3571-34-4

Basic information

• Product Name: dopachrome
• Synonyms: dopachrome;2,3,5,6-Tetrahydro-5,6-dioxo-1H-indole-2-carboxylic acid;5,6-Dihydro-5,6-dioxoindoline-2-carboxylic acid;5,6-Dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acid;Dopachrom;DopachroMe Discontinued;5,6-dioxo-2,3-dihydro-1H-indole-2-carboxylic acid
• CAS NO: 3571-34-4
• Molecular Formula: C₉H₇NO₄
• Molecular Weight: 193.15618
• Product Categories: Amino Acids & Derivatives, Neurochemicals, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 3571-34-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 481.1°Cat760mmHg
• Flash Point: 244.8°C
• Appearance: /
• Density: 1.56g/cm³
• Vapor Pressure: 1.41E-10mmHg at 25°C
• Refractive Index: 1.639
• PKA: 1.97±0.20(Predicted)
• CAS DataBase Reference: dopachrome(CAS DataBase Reference)
• NIST Chemistry Reference: dopachrome(3571-34-4)
• EPA Substance Registry System: dopachrome(3571-34-4)

Safety Data

• Hazardous Substances Data: 3571-34-4(Hazardous Substances Data)

Usage

Description

Dopachrome, also known as cyclo-DOPA or 5,6-dihydroxyindole-2-carboxylic acid, is a cyclized product of L-DOPA and serves as an intermediate in the biosynthesis of melanin. It plays a crucial role in the pigmentation process and has potential applications in various industries due to its unique properties.

Uses

Used in Pharmaceutical Industry:
Dopachrome is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly those related to melanin production and regulation. Its involvement in the melanin biosynthesis pathway makes it a valuable compound for studying and treating conditions related to pigmentation disorders.
Used in Cosmetics Industry:
In the cosmetics industry, dopachrome is used as an ingredient in skin care products and formulations designed to address pigmentation issues, such as hyperpigmentation and uneven skin tone. Its role in melanin production allows for the development of products that can help regulate and balance skin pigmentation.
Used in Research and Development:
Dopachrome is utilized in research and development for the study of melanin biosynthesis, pigmentation processes, and related biological mechanisms. Understanding the role of dopachrome in these processes can lead to the discovery of new therapeutic approaches for pigmentation-related conditions and the development of novel cosmetic products.

InChI:InChI=1/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10H,1H2,(H,13,14)

Upstream product

• 60-18-4 L-tyrosine 
• 59-92-7 levodopa 

Downstream Products

• 3131-52-0 1H-indole-5,6-diol 
• 4790-08-3 5,6-dihydroxy-2-carboxyindole 

Relevant articles and documents

Continuous-flow step gradient mass spectrometry based method for the determination of kinetic parameters of immobilized mushroom tyrosinase in equilibrating conditions: Comparison with free enzyme

A mass spectrometry (MS)-based methodology for enzymatic assay in equilibrium conditions was designed and evaluated. This on-line assay involves the introduction of a continuous-flow step gradient (CFSG) of a substrate solution in the column containing immobilized enzyme and the simultaneous tracking of the product formation. We showed that the constant concentration of substrate in the entire bioreactor for an appropriate duration ensures the equilibration of the studied enzyme (mushroom tyrosinase). Under these conditions, it was demonstrated also that the kinetic and enzymatic parameters (Michaelis-Menten constant, KM, the maximal specific activity, SAmax) are independent of the flow rate of the mobile phase. The feasibility of the mentioned approach for inhibitory tests was also investigated. The coupling of the mass spectrometer to the bio-reactor allows the selective monitoring of the enzymatic reaction products and increases their detection level. Very high sensitivity, 500 pmol/min/column, and selective monitoring of the products of the enzymatic reaction are allowed by MS detection. The methodology developed here constitutes a sensitive analytical tool to study enzymes requiring long equilibration times. Copyright

HAIR DYE COMPOSITION

An air-oxidative type hair dye composition containing a melanin precursor prepared by a process including (A) an oxidation step for converting, into the melanin precursor, a tyrosine or derivative thereof used as a starting substance with an enzyme or cell that is derived from a fungus selected from the group consisting of fungi belonging to the genera Aspergillus, Neurospora, Rhizomucor, Trichoderma, and Penicillium and that exhibits a catechol oxidase activity.