19641-92-0

Basic information

• Product Name: Cysteinyldopa
• Synonyms: Cysteinyldopa
• CAS NO: 19641-92-0
• Molecular Formula: C₁₂H₁₆N₂O₆S
• Molecular Weight: 316.33
• Mol File: 19641-92-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 599.9°Cat760mmHg
• Flash Point: 316.6°C
• Appearance: /
• Density: 1.63g/cm³
• Refractive Index: 1.651
• CAS DataBase Reference: Cysteinyldopa(CAS DataBase Reference)
• NIST Chemistry Reference: Cysteinyldopa(19641-92-0)
• EPA Substance Registry System: Cysteinyldopa(19641-92-0)

Safety Data

• Hazardous Substances Data: 19641-92-0(Hazardous Substances Data)

Usage

Description

Cysteinyldopa is a chemical compound that is formed during the metabolism of the amino acid tyrosine in the human body. It serves as an intermediate in the production of melanin, which is the pigment responsible for the coloration of the skin, hair, and eyes. Cysteinyldopa has been linked to the development of skin disorders such as vitiligo and melanoma, with elevated levels observed in individuals affected by these conditions. Furthermore, cysteinyldopa has emerged as a potential biomarker for the diagnosis and monitoring of melanoma, garnering interest in medical research for improving the understanding and treatment of skin-related diseases.

Uses

Used in Medical Research:
Cysteinyldopa is used as a biomarker for the diagnosis and monitoring of melanoma, a type of skin cancer. Its elevated levels in individuals with melanoma make it a valuable tool in medical research aimed at better understanding and treating skin-related diseases.
Used in Dermatology:
In the field of dermatology, cysteinyldopa is used for studying the development of skin disorders such as vitiligo and melanoma. Its involvement in these conditions helps researchers and medical professionals to explore potential treatments and management strategies for affected individuals.

InChI:InChI=1/C12H16N2O5S/c13-7(5-20)11(17)14-8(12(18)19)3-6-1-2-9(15)10(16)4-6/h1-2,4,7-8,15-16,20H,3,5,13H2,(H,14,17)(H,18,19)

Upstream product

• 59-92-7 levodopa 
• 52-89-1 l-cysteine hydrochloride 
• 19641-91-9 N-acetyl-3,4-dihydroxyphenylalanine ethylester 
• 56-89-3 L-cystine 
• 52-90-4 L-Cysteine 
• 4430-97-1 L-dopaquinone 

Related news

General paperNon-enzymic oxidation of Cysteinyldopa (cas 19641-92-0) catalyzed by metallic ions09/03/2019

1.1. Evidence is presented that under physiological conditions cysteinyldopa behaves similarly to catecholamines, e.g. adrenaline, in forming reversible complexes with various metallic cations.2.2. As a rule, these complexes are stable under anaerobic conditions, but readily autoxidize in the pr...detailed

Presence of Cysteinyldopa (cas 19641-92-0) in the mature bovine eye09/01/2019

The concentration of dopa, dopamine and cysteinyldopa were measured in various parts of the mature bovine eye, using a fluorescent assay. Special attention was paid to cysteinyldopa levels, since this compound is thought to be a specific marker of melanin turnover. Levels of cysteinyldopa in the...detailed

Relevant articles and documents

One-step synthesis of (2-amino-2-carboxyethylthio)dopas (cys-dopas) from dopa and cysteine by hydrogen peroxide in the presence of iron-EDTA complex

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Inhibition effects of 5-S-glutathionyl-N-β-alanyl-L-dopa analogues against Src protein tyrosine kinase

Twelve analogues of the antibacterial phenolic peptide 5-S- glutathionyl-N-β-alanyl-L-dopa (5-S-GA-L-D, 1) were synthesized via orthoquinone using tyrosinase. Several synthesized compounds inhibited the v- Src autophosphorylation tyrosine kinase reaction with an IC50 value comparable to that of herbimycin A. The inhibition of c-Src substrate phosphorylation was much less active than v-Src autophosphorylation inhibition. 5-S-GAL-D (1) and its analogous competed with peptide substrate and non-competed with ATP. The analogues showed no effects on substrate phosphorylation by epidermal growth factor receptor (EGFR), and this selectivity is the most characteristic feature of the 5-S-GA-L-D and its analogues (1 - 12).

Synthesis and Antitumor activity of Cysteinyl-3,4-dihydroxyphenylalanines and Related Compounds

The natural catecholic amino acid 5-S-cysteinyl-3,4-dihydroxyphenylalanine (1) was selectively toxic to a variety of human tumor cell lines in culture and exhibited antitumor activity against L1210 leukemia and B-16 melanoma in mice at doses which were not toxic to the host.Structural analogues of 5-S-cysteinyl-3,4-dihydroxyphenylalanine, including several new compounds, were synthesized and tested for growth inhibition of cultured cells of human neuroblastoma YT-nu and Chinese hamster fibroblast Don-6.Some were also examined for antitumor activity against L1210 and B-16 in vivo. 4-S-Cysteinylcatechols and 2- and 4-S-cysteinylphenols, which cannot be prepared by conventional methods, were synthesized by the reaction of catechols and phenols with cystine in boiling aqueous HBr. 5-S-Cysteinyl and 2-S-cysteinyl-3,4-dihydroxyphenylalanine (1 and 2), L-3,4-dihydroxyphenylalanine (L-Dopa), and 2- and 4-S-cysteinylphenol (14 and 15) were toxic to the YT-nu cell line only, while 4-S-cysteinylcatechol (6), 3-S-cysteinyl-5-methylcatechol (8), 5-S-cysteaminyldopamine (9), and 4-methylcatechol were strongly toxic to both cell lines.Compounds 1 (1000 mg/kg), 6 (500 mg/kg), and 8 (400 mg/kg) increased the life span of L1210-bearing mice by 50, 50, and 43percent, respectively, and compounds 1 and 8 were marginally effective against B-16 melanoma as well.Compound 9 was too toxic to show any activity.There was good correlation between the cytotoxicity and the in vivo activity.