F7626
6-Fluoro-DL-tryptophan
crystalline
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About This Item
Empirical Formula (Hill Notation):
C11H11FN2O2
CAS Number:
Molecular Weight:
222.22
UNSPSC Code:
12352200
PubChem Substance ID:
EC Number:
231-788-6
MDL number:
form
crystalline
mp
280-285 °C (dec.) (lit.)
storage temp.
−20°C
SMILES string
NC(Cc1c[nH]c2cc(F)ccc12)C(O)=O
InChI
1S/C11H11FN2O2/c12-7-1-2-8-6(3-9(13)11(15)16)5-14-10(8)4-7/h1-2,4-5,9,14H,3,13H2,(H,15,16)
InChI key
YMEXGEAJNZRQEH-UHFFFAOYSA-N
Application
6-Fluoro-DL-tryptophan (6-F-TRP), a serotonin (5-HT) synthesis inhibitor, is metabolized in the brain and may be useful for tracing neuronal serotoninergic pools. 6-F-TRP is used as a competitive inhibitor of tryptophan binding to albumin and passage through the blood brain barrier (BBB).
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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A H Baugher et al.
Biophysical journal, 75(5), 2574-2576 (1998-10-28)
Rotational-echo double-resonance (REDOR) 13C NMR spectra (with 19F dephasing) have been obtained of 6-fluorotryptophan complexed by a polymeric amphiphilic nanosphere consisting of a polystyrene core covalently attached to a poly(acrylic acid)-polyacrylamide shell. The REDOR spectra show that aromatic carbons from
Induction of anthranilate synthase activity by elicitors in oats.
Matsukawa T, Ishihara A, Iwamura H.
Zeitschrift fur Naturforschung, 57, 121-128 (2002)
Albumin binding and brain uptake of 6-fluoro-DL-tryptophan: competition with L-tryptophan.
Chanut E, Zini R, Trouvin JH, Riant P, et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 44, 2082-2085 (1992)
F Richard et al.
Brain research, 536(1-2), 41-45 (1990-12-17)
An immunoblot procedure was developed to quantify the amount of tryptophan hydroxylase (TpOH), the rate limiting enzyme in the synthesis of serotonin, in the rat raphe dorsalis nucleus (NRD). Using this method we have studied the time course variations in
E Li et al.
The Journal of biological chemistry, 265(20), 11549-11554 (1990-07-15)
Rat cellular retinol binding protein (CRBP II) is a 134-amino acid intracellular protein synthesized in the polarized absorptive cells of the intestine. We have previously used 19F nuclear magnetic resonance (NMR) spectroscopy to survey the structural effects of ligand binding
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