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MilliporeSigma

284785

(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
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24857178
EC Number:
244-838-7
Beilstein/REAXYS Number:
3591068
MDL number:
MFCD00010500
Assay:
98%

Key Documents

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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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This Item
N8280PHR1040N-042
(S)-(+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid 98%

Sigma-Aldrich

284785

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

Naproxen meets USP testing specifications

Sigma-Aldrich

N8280

Naproxen

Naproxen Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1040

Naproxen

Naproxen solution 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®

Supelco

N-042

Naproxen solution

assay

98%

assay

-

assay

-

assay

-

Quality Level

200

Quality Level

200

Quality Level

300

Quality Level

300

mp

152-154 °C (lit.)

mp

152-154 °C (lit.)

mp

152-154 °C (lit.)

mp

-

optical activity

[α]25/D +66°, c = 1 in chloroform

optical activity

-

optical activity

-

optical activity

-

functional group

carboxylic acid

functional group

-

functional group

-

functional group

-

Gene Information

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

Gene Information

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

Gene Information

human ... PTGS1(5742), PTGS2(5743)

Gene Information

human ... PTGS1(5742), PTGS2(5743)

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.[1][2]

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.[3][4]

signalword

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

11 - Combustible Solids

wgk

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV6308
MKCR5972
MKCR2183
MKCN6736
MKCM9228

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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)
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)
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)
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
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