27172-85-6

Basic information

• Product Name: 3-phenyl-DL-alanine hydrochloride
• Synonyms: 3-phenyl-DL-alanine hydrochloride;DL-Phenylalanine hydrochloride
• CAS NO: 27172-85-6
• Molecular Formula: C₉H₁₁NO₂*ClH
• Molecular Weight: 201.65008
• EINECS: 248-285-2
• Mol File: 27172-85-6.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 307.5°Cat760mmHg
• Flash Point: 139.8°C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 3-phenyl-DL-alanine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-DL-alanine hydrochloride(27172-85-6)
• EPA Substance Registry System: 3-phenyl-DL-alanine hydrochloride(27172-85-6)

Safety Data

• Hazardous Substances Data: 27172-85-6(Hazardous Substances Data)

Usage

General Description

3-phenyl-DL-alanine hydrochloride, also known as DL-3-phenylalanine hydrochloride, is a chemical compound consisting of an amino acid derivative with a phenyl group attached to the alpha carbon of the alanine molecule. It is commonly used as a chiral building block in the synthesis of pharmaceuticals and other organic compounds. As a hydrochloride salt, it is highly soluble in water and commonly used in laboratory and industrial settings. The compound has several potential uses in medicinal chemistry and as a precursor in the production of various drugs and biologically active molecules. Additionally, it can also be used in research and development activities related to organic chemistry and drug discovery.

Upstream product

• 127556-12-1 N-<(S)-2'-amino-3-phenylpropanoyl>bornane-2,10-sultam hydrochloride 
• 4530-18-1 2-(tert-butoxycarbonylamino)-3-phenylpropionic acid 
• 70288-60-7 methyl 2-bromo-3-phenylpropionate 
• 101308-40-1 ethyl 2-bromo-3-phenylpropionate 
• 138286-83-6 Ethyl N-(trichloroacetyl)-2-amino-3-phenylpropanoate 
• 15167-27-8 N-trichloroacetyl-DL-phenylalanine 
• 70288-75-4 2-(Methoxycarbonalamino)-3-phenylpropionsaeure-methylester 
• 19256-31-6 1,1-diethoxy-3-phenylpropane-2-one 
• 2566-22-5 N-benzoyl-L-phenylalanine 
• 35593-57-8 (S)-N-(1-oxo-3-phenylpropan-2-yl)benzamide 
• 1544699-35-5 C₂₀H₂₅NO₃ 
• 346611-16-3 (S)-2-(N,N-dibenzyl)amino-3-phenylpropanal diethyl acetal 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 111060-52-7 (S)-2-(dibenzylamino)-3-phenylpropan-1-ol 

Downstream Products

• 50300-49-7 Z-Ala-Ala-Phe-OH 
• 24955-20-2 Cbz-glycyl-leucyl-phenylalanine 
• 119590-67-9 (2S,2'S)-2,2'-(ethane-1,2-diylbis(azanediyl))bis(3-phenylpropanoic acid) 
• 158174-67-5 H-L-Phe-NH(CH₂)3NMe₂ 
• 1043893-04-4 2-{1-[7-(N,N-dimethylamino)-2,4-dioxochroman-(3E)-ylidene]ethylamino}-3-phenylpropionic acid 
• 1043893-09-9 2-(3-acetyl-7-(N,N-dimethylamino)-2-oxo-2H-chromen-4-ylamino)-3-phenylpropionic acid 
• 123760-79-2 N-(1-adamantylmethyl)-L-phenylalanine 
• 95713-60-3 L-Phe-L-FDAA 
• 95713-61-4 L-FDAA-D-Phe 
• 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 
• 5619-07-8 methyl 2-amino-3-phenylpropanoate hydrochloride 
• 111753-78-7 Phe-O-butyl ester hydrochloride 
• 21156-62-7 N-acetylphenylalanine methyl ester 
• 194661-20-6 butyl 2-acetylamino-3-phenylpropanoate 

Relevant articles and documents

Economical Synthesis of α-Amino Acids from a Novel Family of Easily Available Schiff Bases of Glycine Esters and 2-Hydroxybenzophenone

We report a novel, efficient, and easily prepared substrate/precursor family of Schiff bases of various glycine esters with 2-hydroxybenzophenone, and their use for the synthesis of amino acids in quantitative yields. The Michael addition of the substrates to methyl acrylate gave two different types of product (cyclic or chain), depending on the nature of the base. Also, we demonstrated that one of the new substrates could be involved in an asymmetric version of the alkylation reaction (70% ee).

Synthesis and anti-parasitic activity of C-benzylated (N-arylcarbamoyl)alkylphosphonate esters

Unexpected substituent-dependent regioselectivty challenges in the synthesis of C-benzylated (N-arylcarbamoyl)phosphonate esters have been resolved. The C-benzylated N-furfurylcarbamoyl derivative showed low micromolar PfLDH inhibition, while one of the C-benzylated N-arylcarbamoyl analogues was active against Nagana Trypanosoma brucei parasites which are responsible for African trypanosomiasis in cattle.

LAT1 activity of carboxylic acid bioisosteres: Evaluation of hydroxamic acids as substrates

Large neutral amino acid transporter 1 (LAT1) is a solute carrier protein located primarily in the blood–brain barrier (BBB) that offers the potential to deliver drugs to the brain. It is also up-regulated in cancer cells, as part of a tumor's increased metabolic demands. Previously, amino acid prodrugs have been shown to be transported by LAT1. Carboxylic acid bioisosteres may afford prodrugs with an altered physicochemical and pharmacokinetic profile than those derived from natural amino acids, allowing for higher brain or tumor levels of drug and/or lower toxicity. The effect of replacing phenylalanine's carboxylic acid with a tetrazole, acylsulfonamide and hydroxamic acid (HA) bioisostere was examined. Compounds were tested for their ability to be LAT1 substrates using both cis-inhibition and trans-stimulation cell assays. As HA-Phe demonstrated weak substrate activity, its structure–activity relationship (SAR) was further explored by synthesis and testing of HA derivatives of other LAT1 amino acid substrates (i.e., Tyr, Leu, Ile, and Met). The potential for a false positive in the trans-stimulation assay caused by parent amino acid was evaluated by conducting compound stability experiments for both HA-Leu and the corresponding methyl ester derivative. We concluded that HA's are transported by LAT1. In addition, our results lend support to a recent account that amino acid esters are LAT1 substrates, and that hydrogen bonding may be as important as charge for interaction with the transporter binding site.