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SMB00930

Sigma-Aldrich

5-Methoxy-L-tryptophan

98-102%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C12H14N2O3
CAS Number:
25197-96-0
Molecular Weight:
234.25
UNSPSC Code:
12352209
NACRES:
NA.26

Quality Level

100

Assay

98-102%

form

solid

optical activity

[α]20/D -30 to -28° in water

color

off-white to light yellow

storage temp.

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

InChI key

KVNPSKDDJARYKK-JTQLQIEISA-N

General description

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.

Features and Benefits

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

Other Notes

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

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000369622
0000364210
0000369622
0000364210
0000248294

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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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