17585-69-2

Basic information

• Product Name: L-Phenylalanine hydrochloride
• Synonyms: l-phenylalaninehydrochloridesolution;3-phenyl-L-alanine hydrochloride;L-Phenylalanine hydrochloride;Phenylalanine·hydrochloride;Phe-OH·Hydrochloride;(S)-2-aMino-3-phenylpropanoic acid hydrochloride;L-Phe.hcl
• CAS NO: 17585-69-2
• Molecular Formula: C₉H₁₁NO₂*ClH
• Molecular Weight: 201.65
• EINECS: 241-554-5
• Product Categories: Amino Acids, Peptides and Proteins;Amino AcidsAlphabetic;Life Sciences Standards;P;PER - POLA
• Mol File: 17585-69-2.mol
• Article Data: 24

Chemical Properties

• Melting Point: 244-245 °C
• Boiling Point: 307.5 °C at 760 mmHg
• Flash Point: 139.8 °C
• Appearance: /
• Density: 1.268 g/cm3
• Vapor Pressure: 0.000313mmHg at 25°C
• Storage Temp.: 2-8°C
• BRN: 8584529
• CAS DataBase Reference: L-Phenylalanine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine hydrochloride(17585-69-2)
• EPA Substance Registry System: L-Phenylalanine hydrochloride(17585-69-2)

Safety Data

• WGK Germany: 2
• F: 10
• Hazardous Substances Data: 17585-69-2(Hazardous Substances Data)

Usage

General Description

L-Phenylalanine hydrochloride is a chemical compound that is derived from the essential amino acid phenylalanine. It is often used as a dietary supplement to boost levels of phenylalanine in the body, and is also used in the production of food and pharmaceuticals. L-Phenylalanine hydrochloride is known for its role in the synthesis of important neurotransmitters such as dopamine, norepinephrine, and epinephrine, which are essential for regulating mood, motivation, and stress response. It is also used in the treatment of phenylketonuria, a rare genetic disorder that affects the body's ability to metabolize phenylalanine. L-Phenylalanine hydrochloride has been found to have potential benefits for improving cognitive function and mental alertness, and may also play a role in managing symptoms of depression and anxiety. However, it should be used with caution and under the supervision of a healthcare professional, as excessive levels of phenylalanine can have detrimental effects on health.

InChI:InChI=1/C9H11NO2.ClH/c10-8(9(11)12)6-7-4-2-1-3-5-7;/h1-5,8H,6,10H2,(H,11,12);1H/t8-;/m0./s1

Upstream product

• 5619-07-8 methyl 2-amino-3-phenylpropanoate hydrochloride 
• 169221-13-0 (R)-3-hydroxy-4,4-dimethyl-1-phenylpyrrolidin-2-one 
• 56271-33-1 3-phenyl-2-(phthalimido)propanoyl chloride 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 122-78-1 phenylacetaldehyde 
• 1186048-83-8 desmocyclopeptide 
• 15180-22-0 (3S,6S)-3-methyl-6-(phenylmethyl)piperazine-2,5-dione 
• 111060-52-7 (S)-2-(dibenzylamino)-3-phenylpropan-1-ol 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 346611-16-3 (S)-2-(N,N-dibenzyl)amino-3-phenylpropanal diethyl acetal 
• 1544699-35-5 C₂₀H₂₅NO₃ 
• 35593-57-8 (S)-N-(1-oxo-3-phenylpropan-2-yl)benzamide 
• 2566-22-5 N-benzoyl-L-phenylalanine 

Downstream Products

• 137282-27-0 (2S)-2-(1-oxo-2,3-dihydro-1H-benzisoquinolin-2-yl)-3-phenylpropionic acid 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 50300-49-7 Z-Ala-Ala-Phe-OH 
• 24955-20-2 Cbz-glycyl-leucyl-phenylalanine 
• 14825-82-2 L-phenylalanine-N-carboxyanhydride 
• 1202-31-9 (S)-2-hydrazinyl-3-phenylpropanoic acid 
• 137282-02-1 (3S)-4-cyclohexyl-2-hydroxy-3-<<(2S)-4-methyl-2-<<(2S)-2-(1-oxo-2,3-dihydro-1H-benzisoquinolin-2-yl)-3-phenylpropionyl>amino>pentanoyl>amino>butyric acid isopropyl ester 
• 123760-79-2 N-(1-adamantylmethyl)-L-phenylalanine 
• 35661-40-6 N-Fmoc L-Phe 
• 172097-41-5 (S)-1-diazo-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-phenylbutan-2-one 
• 1131444-48-8 methyl (2-ethoxy-2-oxoacetyl)-L-phenylalaninate 
• 16257-32-2 L-N-(tert-butoxycarbonylamino)phenylalanine 
• 2566-22-5 N-benzoyl-L-phenylalanine 
• 1415246-55-7 (S)-methyl 2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((tert-butoxycarbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)-pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoate 

Relevant articles and documents

New Efficient Route to α-Nitro Acids. Oxidation of Amino Acids with HOF*CH3CN

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LAT-1 activity of meta-substituted phenylalanine and tyrosine analogs

The transporter protein Large-neutral Amino Acid Transporter 1 (LAT-1, SLC7A5) is responsible for transporting amino acids such as tyrosine and phenylalanine as well as thyroid hormones, and it has been exploited as a drug delivery mechanism. Recently its role in cancer has become increasingly appreciated, as it has been found to be up-regulated in many different tumor types, and its expression levels have been correlated with prognosis. Substitution at the meta position of aromatic amino acids has been reported to increase affinity for LAT-1; however, the SAR for this position has not previously been explored. Guided by newly refined computational models of the binding site, we hypothesized that groups capable of filling a hydrophobic pocket would increase binding to LAT-1, resulting in improved substrates relative to parent amino acid. Tyrosine and phenylalanine analogs substituted at the meta position with halogens, alkyl and aryl groups were synthesized and tested in cis-inhibition and trans-stimulation cell assays to determine activity. Contrary to our initial hypothesis we found that lipophilicity was correlated with diminished substrate activity and increased inhibition of the transporter. The synthesis and SAR of meta-substituted phenylalanine and tyrosine analogs is described.

Recyclable Ligands for the Non-Enzymatic Dynamic Kinetic Resolution of Challenging α-Amino Acids

Structurally simple and inexpensive chiral tridentate ligands were employed for substantially advancing the purely chemical dynamic kinetic resolution (DKR) of unprotected racemic tailor-made α-amino acids (TM-α-AAs), enabling the first DKR of TM-α-AAs bearing tertiary alkyl chains as well as multiple unprotected functional groups. Owing to the operationally convenient conditions, virtually complete stereoselectivity, and full recyclability of the source of chirality, this method should find wide applications for the preparation of TM-α-AAs, especially on large scale. The non-enzymatic dynamic kinetic resolution of racemic α-amino acids bearing tertiary alkyl chains and multiple unprotected functional groups is based on the enantioselective formation of nickel(II) complexes and their hydrolysis under convenient conditions. The specially designed chiral ligands are inexpensive and can be quantitatively recycled.