21598-06-1

Basic information

• Product Name: 5-Hydroxyindole-2-carboxylic acid
• Synonyms: 5-HYDROXYINDOLE-2-CARBOXYLIC ACID;5-HYDROXY-1H-INDOLE-2-CARBOXYLIC ACID;5-HYDROXY-2-INDOLECARBOXYLIC ACID;5-Hydroxyindole-2-carboxylicacid,97%;5-HO-ICA;5-Hydroxy-2-indolecarboxylic acid 98%;5-HYDROXYINDOLE-2-CARBOXYLIC ACID(5OHI2CA);5-Hydroxy-2-indolecarboxylic acid,98%
• CAS NO: 21598-06-1
• Molecular Formula: C₉H₇NO₃
• Molecular Weight: 177.16
• EINECS: 244-468-6
• Product Categories: Indoles and derivatives;Indole;Organic acids;Heterocyclic Compounds;Indoles;Building Blocks;Heterocyclic Building Blocks;Building Blocks;C7 to C9;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 21598-06-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 249 °C (dec.)(lit.)
• Boiling Point: 309.06°C (rough estimate)
• Flash Point: 263.1 °C
• Appearance: Clear colorless to slightly yellow/Fuming Liquid
• Density: 1.3312 (rough estimate)
• Vapor Pressure: 2.79E-11mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Refrigerator (+4°C)
• Solubility: chloroform/ethanol (1:1): soluble50mg/mL, clear to slightly hazy
• PKA: 4.38±0.30(Predicted)
• BRN: 153214
• CAS DataBase Reference: 5-Hydroxyindole-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxyindole-2-carboxylic acid(21598-06-1)
• EPA Substance Registry System: 5-Hydroxyindole-2-carboxylic acid(21598-06-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-21/22
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 21598-06-1(Hazardous Substances Data)

Usage

Description

5-Hydroxyindole-2-carboxylic acid is a light yellow to beige crystalline powder that serves as a versatile reactant in the synthesis of various compounds with potential applications in pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
5-Hydroxyindole-2-carboxylic acid is used as a reactant for the preparation of indole C5-O-substituted seco-cyclopropylindole analogs, which are potential anticancer agents.
5-Hydroxyindole-2-carboxylic acid is used as a reactant for microwave combinatorial synthesis of indolic arylpiperazine derivatives, which serve as ligands for 5-HT1A, 5-HT2A, and 5-HT2C receptors.
5-Hydroxyindole-2-carboxylic acid is used as a reactant for the preparation of 5-Hydroxyindole-2-carboxylic acid amides, which act as histamine-3 receptor inverse agonists for the treatment of obesity.
5-Hydroxyindole-2-carboxylic acid is used as a reactant for the preparation of melanins, which are novel nature-inspired radioprotectors.
Used in Neuroprotection:
5-Hydroxyindole-2-carboxylic acid acts as a competitive antagonist of potentiation by glycine at the N-methyl-D-aspartate receptors, which are linked to neuronal death and associated with afflictions such as stroke and epilepsy.
Used in Analytical Chemistry:
5-Hydroxyindole-2-carboxylic acid was used in HPLC-amperometric detection of serotonin in plasma, platelets, and urine.
Chemical Properties:
Upon oxidation with KMnO4, 5-Hydroxyindole-2-carboxylic acid yields pyrrole-2,3,5-tricarboxylic acid.

InChI:InChI=1/C9H7NO3/c11-6-1-2-7-5(3-6)4-8(10-7)9(12)13/h1-4,10-11H,(H,12,13)/p-1

Upstream product

• 6640-09-1 5-benzyloxy-1H-indole-2-carboxylic acid 
• 412284-26-5 (5-hydroxy-2-nitro-phenyl)-pyruvic acid 
• 2581-34-2 3-methyl-4-nitrophenol 
• 22424-58-4 5-benzyloxy-2-nitrotoluene 
• 22424-59-5 (5-benzyloxy-2-nitro-phenyl)-pyruvic acid 
• 1256496-85-1 C₁₀H₉N₃O₃ 
• 51991-39-0 5-Hydroxy-1H-indole-2-carboxylic acid methyl ester 
• 100-83-4 meta-hydroxybenzaldehyde 
• 4382-54-1 5-methoxy-1H-indole-2-carboxylic acid 

Downstream Products

• 1953-54-4 indol-5-ol 
• 143268-07-9 5-oxo-1-(tert-butoxycarbonyl)-2,3,3a,4,5,6,7,7a-octahydroindole 
• 136816-97-2 1-[5-hydroxyindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine 
• 265311-80-6 5-hydroxy-1H-indole-2-carboxylic acid 2-methoxy-benzylamide 
• 265311-88-4 4-{[(5-hydroxy-1H-indole-2-carbonyl)-amino]-methyl}-benzoic acid methyl ester 
• 265311-75-9 5-hydroxy-1H-indole-2-carboxylic acid (3-methoxy-phenyl)-amide 
• 265311-82-8 5-hydroxy-1H-indole-2-carboxylic acid 4-methoxy-benzylamide 
• 952140-13-5 methyl 3-[(5-hydroxyindol-2-yl)carbonyl]-1-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate 
• 952140-59-9 methyl 3-[(5-hydroxyindol-2-yl)carbonyl]-1-(chloromethyl)-5-benzyloxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-carboxylate 

Relevant articles and documents

AROMATIC RING DERIVATIVE AS IMMUNOREGULATION AND PREPARATION METHOD AND APPLICATION OF AROMATIC RING DERIVATIVE

Relating to a compound represented by formula (I) and a pharmaceutically acceptable salt of the compound, and an application of the compound as an S1P1 agonist.

Product based on inorganic or organic lamellar particles, containing a melanotic pigment, process for preparing it and its use in cosmetics

The invention relates to a product in powder form consisting of organic or inorganic particles having a lamellar structure, having a size of less than 50 microns and containing at least one synthetic melanotic pigment formed in situ by oxidation of an indole compound, and to its use for the protection of the human epidermis, in make-up products and for dyeing hair.

Process for dyeing keratinous fibres with a hydroxyindole in combination with a quinone derivative; and novel 1,4-benzoquinones

Process for dyeing keratinous fibres, comprising the step of applying to these fibres at least one composition A containing, in a medium appropriate for dyeing, at least one mono- or di-hydroxyindole the application of the composition A being preceded or followed by the application of a composition B containing, in a medium appropriate for dyeing, at least one quinone derivative chosen from ortho- or para-benzoquinones, monoimines or diimines of ortho- or para-benzoquinones, 1,2- or 1,4-naphthoquinones, sulphonimides of ortho- or para-benzoquinones, α, ω-alkylene-bis-1,4-benzoquinones, or 1,2- or 1,4-naphthoquinone-monoimines or -diimines; the mono- or di-hydroxyindoles and the quinone derivatives being chosen such that the oxidation-reduction potential difference ΔE between the oxidation-reduction potential Ei of the mono- or di-hydroxyindoles, determined at pH 7 in a phosphate medium on a vitreous carbon electrode by voltametry, and the oxidation-reduction potential Eq of the quinone derivative determined at pH 7 in a phosphate medium by polarography on a mercury electrode and relative to a saturated calomel electrode is such that