N-Acetyl-L-cysteine ethyl ester is the esterified form of NAC. N-Acetyl-L-cysteine ethyl ester displays enhanced cell permeability and produces NAC and cysteine. N-Acetyl-L-cysteine ethyl ester increases hydrogen sulfide (H2S) recycling. N-Acetyl-L-cysteine ethyl ester may be used to replace NAC as a viscosolvent and glutathione-related antioxidant (antioxidant).

Physicochemical Properties

Molecular Formula	C7H13NO3S
Molecular Weight	191.25
Exact Mass	191.062
CAS #	59587-09-6
PubChem CID	148861
Appearance	White to off-white solid powder
Density	1.138g/cm3
Boiling Point	337.6ºC at 760 mmHg
Flash Point	158ºC
Index of Refraction	1.48
LogP	0.824
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Heavy Atom Count	12
Complexity	172
Defined Atom Stereocenter Count	1
SMILES	CCOC(=O)[C@H](CS)NC(=O)C
InChi Key	MSMRAGNKRYVTCX-LURJTMIESA-N
InChi Code	InChI=1S/C7H13NO3S/c1-3-11-7(10)6(4-12)8-5(2)9/h6,12H,3-4H2,1-2H3,(H,8,9)/t6-/m0/s1
Chemical Name	ethyl (2R)-2-acetamido-3-sulfanylpropanoate
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro

N-acetyl-L-cysteine ethyl ester is N-acetyl-L-cysteine (NAC) in an esterified form. N-Acetyl-L-cysteine ethyl ester produces cysteine and NAC and shows increased cell permeability. N-Acetyl-L-cysteine ethyl ester can be employed as an H2S producer and raises the amount of hydrogen sulfide (H2S) in the air. As a mucolytic agent and GSH-related antioxidant, N-Acetyl-L-cysteine ethyl ester may replace NAC[1].

References

[1]. N-Acetylcysteine ethyl ester (NACET): a novel lipophilic cell-permeable cysteine derivative with an unusual pharmacokinetic feature and remarkable antioxidant potential. Biochem Pharmacol. 2012 Dec 1;84(11):1522-33.

Solubility Data

Solubility (In Vitro)

H2O: ≥ 100 mg/mL (522.88 mM) DMSO: 50 mg/mL (261.44 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (13.07 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 2: ≥ 1 mg/mL (5.23 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 3: ≥ 1 mg/mL (5.23 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.2288 mL	26.1438 mL	52.2876 mL
	5 mM	1.0458 mL	5.2288 mL	10.4575 mL
	10 mM	0.5229 mL	2.6144 mL	5.2288 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.