2-VALERYLOXYBENZOIC ACID
2-VALERYLOXYBENZOIC ACID Basic information
- Product Name:
- 2-VALERYLOXYBENZOIC ACID
- Synonyms:
-
- VSA
- VALERYL SALICYLATE
- VALERYLSALICYLIC ACID
- VALEROYL SALICYLATE
- salicylicacid,valerate
- 2-[(1-OXOPENTYL)OXY]-BENZOIC ACID
- 2-VALERYLOXYBENZOIC ACID
- WJHZBTMHUNVIKC-UHFFFAOYSA-N
- CAS:
- 64206-54-8
- MF:
- C12H14O4
- MW:
- 222.24
- Mol File:
- 64206-54-8.mol
2-VALERYLOXYBENZOIC ACID Chemical Properties
- 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
- pka
- 3.01±0.36(Predicted)
- form
- A crystalline solid
- color
- white
Safety Information
- Safety Statements
- 22-24/25
- WGK Germany
- 3
MSDS
- Language:English Provider:SigmaAldrich
2-VALERYLOXYBENZOIC ACID Usage And Synthesis
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].
in vivo
Valeryl salicylate (3, 10, 30 mg/kg; i.p.) shows anti-inflammatory effect in arachidonic acid (HY-109590)-induced ear oedema and Carrageenan (HY-125474)-induced paw oedema[1].
| Animal Model: | 25-30g, Swiss male mice (arachidonic acid induces Ear oedema)[1] |
| Dosage: | 1.5, 4.5, 15, 45 μg per ear |
| Administration: | |
| Result: | Showed the anti-inflammatory effect of topical administration and resulted in significant inhibition of the ear oedema of28, 36, 40, and 58% at 1.5, 4.5, 15, 45 μg per ear. |
| Animal Model: | 25-30g, Swiss male mice (Carrageenan-induced paw oedema)[1] |
| Dosage: | 3, 10, 30 mg/kg |
| Administration: | I.p. |
| Result: | Promoted a significant inhibition of 43.3, 53.3 and 66.6% at 3, 10, 30 mg/kg, respectively. |
IC 50
COX-1
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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