Synonym
Xylocoumarol; BS 7173-D; Xilocumarol.
IUPAC/Chemical Name
4-Hydroxy-3-(3,5-xylyl)coumarin
InChi Key
MEGNNNHOKFVHGC-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H14O3/c1-10-7-11(2)9-12(8-10)15-16(18)13-5-3-4-6-14(13)20-17(15)19/h3-9,18H,1-2H3
SMILES Code
O=C1OC2=C(C=CC=C2)C(O)=C1C3=CC(C)=CC(C)=C3
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
266.30
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Rayar AM, Lagarde N, Martin F, Blanchard F, Liagre B, Ferroud C, Zagury JF, Montes M, Sylla-Iyarreta Veitía M. New selective cyclooxygenase-2 inhibitors from cyclocoumarol: Synthesis, characterization, biological evaluation and molecular modeling. Eur J Med Chem. 2018 Feb 25;146:577-587. doi: 10.1016/j.ejmech.2018.01.054. Epub 2018 Jan 31. PubMed PMID: 29407982.
2: He M, Korzekwa KR, Jones JP, Rettie AE, Trager WF. Structural forms of phenprocoumon and warfarin that are metabolized at the active site of CYP2C9. Arch Biochem Biophys. 1999 Dec 1;372(1):16-28. PubMed PMID: 10562412.
3: Maurer HH, Arlt JW. Detection of 4-hydroxycoumarin anticoagulants and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation. J Chromatogr B Biomed Sci Appl. 1998 Sep 4;714(2):181-95. PubMed PMID: 9766858.
4: Bourinbaiar AS, Tan X, Nagorny R. Inhibitory effect of coumarins on HIV-1 replication and cell-mediated or cell-free viral transmission. Acta Virol. 1993 Aug;37(4):241-50. PubMed PMID: 7905238.
5: Heimark LD, Trager WF. Stereoselective metabolism of conformational analogues of warfarin by beta-naphthoflavone-inducible cytochrome P-450. J Med Chem. 1985 Apr;28(4):503-6. PubMed PMID: 3981543.
6: Heimark LD, Trager WF. The preferred solution conformation of warfarin at the active site of cytochrome P-450 based on the CD spectra in octanol/water model system. J Med Chem. 1984 Aug;27(8):1092-5. PubMed PMID: 6747992.
7: BRUNTON L, LOWENSTEIN L, SHAPIRO L. Some experience with the anticoagulant cyclocumarol. Can Med Assoc J. 1955 Sep 1;73(5):392-5. PubMed PMID: 13250469; PubMed Central PMCID: PMC1826335.
8: MARION P, COLPRON G, LONG LA. [Study of cyclocumarol, its clinical aspects and its depressive action on prothrombin and on proconvertin]. Union Med Can. 1955 Apr;84(4):426-30. French. PubMed PMID: 14386612.
9: NEW and nonofficial remedies: cyclocumarol. J Am Med Assoc. 1952 Mar 15;148(11):939. PubMed PMID: 14897693.
10: SHAPIRO S. The hypoprothrombinemia-inducing activity of Link's compound 63 (methopyranorin). Acta Haematol. 1951 Sep;6(3):129-40. PubMed PMID: 14877466.