6-METHOXY-2-NAPHTHYLACETIC ACID Property

Melting point:

170-172°C

Boiling point:

408.8±20.0 °C(Predicted)

Density 

1.235

RTECS 

QJ1045000

storage temp. 

Sealed in dry,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

4.35±0.30(Predicted)

form 

Off-white solid.

color 

Off-White to Yellow

Safety

Hazard Codes 

Xn,Xi,N

Risk Statements 

22-36/37/38-37/38-41-50

Safety Statements 

26-39-61

HS Code 

2916399090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

6-METHOXY-2-NAPHTHYLACETIC ACID Chemical Properties,Usage,Production

Chemical Properties

Yellow Solid

Uses

A metabolite of Nabumetone. A competitive, non-selective COX inhibitor.

Definition

ChEBI: (6-methoxy-2-naphthyl)acetic acid is a monocarboxylic acid consisting of 2-naphthylacetic acid having a methoxy substituent at the 6-position. The active metabolite of the prodrug nabumetone. It has a role as an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, a drug metabolite and a xenobiotic metabolite. It is a monocarboxylic acid and a methoxynaphthalene. It is functionally related to a 2-naphthylacetic acid.

Biological Activity

6-methoxy naphthalene acetic acid is a competitive and non-selective cox inhibitor with ki values of 21 and 19 μm for ovine cox-1 and -2, respectively [1][2][3].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].6-methoxy naphthalene acetic acid (6-mna) is a competitive and non-selective cox inhibitor with ki values of 21 and 19 μm for ovine cox-1 and -2, respectively [1][2]. 6-mna is a metabolite of nebumetome. 6-mna inhibited human recombinant cox-1 and -2 with ic50 values of 70 and 20 μm, respectively [1].

References

[1]. barnett j, chow j, ives d, et al. purification, characterization and selective inhibition of human prostaglandin g/h synthase 1 and 2 expressed in the baculovirus system. biochim biophys acta. 1994 nov 16;1209(1):130-9.
[2]. 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.
[3]. laneuville o1, breuer dk, dewitt dl, et al. differential inhibition of human prostaglandin endoperoxide h synthases-1 and -2 by nonsteroidal anti-inflammatory drugs. j pharmacol exp ther. 1994 nov;271(2):927-34.