| Identification | Back Directory | [Name]
2-VALERYLOXYBENZOIC ACID | [CAS]
64206-54-8 | [Synonyms]
VSA
VALERYL SALICYLATE
VALEROYL SALICYLATE
VALERYLSALICYLIC ACID
salicylicacid,valerate
2-VALERYLOXYBENZOIC ACID
WJHZBTMHUNVIKC-UHFFFAOYSA-N
2-[(1-OXOPENTYL)OXY]-BENZOIC ACID
Benzoic acid, 2-[(1-oxopentyl)oxy]-
2-Valeryloxybenzoic acid, Valerylsalicylic acid, vsa | [Molecular Formula]
C12H14O4 | [MDL Number]
MFCD00041466 | [MOL File]
64206-54-8.mol | [Molecular Weight]
222.24 |
| Chemical Properties | Back Directory | [Melting point ]
86-87 °C(lit.) | [Boiling point ]
357.6±25.0 °C(Predicted) | [density ]
1.175±0.06 g/cm3(Predicted) | [storage temp. ]
Room temperature | [solubility ]
DMSO: 24 mL/mL | [form ]
A crystalline solid | [pka]
3.01±0.36(Predicted) | [color ]
white |
| Hazard Information | Back Directory | [Uses]
Valeryl salicylate is a selective inhibitor of Cox-1. | [Definition]
ChEBI: A valerate ester that is salicylic acid in which the phenolic hydrogen is replaced by a valeryl (pentanoyl) group. | [Biological Activity]
valeroyl salicylate is an irreversible and selective inhibitor of cyclooxygenase-1 (cox-1) with ic50 values of 0.8 and 15 mm for ovine cox-1 and -2, respectively [1].cyclooxygenase (cox), also known as prostaglandin-endoperoxide synthase (ptgs, pghs), is an enzyme responsible for formation of prostanoids, including thromboxane and prostaglandins such as prostacyclin. cox-1 is the constitutive isoform and is mainly responsible for the synthesis of cytoprotective prostaglandins in the gastrointestinal tract (gi) and of the proaggregatory thromboxane in blood platelets. cox-2 is inducible and short-lived that is stimulated by endotoxin, cytokines, and mitogens. cox-2 plays important roles in prostaglandin biosynthesis in inflammatory cells the central nervous system [1][2].valeroyl salicylate is an irreversible and selective inhibitor of cyclooxygenase-1 (cox-1) with ic50 values of 0.8 and 15 mm for ovine cox-1 and -2, respectively. in cos-1 cells expressing either cox-1 or -2, 500 μm of valeroyl salicylate inhibited human cox-1 and -2 by 85% and 15%, respectively. the half-lives for inactivation of human recombinant cox-1 in the presence of 500 μm valeroyl salicylate was 12 minutes [2]. | [References]
[1]. johnson jl, wimsatt j, buckel sd, et al. purification and characterization of prostaglandin h synthase-2 from sheep placental cotyledons. arch biochem biophys. 1995 dec 1;324(1):26-34.
[2]. bhattacharyya dk, lecomte m, dunn j, et al. selective inhibition of prostaglandin endoperoxide synthase-1 (cyclooxygenase-1) by valerylsalicylic acid. arch biochem biophys. 1995 feb 20;317(1):19-24. |
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