4790-08-3

Basic information

• Product Name: 5,6-dihydroxy-1H-indole-2-carboxylic acid
• Synonyms: 5,6-dihydroxy-1H-indole-2-carboxylic acid;5,6-Dihydroxyindole-2-carboxylic acid;5,6-dihydroxy-2-indolylcarboxylic acid;1H-Indole-2-carboxylicacid, 5,6-dihydroxy-;2-Carboxy-5,6-dihydroxyindole;5,6-Dihydroxy-2-carboxyindole
• CAS NO: 4790-08-3
• Molecular Formula: C₉H₇NO₄
• Molecular Weight: 193.15618
• Product Categories: Aromatics;Heterocycles;Indole Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 4790-08-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 234 °C (decomp)
• Boiling Point: 578.6 °C at 760 mmHg
• Flash Point: 303.8 °C
• Appearance: /
• Density: 1.736 g/cm³
• Vapor Pressure: 3.13E-14mmHg at 25°C
• Refractive Index: 1.838
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.52±0.30(Predicted)
• Stability: Air Sensitive
• CAS DataBase Reference: 5,6-dihydroxy-1H-indole-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-dihydroxy-1H-indole-2-carboxylic acid(4790-08-3)
• EPA Substance Registry System: 5,6-dihydroxy-1H-indole-2-carboxylic acid(4790-08-3)

Safety Data

• Hazardous Substances Data: 4790-08-3(Hazardous Substances Data)

Usage

Description

5,6-dihydroxy-1H-indole-2-carboxylic acid, also known as 5,6-dihydroxyindole-2-carboxylic acid, is a dihydroxyindole derivative characterized by the presence of hydroxy groups at positions 5 and 6 on the indole-2-carboxylic acid structure. This organic compound serves as a precursor to melanin and has potential applications as an HIV-1 integrase inhibitor.

Uses

Used in Pharmaceutical Industry:
5,6-dihydroxy-1H-indole-2-carboxylic acid is used as a precursor for melanin, which is essential for the pigmentation of skin, hair, and eyes. It plays a crucial role in the synthesis of melanin, making it a significant compound in the study and treatment of pigmentation disorders.
Used in Antiviral Applications:
In the field of antiviral research, 5,6-dihydroxy-1H-indole-2-carboxylic acid is used as a potential HIV-1 integrase inhibitor. Integrase is an enzyme that the HIV virus relies on to integrate its genetic material into the host cell's DNA. By inhibiting this enzyme, the compound can help prevent the replication and spread of the virus, offering a potential therapeutic approach to combat HIV.
Used in Cosmetics Industry:
Due to its role in melanin synthesis, 5,6-dihydroxy-1H-indole-2-carboxylic acid can also be utilized in the cosmetics industry for the development of products aimed at enhancing or regulating skin pigmentation. This can be particularly useful in products designed to address issues such as hyperpigmentation, uneven skin tone, or the desire for a more even complexion.

InChI:InChI=1/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1-3,10-12H,(H,13,14)

Upstream product

• 13520-94-0 Dopachrome 
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• 59-92-7 levodopa 
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• 18766-65-9 O,O,N-triacetyl cycloDOPA methyl ester 
• 1275548-77-0 (S)-cyclo-DOPA-methylester hydrochloride 

Downstream Products

• 3131-52-0 1H-indole-5,6-diol 

Relevant articles and documents

pH stability and antioxidant power of CycloDOPA and its derivatives

CycloDOPA (leukodopachrome), a well known metabolite of tyrosine, is a precursor of melanine in mammalian organisms and of the pigment betalain in plants. However, the isolation of cycloDOPA from natural sources has not been widely reported. In the present work, the stabilities of cycloDOPA and cycloDOPA methyl ester at various pH levels were studied. Both compounds were stable under acidic conditions. By contrast, both compounds were unstable when the pH was shifted from neutral to basic to form indole derivatives as major products. Based on the pH stability, cycloDOPA and its derivatives were subjected to the DPPH radical scavenging assay for the first time.

Oxidative Degradation of Melanins to Pyrrole Acids: a Model Study.

The origin of pyrrole-2,3,5-tricarboxylic acid (PTCA), the most characteristic degradation product of melanins, was investigated by use of synthetic pigments prepared from the major biosynthetic precursors, 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA).Under the reported conditions, i.e. acidic permanganate, oxidative degradation of DHI- and DHICA-melanins afforded PTCA in 0.15 and 3.0percent w/w yield, respectively.A significant improvement of PTCA yields up to 7percent was obtained using alkaline hydrogen peroxide as the oxidising agent.Under these conditions pyrrole-2,3-dicarboxylic acid (PDCA) was also obtained in significant yields.Investigations of the oxidative degradation of some model indole obligomers (1-4) provided unambiguous evidence that PTCA may originate from 2-linked DHI-units in the pigment polymer as well as from DHICA-derived units, whereas PDCA arises from DHI-units not substituted at 2-position.Monitoring of the oxidation of dimer 1 to PTCA showed the intermediate formation of DHICA.Accordingly, a mechanistic route is proposed for the degradation of 2-substituted DHI-units in melanin polymer to PTCA, which also accounts for the observed yields of formation of the pyrrole acid from the model oligomers.