| Identification | Back Directory | [Name]
PHENPROCOUMON | [CAS]
435-97-2 | [Synonyms]
MARCUMA
Fencumar
Liquamar
Marcumar
Marcoumar
RO 1-4849
Falithiom
Falithrom
Phenprocumon
PHENPROCOUMON
Phenprocumone
Phenprocoumarol
Phenprocoumarole
Phenprocoumon (Marcumar)
PHENYLPROPYL-4-HYDROXYCOUMARIN
3-(1'-Phenyl-propyl)-4-oxycoumarin
3-(α-Ethylbenzyl)-4-hydroxycoumarin
3-(1-Phenylpropyl)-4-hydroxycoumarin
4-hydroxy-3-(1-phenylpropyl)coumarin
3-(alpha-Ethylbenzyl)-4-hydroxycoumarin
Coumarin, 3-(alpha-ethylbenzyl)-4-hydroxy-
4-Hydroxy-3-(1-phenylpropyl)-2H-chromen-2-on
4-Hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one
4-Hydroxy-2-oxo-3-(1-phenylpropyl)-2H-chromene
2-hydroxy-3-[(1S)-1-phenylpropyl]-4H-chroMen-4-one
4-Hydroxy-3-(1-phenylpropyl)-2H-1-benzopyran-2-one
2H-1-Benzopyran-2-one, 4-hydroxy-3-(1-phenylpropyl)- | [EINECS(EC#)]
207-108-9 | [Molecular Formula]
C18H16O3 | [MDL Number]
MFCD00865273 | [MOL File]
435-97-2.mol | [Molecular Weight]
280.32 |
| Chemical Properties | Back Directory | [Melting point ]
179-180° | [Boiling point ]
463.2±45.0 °C(Predicted) | [density ]
1.261±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
4.50±1.00(Predicted) | [color ]
White to Off-White | [EPA Substance Registry System]
Phenprocoumon (435-97-2) |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Originator]
Liquamar ,Organon ,US,1958 | [Uses]
Phenprocoumon is known for being an oral anti-coagulant. | [Definition]
ChEBI: A hydroxycoumarin that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenylpropyl group. | [Manufacturing Process]
8.3 parts by weight of powdered sodium in 300 parts by volume of benzene, 100 parts by weight of diethyl (1'-phenylpropyl)-malonate and 72 parts by weight of acetylsalicylic acid chloride are reacted together to form diethyl 1(o-acetoxybenzoy1)-1-(1'-phenylpropyl)malonate, which boils at 195°198°C/0.03 mm Hg.
10.3 parts of weight of diethyl 1-(o-acetoxybenzoyl)-1-(1'-phenylpropyl)malonate are dissolved in 60 parts by volume of absolute ether and to this solution are added portion. wise at 10°C, while stirring, 2.6 parts by weight of sodium methylate. The reaction mixture is stirred for 4 hours, whereupon it is poured into ice water. The ether solution is washed neutral with ice water. After having distilled off the ether, a thick oil consisting of 3-carbethoxy-3-(1'phenylpropyl)-4-oxo-dihydrocoumarinis obtained. This compound crystallized in butyl oxide and has a MP of 108°-109°C.
The 3-carbethoxy-3-(1'-phenylpropyl)-4-oxo-dihydrocoumarinmay be hydrolyzed and decarboxylated as follows. The crude product is heated to 85°C for 1/2 hour with 100 parts by volume of 5% aqueous sodium hydroxide, while agitating or stirring. To remove traces of undissolved oil, the cooled solution is treated with 1 part by weight of charcoal, whereupon it is filtrated and acidified to Congo reaction with dilute sulfuric acid. The 3-(1'phenylpropyl)-4-hydroxycoumarin formed is separated off and recrystallized in 80% ethanol, whereupon it melts at 178°-179°C according to US Patent 2,701,804. | [Brand name]
Liquamar (Organon). | [Therapeutic Function]
Anticoagulant | [Biological Activity]
Phenprocoumon is a coumarin derivative th at inhibits vitamin K and acts as a long acting oral anticoagulant. It was recently found to act synergistically with flutamide to modulate the stability of the androgen receptor (AR) and resensitize AR-mutant prostate cancer cells to flutamide. | [Synthesis]
Phenprocoumon, 3-(|á-ethylbenzyl)-4-hydroxycoumarin (24.1.14), is
synthesized by acylating sodium salts of diethyl ester (1-phenylpropyl)butyric acid with
acetylsalicylic acid chloride, which forms the compound 24.1.12, which upon reaction
with sodium ethoxide cyclizes to 3-(|á-ethylbenzyl)-2-carboethoxy-4-hydroxycoumarin
(24.1.13). Alkaline hydrolysis of this product and further decarboxylation gives phenprocoumon(24.1.14).
| [storage]
Store at -20°C |
|
| Company Name: |
LGM Pharma
|
| Tel: |
1-(800)-881-8210 |
| Website: |
www.lgmpharma.com |
|