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Application Area

L-Cysteine Ethyl Ester Hydrochloride

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

L-Cysteine ethyl ester hydrochloride is widely used in food additive, cosmetic, pharmaceutical area.

Category

L-Amino Acids

Catalog number

BAT-003968

CAS number

868-59-7

Molecular Formula

C5H12ClNO2S

Molecular Weight

185.67

IUPAC Name

ethyl (2R)-2-amino-3-sulfanylpropanoate;hydrochloride

Synonyms

Cystanin; Ethyl L-cysteinate hydrochloride; Ethyl cysteinate hydrochloride; NSC 117387; NSC 519837

Related CAS

3411-58-3 (free base)

Appearance

White crystalline powder

Purity

≥ 99% (Titration)

Density

1.391 g/cm3

Melting Point

123-125 °C

Boiling Point

205.9°C at 760 mmHg

Storage

Store at -20°C

InChI

InChI=1S/C5H11NO2S.ClH/c1-2-8-5(7)4(6)3-9;/h4,9H,2-3,6H2,1H3;1H/t4-;/m0./s1

InChI Key

JFKJWWJOCJHMGV-WCCKRBBISA-N

Canonical SMILES

CCOC(=O)C(CS)N.Cl

L-Cysteine Ethyl Ester Hydrochloride, a derivative of the amino acid L-cysteine, finds wide-ranging applications across scientific and industrial domains. Here are four key applications of L-Cysteine Ethyl Ester Hydrochloride:

Pharmaceuticals: Embedded within the realm of pharmaceuticals, L-Cysteine Ethyl Ester Hydrochloride emerges as a pivotal element in drug formulation, serving as a precursor for crafting anti-inflammatory and mucolytic agents. Its role extends to enhancing the bioavailability and stability of active compounds, ultimately elevating their therapeutic effectiveness. This compound plays a crucial role in the development of treatments for chronic respiratory afflictions like bronchitis and cystic fibrosis, reshaping the landscape of respiratory health therapies.

Cosmetics and Personal Care: Delving into the cosmetics sphere, L-Cysteine Ethyl Ester Hydrochloride infiltrates hair care and skin care products, fostering the fortification of hair fibers and bolstering the growth and elasticity of keratin, the primary structural protein in hair and skin. Its antioxidative prowess contributes to shielding skin cells from environmental onslaughts, nurturing a rejuvenated appearance that exudes vitality and resilience.

Nutritional Supplements: Positioned at the intersection of nutrition and health, L-Cysteine Ethyl Ester Hydrochloride assumes a crucial role in dietary supplements aimed at promoting holistic well-being. Its involvement in glutathione synthesis, a potent antioxidant pivotal for cellular defense against oxidative stress, underscores its significance. Often integrated into formulations designed to augment immune functionality and facilitate detoxification processes, this compound stands as a cornerstone in the realm of nutritional support systems.

Biochemical Research: Within the confines of cutting-edge biochemical research, L-Cysteine Ethyl Ester Hydrochloride emerges as a versatile reagent employed in a myriad of assays and investigations. Its attribution as a reducing agent lends it immense value in experiments focused on protein folding dynamics and thiol group safeguarding. Researchers leverage its unique properties to probe the redox equilibrium of cells, unravel the intricacies of protein structure, and decipher functional intricacies, propelling forward the frontiers of biochemical inquiry and understanding.

1.Facile synthesis of cysteine and triethanolamine capped CdTe nanoparticles.

Mntungwa N1, Pullabhotla VS, Revaprasadu N. Colloids Surf B Biointerfaces. 2013 Jan 1;101:450-6. doi: 10.1016/j.colsurfb.2012.07.010. Epub 2012 Jul 28.

Cysteine and triethanolamine capped CdTe nanoparticles have been synthesized using a simple aqueous solution based method. This method involves the reaction of tellurium powder with sodium borohydride (NaBH(4)) in water to produce telluride ions (Te(2-)), followed by the simultaneous addition of an aqueous solution of cadmium chloride or other cadmium source (acetate, carbonate and nitrate) and solution of L-cysteine ethyl ester hydrochloride or triethanolamine. The effect of capping agent on the size, structure and morphology of the as-synthesized nanoparticles was investigated. The particles were characterized using optical spectroscopy, transmission electron microscopy (TEM), high-resolution TEM (HRTEM), X-ray diffraction (XRD) and Fourier transform infrared (FT-IR) spectroscopy.

2.Preparation and properties of S-nitroso-L-cysteine ethyl ester, an intracellular nitrosating agent.

Clancy R1, Cederbaum AI, Stoyanovsky DA. J Med Chem. 2001 Jun 7;44(12):2035-8.

In this report, a protocol for the preparation of the hydrochloride of S-nitroso-L-cysteine ethyl ester (SNCEE.HCl; 2) is presented. The synthesis of 2 has been targeted because S-nitroso-L-cysteine (SNC; 2b), which is extensively used for trans-S-nitrosation of thiol-containing proteins, has a limited ability of crossing cellular membranes. The nitrosothiol 2 was prepared via direct S-nitrosation of the hydrochloride of L-cysteine ethyl ester (CEE.HCl; 1a) with ethyl nitrite. 2 is relatively stable in crystal form and when neutralized to SNCEE (2a) in aqueous solutions treated with chelators of metal ions. Traces of metal ions, however, triggered the decomposition of 2a to nitric oxide and a S-centered radical, which were detected by ESR spectrometry. In contrast to 2b, 2a is a lipophilic compound that was taken up by human neutrophils. The latter process was paralleled by inhibition of the NADPH oxidase-dependent generation of superoxide anion radicals, presumably via reaction(s) of intracellular trans-S-nitrosation.

3.The solid-state molecular structure of the S-nitroso derivative of L-cysteine ethyl ester hydrochloride.

Yi J1, Khan MA, Lee J, Richter-Addo GB. Nitric Oxide. 2005 Jun;12(4):261-6.

Nitrosation of protein sulfhydryl groups to form thionitrites (S-nitrosothiols) has been reported to be important in the biochemistry of nitric oxide. Such S-nitrosation of protein thiol residues has been shown to alter the function of some proteins. In this brief communication, we report the X-ray crystal structure of S-nitroso-L-cysteine ethyl ester hydrochloride. Two rotamers with respect to the NCCS moiety are present in the crystal: the major rotamer is in the gauche+ conformation, and the minor rotamer is in the rare anti (trans, antiperiplanar) conformation for a cysteinyl compound. Importantly, the CSNO groups for both rotamers are in the syn (cis, synperiplanar) form. To the best of our knowledge, this is the first reported high-resolution solid-state structure of an S-nitroso derivative of a cysteine or cysteinyl-containing compound.

4.Ultraviolet A regulates the stemness of human adipose tissue-derived mesenchymal stem cells through downregulation of the HIF-1α via activation of PGE(2)-cAMP signaling.

Lee J1, Jung E, Hyun JW, Park D. J Cell Biochem. 2012 Dec;113(12):3681-91. doi: 10.1002/jcb.24241.

Ultraviolet A (UVA) irradiation is responsible for a variety of changes in cell biology. The purpose of this study was to investigate the effects of UVA irradiation on the stemness properties of human adipose tissue-derived mesenchymal stem cells (hAMSCs). Furthermore, we examined the UVA-antagonizing effects of L-cysteine ethylester hydrochloride (ethylcysteine) and elucidated its action mechanisms. The results of this study showed that UVA reduced the proliferative potential and stemness of hAMSCs, as evidenced by reduced proliferative activity in the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and downregulation of OCT4, NANOG, and SOX2, stemness-related genes. The mRNA level of hypoxia-inducible factor (HIF)-1α, but not HIF-2α was reduced by UVA. Moreover, the knockdown of HIF-1α using small interfering RNA (siRNA) for HIF-1α was found to downregulate stemness genes, suggesting that UVA reduces the stemness through downregulation of HIF-1α.