H-DL-Trp-OH is a mixture of tryptophan isomers, an essential amino acid that plays a key role in protein synthesis and serves as a precursor for serotonin and melatonin, important for regulating sleep, mood, and cognitive functions." />

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Chemical Structure| 54-12-6 Chemical Structure| 54-12-6
Chemical Structure| 54-12-6

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CAS No.: 54-12-6

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H-DL-Trp-OH is a mixture of tryptophan isomers, an essential amino acid that plays a key role in protein synthesis and serves as a precursor for serotonin and melatonin, important for regulating sleep, mood, and cognitive functions.

Synonyms: (±)-Tryptophan; NSC 13118; (R,S)-Tryptophan

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Product Details of H-DL-Trp-OH

CAS No. :54-12-6
Formula : C11H12N2O2
M.W : 204.23
SMILES Code : NC(CC1=CNC2=C1C=CC=C2)C(O)=O
Synonyms :
(±)-Tryptophan; NSC 13118; (R,S)-Tryptophan
MDL No. :MFCD00064339
InChI Key :QIVBCDIJIAJPQS-UHFFFAOYSA-N
Pubchem ID :1148

Safety of H-DL-Trp-OH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of H-DL-Trp-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 54-12-6 ]

[ 54-12-6 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 64-18-6 ]
  • [ 54-12-6 ]
  • [ 16108-03-5 ]
  • 2
  • nickel(II) nitrate hexahydrate [ No CAS ]
  • [ 96293-17-3 ]
  • [ 54-12-6 ]
  • [Ni(C6H5CN(CH(CH2C8H6N)CO2)C6H4NC(O)CHC3H6N(CH2C6H5))] [ No CAS ]
  • [Ni(C6H5CN(CH(CH2C8H6N)CO2)C6H4NC(O)CHC3H6N(CH2C6H5))]*1.5C6H6 [ No CAS ]
  • 3
  • [ 64-17-5 ]
  • [ 54-12-6 ]
  • [ 6519-67-1 ]
  • 4
  • methoxytryptophane [ No CAS ]
  • [ 54-12-6 ]
  • [ 406938-53-2 ]
YieldReaction ConditionsOperation in experiment
With LiOH; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; Synthesis of Cbz-protected methoxytryptophane 10 Trifluoroacetic acid (0.5 mL) was added dropwise to a solution of methoxytryptophane 9 (95 mg, 0.20 mmol) in dichloromethane (4 mL) at 0 C. The reaction mixture was stirred for 3.5 hours at room temperature. The solution was concentrated by co-evaporation with toluene (3 x 5 mL) and the resulting deprotected tryptophane was used directly in the next step. A 0.5 N aqueous solution of LiOH (0.8 mL, 0.4 mmol) was added to a solution of the deprotected tryptophane in tetrahydrofurane/methanol/water (7:1.3:4 mL) at 0 C. The reaction mixture was warmed to room temperature and stirred for 2 hours. The solution was partitioned between 0.1 N aqueous HCl (15 mL) and dichloromethane (15 mL). The aqueous layer was extracted with dichloromethane (2 x 15 mL) and the organic layers were combined, dried (Na2SO4) and concentrated. The residue was purified by column chromatography (dichloromethane with a gradient of 1 to 5% methanol) to give 51 mg of Cbz-protected methoxytryptophane 10 as a white solid (0.14 mmol, 70%, 2 steps). Rf = 0.27 (Ethyl acetate /n-hexane 3:1, with 1% acetic acid);
 

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