614-03-9

Basic information

• Product Name: L -PHENYLEPHRINE
• Synonyms: (S)-3-hydroxy-alpha-[(methylamino)methyl]benzyl alcohol;L-Phenylephrinefreebase;Benzenemethanol, 3-hydroxy-a-[(methylamino)methyl]-, (aS)- (9CI);Benzenemethanol, 3-hydroxy-a-[(methylamino)methyl]-, (S)-;d-Phenylephrine;[S,(+)]-m-Hydroxy-α-[(methylamino)methyl]benzyl alcohol;3-[(S)-1-Hydroxy-2-(methylamino)ethyl]phenol;3-[(1S)-1-hydroxy-2-(methylamino)ethyl]phenol
• CAS NO: 614-03-9
• Molecular Formula: C₉H₁₃NO₂
• Molecular Weight: 167.20502
• EINECS: 210-367-0
• Mol File: 614-03-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 341.1°C at 760 mmHg
• Flash Point: 163.4°C
• Appearance: /
• Density: 1.159g/cm³
• Vapor Pressure: 3.18E-05mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: L -PHENYLEPHRINE(CAS DataBase Reference)
• NIST Chemistry Reference: L -PHENYLEPHRINE(614-03-9)
• EPA Substance Registry System: L -PHENYLEPHRINE(614-03-9)

Safety Data

• Hazardous Substances Data: 614-03-9(Hazardous Substances Data)

Usage

General Description

L-Phenylephrine is a sympathomimetic compound that acts as a selective α1-adrenergic receptor agonist. It is widely used as a nasal decongestant to relieve nasal congestion caused by colds, allergies, or sinusitis. L-Phenylephrine works by constricting blood vessels in the nasal passages, reducing swelling and promoting drainage. In addition to its nasal decongestant properties, L-Phenylephrine is also used in ophthalmic solutions to dilate the pupil during eye examinations and to treat hypotension as a vasopressor. While generally considered safe when used as directed, L-Phenylephrine may cause side effects such as nervousness, dizziness, and increased heart rate when used in excessive amounts. It is important to always follow the recommended dosage and usage instructions when using L-Phenylephrine-containing products.

InChI:InChI=1/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m1/s1

Upstream product

• 1280541-43-6 (S)-phenylephrine-(R)-naproxen 
• 154-86-9 phenylephrine hydrochloride 
• 939-38-8 (+)-Phenylephrine hydrochloride 
• 52093-42-2 Neosynephrine ketone 
• 286426-31-1 C₁₆H₁₉NO₂ 
• 94240-17-2 3-Hydroxyphenyl-ω-methylaminoacetophenone hydrochloride 
• 1477-63-0 Phenylephrine 

Downstream Products

• 59-42-7 Phenylephrin 
• 63991-22-0 (+)-1-acetoxy-1-(3-acetoxy-phenyl)-2-methylamino-ethane 
• 94092-15-6 (R)-1-acetoxy-1-(3-acetoxy-phenyl)-2-(acetyl-methyl-amino)-ethane 
• 94092-15-6 (S)-1-acetoxy-1-(3-acetoxy-phenyl)-2-(acetyl-methyl-amino)-ethane 
• 25333-66-8 (S)-1-(3-acetoxy-phenyl)-2-(acetyl-methyl-amino)-ethanol 
• 25333-66-8 (R)-1-(3-acetoxy-phenyl)-2-(acetyl-methyl-amino)-ethanol 
• 51-43-4 L-epinephrine 

Relevant articles and documents

Enantioselective synthesis of (S)-phenylephrine by recombinant Escherichia coli cells expressing the short-chain dehydrogenase/reductase gene from Serratia quinivorans BCRC 14811

Background An amino alcohol dehydrogenase gene (RE-AADH) from Rhodococcus erythropolis BCRC 10909 has been used for the conversion of 1-(3-hydroxyphenyl)- 2-(methylamino) ethanone (HPMAE) to (S)-phenylephrine [(S)-PE]. However RE-AADH uses NADPH as cofactor, and only limited production of (S)-PE from HPMAE is achieved. Methods A short-chain dehydrogenase/reductase gene (SQ-SDR) from Serratia quinivorans BCRC 14811 was expressed in Escherichia coli BL21 (DE3) for the conversion of HPMAE to (S)-PE. Results The SQ-SDR enzyme was capable of converting HPMAE to (S)-PE in the presence of NADH and NADPH, with specific activities of 26.5 ± 2.3 U/mg protein and 0.24 ± 0.01 U/mg protein, respectively, at 30 C and at a pH of 7.0. The E. coli BL21 (DE3), expressing NADH-preferring SQ-SDR, converted HPMAE to (S)-PE with more than 99% enantiomeric excess, a conversion yield of 86.6% and a productivity of 20.2 mmol/l h, which was much higher than our previous report using E. coli NovaBlue expressing NADPH-dependent RE-AADH as the biocatalyst. Conclusion The SQ-SDR enzyme with its high catalytic activity and strong preference for NADH as a cofactor provided a significant advantage in bioreduction.

A feasibility study on the synthesis of phenylephrine via ruthenium-catalyzed homogeneous asymmetric hydrogenation

We report a feasibility study on a new route to (R)-phenylephrine, based on the ruthenium-catalyzed asymmetric hydrogenation of an aminoketone precursor. The direct and fast asymmetric reduction of aminoketones or their hydrochloride salts is achievable at low catalyst loadings (molar substrate to catalyst ratio, S/C, >25,000/1, TOF up to 25,000 h-1) with high enantioselectivity (>95% ee), without the need for N-protection nor isolation of the free base prior to reaction.

PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE 2-AMINO-1-PHENYLETHANOLS

Optically active 2-amino-l-phenylethanols of formula (I) or its mirror image, wherein R1 is hydrogen, C1-6alkyl or aryl-substituted C1-6alkyl and R2 through R6 are independently hydrogen, hydroxy or C1-6alkoxy, or salts thereof are prepared by asymmetric hydrogenation of the corresponding 2-aminoacetophenones in the presence of a ruthenium complex catalyst comprising a chiral phosphine ligand.