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284785

Sigma-Aldrich

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

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
Beilstein:
3591068
EC Number:
244-838-7
MDL number:
MFCD00010500
UNSPSC Code:
12352005
PubChem Substance ID:
24857178
NACRES:
NA.22

Assay

98%

optical activity

[α]25/D +66°, c = 1 in chloroform

mp

152-154 °C (lit.)

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)

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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.

Signal Word

Warning

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 Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

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Enzymatic resolution of naproxen
Koul S, et al.
Tetrahedron Asymmetry, 14(16), 2459-2465 (2003)
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
Jiayang Li et al.
Journal of the American Chemical Society, 135(2), 542-545 (2012-11-10)
As systemically used therapeutics for treating acute or chronic pains or inflammations, nonsteroidal anti-inflammatory drugs (NSAIDs) also associate with the adverse gastrointestinal and renal effects and cardiovascular risks. Thus, it is beneficial to develop topical gels that selectively inhibit cyclooxygenase-2
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
Dong Qing Zhang et al.
Chemosphere, 91(1), 14-21 (2012-12-27)
Scirpus validus was grown hydroponically and exposed to the pharmaceuticals, carbamazepine and naproxen at concentrations of 0.5-2.0 mg L(-1) for an exposure duration of up to 21 d. By the end of experiment, carbamazepine elimination from the nutrient solution reached
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Chromatograms

application for HPLC

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