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51145

Supelco

L-Tryptophan

certified reference material, TraceCERT®

Synonym(s):
L-α-Amino-3-indolepropionic acid, (S)-2-Amino-3-(3-indolyl)propionic acid
Empirical Formula (Hill Notation):
C11H12N2O2
CAS Number:
Molecular Weight:
204.23
Beilstein:
86197
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.24

Quality Level

grade

certified reference material
TraceCERT®

product line

TraceCERT®

form

neat

analyte chemical class(es)

amino acids, peptides, proteins

application(s)

HPLC: suitable
gas chromatography (GC): suitable

color

white

mp

280-285 °C (dec.) (lit.)

Featured Industry

Food and Beverages

format

neat

storage temp.

20-25°C

SMILES string

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

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

InChI key

QIVBCDIJIAJPQS-VIFPVBQESA-N

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General description

This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO 17034. This CRM is traceable to primary material from an NMI, e.g. NIST or NMIJ.
Certified content by quantitative NMR incl. uncertainty and expiry date are given on the certificate.
Download your certificate at: http://www.sigma-aldrich.com.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Amino acid precursor of serotonin and melatonin

Caution

Store under Argon

Legal Information

TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 1

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Dirk E M Geurts et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(48), 18932-18939 (2013-11-29)
Adaptive decision-making involves interaction between systems regulating Pavlovian and instrumental control of behavior. Here we investigate in humans the role of serotonin in such Pavlovian-instrumental transfer in both the aversive and the appetitive domain using acute tryptophan depletion, known to...
Kei Hiruma et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(23), 9589-9594 (2013-05-23)
The hypersensitive response (HR) is a type of strong immune response found in plants that is accompanied by localized cell death. However, it is unclear how HR can block a broad range of pathogens with different infective modes. In this...
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...
George Anderson et al.
Advances in protein chemistry and structural biology, 88, 27-48 (2012-07-21)
A recent study--comparing those with depression, somatization, comorbid depression+somatization, and controls--showed specific changes in the tryptophan catabolite (TRYCAT) pathway in somatization, specifically lowered tryptophan and kynurenic acid, and increased kynurenine/kynurenic acid (KY/KA) and kynurenine/tryptophan ratios. These findings suggest that somatization...
Michael Platten et al.
Cancer research, 72(21), 5435-5440 (2012-10-24)
Tryptophan catabolism in cancer is increasingly being recognized as an important microenvironmental factor that suppresses antitumor immune responses. It has been proposed that the essential amino acid tryptophan is catabolized in the tumor tissue by the rate-limiting enzyme indoleamine-2,3-dioxygenase (IDO)...

Protocols

GC Analysis of Amino Acids (as TBDMS Derivatives) on SLB®-5ms (20 m x 0.18 mm I.D., 0.18 μm), Fast GC Analysis

Separation of L-Alanine; Glycine; L-Valine; L-Leucine; L-Isoleucine; L-Proline; L-Methionine; L-Serine; L-Threonine; L-Phenylalanine; L-Aspartic acid; L-4-Hydroxyproline; L-Cysteine; L-Glutamic acid; L-Asparagine; L-Lysine; L-Glutamine; L-Histidine; L-Tyrosine; L-Tryptophan; L-Cystine

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