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469971

Sigma-Aldrich

L-Tryptophanol

97%

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About This Item

Empirical Formula (Hill Notation):
C11H14N2O
CAS Number:
Molecular Weight:
190.24
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

optical activity

[α]20/D −20.5°, c = 1 in methanol

reaction suitability

reaction type: solution phase peptide synthesis

mp

73-77 °C (lit.)

application(s)

peptide synthesis

SMILES string

N[C@H](CO)Cc1c[nH]c2ccccc12

InChI

1S/C11H14N2O/c12-9(7-14)5-8-6-13-11-4-2-1-3-10(8)11/h1-4,6,9,13-14H,5,7,12H2/t9-/m0/s1

InChI key

UDQCRUSSQAXPJY-VIFPVBQESA-N

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Mercedes Amat et al.
The Journal of organic chemistry, 74(3), 1205-1211 (2008-12-17)
The enantioselective construction of the 3-ethylindolo[2,3-a]quinolizidine moiety present in numerous indole alkaloids is reported, the key steps being a stereoselective cyclocondensation of (S)-tryptophanol with an appropriate racemic delta-oxoester and a regio- and stereoselective cyclization of the resulting oxazolopiperidones on the
G M Beck et al.
Chirality, 8(7), 503-510 (1996-01-01)
Lambda-carrageenan, a linear high molecular weight sulfated polysaccharide, has been employed as a chiral selector in capillary electrophoresis for the separation of enantiomers of weakly basic pharmaceutical compounds. The racemic compounds that were enantioresolved included propranolol, pindolol, tryptophanol, laudanosine and
Nicholas A Barnes et al.
Journal of immunology (Baltimore, Md. : 1950), 183(9), 5768-5777 (2009-10-16)
Catabolism of tryptophan by IDO1 plays an important role in the control of immune responses. Activation of the eukaryotic initiation factor 2alpha (eIF2alpha) kinase general control nonderepressible-2 (GCN2) following tryptophan depletion is a major pathway mediating this effect. However, immunomodulatory
Mariia Pushina et al.
Chemical communications (Cambridge, England), 55(31), 4495-4498 (2019-03-29)
The determination of enantiomeric excess (ee) in various groups of chiral compounds, namely amines, amino alcohols, diols, and hydroxy acids is performed using a dual chromophore FRET/PET based sensor ensemble. The sensing ensemble utilizes fluorescence changes from two chromophores (indicators)
Theodoros Eleftheriadis et al.
International journal of molecular medicine, 42(1), 557-568 (2018-04-26)
It is generally hypothesized in the literature that indoleamine 2,3‑dioxygenase (IDO), by degrading L‑tryptophan along the kynurenine pathway, suppresses CD4+ T‑cell function by inducing apoptosis, inhibiting proliferation and promoting differentiation towards a regulatory phenotype. These effects are either accompanied or

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