(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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All Photos(2)

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

Product Name

(S)-(+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid, 98%

InChI key

CMWTZPSULFXXJA-VIFPVBQESA-N

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

SMILES string

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

assay

98%

optical activity

[α]25/D +66°, c = 1 in chloroform

mp

152-154 °C (lit.)

functional group

carboxylic acid

Quality Level

200

Gene Information

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

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Related Categories

Catalysts

Chiral Catalysts & Ligands

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.

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.

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)

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)

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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