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Merck

T3300

DL-Tryptophan

≥99% (HPLC)

Synonym(s):

(±)-α-Amino-3-indolepropionic acid, (±)-2-Amino-3-(3-indolyl)propionic acid, DL-3β-Indolylalanine

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About This Item

Empirical Formula (Hill Notation):
C11H12N2O2
CAS Number:
54-12-6
Molecular Weight:
204.23
NACRES:
NA.26
PubChem Substance ID:
24900128
UNSPSC Code:
12352209
EC Number:
200-194-9
MDL number:
MFCD00064339
Beilstein/REAXYS Number:
86199

Key Documents

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Product Name

DL-Tryptophan, ≥99% (HPLC)

InChI key

QIVBCDIJIAJPQS-UHFFFAOYSA-N

InChI

1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)

SMILES string

NC(Cc1c[nH]c2ccccc12)C(O)=O

assay

≥99% (HPLC)

form

powder

color

white to off-white

mp

289-290 °C (dec.) (lit.)

solubility

methanol: water (7:3): soluble

Quality Level

200

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General description

Tryptophan is the precursor for 5-hydroxy-tryptamin and an essential α-amino acid. DL-Tryptophan exists as a zwitterion during crystallization.

Application

DL-Tryptophan has been used:
  • as a medium supplement in Psilocybe atrobrunnea and Psilocybe serbica for the synthesis of psychotropic compounds
  • as an optimal medium supplement for culturing yeast, Pichia stipitis
  • for chiral separation experiments using Hewlett-Packard HP3D CE capillary electrophoresis system(HPCE)

Biochem/physiol Actions

DL-Tryptophan binding to bovine serum albumin is employed for its affinity based chromatographic purification. Supplementation of tryptophan in diets of rat induce bladder tumor.

Preparation Note

Prepared from L-tryptophan produced by fermentation

Other Notes

Amino acid precursor of serotonin and melatonin

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000173275
0000173269
SLCR5001
SLBX6143
0000173275

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Promoting effect of saccharin and DL-tryptophan in urinary bladder carcinogenesis
Cohen SM, et al.
Cancer Research, 39(4), 1207-1217 (1979)
Chiral separation of aromatic amino acids by capillary electrophoresis
Bjergegaard C, et al.
Journal of Chromatography A, 836(1), 137-146 (1999)
Crystal structure of DL-Tryptophan at 173K
Hubschle CB, et al.
Crystal Research and Technology, 39(3), 274-278 (2004)
Phylogenetic and chemical studies in the potential psychotropic species complex of Psilocybe atrobrunnea with taxonomic and nomenclatural notes
Borovivcka J, et al.
Persoonia, 34(4), 1-1 (2015)
Culture nutrition and physiology impact the inhibitor tolerance of the yeast Pichia stipitis NRRL Y-7124
Slininger PJ, et al.
Biotechnology and Bioengineering, 102(3), 778-790 (2009)
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