5-Hydroxyindole-3-acetic acid

Base Information

• Chemical Name: 5-Hydroxyindole-3-acetic acid
• CAS No.: 54-16-0
• Deprecated CAS: 113303-91-6,1321-73-9,99155-61-0
• Molecular Formula: C10H9 N O3
• Molecular Weight: 191.186
• Hs Code.: 29339980
• European Community (EC) Number: 200-195-4
• NSC Number: 90432
• UNII: YHC763JY1P
• DSSTox Substance ID: DTXSID50861582
• Nikkaji Number: J11.030B
• Wikipedia: 5-Hydroxyindoleacetic_acid
• Wikidata: Q238532
• NCI Thesaurus Code: C28157
• Metabolomics Workbench ID: 37412
• ChEMBL ID: CHEMBL395915
• Mol file: 54-16-0.mol

Synonyms:5 Hydroxy 3 Indoleacetic Acid;5 Hydroxyindolamine Acetic Acid;5-HIAA;5-Hydroxy-3-Indoleacetic Acid;5-Hydroxyindolamine Acetic Acid;Acetic Acid, 5-Hydroxyindolamine;Acid, 5-Hydroxy-3-Indoleacetic;Acid, 5-Hydroxyindolamine Acetic;Acid, Hydroxyindoleacetic;Hydroxyindoleacetic Acid

Chemical Property of 5-Hydroxyindole-3-acetic acid

Chemical Property:

• Vapor Pressure: 1.07E-10mmHg at 25°C
• Melting Point: 161-164 °C (dec.)(lit.)
• Refractive Index: 1.5310 (estimate)
• Boiling Point: 497.1°Cat760mmHg
• PKA: 4.54±0.30(Predicted)
• Flash Point: 254.4°C
• PSA: 73.32000
• Density: 1.496g/cm³
• LogP: 1.50060
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in ethanol (50 mg/ml).
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 191.058243149
• Heavy Atom Count: 14
• Complexity: 231

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Hydroxyindole-3-acetic Acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Plant Growth Regulators
• Canonical SMILES: C1=CC2=C(C=C1O)C(=CN2)CC(=O)O
• Description: 5-hydroxy Indole-3-acetic acid (5-HIAA) is the primary metabolite of serotonin (5-HT; ). It is formed when 5-HT is metabolized by monamine oxidase and aldehyde dehydrogenase in the liver. 5-HIAA is excreted in urine and has been used as a biomarker for detection of neuroendocrine tumors and an internal standard for the quantification of serotonin metabolism in rat brain using mass spectrometry. 5-HIAA has also been associated with autism, insomnia, and chronic migraine.
• Uses: 5-Hydroxyindole-3-acetic acid is a major serotonin metabolite.

Technology Process of 5-Hydroxyindole-3-acetic acid

There total 7 articles about 5-Hydroxyindole-3-acetic acid 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:

2-(5-benzyloxy-1H-indol-3-yl)acetic acid (4382-53-0) → 5-Hydroxyindole-3-acetic acid (54-16-0,1321-73-9)

Guidance literature:

With palladium on activated charcoal; ethyl acetate;

DOI:10.1021/jo01084a008 DOI:10.1021/ja01651a001

Reference yield:

5-benzyloxygramine (1453-97-0) → 5-Hydroxyindole-3-acetic acid (54-16-0,1321-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaCN; aqueous ethanol

2: palladium/charcoal; ethanol

With palladium on activated charcoal; ethanol; sodium cyanide;

DOI:10.1021/jo01084a008 DOI:10.1021/ja01651a001

Reference yield:

5-benzyloxy-1H-indole (1215-59-4) → 5-Hydroxyindole-3-acetic acid (54-16-0,1321-73-9)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; dioxane

2: NaCN; aqueous ethanol

3: palladium/charcoal; ethanol

With 1,4-dioxane; palladium on activated charcoal; ethanol; sodium cyanide; acetic acid;

DOI:10.1021/ja01651a001

upstream raw materials:

5-methoxy-1H-indole-3-acetic acid

2-(5-benzyloxy-1H-indol-3-yl)acetic acid

5-methoxyindole-3-acetonitrile

5-benzyloxy-1H-indole

Downstream raw materials:

5-hydroxytryptophol

Refernces