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284785

Sigma-Aldrich

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

98%

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Synonym(s):
Naproxen, (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid
Linear Formula:
CH3OC10H6CH(CH3)CO2H
CAS Number:
Molecular Weight:
230.26
Beilstein/REAXYS Number:
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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1 of 4

This Item
375160318035N0250000
vibrant-m

375160

(S)-(+)-Ibuprofen

vibrant-m

N0250000

Naproxen

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

-

mp

152-154 °C (lit.)

mp

49-53 °C (lit.)

mp

46-49 °C (lit.)

mp

152-154 °C (lit.)

optical activity

[α]25/D +66°, c = 1 in chloroform

optical activity

[α]20/D +59°, c = 2 in ethanol

optical activity

[α]18/D −72°, c = 1.6 in methanol

optical activity

-

Gene Information

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

Gene Information

human ... IL8RA(3577), PTGS1(5742), PTGS2(5743)

Gene Information

-

Gene Information

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

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.

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_germany

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)
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)
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)
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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