93659

Sigma-Aldrich

L-Tryptophan

BioUltra, ≥99.5% (NT)

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/REAXYS Number:
86197
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26
Pricing and availability is not currently available.

product line

BioUltra

Quality Level

assay

≥99.5% (NT)

form

powder or crystals

optical activity

[α]20/D −31.5±1°, c = 1% in H2O

application(s)

cell analysis: suitable

impurities

insoluble matter, passes filter test

ign. residue

≤0.1%

loss

≤0.1% loss on drying, 20 °C (HV)

color

white

mp

280-285 °C (dec.) (lit.)

solubility

0.5 M HCl: 0.1 g/mL at 20 °C, clear, colorless to faintly yellow

anion traces

chloride (Cl-): ≤50 mg/kg
sulfate (SO42-): ≤50 mg/kg

cation traces

Al: ≤5 mg/kg
As: ≤0.1 mg/kg
Ba: ≤5 mg/kg
Bi: ≤5 mg/kg
Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤50 mg/kg
Li: ≤5 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Mo: ≤5 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Sr: ≤5 mg/kg
Zn: ≤5 mg/kg

absorption

cut-off at 326 nm in 0.5 M HCl at 0.5 M

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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Application

L-Tryptophan has been used as a nutritional supplement to study its effect on the circadian clock of primary cell lines. It has also been used as a test amino acid aerosol to study the variation in the fluorescence intensity of thermally-exposed bacterial bioaerosols.

Biochem/physiol Actions

Tryptophan (Trp) is one of the functional amino acids that are associated with growth, reproduction, maintenance and immunity. Increased Trp availability is necessary for the regulation of mood, cognition and behaviour. It is hypothesised that L-Trp might be useful in inducing sleep in healthy adults against the normal circadian rhythm. Trp uptake by the brain depends on the plasma ratio of Trp to all of the other LNAAs (large neutral amino acids). Higher the Trp:LNAAs ratio, greater is the Trp uptake.

Other Notes

Amino acid precursor of serotonin and melatonin
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 93659.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
In tryptophan-substituted Sephadex® and Sepharose® for the improved chromatographic separation of cellulases; As spacer in isotachophoresis of serum proteins; Growth requirement of various microorganisms.

Legal Information

Sephadex is a registered trademark of Cytiva
Sepharose is a registered trademark of Cytiva

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Variation in the fluorescence intensity of thermally-exposed bacterial bioaerosols
Jae HeeJung and Jung EunLee
Journal of Aerosol Science, 65, 101-110 (2013)
Long-lasting effect of perinatal exposure to L-tryptophan on circadian clock of primary cell lines established from male offspring born from mothers fed on dietary protein restriction.
Nascimento E
PLoS ONE, 8(2), 1-14 (2013)
CRC Handbook of Microbiology, 4, 1-1 (1974)
M A Vijayalakshmi et al.
Journal of chromatography, 177(2), 201-208 (1979-09-21)
The adsorption of tyrosine, tryptophan and some related compounds on tryptophan and tryptophanyltryptophan gels is similar to but much stronger than that observed with the parent gel Sephadex G-25. The adsorption has been attributed mainly to charge transfer or redistribution...
T. Hine et al.
Electrophoresis ?83, 541-541 (1984)

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