Molecular structure of 5,6-Dihydroxyindole-2-carboxylic Acid, CAS Number: 4790-08-3
5,6-Dihydroxyindole-2-carboxylic Acid (CAS 4790-08-3)
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Alternate Names:
5,6-Dihydroxyindole-2-carboxylic Acid is also known as DHICA.
Application:
5,6-Dihydroxyindole-2-carboxylic Acid is an intermediate in the process of melanin synthesis, able to tautomerize into Dopachrome.
CAS Number:
4790-08-3
Molecular Weight:
193.16
Molecular Formula:
C9H7NO4
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
5,6-Dihydroxyindole-2-carboxylic Acid is an intermediate in the process of melanin synthesis. 5,6-Dihydroxyindole-2-carboxylic Acid highly reactive and an important intermediate in the enzymatic pathways that lead to the formation of various types of melanin, including eumelanin, which provides brown to black pigmentation. 5,6-Dihydroxyindole-2-carboxylic Acid′s role in melanin synthesis is useful in the study of pigment-related biological processes. It serves as a substrate for the enzyme tyrosinase, which catalyzes its oxidation among other steps in the melanin synthesis pathway. Understanding the behavior and reactivity of 5,6-Dihydroxyindole-2-carboxylic Acid within this pathway is for insights into how melanin′s chemical composition and properties are determined.
5,6-Dihydroxyindole-2-carboxylic Acid (CAS 4790-08-3) References
- The 5,6-dihydroxyindole-2-carboxylic acid (DHICA) oxidase activity of human tyrosinase. | Olivares, C., et al. 2001. Biochem J. 354: 131-9. PMID: 11171088
- Regulation of the final phase of mammalian melanogenesis. The role of dopachrome tautomerase and the ratio between 5,6-dihydroxyindole-2-carboxylic acid and 5,6-dihydroxyindole. | Aroca, P., et al. 1992. Eur J Biochem. 208: 155-63. PMID: 1511683
- 5,6-Dihydroxyindole-2-carboxylic acid is incorporated in mammalian melanin. | Tsukamoto, K., et al. 1992. Biochem J. 286 (Pt 2): 491-5. PMID: 1530581
- The Tyrosinase-tyrosine Reaction: Production from Tyrosine of 5: 6-Dihydroxyindole and 5: 6-Dihydroxyindole-2-carboxylic Acid-the Precursors of Melanin. | Raper, HS. 1927. Biochem J. 21: 89-96. PMID: 16743827
- The eumelanin intermediate 5,6-dihydroxyindole-2-carboxylic acid is a messenger in the cross-talk among epidermal cells. | Kovacs, D., et al. 2012. J Invest Dermatol. 132: 1196-205. PMID: 22297637
- Roles of reactive oxygen species in UVA-induced oxidation of 5,6-dihydroxyindole-2-carboxylic acid-melanin as studied by differential spectrophotometric method. | Ito, S., et al. 2016. Pigment Cell Melanoma Res. 29: 340-51. PMID: 26920809
- Preparation of eumelanin-related metabolites 5,6-dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, and their O-methyl derivatives. | Wakamatsu, K. and Ito, S. 1988. Anal Biochem. 170: 335-40. PMID: 3394933
- Photoreactivity and phototoxicity of experimentally photodegraded hair melanosomes from individuals of different skin phototypes. | Mokrzyński, K., et al. 2023. J Photochem Photobiol B. 243: 112704. PMID: 37030132
- A new enzymatic function in the melanogenic pathway. The 5,6-dihydroxyindole-2-carboxylic acid oxidase activity of tyrosinase-related protein-1 (TRP1). | Jiménez-Cervantes, C., et al. 1994. J Biol Chem. 269: 17993-8000. PMID: 8027058
- Polymerization of 5,6-dihydroxyindole-2-carboxylic acid to melanin by the pmel 17/silver locus protein. | Chakraborty, AK., et al. 1996. Eur J Biochem. 236: 180-8. PMID: 8617263
- Chemical characterization of eumelanins with special emphasis on 5,6-dihydroxyindole-2-carboxylic acid content and molecular size. | Ozeki, H., et al. 1997. Anal Biochem. 248: 149-57. PMID: 9177734
- Coordinated microRNA/mRNA Expression Profiles Reveal Unique Skin Color Regulatory Mechanisms in Chinese Giant Salamander (Andrias davidianus) | by Yanjie Guo, et al. 2023,. Animals. 3(7),: 11811.
- The elastase and melanogenesis inhibitory and anti-inflammatory activities of phosvitin phosphopeptides produced using HTMP pre-treatment and enzyme hydrolysis combinations | JE Lee, BJ An, C Jo, B Min, HD Paik, DU Ahn -. 5 April 2023,. Poultry Science. 102680.
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
5,6-Dihydroxyindole-2-carboxylic Acid, 10 mg | sc-499091 | 10 mg | $364.00 | |||
5,6-Dihydroxyindole-2-carboxylic Acid, 100 mg | sc-499091A | 100 mg | $2507.00 |