14907-27-8

Basic information

• Product Name: D-Tryptophan methyl ester hydrochloride
• Synonyms: D-TRYPTOPHAN METHYL ESTER HYDROCHLORIDE 99%;D-TRP.OME.HCL;(S)-2-Amino-3-(1H-indol-3-yl)-propionic acid methyl ester hydrochloride;Methyl (2R)-2-amino-3-(1H-indol-3-yl)propanoate hydrochloride;D-Tryptophane methyl ester hydrochloride;Trp-OMe;(R)-Tryptophan Methyl Ester Monohydrochloride;Methyl D-Tryptophanate Hydrochloride
• CAS NO: 14907-27-8
• Molecular Formula: C₁₂H₁₄N₂O₂*ClH
• Molecular Weight: 254.71
• EINECS: 231-385-5
• Product Categories: Amino Acids Derivatives;Amino Acids;Tryptophan [Trp, W];Amino Acids and Derivatives;Amino Acids 13C, 2H, 15N;Amino Acid Methyl Esters;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Amino Acids & Derivatives;Amino Acid Derivatives;Peptide Synthesis;Tryptophan;Intermediate of Tadalafil;tadalafil intermediate
• Mol File: 14907-27-8.mol

Chemical Properties

• Melting Point: 213-216 °C(lit.)
• Boiling Point: 390.6 °C at 760 mmHg
• Flash Point: 190 °C
• Appearance: off-white crystalline solid
• Density: 1.337g/cm3 at 20℃
• Vapor Pressure: 2.62E-06mmHg at 25°C
• Refractive Index: -19 ° (C=5, MeOH)
• Storage Temp.: 2-8°C
• Solubility: DMSO, (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility: Soluble in water (150 mg/ml), dimethyl sulfoxide and methanol (50 mg/ml).
• CAS DataBase Reference: D-Tryptophan methyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: D-Tryptophan methyl ester hydrochloride(14907-27-8)
• EPA Substance Registry System: D-Tryptophan methyl ester hydrochloride(14907-27-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 14907-27-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
D-Tryptophan methyl ester hydrochloride is used as an intermediate for the synthesis of Tryptophan derivatives, which are essential in the development of various pharmaceutical products. These derivatives have potential applications in the treatment of numerous medical conditions, including neurological disorders, mood regulation, and other health-related issues.
Used in Chemical Synthesis:
D-Tryptophan methyl ester hydrochloride is also used as a key building block in the chemical synthesis of various compounds with diverse applications. Its unique structure allows for further modification and functionalization, making it a valuable component in the creation of new molecules with specific properties and potential uses in different industries.

InChI:InChI=1/C12H14N2O2.ClH/c1-16-12(15)10(13)6-8-7-14-11-5-3-2-4-9(8)11;/h2-5,7,10,14H,6,13H2,1H3;1H/t10-;/m1./s1

Upstream product

• 118553-32-5 Methyl N-(diphenylmethylene)-D,L-tryptophanates 
• 67-56-1 methanol 
• 54-12-6 Trp 
• 120-72-9 indole 
• 73-22-3 L-Tryptophan 
• 6159-33-7 L-tryptophan hydrochloride 
• 5619-09-0 methyl tryptophanate hydrochloride 
• 153-94-6 D-tryptophan 
• 141595-98-4 D-tryptophan benzyl ester 
• 153-94-6 D-tryptophan 
• 141215-69-2 methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate 
• 1198605-52-5 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate 

Downstream Products

• 141215-69-2 N-(tert-butyloxycarbonyl)-2-(3-indolyl)glycin methyl ester 
• 145401-81-6 (R)-α-methylbenzylcarbamoyl-DL-tryptophan methyl ester 
• 77714-32-0 3-(1H-Indol-3-yl)-2-((Z)-3-oxo-propenylamino)-propionic acid methyl ester 
• 77714-32-0 3-(1H-Indol-3-yl)-2-((E)-3-oxo-propenylamino)-propionic acid methyl ester 
• 79397-25-4 2-[2-(4-Chloro-phenoxy)-acetylamino]-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 79397-35-6 2-[(Z)-2-(4-Chloro-phenoxy)-3-(4-nitro-phenyl)-acryloylamino]-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 144426-38-0 3-(1H-Indol-3-yl)-2-{2-[4-((E)-styryl)-phenoxy]-acetylamino}-propionic acid methyl ester 
• 144426-46-0 2-(2-{4-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenoxy}-acetylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 144426-47-1 3-(1H-Indol-3-yl)-2-{2-[4-((E)-styryl)-phenoxy]-propionylamino}-propionic acid methyl ester 
• 7303-49-3 DL-tryptophan methyl ester 
• 53399-48-7 trans-(3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol-1-yl)(2-nitrobenzene) 
• 53399-48-7 cis-(3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indol-1-yl)(2-nitrobenzene) 
• 79659-73-7 methyl 2-(4-methylphenylsulfonamido)-3-(1H-indol-3-yl)propanoate 
• 144599-95-1 3-(2-tert-butoxycarbonylamino-2-carboxy-ethyl)-indole-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Convenient method for the synthesis of some novel chiral methyl 2-(2-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)propanoate derivatives and biological evaluation of their antioxidant, cytotoxic, and molecular docking properties

Ten chiral methyl 2-(2-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)propanoate derivatives 6a-6j have been synthesized from optically pure amino methyl phenol 5 and 4-nitrophenyl chloroformate. These derivatives 6a-6j are characterized by 1H NMR, 13C NMR, FT-IR, and HRMS spectral techniques. Optical purity of these derivatives was confirmed by chiral HPLC method. Ten synthesized ester derivatives 6a-6j were screened for their in vitro antioxidant activity. Among the compounds 6b-d and 6h-j have exhibited comparable antioxidant activity with ascorbic acid as a standard. Compounds 6a and 6e-g have shown moderate antioxidant activity. Further, the in vitro cytotoxicity of these compounds were studied through MTT cell proliferation assay in addition the effect on LDH leakage and NO release. Among the derivatives, 6j showed extremely best activity and the IC50 value (12.54 ± 0.71 μM) is very close to doxorubicin (7.2 ± 0.58 μM) as a standard. Compounds 6b, 6h, and 6i showed better inhibition next to compound 6j on the viability of HepG2 cells with an IC50 value (μM) of 56.02 ± 1.4, 41.76 ± 0.58, and 38.17 ± 0.34, respectively. Also, molecular docking studies have been carried out with STAT-3 (PDB ID: 1BG1) and BCL-2 (PDB ID: 4AQ3) proteins against the four active compounds 6b, 6h, 6i, and 6j. The binding energies of the tested compounds were in the range of ?7.76 to ?8.41 kcal/mol, which is very close to doxorubicin (?8.53 kcal/mol) as a standard. These molecular docking results are in good agreement with the in vitro studies.

Preparation method of phosphodiesterase inhibitor

The invention discloses a preparation method of a phosphodiesterase inhibitor and belongs to the field of medicinal chemistry. The preparation method comprises the following steps: starting the raw material 1 and methanol to prepare the intermediate I without adding organic solvent crystallization. After the series of centrifugation, washing and drying, the intermediate II is directly condensed and cyclized with piperonal, and a final product tadalafil is prepared by chloroacetylation, aminolysis and refining steps. The method improves the product yield and quality, greatly shortens the reaction period, reduces the operation steps and the production cost, and is suitable for industrial mass production.

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Translation of Mycobacterium Survival Strategy to Develop a Lipo-peptide based Fusion Inhibitor**

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(2S, 3R)-3-amino-2-hydroxy-4-phenylbutyrylamide derivative as well as preparation method and application thereof

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Enhancement of the chiroptical response of α-amino acids via N-substitution for molecular structure determination using vibrational circular dichroism

The chiroptical response in the form of vibrational circular dichroism (VCD) in the midinfrared region is found to be enhanced when a hydrogen of amino group of l-tryptophan is substituted with acetyl, acryloyl, or maleyl group. The order of preference for VCD enhancement is found to be acryloyl > acetyl > maleyl group. The resulting experimental VCD spectra are also found to be satisfactorily reproduced by the quantum mechanical (QM) predicted spectra. The QM predicted spectra were simulated using the conformer populations, (a) predicted by Gibbs energies and (b) optimized to maximize the similarity between experimental and predicted VCD spectra. It is found that the conformer populations predicted by Gibbs energies do not yield the maximum possible similarity between experimental and the QM predicted spectra. This work identifies the N-substitution of α-amino acids and determining the conformer populations that best reproduce the experimental spectra as two new approaches for molecular structure determination.