38520-57-9

Basic information

• Product Name: N-Acetylcysteine amide
• Synonyms: N-ACETYL-L-CYSTINE;(R)-2-acetaMido-3-MercaptopropanaMide;PropanaMide,2-(acetylaMino)-3-Mercapto-, (2R)-;N-Acetylcysteine amide Synonyms N-Acetyl-L-cysteinamide;(R)- 2-(Acetylamino)-3-mercapto-Propanamide;acetylcysteinamide;AD4;NACA
• CAS NO: 38520-57-9
• Molecular Formula: C₅H₁₀N₂O₂S
• Molecular Weight: 282.33716
• Mol File: 38520-57-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 147-149 °C(Solv: ethanol (64-17-5))
• Boiling Point: 441.0±40.0 °C(Predicted)
• Appearance: white to off-white/
• Density: 1.226±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: H2O: ≥20mg/mL
• PKA: 9.21±0.10(Predicted)
• CAS DataBase Reference: N-Acetylcysteine amide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetylcysteine amide(38520-57-9)
• EPA Substance Registry System: N-Acetylcysteine amide(38520-57-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 38520-57-9(Hazardous Substances Data)

Usage

Uses

N-acetylcysteine amide has been used:to protect retinal pigment epithelium (RPE) from oxidative stressto show that increased expression of cell adhesion molecule 4 (CADM4) in oligodendrocytes inhibits myelinationto protect cells from apoptosis induced by shikonin plus erlotinib/gefitinibas a component in various culture media

Biochem/physiol Actions

N-acetylcysteine amide is a membrane penetrating antioxidant with antiinflamatory activity through regulation of activation of NF-κB and HIF-1α as well as modulation of ROS. The compound readily crosses cell membranes, replenishes intracellular GSH, and defends the cell from oxidative stress. In contrast to DTT, AD4 is able to directly reduce intracellularl GSSG to GSH without the involvement of glutathione peroxidase. Such direct thiol exchange might have a protective effect. This compound has a potential in research and exploration for treatment of neurodegeneration, radiation exposure, and other oxidation-mediated disorders.

Upstream product

• 7652-46-2 Ac-Cys-OMe 
• 108-24-7 acetic anhydride 
• 74401-72-2 L-cysteinamide 

Downstream Products

• 1028450-42-1 C₁₉H₂₈N₂O₁₁S₂ 
• 16359-16-3 (2R,2R’)-3,3’-disulfanediyl bis(2 acetamidopropanamide) 

Relevant articles and documents

ANTIBACTERIAL AGENT

The invention provides a compound which is a peptide derivative of formula (1) as defined in the claims or a salt thereof: RG is H, -CH2-RGA or C1-12 hydrocarbyl optionally substituted with 1 to 4 substituents selected from -OR', -NO2, -CN, halogen and 5-6 membered heterocyclyl; or RG and RN1 together form a 5-6 membered heterocyclic ring which is optionally substituted with 1 to 3 substituents selected from Ra, -OR' and halogen; RGA is C1-11 hydrocarbyl optionally substituted with 1 to 4 substituents selected from -NR'R", -OR', -NO2, -CN, halogen and 5-6 membered heterocyclyl; RSis C1-16 hydrocarbyl, a 5-10 membered heterocyclyl or heteroaryl group, -(C1-4 alkylene)-RSA or -(C1-4 alkylene)-L-RSA; RSA is C1-16 hydrocarbyl, or a 5-10 membered heterocyclyl or heteroaryl group; L is -SO2-; and wherein RS and RSA are optionally substituted with a group Rb and/or from 1 to 5 substituents selected from Ra, -NR'R", -OR', -NO2, -CN, -C(O)R', -C(O)OR', -C(O)NR'R", -0-C(0)R', -N(R')-C(0)R", -SR', -S(O)R', -S(O)2R', -S(O)2OR', -P(O)(OR')(OR"), =O, -SiR'R"R" and halogen; or Rs and an RC1 together form a 5-6 membered heterocyclyl ring which is optionally substituted with 1 to 3 substituents selected from Ra, -OR' and halogen; Rb is phenyl, benzyl, C3-6 cycloalkyl or 5-6 membered heterocyclyl; Q is -C(O)-N(RN2)-, -C(O)-C(R'R")-, -C(O)-O- -N(RN2)-C(O)-, -C(R'R")- C(O)-, -O-C(O)-, -C(R'R")-C(R"'R"")-, -C(R'R")-O- -O-C(R'R")-, -C(R'R")-N(RN2)-, -N(RN2)-C(R'R")- or -C(R')=C(R")-; Z is a group selected from -C(O)-O-RO and -CN4R' (tetrazolyl); RO is H or C1-12 hydrocarbyl optionally substituted with 1 to 4 substituents selected from -NR'R", -OR', -NO2, -CN, -C(O)R', -C(O)OR', -C(O)NR'R", -O-C(O)R', -N(R')- C(O)R", -SR', -S(O)R', -S(O)2R', -S(O)2OR', -P(O)(OR')(OR"), =O, halogen and 5-6 membered heterocyclyl; or RO and an RC2 together form a 5-6 membered heterocyclyl ring which is optionally substituted with 1 to 3 substituents selected from Ra, -OR' and halogen; each RN1 and RN2 is independently H or C1-4 alkyl; each RC1, RC2, R', R", R" and R"" is independently H or C1-4 alkyl and is optionally substituted with 1 to 3 substituents selected from halogen, -OH and -O-C1-4 alkyl; and each Ra is independently C1-4 alkyl which is optionally substituted with 1 to 3 halogen atoms.

METHOD FOR THE PREPARATION OF N-ACETYL CYSTEINE AMIDE

The present application discloses an efficient process for the preparation of N-acetyl-L-cysteine amide (NACA) starting with N-acetyl-L-cysteine.

From disulfide- to thioether-linked glycoproteins

(Chemical Presented) Strengthening the bond: The introduction of a thiol tag in combination with chemoselective ligation to form a disulfide-linked bioconjugate is a selective and useful method for site-selective protein glycosylation. The phosphine-mediated desulfurization of such glycoconjugates to their reductant-resistant thioether-linked counterparts completes a convergent, site-selective synthesis of thioether-linked glycoproteins (see scheme).