93659

L-Tryptophan

BioUltra, ≥99.5% (NT)

• Synonym(s): (S)-2-Amino-3-(3-indolyl)propionic acid, L-α-Amino-3-indolepropionic acid
• Empirical Formula (Hill Notation): C₁₁H₁₂N₂O₂
• CAS Number: 73-22-3
• Molecular Weight: 204.23
• Beilstein: 86197
• EC Number: 200-795-6
• MDL number: MFCD00064340
• eCl@ss: 32160406
• PubChem Substance ID: 57653570
• NACRES: NA.26

Properties

• product line: BioUltra
• Quality Level: 100
• assay: ≥99.5% (NT)
• form: powder or crystals
• optical activity: [α]20/D −31.5±1°, c = 1% in H₂O
• 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 (SO₄^2-): ≤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
• application(s): cell analysis
• 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

Description

Application

L-Tryptophan has been used as a nutritional supplement to study its effect on the circadian clock of primary cell lines.[97] It has also been used as a test amino acid aerosol to study the variation in the fluorescence intensity of thermally-exposed bacterial bioaerosols.[98]

Biochem/physiol Actions

Tryptophan (Trp) is one of the functional amino acids that are associated with growth, reproduction, maintenance and immunity.[95] 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.[51]

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[74]; As spacer in isotachophoresis of serum proteins[75]; Growth requirement of various microorganisms[76].

Legal Information

Sephadex is a registered trademark of Cytiva

Sepharose is a registered trademark of Cytiva

Safety Information

• Storage Class Code: 13 - Non Combustible Solids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves