25565-17-7

Basic information

• Product Name: 2-S-cysteinyldopa
• Synonyms: 2-S-cysteinyldopa
• CAS NO: 25565-17-7
• Molecular Formula: C₁₂H₁₆N₂O₆S
• Molecular Weight: 316.33024
• Mol File: 25565-17-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 593.2°Cat760mmHg
• Flash Point: 312.6°C
• Appearance: /
• Density: 1.63g/cm³
• Vapor Pressure: 6.42E-15mmHg at 25°C
• Refractive Index: 1.714
• PKA: 2.04±0.10(Predicted)
• CAS DataBase Reference: 2-S-cysteinyldopa(CAS DataBase Reference)
• NIST Chemistry Reference: 2-S-cysteinyldopa(25565-17-7)
• EPA Substance Registry System: 2-S-cysteinyldopa(25565-17-7)

Safety Data

• Hazardous Substances Data: 25565-17-7(Hazardous Substances Data)

Usage

Description

2-S-Cysteinyldopa is an L-tyrosine derivative in which the hydrogen at position 2 on the phenyl ring is replaced by a cysteinyl group. It is a biomarker found in the urine of patients with melanoma, indicating its potential use in the detection and monitoring of this specific type of cancer.

Uses

Used in Medical Industry:
2-S-Cysteinyldopa is used as a biomarker for the detection and monitoring of melanoma in patients. Its presence in urine samples can help in the early identification of the disease, allowing for timely intervention and treatment.
Used in Research and Development:
2-S-Cysteinyldopa can be utilized in research to better understand the biochemical processes involved in melanoma development and progression. This knowledge can contribute to the development of novel therapeutic strategies and targeted treatments for melanoma patients.
Used in Diagnostic Tests:
2-S-Cysteinyldopa can be incorporated into diagnostic tests to specifically identify melanoma in patients. These tests can help in the accurate diagnosis of the disease, which is crucial for determining the appropriate treatment plan and improving patient outcomes.

InChI:InChI=1/C12H16N2O6S/c13-6(11(17)18)3-5-1-2-8(15)9(16)10(5)21-4-7(14)12(19)20/h1-2,6-7,15-16H,3-4,13-14H2,(H,17,18)(H,19,20)/t6-,7-/m0/s1

Upstream product

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

Relevant articles and documents

The first expedient entry to the human melanogen 2-S-cysteinyldopa exploiting the anomalous regioselectivity of 3,4-dihydroxycinnamic acid-thiol conjugation

The first convenient synthesis of 2-S-cysteinyl-3,4-dihydroxyphenylalanine (2-S-cysteinyldopa) in 30% overall yield is reported, which capitalizes on the anomalous regiochemistry of the oxidative coupling of 3,4-dihydroxycinnamic acid derivatives with thi

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.