5-Hydroxyindole-2-carboxylic acid

Base Information

• Chemical Name: 5-Hydroxyindole-2-carboxylic acid
• CAS No.: 21598-06-1
• Molecular Formula: C9H7NO3
• Molecular Weight: 177.159
• Hs Code.: 29339900
• European Community (EC) Number: 244-468-6
• NSC Number: 117338
• UNII: 5XP5R85YFD
• DSSTox Substance ID: DTXSID50175959
• Nikkaji Number: J226.235E
• Wikidata: Q72484502
• ChEMBL ID: CHEMBL1368373
• Mol file: 21598-06-1.mol

Synonyms:21598-06-1;5-Hydroxyindole-2-carboxylic acid;5-Hydroxy-1H-indole-2-carboxylic acid;5-Hydroxy-2-indolecarboxylic acid;5XP5R85YFD;MFCD00005615;NSC 117338;NSC-117338;1H-Indole-2-carboxylic acid, 5-hydroxy-;5-Hydroxyindole-2-carboxylicacid;NSC117338;5-Hydroxyindole-2-carboxylic acid hemihydrate;UNII-5XP5R85YFD;5-HO-ICA;Oprea1_412252;SCHEMBL61386;cid_88958;CHEMBL1368373;BDBM41958;DTXSID50175959;CHEBI:167509;5-hydroxy-indole-2-carboxylic acid;5-Hydroxyindole -2-carboxylic acid;AMY31765;EINECS 244-468-6;LH0055;STK530105;5-Hydroxy-1H-2-indolecarboxylic acid;AKOS002664591;Indole-2-carboxylic acid, 5-hydroxy-;CS-W017375;GS-6045;5-oxidanyl-1H-indole-2-carboxylic acid;5-Hydroxyindole-2-carboxylic acid, 98%;AC-22683;SY039818;5-Hydroxy-1H-indole-2-carboxylic acid #;A4642;FT-0620487;EN300-380953;H-6300;H-6310;F1920-0039;Z2894427530;45542C1F-1243-4363-9F29-ED2B251C6D36

Chemical Property of 5-Hydroxyindole-2-carboxylic acid

Chemical Property:

• Appearance/Colour: light yellow to beige crystalline powder
• Vapor Pressure: 2.79E-11mmHg at 25°C
• Melting Point: 249 °C (dec.)(lit.)
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 511.4 °C at 760 mmHg
• PKA: 4.38±0.30(Predicted)
• Flash Point: 263.1 °C
• PSA: 73.32000
• Density: 1.57 g/cm³
• LogP: 1.57170
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: chloroform/ethanol (1:1): soluble50mg/mL, clear to slightly hazy
• XLogP3: 2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 177.042593085
• Heavy Atom Count: 13
• Complexity: 219

Purity/Quality:

99% ^*data from raw suppliers

5-Hydroxyindole-2-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-21/22
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=C1O)C=C(N2)C(=O)O
• Uses: ? ;Reactant for preparation of indole C5-O-substituted seco-cyclopropylindole analogs as potential anticancer agents? ;Reactant for microwave combinatorial synthesis of indolic arylpiperazine derivatives as ligands for 5-HT1A, 5-HT2A, and 5-HT2C receptors1? ;Reactant for preparation of melanins as novel nature-inspired radioprotectors2? ;Reactant for preparation of 5-Hydroxyindole-2-carboxylic acid amides as histamine-3 receptor inverse agonists for the treatment of obesity3? ;Reactant for preparation of conformationally constrained peptidomimetic inhibitors of signal A competitive antagonist of potentiation by glycine at the N-methyl-D-aspartate receptors that have been linked to neuronal death, assiciated to such afflictions as stroke and epilepsy. 5-Hydroxyindole-2-carboxylic acid was used in HPLC-amperometric detection of serotonin in plasma, platelets and urine.

Technology Process of 5-Hydroxyindole-2-carboxylic acid

There total 10 articles about 5-Hydroxyindole-2-carboxylic 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: 98.0%

5-Hydroxy-1H-indole-2-carboxylic acid methyl ester (51991-39-0) → 5-hydroxyindole-2-carboxylic acid (21598-06-1)

Guidance literature:

5-Hydroxy-1H-indole-2-carboxylic acid methyl ester; With sodium hydroxide; In methanol; at 60 ℃; for 1h;

With hydrogenchloride; In methanol; water;

DOI:10.3390/molecules15117971

Reference yield:

5-methoxy-1H-indole-2-carboxylic acid (4382-54-1) → 5-hydroxyindole-2-carboxylic acid (21598-06-1)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 ℃; for 1h;

Reference yield:

C10H9N3O3 (1256496-85-1) → 5-hydroxyindole-2-carboxylic acid (21598-06-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 5,5-dimethyl-1,3-cyclohexadiene / 1 h / Reflux

2: sodium hydroxide / methanol / 1 h / 60 °C

With sodium hydroxide; In methanol; 5,5-dimethyl-1,3-cyclohexadiene;

DOI:10.3390/molecules15117971

upstream raw materials:

5-benzyloxy-1H-indole-2-carboxylic acid

(5-hydroxy-2-nitro-phenyl)-pyruvic acid

3-methyl-4-nitrophenol

5-benzyloxy-2-nitrotoluene

Downstream raw materials:

5-hydroxy-1H-indole-2-carboxylic acid 2-methoxy-benzylamide

4-{[(5-hydroxy-1H-indole-2-carbonyl)-amino]-methyl}-benzoic acid methyl ester

5-hydroxy-1H-indole-2-carboxylic acid (3-methoxy-phenyl)-amide

5-hydroxy-1H-indole-2-carboxylic acid 4-methoxy-benzylamide

Refernces

• 1、 Choi, Taeyoung,Ma, Eunsook. "Structural necessity of indole C5-O-substitution of seco-duocarmycin analogs for their cytotoxic activity". . p. 7971 - 7984. Retrieved 2011/03/22.
• 2、 -. "Process for dyeing keratin fibres with a monohydroxyindole associated with an iodide and hydrogen peroxide". . . Retrieved 2008/06/13.