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284785

(S)-(+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid

Name: (<I>S</I>)-(+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid
Brand: ALDRICH

98%

Synonym(s):

Naproxen, (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid

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About This Item

Linear Formula:

CH₃OC₁₀H₆CH(CH₃)CO₂H

CAS Number:

22204-53-1

Molecular Weight:

230.26

UNSPSC Code:

12352005

NACRES:

NA.22

PubChem Substance ID:

24857178

EC Number:

244-838-7

Beilstein/REAXYS Number:

3591068

MDL number:

MFCD00010500

Assay:

98%

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Properties

assay

98%

optical activity

[α]25/D +66°, c = 1 in chloroform

mp

152-154 °C (lit.)

functional group

carboxylic acid

SMILES string

COc1ccc2cc(ccc2c1)[C@H](C)C(O)=O

InChI

1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1

InChI key

CMWTZPSULFXXJA-VIFPVBQESA-N

Gene Information

human ... MAPK14(1432), PTGS1(5742), PTGS2(5743)
rat ... Alox5(25290), Ptgs1(24693)

Description

General description

(S)-(+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid is a nonsteroidal anti-inflammatory molecule (NSAID). The (S)-enantiomer is 30 times more active than the (R)-enantiomer.

Application

(S)-(+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid can be used as a chiral ligand in the synthesis of organotin (IV) carboxylate metal complexes.

Biochem/physiol Actions

Non-selective cyclooxygenase (COX-1 and COX-2) inhibitor.

pictograms

GHS08,GHS07,GHS09

signalword

Warning

hcodes

H302,H315,H319,H335,H361fd,H411

pcodes

P202 - P273 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

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Enzymatic resolution of naproxen

Koul S, et al.

Tetrahedron Asymmetry, 14(16), 2459-2465 (2003)

Renal effects of selective cyclooxygenase-2 inhibition in normotensive salt-depleted subjects.

J Rossat et al.

Clinical pharmacology and therapeutics, 66(1), 76-84 (1999-08-03)

To compare the renal hemodynamic and tubular effects of celecoxib, a selective inhibitor of cyclooxygenase-2 (COX-2) to those of naproxen, a nonselective inhibitor of cyclooxygenases in salt-depleted subjects. Forty subjects were randomized into four parallel groups to receive 200 mg

A hydrogen sulfide-releasing cyclooxygenase inhibitor markedly accelerates recovery from experimental spinal cord injury.

Michela Campolo et al.

FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 27(11), 4489-4499 (2013-08-01)

Spinal cord trauma causes loss of motor function that is in part due to the ensuing inflammatory response. Hydrogen sulfide (H2S) is a potent, endogenous anti-inflammatory and neuroprotective substance that has been explored for use in the design of novel

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Global Trade Item Number

SKU	GTIN
284785-25G	04061826259504
284785-5G	04061826259511