3-(ALPHA-ACETONYLBENZYL)-4-HYDROXYCOUMARIN (WARFARIN)

WARFARIN

PRODUCT IDENTIFICATION

CAS NO.

81-81-2; 5543-56-6; 56573-89-8

WARFARIN

EINECS NO. 201-377-6

FORMULA C₁₉H₁₆O₄

MOL WT. 308.33

H.S. CODE

2932.29

TOXICITY

DERIVATION

SYNONYMS 3-(alpha-acetonylbenzyl) -4 -hydroxycoumarin;

4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-Benzopyran-2-one; Coumadin; 3-(a-phenyl-b-acetylethyl)-4-hydroxycoumarin; 3-(1'-phenyl-2'-acetylethyl)-4- Hydroxycoumarin; 4-hydroxy-3-(3-oxo-1-phenylbutyl)-Benzopyran-2-one;

CLASSIFICATION

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white to off-white crystalline powder

MELTING POINT 161 C

BOILING POINT

SPECIFIC GRAVITY

SOLUBILITY IN WATER Insoluble (Soluble in acetone, alkalinesolutions )

VAPOR DENSITY

AUTOIGNITION

REFRACTIVE INDEX

NFPA RATINGS

FLASH POINT

STABILITY Stable under ordinary conditions

APPLICATIONS

Warfarin is a synthetic coumarin anticoagulant which inhibits the hepatic synthesis of the vitamin K–dependent coagulation factors. Its chemical designation is 3-(alpha-acetonylbenzyl) -4 -hydroxycoumarin; racemic mixture of the R and S enantiomers. It is also used as a rodenticide due to the property of causing fatal hemorrhaging. Its salts (sodium or potassium) of warfarin are administered orally, intravenously, or intramuscularly. Warfarin sodium is a white, odorless, crystalline powder; soluble in water, in alcohol; slightly soluble in chloroform and in ether.

Members of anticoagulant ingredient

Product	CAS RN
1-(2-Amino-3-phenyl-propanoyl)-N-[5-(diaminomethylideneamino)-1- oxo-pentan-2-yl]pyrrolidine-2-carboxamide	60503-05-1
1,2-Di(5-amidino-2-benzofuranyl)ethane	66639-67-6
1-Butyl-3-(6,7-dimethoxy-2-naphthylsulfonyl)amino-3-(3- guanidinopropyl)-2-pyrrolidinone hydrochloride	173440-64-7
2,3,5,6-Tetrachloro-4-pyridinol	2322-38-5
2-Hydroxychromone	22105-09-5
2-Isovalerylindane-1,3-dione	83-28-3
2-Methyl-2-tert-butyl-ketolactone	26687-80-9
3,4-Dihydroxyphenyllactic acid	23028-17-3
3-Phenyl-5,6-benzocoumarin	13759-56-3
4',5,6,7-Tetramethoxyflavone	1168-42-9
4-Acetylpyridine	1122-54-9
5,6-Benzocoumarin-3-carboxylic acid ethyl ester	734-88-3
5-Phenyl-3-(1-phenylpropyl)tetronic acid	69354-73-0
7-Amino-4-chloro-3-(3-isothiureidopropoxy)isocoumarin	113251-07-3
Abciximab	143653-53-6
Acenocoumarol	152-72-7
Ancrod	9046-56-4
Antistasin	110119-38-5
Antithrombin III	9000-94-6
Aprosulate sodium	123072-45-7
Argatroban	74863-84-6
Argatroban	141396-28-3
Bephedon	1174-99-8
Bivalirudin	128270-60-0
Breviscapine	116122-36-2
Brodifacoum	56073-10-0
Bromadiolone	28772-56-7
Bromindione	1146-98-1
Bufrudin	137879-02-8
Butolame	150748-23-5
Calophyllolid	548-27-6
Chlorazol fast pink	25255-10-1
Chlorophacinone	3691-35-8
Citrate phosphate dextrose	51404-37-6
Citric acid	77-92-9
Clocoumarol	35838-63-2
Clorindione	1146-99-2
Coumachlor	81-82-3
Coumarin	91-64-5
Coumetarol	4366-18-1
Cyclocumarol	518-20-7
Danaparoid Sodium	57459-72-0
Danaparoid	83513-48-8
Depogen	61954-97-0
Dermatan sulfate	24967-94-0
Desirudin	120993-53-5
Dextran 40	9004-54-0
Dextran sulfate	9042-14-2
Dextrose citric acid complex	13838-07-8
Dicumarol	66-76-2
Difenacoum	56073-07-5
Difethialone	104653-34-1
Diphacinone	82-66-6
Edetic acid	60-00-4
Efegatran	105806-65-3
Eleparon	37187-54-5
Etersalate	62992-61-4
Ethyl biscoumacetate	548-00-5
Ferulic acid	1135-24-6
Fidexaban	183305-24-0
Flocoumafen	90035-08-8
Fluindione	957-56-2
Fondaparinux	104993-28-4
Fucoidan	9072-19-9
Gabexate	39492-01-8
Glucuronyl glucosamine glycan sulfate	58915-48-3
Glycyl-prolyl-glycyl-glycine	13054-03-0
Hemovasal	61461-86-7
Heparin	9005-49-6
Heparin sodium	9041-08-1
Hexolame	110346-23-1
Isoeruboside B	72994-87-7
Isopropoxygermatrane	6068-14-0
Lamifiban	144412-49-7
Laminaran	9008-22-4
Lepirudin	138068-37-8
Lyapolate sodium	25053-27-4
Melagatran	159776-70-2
Moroxybrate	79990-42-4
N(alpha)-Tosyl-glycyl-3-amidinophenylalanine	133397-82-7
N(alpha)-Tosylglycyl-3-amidinophenylalanine methyl ester	133397-81-6
Nafamostat	81525-10-2
Nafamostat mesylate	82956-11-4
N-Benzoyl-L-isoleucyl-5-oxo-5-(1-piperidinyl)-L-norvalylglycyl- N-(4-nitrophenyl)-L-argininamide	67608-06-4
Nitrofarin	17298-36-1
N-Methylphenylalanyl-prolyl-arginine	162435-91-8
Omephine	151-88-2
Oxazidione	27591-42-0
Oxovinca	54341-01-4
Pentolame	150748-24-6
Pentosan sulfuric polyester	37300-21-3
Phenindione	83-12-5
Phenprocoumon	435-97-2
Phentolacin	7443-17-6
Phenylalanyl-prolyl-arginine	79338-56-0
Phepromaron	15620-34-5
Phlebex	37317-65-0
Pindone	83-26-1
Plumbagin	481-42-5
Poly(anetholesulfonic acid)	63589-56-0
Prolame	99876-41-2
Protocatechualdehyde	139-85-5
Raparin	139352-36-6
Razaxaban Hydrochloride	405940-76-3
Salvianolic acid A	96574-01-5
Silatrane	283-60-3
Sodium amylosulfate	9010-01-9
Sodium Citrate	68-04-2
Streptoverticillium anticoagulant protein	155775-04-5
Tanshinone I	568-73-0
tert-Butyloxycarbonyl-phenylalanyl-prolyl-arginal	69201-89-4
Tetrathionic acid	13760-29-7
Thrombin aptamer	145563-68-4
Thrombolytin	9049-24-5
Tifacogin	148883-56-1
Tioclomarol	22619-35-8
Tocopherylquinone	7559-04-8
Troxerutin	7085-55-4
Troxevasin	84932-19-4
Warfarin sodium	129-06-6
Warfarin	81-81-2
Ximelagatran	192939-46-1
(1-4)-2-Amino-2-deoxy-beta-glucopyranuronan	60182-07-2
(1-4)-2-Deoxy-2-sulfoamino-beta-D-glucopyranuronan	76081-95-3
(1-6)-Mannopyranan sulfate	136331-89-0
-(4-((1-Acetimidoyl-3-pyrrolidinyl)oxy)phenyl)-3-(7-amidino-2-naphthyl) propanoic acid hydrocloride pentahydrate	155204-81-2
(S-(R',R'))-N-(4-((aminoiminomethyl)amino)-1-formylbutyl)-1- (1-oxo-3-phenylpropyl)- 2-pyrrolidinecarboxamide	146763-81-7

SALES SPECIFICATION

APPEARANCE

white to off-white crystalline powder

ASSAY

98.0% min

LOSS ON DRYING

1.0% max

TRANSPORTATION

PACKING

HAZARD CLASS 6.1 (Packing group: I)

UN NO. 3027

OTHER INFORMATION

Hazard Symbols: XN, Risk Phrases: 22/36/38, Safety Phrases: 24/25

GENERAL DESCRIPTION OF COUMARIN

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.