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SMB00930

Sigma-Aldrich

5-Methoxy-L-tryptophan

98-102%

Synonyme(s) :

5-Methoxy-L-tryptophan, L-2-Amino-3-(5-methoxyindolyl)propionic acid

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About This Item

Formule empirique (notation de Hill):
C12H14N2O3
Numéro CAS:
25197-96-0
Poids moléculaire :
234.25
Code UNSPSC :
12352209
Nomenclature NACRES :
NA.26

Niveau de qualité

100

Pureté

98-102%

Forme

solid

Activité optique

[α]20/D -30 to -28° in water

Couleur

off-white to light yellow

Température de stockage

2-8°C

InChI

1S/C12H14N2O3/c1-17-8-2-3-11-9(5-8)7(6-14-11)4-10(13)12(15)16/h2-3,5-6,10,14H,4,13H2,1H3,(H,15,16)/t10-/m0/s1

Clé InChI

KVNPSKDDJARYKK-JTQLQIEISA-N

Description générale

5-Methoxy-L-tryptophan is a L-tryptophan metabolite that exhibits anti-inflammatory and tumor-suppressing activities. 5-Methoxy-L-tryptophan is synthesized by tryptophan hydroxylase (TPH) and hydroxyindole O-methyltransferase (HIOMT). A recent study indicates 5-methoxytryptophan as a biomarker of the progression of chronic kidney disease (CKD). Its levels decrease during disease and treatment with 5-methoxytryptophan ameliorates kidney fibrosis in mice model of CKD. 5-Methoxytryptophan appears to inhibit IκB/NFκB signaling and enhances Keap1/Nrf2 signaling in mice models of unilateral ureteral obstruction.

Application

5-Methoxy-L-tryptophan finds application in cell biology, biochemical and metabolomics research.

Caractéristiques et avantages

  • Can be used in Metabolomics and Biochemical research
  • High-quality compound suitable for multiple research applications

Autres remarques

For additional information on our range of Biochemicals, please complete this form.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000369622
0000364210
0000369622
0000364210
0000248294

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Consulter la Bibliothèque de documents

Hua-Ling Chen et al.
The Journal of biological chemistry, 293(28), 11131-11142 (2018-05-26)
5-Methoxytryptophan (5-MTP) is a tryptophan metabolite with recently discovered anti-inflammatory and tumor-suppressing activities. Its synthesis is catalyzed by a hydroxyindole O-methyltransferase (HIOMT)-like enzyme. However, the exact identity of this HIOMT in human cells remains unclear. Human HIOMT exists in several
Huei-Hsuan Cheng et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(33), 13231-13236 (2012-08-02)
Cyclooxygenase-2 (COX-2) expression is induced by mitogenic and proinflammatory factors. Its overexpression plays a causal role in inflammation and tumorigenesis. COX-2 expression is tightly regulated, but the mechanisms are largely unclear. Here we show the control of COX-2 expression by
Dan-Qian Chen et al.
Nature communications, 10(1), 1476-1476 (2019-04-02)
Early detection and accurate monitoring of chronic kidney disease (CKD) could improve care and retard progression to end-stage renal disease. Here, using untargeted metabolomics in 2155 participants including patients with stage 1-5 CKD and healthy controls, we identify five metabolites

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