(R)-2-(6-Methoxynaphthalen-2-yl)propanoic acid

Modify Date: 2025-08-24 09:21:27

(R)-2-(6-Methoxynaphthalen-2-yl)propanoic acid Structure
(R)-2-(6-Methoxynaphthalen-2-yl)propanoic acid structure
Common Name (R)-2-(6-Methoxynaphthalen-2-yl)propanoic acid
CAS Number 23979-41-1 Molecular Weight 230.259
Density 1.2±0.1 g/cm3 Boiling Point 403.9±20.0 °C at 760 mmHg
Molecular Formula C14H14O3 Melting Point 156-158ºC(lit.)
MSDS Chinese USA Flash Point 154.5±15.3 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of (R)-2-(6-Methoxynaphthalen-2-yl)propanoic acid


l-Naproxen ((R)-Naproxen) is an enantiomer of (S)-Naproxen. l-Naproxen can inhibit Cdc42 and Rac1 (EC50=96 μM and 212 μM, respectively), and show anti-tumor activity[1][2][3].

 Names

Name (r)-naproxen
Synonym More Synonyms

  Biological Activity

Description l-Naproxen ((R)-Naproxen) is an enantiomer of (S)-Naproxen. l-Naproxen can inhibit Cdc42 and Rac1 (EC50=96 μM and 212 μM, respectively), and show anti-tumor activity[1][2][3].
Related Catalog
In Vitro l-Naproxen (30-1000 μM; 2 h) inhibits Rac1 and Cdc42 activity selectively in cells[3]. l-Naproxen (0-300 μM; 48 h) inhibits migration of immortalized human ovarian cancer cells[3]. l-Naproxen (300 μM; 48 h) shows activity via a COX-independent mechanism[3]. Cell Viability Assay[3] Cell Line: HeLa cells Concentration: 30-1000 μM Incubation Time: 2 hour Result: Inhibited Rac1 and Cdc42 activity in a dose dependent manner with the EC50 values of 212 μM and 96 μM, respectively. Cell Migration Assay [3] Cell Line: OvCa429 and OvCa433 cells Concentration: 0-300 μM Incubation Time: 48 hour Result: Had a statistically significant inhibitory effect at 300 μM compared to untreated controls. Western Blot Analysis[3] Cell Line: OvCa433 cells Concentration: 300 μM Incubation Time: 48 hour Result: Exhibited higher levels of phosphorylated EGFR (pEGFR) and (pERK) compared to unstimulated controls.
References

[1]. Sonika Batra, et al. Enantiomeric Resolution of (RS)-Naproxen and Application of (S)- Naproxen in the Direct and Indirect Enantioseparation of Racemic Compounds by Liquid Chromatography: A Review. Curr Med Chem. 2017;24(8):758-780.

[2]. M Iwaki, et al. Stereoselective disposition of naproxen glucuronide in the rat. Drug Metab Dispos. 1995 Oct;23(10):1099-103.

[3]. Tudor I Oprea, et al. Novel Activities of Select NSAID R-Enantiomers against Rac1 and Cdc42 GTPases. PLoS One. 2015 Nov 11;10(11):e0142182.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 403.9±20.0 °C at 760 mmHg
Melting Point 156-158ºC(lit.)
Molecular Formula C14H14O3
Molecular Weight 230.259
Flash Point 154.5±15.3 °C
Exact Mass 230.094299
PSA 46.53000
LogP 3.00
Vapour Pressure 0.0±1.0 mmHg at 25°C
Index of Refraction 1.609
InChIKey CMWTZPSULFXXJA-SECBINFHSA-N
SMILES COc1ccc2cc(C(C)C(=O)O)ccc2c1
Storage condition 2-8°C

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn
Risk Phrases R22
Safety Phrases S36/S37
RIDADR UN 2811 6.1/PG 3
WGK Germany 3.0
HS Code 2918990090

 Synthetic Route

 Customs

HS Code 2918990090
Summary 2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

 Bioassay

View more

Name: Selectivity ratio of IC50 for inhibition of COX1 in ram seminal vesicles to IC50 for ...
Source: ChEMBL
Target: N/A
External Id: CHEMBL4428996
Name: Selectivity ratio of IC50 for COX2 (unknown origin) to IC50 for human recombinant AKR...
Source: ChEMBL
Target: N/A
External Id: CHEMBL4428997
Name: Binding affinity to human DHFR at 5 mM in presence of MFM by NMR spectroscopy
Source: ChEMBL
Target: Dihydrofolate reductase
External Id: CHEMBL4621661
Name: Chemical Probes of Kaposi's Sarcoma Herpes Virus Latent Infection
Source: ICCB-Longwood/NSRB Screening Facility, Harvard Medical School
Target: ORF 73 [Human herpesvirus 8 type M]
External Id: HMS791
Name: Inhibition of human recombinant AKR1C3 using S-tetralol as substrate assessed as redu...
Source: ChEMBL
Target: Aldo-keto reductase family 1 member C3
External Id: CHEMBL4428988
Name: Inhibition of human recombinant AKR1C2 using S-tetralol as substrate assessed as redu...
Source: ChEMBL
Target: Aldo-keto reductase family 1 member C2
External Id: CHEMBL4428989
Name: Selectivity ratio of IC50 for human recombinant AKR1C2 to IC50 for human recombinant ...
Source: ChEMBL
Target: N/A
External Id: CHEMBL4428990
Name: S-Tetralol Oxidation Assay from US Patent US11459295: "2-beta-naphthyl-acetic acid an...
Source: BindingDB
Target: N/A
External Id: BindingDB_10852_1
Name: Contractile Force Screening of Prestwick Library for asthma drug discovery
Source: 24015
Target: N/A
External Id: HSPH_Screening_CFS_001
Name: Inhibition of COX1 in ram seminal vesicles using arachidonic acid as substrate assess...
Source: ChEMBL
Target: Prostaglandin G/H synthase 1
External Id: CHEMBL4428992
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 Synonyms

piproxen
(+)-(S)-Naproxen
Anaprox
(R)-Naproxen
MFCD00870716
(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
(2R)-2-(6-Methoxy-2-naphthyl)propanoic acid
NAPRELAN
(2S)-2-(6-Methoxy-2-naphthyl)propanoic acid
(2S)-2-(6-Methoxynaphth-2-yl)propanoic acid
Naproxen
Apronax
EINECS 245-966-6
(+)-NAPROXEN
(S)-(+)-6-methoxy-α-methyl-2-naphthaleneacetic acid
(S)-(+)-Naproxen
ALEVE
(S)-naproxen
Naprosyn
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