17469-89-5

Basic information

• Product Name: N,N-DIMETHYL-L-PHENYLALANINE
• Synonyms: N,N-DiMethyl-L-phenylalanine 99%;(s)-2-Dimethylamino-3-phenyl-propionic acid;Alanine, N,N-dimethyl-3-phenyl-, L-;L-Phenylalanine, N,N-dimethyl-;N,N-Dimethylphenylalanine;N,N-DIME-PHE-OH;N,N-DIMETHYL-L-PHENYLALANINE;N,N-DIMETHYL-L-PHE-OH
• CAS NO: 17469-89-5
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• Product Categories: N-Methyl Amino Acids;Amino Acid Derivatives;Peptide Synthesis
• Mol File: 17469-89-5.mol

Chemical Properties

• Melting Point: 225-227 °C(lit.)
• Boiling Point: 308.067 °C at 760 mmHg
• Flash Point: 140.114 °C
• Appearance: White to off-white/Powder
• Density: 1.11 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.544
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.24±0.11(Predicted)
• BRN: 2966581
• CAS DataBase Reference: N,N-DIMETHYL-L-PHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIMETHYL-L-PHENYLALANINE(17469-89-5)
• EPA Substance Registry System: N,N-DIMETHYL-L-PHENYLALANINE(17469-89-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 17469-89-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N,N-DIMETHYL-L-PHENYLALANINE is used as a chiral mobile phase additive for the resolution of enantiomers, particularly in the preparation of Cu(II)-L-amino acid complex. This application is essential in the development of enantiomerically pure drugs, which are crucial for ensuring the desired therapeutic effects and minimizing potential side effects.
Used in Chemical Synthesis:
N,N-DIMETHYL-L-PHENYLALANINE is used as a key intermediate in the total synthesis of complex organic molecules, such as (+)-paliurine E and almazole D. These compounds have potential applications in various fields, including pharmaceuticals and agrochemicals, due to their unique biological activities.

InChI:InChI=1/C11H15NO2/c1-12(2)10(11(13)14)8-9-6-4-3-5-7-9/h3-7,10H,8H2,1-2H3,(H,13,14)/t10-/m0/s1

Upstream product

• 50-00-0 formaldehyd 
• 63-91-2 L-phenylalanine 
• 24268-81-3 DL-N,N-dimethylphenylalanine 
• 64-18-6 formic acid 

Downstream Products

• 27720-05-4 N,N-dimethyl-L-phenylalanine methyl ester 
• 19704-85-9 N_.N-Dimethyl-L-phenylalanin-N-oxid 
• 97800-80-1 (S)-2-Dimethylamino-3-phenyl-thiopropionic acid S-pyridin-2-yl ester 
• 97800-79-8 N,N-Dimethylphenylalanin-(pentafluorphenyl)ester 
• 27720-03-2 S-2-(Dimethylamino)-3-phenyl-1-propanol 
• 97800-81-2 (S)-2-Dimethylamino-3-phenyl-thiopropionic acid S-(3-cyano-4,6-dimethyl-pyridin-2-yl) ester 
• 107462-36-2 sanjoinine G₁ 
• 19526-09-1 sanjoinine A 
• 74492-07-2 diphenylphosphine 
• 74492-03-8 (S)-(+)-2-N,N-dimethylamino-3-phenyl-1-propylchloride hydrochloride 
• 97800-66-3 (Me)2Phe-Phe-OiPr 
• 161068-70-8 prealmazole C 

Relevant articles and documents

Iheyamides A-C, Antitrypanosomal Linear Peptides Isolated from a Marine Dapis sp. Cyanobacterium

Iheyamides A (1), B (2), and C (3), new linear peptides, were isolated from a marine Dapis sp. cyanobacterium. Their structures were elucidated by spectroscopic analyses and degradation reactions. Iheyamide A (1) showed moderate antitrypanosomal activities against Trypanosoma brucei rhodesiense and Trypanosoma brucei brucei (IC50 = 1.5 μM), but the other two analogues, iheyamides B (2) and C (3), did not (IC50 > 20 μM, respectively). The structure-activity relationship clarified that an isopropyl-O-Me-pyrrolinone moiety was necessary for the antitrypanosomal activity. Furthermore, the cytotoxicity of 1 against normal human cells, WI-38, was 10 times weaker than its antitrypanosomal activity (IC50 = 18 μM).

Isolation and structure elucidation of cyclopeptide alkaloids from the leaves of Heisteria parvifolia

Heisteria parvifolia Sm. is prescribed in traditional medecine against numerous diseases in C?te d'Ivoire. Due to the shortcoming in scientifical knowledge of use of this species, our investigations revealed five undescribed cyclopeptide alkaloids added to one known derivative namely anorldianine. These compounds were elucidated by 1D and 2D-NMR experiments and comparison with literature data, and confirmed by HR-ESI-MS. Cytotoxic activity evaluation of these compounds against the chronic myeloid leukemia (K565) cell line exhibited an antiproliferative activity with cell growth inhibition from 13% to 46%.

Compound for treating metabolic diseases as well as preparation method and application thereof

The invention provides a compound for treating metabolic diseases, the compound has a structure represented by formula (I) or formula (II), or a racemate, a stereoisomer, a geometric isomer, a tautomer, a solvate, a hydrate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof. The compounds provided by the invention are FXR and/or TGR5 receptor activators, and the compounds havethe activity of activating FXR and/or TGR5 receptors, and can be used for preparing medicines for treating chronic liver diseases, metabolic diseases or portal hypertension.

Synthetic method of L-N,N-dimethylphenylalanine

The invention discloses a synthetic method of L-N,N-dimethylphenylalanine. The synthetic method comprises the following steps: in a solvent, a compound I, formaldehyde and a hydroboration reagent aresubjected to a reaction so as to obtain a compound II. T

Palladium Nanoparticle Loaded Bifunctional Silica Hybrid Material: Preparation and Applications as Catalyst in Hydrogenation Reactions

Bifunctional mesoporous silica was prepared by co-condensation of tetraethyl orthosilicate (TEOS) with functionalized organosilanes containing azides or alkoxyamines. Orthogonal functional groups at the particles were selectively addressed in subsequent chemical modifications through “click”-chemistry (“click to ligand” strategy) and radical nitroxide exchange. Palladation with PdCl2 delivered Pd nanoparticle-loaded silica material bearing sulfoxides and additional aminoamides as stabilizing ligands by means of in situ reduction of the PdII-salt. These functional particles were successfully applied to the hydrogenation of alkynes and alkenes. Aldehyde hydrodeoxygenation and benzyl ether cleavage were achieved with these hybrid catalysts under mild conditions. Particles were analyzed by IR, TEM/STEM, EDX, and solid-state NMR spectroscopy.

Characterization of N,N-dimethyl amino acids by electrospray ionization-tandem mass spectrometry

Methylation is an essential metabolic process for a number of critical reactions in the body. Methyl groups are involved in the healthy function of the body life processes, by conducting methylation process involving specific enzymes. In these processes, various amino acids are methylated, and the occurrence of methylated amino acids in nature is diverse. Nowadays, mass-spectrometric-based identification of small molecules as biomarkers for diseases is a growing research. Although all dimethyl amino acids are metabolically important molecules, mass spectral data are available only for a few of them in the literature. In this study, we report synthesis and characterization of all dimethyl amino acids, by electrospray ionization-tandem mass spectrometry (MS/MS) experiments on protonated molecules. The MS/MS spectra of all the studied dimethyl amino acids showed preliminary loss of H2O+CO to form corresponding immonium ions. The other product ions in the spectra are highly characteristic of the methyl groups on the nitrogen and side chain of the amino acids. The amino acids, which are isomeric and isobaric with the studied dimethyl amino acids, gave distinctive MS/MS spectra. The study also included MS/MS analysis of immonium ions of dimethyl amino acids that provide information on side chain structure, and it is further tested to determine the N-terminal amino acid of the peptides.

Catalyst-free one-pot reductive alkylation of primary and secondary amines and N,N-dimethylation of amino acids using sodium borohydride in 2,2,2-trifluoroethanol

A simple and convenient procedure for the reductive alkylation of primary and secondary amines and N,N-dimethylation of amino acids is described using sodium borohydride as a reducing agent in 2,2,2- trifluoroethanol without use of a catalyst or any other additive. The solvent can be readily recovered from reaction products in excellent purity for direct reuse. Georg Thieme Verlag Stuttgart - New York.

Cyclopeptide alkaloids of Zizyphus xylopyra

14-Membered cyclopeptide alkaloids, franganine, frangufoline, amphibine-D and mauritine-A has been isolated from the whole plant of Zizyphus xylopyra and their structures established by spectral evidences. This is the first report of these alkaloids from Z. xylopyra.

Resolution of racemic N-benzyl α-amino acids by liquid-liquid extraction: A practical method using a lipophilic chiral cobalt(III) salen complex and mechanistic studies

The efficient resolution of racemic N-benzyl α-amino acids (N-Bn-AA) has been achieved by a liquid-liquid extraction process using the lipophilic chiral salen-cobalt(III) complex [CoIII(3)(OAc)]. As a result of the resolution by extraction, one enantiomer (S) of the N-benzyl α-amino acid predominated in the aqueous phase, while the other enantiomer (R) was driven into the organic phase by complexation to cobalt. The complexed amino acid (R) was then quantitatively released by a reductive (CoIII→Co II) counter-extraction with aqueous sodium dithionite or L-ascorbic acid in methanol. The reductive cleavage allowed to recover the [Co II(3)] complex in good yield, which could be easily re-oxidized to [CoIII(3)(OAc)] with air/AcOH and reused with essentially no loss of reactivity and selectivity. Investigation on the nitrogen substitution indicates that the presence of a single benzyl group on the amino acid nitrogen is important to obtain high enantioselectivity in the extraction process. The kinetic vs. thermodynamic nature of the resolution process was also investigated with an enantiomeric exchange experiment, which shows that the liquid-liquid extraction with [CoIII(3)-(OAc)] is an equilibrium process operating under thermodynamic control. In the absence of a suitable crystal structure of the [CoIII(3)(N-Bn-AA)] complexes, computational and spectroscopic studies were used to investigate how the N-benzyl α-amino acids are accommodated in the "binding pocket" of the chiral cobalt complex. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Stable-isotope dimethylation labeling combined with LC-ESI MS for quantification of amine-containing metabolites in biological samples

One of the challenges associated with metabolome profiling in complex biological samples is to generate quantitative information on the metabolites of interest. In this work, a targeted metabolome analysis strategy is presented for the quantification of amine-containing metabolites. A dimethylation reaction is used to introduce a stable isotopic tag onto amine-containing metabolites followed by LC-ESI MS analysis. This labeling reaction employs a common reagent, formaldehyde, to label globally the amine groups through reductive animation. The performance of this strategy was investigated in the analysis of 20 amino acids and 15 amines by LC-ESI MS. It is shown that the labeling chemistry is simple, fast (13C-dimethylation does not show any isotope effect on either RPLC or HILIC LC, indicating that 13C-labeling is a preferred approach for relative quantification of amine-containing metabolites in different samples. The isotopically labeled 35 amine-containing analogues were found to be stable and proved to be effective in overcoming matrix effects in both relative and absolute quantification of these analytes present in a complicated sample, human urine. Finally, the characteristic mass difference provides additional structural information that reveals the existence of primary or secondary amine functional groups in amine-containing metabolites. As an example, for a human urine sample, a total of 438 pairs of different amine-containing metabolites were detected, at signal-to-noise ratios of greater than 10, by using the labeling strategy in conjunction with RP LC-ESI Fourier-transform ion cyclotron resonance MS.