4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one

• ChemBase ID: 108455
• Molecular Formular: C19H16O4
• Molecular Mass: 308.32794
• Monoisotopic Mass: 308.10485899
• SMILES: CC(=O)CC(c1ccccc1)c1c(O)c2c(oc1=O)cccc2
• Canonical SMILES: CC(=O)CC(c1c(=O)oc2c(c1O)cccc2)c1ccccc1
• InChI: InChI=1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3
• InChIKey: PJVWKTKQMONHTI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one
• IUPAC Traditional name: warfarin; 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one
• Synonyms: DL-3-(α-ACETONYLBENZYL)-4-HYDROXYCOUMARIN; 4-Hydroxy-3-(3-oxo-1-phenyl-butyl)-2H-1-benzopyran-2-one; 3-(α-Acetonylbenzyl-4-hydroxy-coumarin; Warf compound 42; Rodex; Sakarat X; Warfotox; Warfarin; DL-3-(α-ACETONYLBENZYL)-4-HYDROXYCOUMARIN,TECH; Warfarin™; 4-Hydroxy-3-(3-oxo-1-phenylbutyl)coumarin; Coumafene; Aldocumar; Coumadin; Kumatox; Marevan; Panwarfin; Ratron; Vampirinip; Waran; Zoocoumarin; Warfarin; 4-羟基-3-(3-氧代-1-苯基丁基)-2H-1-苯并吡喃-2-酮; 杀鼠灵钠; 华法林™

Database IDs

• CAS Number: 81-81-2
• EC Number: 201-377-6
• MDL Number: MFCD00006854
• Beilstein Number: 8868198
• PubChem SID: 162094146; 24890636; 24869276; 24899091
• PubChem CID: 54678486

CALCULATED PROPERTIES

• Acid pKa: 6.330688
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.6849828
• LogD (pH = 7.4): 1.6473457
• Log P: 2.7447073
• Molar Refractivity: 86.8601 cm^3
• Polarizability: 33.339684 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dioxane; DMSO
• Apperance: White to Off-White Solid
• Melting Point: 151-153°C; 162-164 °C(lit.)

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: GN4550000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 61-48/25-52/53
• Safety Statements: 53-45-61
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360D-H372-H412
• GHS Precautionary statements: P201-P273-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Clotting factor sythesis inhibitor; Depletes clotting factor-IX; Depletes clotting factor-VII; Depletes clotting factor-X; Interferes withsynthesis of menadione-dependent clotting factors; Prothrombin depletor

Product Information

• Grade: analytical standard; PESTANAL®, analytical standard
• Packaging: ampule of 1000 mg
• Suitability: suitable for 1694 per US EPA
• Description: Rotamers
• Application(s): Anticoagulant; Orally active anticoagulant which depresses synthesis of vitamin K-dependent coagulation factors.; Used in treatment and prophylaxis of thromboembolic disorders
• Empirical Formula (Hill Notation): C19H16O4

DETAILS

MP Biomedicals - 05211609

MP Biomedicals Rare Chemical collection

MP Biomedicals - 05207422

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A2250

法律信息
Warfarin 商标 Wisconsin Alumni Research Foundation

Sigma Aldrich - 45706

Caution
Restricted to professional users. Attention - Avoid exposure - obtain special instructions before use.
Application
Warfarin is an anticoagulant commonly used in the prevention of thrombosis and thromboembolism. Its use is studied in stroke and pulmonary fibrosis patients among many others. It is used to study potential risks and interactions with other drugs and food1.
Biochem/physiol Actions
Warfarin consists of a racemic mixture of two active enantiomers, R- and S- forms. Warfarin is slower-acting than the common anticoagulant heparin. Warfarin inhibits the vitamin K-dependent synthesis of biologically active forms of the calcium-dependent clotting factors II, VII, IX and X. It inhibits regulatory factors protein C, protein S, and protein Z2.
Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH
Warfarin is a trademark of Wisconsin Alumni Research Foundation

Sigma Aldrich - PS104

Legal Information
Warfarin is a trademark of Wisconsin Alumni Research Foundation

Toronto Research Chemicals - W498500

Coumarin anticoagulant. Marketed as the racemate; the S-(-)-form is the more potent isomer. Anticoagulant.

REFERENCES

• Hagan, E.C., et al.: J. Am. Pharm. Assoc. Sci. Ed., 42, 379 (1953)
• Bell, R.G., et al.: Biochemistry, 11, 1959 (1953)
• Valente, J.E., et al.: J. Med. Chem., 20, 1489 (1953)
• Back, N., et al.: Pharmacol. Res. Commun., 10, 445, (1953)
• Babhair, S.A., et al.
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 327A, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1319C, (nmr)
• U.S. Pat., 1947, 2 427 578; CA, 42, 603, (synth)
• Bravic, G. et al., C. R. Hebd. Seances Acad. Sci. Ser. C, 1973, 277, 1215, (cryst struct)
• Valente, E.J. et al., Acta Cryst. B, 1975, 31, 954, (abs config)
• Valente, E.J. et al., J. Med. Chem., 1977, 21, 141; 231, (uv, pmr)
• Chan, K.K. et al., Tetrahedron, 1977, 33, 899, (cmr)
• Babhair, S.A. et al., Anal. Profiles Drug Subst., 1985, 14, 423, (rev, synth, pharmacol, anal)
• Sato, Y. et al., Chem. Pharm. Bull., 1985, 33, 4606, (resoln)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 5126
• Park, B.K., Biochem. Pharmacol., 1988, 37, 19, (rev, metab, props)
• Ivanov, I. et al., Arch. Pharm. (Weinheim, Ger.), 1990, 323, 521, (synth)
• Dangerous Prop. Ind. Mater. Rep., 1991, 11, 163, (rev)
• Pesticide Manual, 9th edn., 1991, No. 12320
• Agrochemicals Handbook, 3rd edn., Royal Society of Chemistry, 1992, A418
• Robinson, A. et al., Tet. Lett., 1996, 37, 8321, (synth)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 964
• Hayes, W.J. et al., Handbook of Pesticide Toxicology, (Eds. Hayes, W.J. et al), Academic Press, 1991, 3, 1291, (tox)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, WAT200; WAT209; WAT220