26159-36-4

Basic information

• Product Name: Naproxol
• Synonyms: Naproxol;(S)-2-(6-Methoxy-2-naphtyl)-1-propanol;[S,(-)]-6-Methoxy-β-methyl-2-naphthaleneethanol;RS-4034;(S)-2-(6-methoxy-naphthalen-2-yl)propan-1-ol;6-Methoxy-2-(2-methylhydroxyethyl)naphthalene
• CAS NO: 26159-36-4
• Molecular Formula: C₁₄H₁₆O₂
• Molecular Weight: 216.278
• Mol File: 26159-36-4.mol

Chemical Properties

• Melting Point: 87 °C
• Boiling Point: 362.9°Cat760mmHg
• Flash Point: 162.6°C
• Appearance: /
• Density: 1.108g/cm³
• Vapor Pressure: 6.67E-06mmHg at 25°C
• Refractive Index: 1.597
• PKA: 14.75±0.10(Predicted)
• CAS DataBase Reference: Naproxol(CAS DataBase Reference)
• NIST Chemistry Reference: Naproxol(26159-36-4)
• EPA Substance Registry System: Naproxol(26159-36-4)

Safety Data

• Hazardous Substances Data: 26159-36-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Naproxol is used as an anti-inflammatory agent for reducing inflammation and pain associated with various conditions such as arthritis, tendonitis, and other musculoskeletal disorders. Its ability to inhibit cyclooxygenase (COX) enzymes helps in decreasing the production of prostaglandins, which are responsible for inflammation and pain.
Naproxol is used as an analgesic for alleviating mild to moderate pain, such as headaches, menstrual cramps, and dental pain. Its pain-relieving properties make it a popular choice for managing various types of discomfort.
Naproxol is used as an antipyretic to reduce fever and lower body temperature in cases of mild to moderate fever caused by infections or other inflammatory conditions.

InChI:InChI=1/C14H16O2/c1-10(9-15)11-3-4-13-8-14(16-2)6-5-12(13)7-11/h3-8,10,15H,9H2,1-2H3/t10-/m1/s1

Upstream product

• 960210-90-6 1-phenylethyl 2-(6-methoxynaphthalen-2-yl)propionate 
• 27602-75-1 2-(6-methoxy-2-naphthyl)propanal 
• 159990-32-6 (S)-2-(6-methoxy-2-naphthyl)-1,2-propanediol 

Downstream Products

• 22204-53-1 (2S)-2-(6-methoxy(2-naphthyl))propanoic acid 
• 23979-41-1 (R)-2-(6-methoxy-2-naphthyl)propionic acid 
• 1198163-33-5 C₄₀H₃₈BrO₃P 

Relevant articles and documents

Chemoenzymatic synthesis of (2S)-2-arylpropanols through a dynamic kinetic resolution of 2-arylpropanals with alcohol dehydrogenases

We applied Horse Liver Alcohol Dehydrogenase (HLADH) to the enantioselective synthesis of six (2S)-2-arylpropanols, useful intermediates in the synthesis of Profens. The influence of substrate structure and reaction conditions on yields and enantioselectivity were investigated. The high yields and high enantioselectivity towards the (S)-enantiomer obtained in the bioreduction of 2-arylpropionic aldehydes, clearly indicate the achievement of a DKR process through a combination of an enzyme-catalyzed kinetic reduction with a chemical base-catalyzed racemization of the unreacted aldehydes. The racemization step is represented by the keto-enol equilibrium of the aldehyde and can be controlled by modulating pH and reaction conditions.

Parallel kinetic resolution of 1-phenylethanol using quasi-enantiomeric active esters

The parallel kinetic resolution of racemic 1-phenylethanol using an equimolar combination of quasi-enantiomeric pentafluorophenyl esters is discussed. The levels of diastereoselectivity were excellent (>88% de) leading to separable quasi-enantiomeric esters in good yields. Georg Thieme Verlag Stuttgart.

Probing the parallel kinetic resolution of 1-phenylethanol using quasi-enantiomeric oxazolidinone adducts

The parallel kinetic resolution of racemic 1-phenylethanol using an equimolar combination of quasi-enantiomeric oxazolidinones is discussed. The levels of diastereoselectivity were high leading to separable quasi-enantiomeric esters in good yield.

Trichosporon beigelli esterase (TBE): A versatile esterase for the resolution of economically important racemates

A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphthyl)ethanol (E ～ 316), 1-(3,4-methylenedioxyphenyl) ethanol and pentanol (E ～ 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E ～ 340), 2-(benzylthio)propanoic acid (E ～ 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2- naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2- naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies.

A modification of the asymmetric dihydroxylation approach to the synthesis of (S)-2-arylpropanoic acids

Catalytic hydrogenolysis of (S)-2-phenyl-1-2-propanediol (2), prepared by an asymmetric dihydroxylation of α-methylstyrene (1) with AD-mix-α, over Pearlman's catalyst gave (S)-2-phenyl-1-propanol (3). This method was applied to the synthesis of optically active 2-arylpropanoic acid antiinflammatory agents, (S)-ibuprofen (8) and (S)-naproxen (13).