CAS 4790-08-3

5,6-Dihydroxyindole-2-carboxylic acid

Description:

5,6-Dihydroxyindole-2-carboxylic acid is an organic compound that belongs to the class of indole derivatives. It features a bicyclic structure characterized by an indole ring system, which is fused with a carboxylic acid group and two hydroxyl groups at the 5 and 6 positions. This compound is known for its role in the biosynthesis of melanin, particularly in the formation of eumelanin, a pigment found in various biological systems. The presence of hydroxyl groups contributes to its potential reactivity and solubility in polar solvents. Additionally, the carboxylic acid functionality can participate in acid-base reactions, making it a weak acid. Its structural features allow it to engage in hydrogen bonding, influencing its interactions in biological and chemical environments. Due to its significance in pigmentation and potential applications in biochemistry and materials science, 5,6-Dihydroxyindole-2-carboxylic acid is of interest in various research fields.

Formula: C₉H₇NO₄

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

InChI key: InChIKey=YFTGOBNOJKXZJC-UHFFFAOYSA-N

SMILES: C(O)(=O)C1=CC=2C(N1)=CC(O)=C(O)C2

Synonyms:

• 1H-indole-2-carboxylic acid, 5,6-dihydroxy-
• 2-Carboxy-5,6-dihydroxyindole
• 5,6-Dihydroxy-2-carboxyindole
• 5,6-Dihydroxyindole-2-carboxylic acid
• Indole-2-carboxylic acid, 5,6-dihydroxy-
• 5,6-Dihydroxy-1H-indole-2-carboxylic acid

5,6-Dihydroxy-1H-indole-2-carboxylic acid

CAS: 4790-08-3

Formula: C₉H₇NO₄

Purity: 95%

Color and Shape: Solid

Molecular weight: 193.1562

Ref: IN-DA00DDBG

DHICA

CAS: 4790-08-3

DHICA

Purity: 95%

Molecular weight: 193.16g/mol

Ref: 54-OR1007070

Levodopa Impurity 4

CAS: 4790-08-3

Formula: C₉H₇NO₄

Color and Shape: Grey Solid

Molecular weight: 193.16

Ref: 4Z-D-3227

5,6-Dihydroxyindole-2-carboxylic Acid

CAS: 4790-08-3

Stability Air Sensitive
Applications 5,6-Dihydroxyindole-2-carboxylic Acid is the indole analogue of DOPA. 5,6-Dihydroxyindole-2-carboxylic Acid is a precursor to melanin as well as potential as HIV-1 integrase inhibitors.
References Hansson, C.: Acta Derm.-Venereol., 63, 147 (1983); Sechi, M. et al.: Antiviral Chem. Chemother., 15, 67 (2004);

Formula: C₉H₇NO₄

Color and Shape: Neat

Molecular weight: 193.16

Ref: TR-D452825

5,6-Dihydroxy-1H-indole-2-carboxylic acid

CAS: 4790-08-3

5,6-Dihydroxy-1H-indole-2-carboxylic acid (5,6 DHICA) is a photosensitizing agent with a long detection time. It has been used in the treatment of cervical cancer and skin cancer. 5,6 DHICA is an inhibitor of tyrosinase, which is responsible for the synthesis of melanin. 5,6 DHICA prevents the conversion of dopachrome to eumelanin by binding to the active site of tyrosinase and inhibiting its activity. This makes it an important drug for the treatment of hyperpigmentation disorders such as vitiligo and melasma.

Formula: C₉H₇NO₄

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 193.16 g/mol

Ref: 3D-FD143496

5,6-Dihydroxy-1H-indole-2-carboxylic acid

CAS: 4790-08-3

Formula: C₉H₇NO₄

Purity: 95%

Color and Shape: Solid

Molecular weight: 193.158

Ref: 10-F232126

DHICA

CAS: 4790-08-3

DHICA (5,6-Dihydroxyindole-2-carboxylic acid) is an intermediate in melanin synthesis and a component of eumelanin, as well as acting as a moderate potency agonist of GPR35. In the U2OS cell line, DHICA demonstrates the ability to induce β-arrestin translocation signaling with an EC50 value of 23.2 μM. Additionally, it plays a significant role in promoting and protecting against DNA damage.

Formula: C₉H₇NO₄

Color and Shape: Solid

Molecular weight: 193.16

Ref: TM-T201499