Merck
All Photos(2)

284785

Sigma-Aldrich

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

98%

Synonym(s):
(S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid, Naproxen
Linear Formula:
CH3OC10H6CH(CH3)CO2H
CAS Number:
Molecular Weight:
230.26
Beilstein:
3591068
EC Number:
MDL number:
PubChem Substance ID:
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

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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.

Packaging

5, 25 g in poly bottle

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Enzymatic resolution of naproxen
Koul S, et al.
Tetrahedron Asymmetry, 14(16), 2459-2465 (2003)
Chiral self-assembly of methyltin (IV)-naproxenates: Combining dative Sn--O bonds, secondary Sn? O interactions and C--H? O hydrogen bonding to make an inter-helical meander-shaped network and a cross-linked Z-shaped ribbon
Deak A and Tarkanyi G
Journal of Organometallic Chemistry, 691(8), 1693-1702 (2006)
Chiral organotin (IV) carboxylates complexes: Syntheses, characterization, and crystal structures with chiral (S)-(+)-6-methoxy-α-methyl-2-naphthaleneaceto acid ligand
Ma C, et al.
Journal of Organometallic Chemistry, 696(10), 2165-2171 (2011)
Development and validation of RP-HPLC methods for simultaneous estimation of naproxen and esomeprazole magnesium trihydrate in combined pharmaceutical formulation
Sojitra C and Rajput S
International Journal of Pharmacy and Pharmaceutical Sciences, 4(Suppl 3), 533-537 (2012)
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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