Ethyl sarcosinate hydrochloride Chemical Properties

Melting point:

~125 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

H₂O: 0.1 g/mL, clear

form 

Crystalline Powder

color 

White to off-white

Water Solubility 

Soluble in water 0.1 g/mL.

Sensitive 

Hygroscopic

BRN 

3911182

InChI

InChI=1S/C5H11NO2.ClH/c1-3-8-5(7)4-6-2;/h6H,3-4H2,1-2H3;1H

InChIKey

NIDZUMSLERGAON-UHFFFAOYSA-N

SMILES

C(=O)(OCC)CNC.Cl

CAS DataBase Reference

52605-49-9(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29299090

MSDS

• Language:English Provider:Sarcosine ethyl ester hydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl sarcosinate hydrochloride Usage And Synthesis

Chemical Properties

white to off-white crystalline solid

Uses

Sarcosine ethyl ester hydrochloride is a metabolite of Sarcosine (S140500), which as been found in starfish and sea urchins. It is used as intermediate in the synthesis of antienzyme agents for toothpaste. Found to be a marker for prostate cancer bioagression.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

Thiophenecarbonyl chloride (65 mL, 900 mmol) was added dropwise to a solution of sarcosine (20.0 g, 224 mmol) in ethanol (250 mL) cooled in an ice-water bath under stirring conditions, and the reaction temperature was maintained at about -10°C. After the dropwise addition was completed, the reaction mixture was gently heated at 55°C overnight until the solution became clear. Upon completion of the reaction, the solvent and residual thionyl chloride were removed by distillation under reduced pressure. The resulting solid residue was washed with ether (3 x 50 mL) and subsequently dried well under vacuum to afford ethyl sarcosinate hydrochloride (33.5 g, 218 mmol) in white powder form in 97% yield. The product could be used in subsequent steps without further purification. The product was characterized as follows: melting point 126°C (literature value 125-127°C); IR (ATR) ν cm?1 2970-2440, 1742, 1229; 1H NMR (CDCl?, 400 MHz) δ 9.64 (br.s, 2H, NH?), 4.24 (q, 2H, 3J = 7.1 Hz, CH?CH?), 3.84 (t, 2H, 3J = 7.1 Hz, CH?CH?), 4.24 (q, 2H, 3J = 7.1 Hz, CH? 3.84 (t, 2H, 3J = 5.7 Hz, NH?CH?), 2.80 (t, 3H, 3J = 5.2 Hz, NH?CH?), 1.26 (t, 3H, 3J = 7.1 Hz, CH?CH?); 13C NMR (CDCl?, 101 MHz) δ 166.18 (CO?), 62.62 (CH?CH?), 48.94 (NH?CH?), 33.34 (NH?CH?), 14.03 (CH?CH?).

References

[1] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 51 - 67
[2] Patent: US4432971, 1984, A
[3] Patent: US4432972, 1984, A

Ethyl sarcosinate hydrochloride(52605-49-9)Related Product Information

• N,N-Dimethyl-1,4-phenylenediamine
• Glycine
• Tris(trimethylsilyl)phosphate
• Aminoacetonitrile hydrochloride
• Ethyl 3-aminopropanoate hydrochloride
• Ethyl acetate
• Ethanol
• Sarcosine
• Glycine ethyl ester hydrochloride
• CREATININE-D3
• SARCOSINE HYDROCHLORIDE
• Ethylparaben
• Sodium lauroylsarcosinate
• ISOXADIFEN-ETHYL
• Sodium sarcosinate
• Ethyl cyanoacetate
• Tris(hydroxymethyl)aminomethane
• Methyl acrylate