Sarcosine

Base Information

• Chemical Name: Sarcosine
• CAS No.: 107-97-1
• Deprecated CAS: 783292-49-9
• Molecular Formula: C3H7NO2
• Molecular Weight: 89.0941
• Hs Code.: 29224995
• European Community (EC) Number: 203-538-6,270-156-4,636-764-2
• NSC Number: 118114
• UNII: Z711V88R5F
• DSSTox Substance ID: DTXSID1047025
• Nikkaji Number: J5.067I
• Wikipedia: Sarcosine
• Wikidata: Q414157
• NCI Thesaurus Code: C113501
• RXCUI: 1362906
• Metabolomics Workbench ID: 37173
• ChEMBL ID: CHEMBL304383
• Mol file: 107-97-1.mol

Synonyms:Sarcosine(8CI);(Methylamino)acetic acid;(Methylamino)ethanoic acid;2-(Methylamino)acetic acid;Acetic acid, (methylamino)-;Methylglycine;N-Methylaminoaceticacid;N-Methylglycine;Sarcosin;Sarcosinic acid;

Chemical Property of Sarcosine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.184mmHg at 25°C
• Melting Point: 208-212 °C (dec.)(lit.)
• Refractive Index: 1.431
• Boiling Point: 195.1 °C at 760 mmHg
• PKA: 2.21(at 25℃)
• Flash Point: 71.8 °C
• PSA: 49.33000
• Density: 1.093 g/cm³
• LogP: -0.31870
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: H2O: 1 M at 20 °C
• Water Solubility.: 1480 g/L (20 ºC)
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 89.047678466
• Heavy Atom Count: 6
• Complexity: 52.8

Purity/Quality:

99% ^*data from raw suppliers

Sarcosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: CNCC(=O)O
• Recent ClinicalTrials: Effect of Sarcosine on Symptomatology, Quality of Life, Oxidative Stress and Glutamatergic Parameters in Schizophrenia
• Description: Sarcosine is the N-methyl derivative of glycine. It can be metabolized to the glycine through sarcosine dehydrogenase. It can be naturally found in many body tissues including muscles. In the laboratory, sarcosine could be synthesized through the reaction between chloroacetic acid and methylamine. Sarcosine is a potential interesting direction for the treatment of mental illness such as schizophrenia, possibly being related to its effect of increasing the glycine content in the brain, which increased the NMDA receptor activity. Sarcosine is also effective in the treatment of depression. Recent study has shown that sarcosine might be an important bio-marker for prostate cancer.
• Biological Functions: Sarcosine reduces dihydrotestosterone (DHT) by inhibiting the enzyme 5 alphareductase. Sebum production is stimulated by androgens. 5 alpha-reductase metabolises testosterone in the skin into its more potent form dihydrotestosterone (DHT) that is responsible for the overproduction of sebum. As a result, sarcosine reduces shine, tightens and reduces pore size, evens tone and complexion.
• Uses: sarcosine is an intermediate in the production glycine from dietary consumption of choline. It is used in making toothpastes and biodegradable surfactants. Sarcosine can be found in foods such as vegetables, ham, egg yolks, turkey and legumes. The normal concentrations of sarcosine in human serum and in human urine are 1.4 μM and 1.6 μM respectively. Sarcosine has been observed to improve treatment of the mental illness known as schizophrenia: 2 g per day consumption of sarcosine (in addition to antipsychotic drug therapy) results in significant additional reductions not only both positive and negative symptoms, but also general psychopathological and neurocognitive symptoms. Sarcosine is thought to work by increasing glycine concentrations in the brain which causes increased NMDA receptor activation. Interestingly, consumption of sarcosine also reduced depressive symptoms in patients with schizophrenia. A clinical study showed sarcosine to be significantly more effective in treating major depression than the established antidepressant drug Citalopram. Has 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. Sarcosine can improve people's intelligence, especially for exams such as the students need to temporarily increase the effectiveness of intelligence is more obvious. sarcosine can increase muscle strength and anaerobic explosiveness.To prevent damage caused by the brain injury. Sarcosine can effectively improve athletic performance,power, and shorten muscle recovery time. sarcosine is a naturally occurring amino acid that is used in cosmetic formulations as a skin conditioner. There are some studies indicating that it is effective for oily skin. Its chemical name is n-methyl glycine.

Technology Process of Sarcosine

There total 105 articles about Sarcosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

hydrogenchloride (7647-01-0,15364-23-5) + N-methyl-N-phenylmethanesulfonyl-glycine (859960-32-0) → sarcosine (107-97-1,25951-24-0) + benzyl chloride (100-44-7)

Guidance literature:

Reference yield:

methoxycarbonylmethylamine (616-34-2) → morpholine-2,5-dione (34037-21-3) + sarcosine (107-97-1,25951-24-0) + N-methylglycine methylester (5473-12-1) + dimethyl iminodiacetate (6096-81-7) + glycine (56-40-6,18875-39-3,25718-94-9)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; at 180 ℃; for 0.166667h; under 300.03 Torr;

DOI:10.1134/S0012500818110071

Reference yield:

perthamide C → sarcosine (107-97-1,25951-24-0) + O-methyl-L-threonine (4144-02-9) + o-hydroxyl-phenylalanine (7423-92-9) + cis-4-methyl-(S)-proline (6734-41-4)

Guidance literature:

With hydrogenchloride; water; at 130 ℃;

DOI:10.1016/j.tet.2009.10.026

upstream raw materials:

creatinine

formaldehyd

methylamine hydrochloride

potassium cyanide

Downstream raw materials:

sarcosine-N-carboxyanhydride

N-oleoylsarcosine

N-acyl sarcosinate

Sarcosine ethyl ester

Refernces

• 1、 Miller, S. L.. "". . p. 2351 - 2361. Retrieved 1955.
• 2、 Sweeley,Horning. "". . p. 2620,2623. Retrieved 1957.
• 3、 Selvi, A. Arul,Manonmani. "Purification and characterization of carbon-phosphorus bond-cleavage enzyme from glyphosate degrading pseudomonas putida T5". . p. 380 - 397. Retrieved 2015.
• 4、 Shibata, Kimihiko,Imanishi, Daiki,Abe, Katsumasa,Suzuki, Masataka,Takahashi, Shouji,Kera, Yoshio. "D-Aspartate N-methyltransferase catalyzes biosynthesis of N-methyl-D-aspartate (NMDA), a well-known selective agonist of the NMDA receptor, in mice". . . Retrieved 2020.
• 5、 Blicke,Norris. "-". . p. 3213. Retrieved 1954.
• 6、 Cocker,Lapworth. "-". . p. 1894,1897. Retrieved 1931.
• 7、 Shah, A. H.,Pandey, V. B.,Eckhardt, G.,Tschesche, R.. "SATIVANINE-C: A CYCLOPEPTIDE ALKALOID FROM THE BARK OF ZIZYPHUS SATIVA". . p. 931 - 933. Retrieved 1984.
• 8、 Yoshii, Tatsuyuki,Onogi, Shoji,Shigemitsu, Hajime,Hamachi, Itaru. "Chemically reactive supramolecular hydrogel coupled with a signal amplification system for enhanced analyte sensitivity". . p. 3360 - 3365. Retrieved 2015.
• 9、 Yin, Shenxiang,Zheng, Qingshu,Chen, Jie,Tu, Tao. "Acceptorless dehydrogenation of primary alcohols to carboxylic acids by self-supported NHC-Ru single-site catalysts". . p. 165 - 172. Retrieved 2022/03/23.