used for the preparation of perfumes, soaps, flavourings. The coumarin nucleus (benzo-2-pyrone) is derived cinnamic acid (phenylacrylic skeleton) in the biosynthesis. Accordingly, the hydroxy group attached to coumarin structure at 7 position is important in biosynthesis pathway. Umbelliferone (7-hydroxy coumarin), esculetin (6,7-Dihydroxycoumarin), scopoletin (7-hydroxy-6-methoxycoumarin) are the widespread coumarins in nature. Synthetic 7-hydroxy coumarins are used to absorb ultraviolet rays in sunscreen cosmetics and used in the synthesis of drugs especially anticancer.

SALES SPECIFICATION

APPEARANCE

white crystalline solid
PURITY (G.C)

99.0% min

MELTING POINT

68 C min

TRANSPORTATION
PACKING  
HAZARD CLASS 6.1 (Packing group: III)
UN NO. 2811
SAFETY INFORMATION

HAZARD OVERVIEW

OSHA Hazards:Target Organ Effect, Toxic by ingestion. Target Organs: Liver, Kidney

GHS

 

SIGNAL WORD Danger

PICTOGRAMS

HAZARD STATEMENTS

H332:  Harmful if inhaled
H312:  Harmful in contact with skin
H302:  Harmful if swallowed
H319:  Causes serious eye irritation
H335:  May cause respiratory irritation
H351:  Suspected of causing cancer
H315:  Causes skin irritation

PRECAUTIONARY STATEMENTS

P280:  Wear protective gloves/protective clothing/eye protection/face protection
P281:  Use personal protective equipment as required
P302 + P352:  IF ON SKIN: Wash with plenty of soap and water
P261:  Avoid breathing dust/fume/gas/mist/vapors/spray
P301+ P312:  IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
P304 + P340:  IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P280:  Wear protective gloves/protective clothing/eye protection/face protection
P305 + P351 + P338:  IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing

EC DIRECTIVES

 

HAZARD CODES

XN Harmful

RISK PHRASES

20/21/22:  Harmful by inhalation, in contact with skin and if swallowed.
36/37/38:  Irritating to eyes, respiratory system and skin.
40:  Limited evidence of a carcinogenic effect.

SAFETY PHRASES

26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
36/37:  Wear suitable protective clothing and gloves.

PRICE INFORMATION