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:
Molecular Weight:
230.26
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
244-838-7
Beilstein/REAXYS Number:
3591068
MDL number:
Assay:
98%
Quality Level
assay
98%
optical activity
[α]25/D +66°, c = 1 in chloroform
mp
152-154 °C (lit.)
functional group
carboxylic acid
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)
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
WGK 3
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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