L-5-Hydroxytryptophan

Base Information

• Chemical Name: L-5-Hydroxytryptophan
• CAS No.: 4350-09-8
• Molecular Formula: C11H12N2O3
• Molecular Weight: 220.228
• Hs Code.: 29339990
• Pharos Ligand ID: VHMXCNDQ1HF6
• Mol file: 4350-09-8.mol

Synonyms:Tryptophan,5-hydroxy-, L- (8CI);(S)-5-Hydroxytryptophan;5-Hydroxy-L-tryptophan;5-Hydroxyl-L-tryptophan;Cincofarm;L-5-HTP;Levothym;Levotinine;Oxitriptan;Oxyfan;Pretonine;Quietim;Serotonyl;Telesol;Tript-Oh;

Chemical Property of L-5-Hydroxytryptophan

Chemical Property:

• Appearance/Colour: white to pale grey powder
• Melting Point: 270 °C (dec.)(lit.)
• Refractive Index: 1.4850
• Boiling Point: 520.6 °C at 760 mmHg
• PKA: 2.22±0.10(Predicted)
• Flash Point: 268.7 °C
• PSA: 99.34000
• Density: 1.484 g/cm³
• LogP: 1.52820
• Storage Temp.: 2-8°C
• Solubility.: H2O: 10 mg/mL
• Water Solubility.: Slightly soluble
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 220.08479225
• Heavy Atom Count: 16
• Complexity: 266

Purity/Quality:

99%, ^*data from raw suppliers

5-Hydroxy-L-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-65-20/21/22-20/21
• Safety Statements: 36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=C1O)C(=CN2)CC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C1=CC2=C(C=C1O)C(=CN2)C[C@@H](C(=O)[O-])[NH3+]
• Uses: 5-Hydroxy-L-Tryptophan is a hydroxylated metabolite of L-Tryptophan 5-Hydroxy-L-tryptophan has been used:to inject experimental mice for serotonin detectionas a precursor of 5-hydroxytryptamine and injected in pregnant mice and neonatal rats for vital neutral red staining of lung slicesas a standard in citrate-acetate buffer for its use in high performance liquid chromatography (HPLC) analysis

Technology Process of L-5-Hydroxytryptophan

There total 29 articles about L-5-Hydroxytryptophan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

indol-5-ol (1953-54-4) + L-serin (56-45-1,83245-15-2) → L-5-HTP (4350-09-8,4298-20-8)

Guidance literature:

indol-5-ol; L-serin; With pyridoxal 5'-phosphate; thermotoga maritima with tryptophan synthase β-subunit from pyrococcus furiosus M145T N167D mutant; In aq. phosphate buffer; water; dimethyl sulfoxide; at 75 ℃; for 2h; pH=8; Sealed tube; Enzymatic reaction;

With hydrogenchloride; In water;

DOI:10.1002/anie.201606242

Reference yield: 43.0%

DL-5-hydroxytryptophane amide (90830-06-1) → L-5-HTP (4350-09-8,4298-20-8)

Guidance literature:

Reference yield: 10.0%

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → 7-Hydroxy-L-tryptophan (25198-02-1) + 4-Hydroxy-L-tryptophan (25242-90-4) + (S)-6-hydroxytryptophan (13567-14-1,1398507-94-2) + L-5-HTP (4350-09-8,4298-20-8)

Guidance literature:

With dihydrogen peroxide; edetate disodium; iron(II) sulfate; ascorbic acid; In water; at 22 ℃; for 0.0416667h;

upstream raw materials:

L-N-benzyloxycarbonyl-5-benzyloxytryptophan

indol-5-ol

L-serin

L-Tryptophan

Downstream raw materials:

3-(2-aminoethyl)-1H-indol-5-ol

Oxyviolacein

violacein

Deoxyviolacein

Refernces

• 1、 Bunn, Brittney M,Xu, Mizhi,Webb, Chase M,Viswanathan, Rajesh. "Biocatalysts from cyanobacterial hapalindole pathway afford antivirulent isonitriles against MRSA". . . Retrieved 2021/04/26.
• 2、 Subedi, Bishnu P.,Fitzpatrick, Paul F.. "Mutagenesis of an Active-Site Loop in Tryptophan Hydroxylase Dramatically Slows the Formation of an Early Intermediate in Catalysis". supporting information. p. 5185 - 5192. Retrieved 2018/04/23.