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Merck

T0254

L-Tryptophan

≥98% (HPLC)

Synonym(s):

(S)-2-Amino-3-(3-indolyl)propionic acid, L-α-Amino-3-indolepropionic acid

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About This Item

Empirical Formula (Hill Notation):
C11H12N2O2
CAS Number:
73-22-3
Molecular Weight:
204.23
NACRES:
NA.26
PubChem Substance ID:
24278135
eCl@ss:
32160406
UNSPSC Code:
12352209
EC Number:
200-795-6
MDL number:
MFCD00064340
Beilstein/REAXYS Number:
86197

Key Documents

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Product Name

L-Tryptophan, reagent grade, ≥98% (HPLC)

form

powder

InChI key

QIVBCDIJIAJPQS-VIFPVBQESA-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)/t9-/m0/s1

SMILES string

N[C@@H](Cc1c[nH]c2ccccc12)C(O)=O

grade

reagent grade

assay

≥98% (HPLC)

color

white to off-white

mp

280-285 °C (dec.) (lit.)

solubility

0.5 M HCl: 50 mg/mL

application(s)

cell analysis

Quality Level

200

Gene Information

human ... TDO2(6999), TPH1(7166), TPH2(121278)

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Application

L-tryptophan has been used for the isolation of bone marrow–derived neutrophils. It has also been used to identify the use of Raman microscopy as a tool to study the network of neurons in pathologically normal retina.

Biochem/physiol Actions

Tryptophan (Trp) is a heterocyclic, essential amino acid associated with growth, reproduction and immunity. Increased availability of tryptophan is necessary for the regulation of mood, cognition and behavior. The uptake of tryptophan by the brain depends on the plasma ratio of Trp to all of the other large neutral amino acids. Higher the ratio, greater is the Trp uptake.

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
BCCG9306
BCCG9305
WXBD6490V
BCCG3733
0000119764

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Raman microscopy of porcine inner retinal layers from the area centralis
J. Renwick
Molecular Vision (2007)
Tryptophan Catabolism Restricts IFN-??Expressing Neutrophils and Clostridium difficile Immunopathology
Mohamad El-Zaatari
Journal of Immunology (2014)
Effects of tryptophan loading on human cognition, mood, and sleep.
Neuroscience and Biobehavioral Reviews, 34(3) (2010)
Amino acids: metabolism, functions, and nutrition.
Wu G
Amino Acids (2009)
Heidi Barth et al.
Critical reviews in microbiology, 40(4), 360-368 (2012-11-24)
Indoleamine-2,3-dioxygenase (IDO) is an enzyme that catabolises tryptophan - an essential amino acid critical for T cell proliferation. Initially recognized as a first line of host defense against infectious pathogens, IDO has been subsequently identified as an important immune-regulator inhibiting
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