Creatine

Base Information

• Chemical Name: Creatine
• CAS No.: 57-00-1
• Deprecated CAS: 2087491-49-2
• Molecular Formula: C4H9N3O2
• Molecular Weight: 131.134
• Hs Code.: 29252900
• European Community (EC) Number: 200-306-6
• NSC Number: 8752
• UNII: MU72812GK0
• DSSTox Substance ID: DTXSID1040451
• Nikkaji Number: J9.321A
• Wikipedia: Creatine
• Wikidata: Q223600
• NCI Thesaurus Code: C37937
• RXCUI: 2907
• Metabolomics Workbench ID: 37054
• ChEMBL ID: CHEMBL283800
• Mol file: 57-00-1.mol

Synonyms:Creatine

Chemical Property of Creatine

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0.00178mmHg at 25°C
• Melting Point: ~295°C (dec.)
• Refractive Index: 1.552
• Boiling Point: 271.6 °C at 760 mmHg
• PKA: 2.63(at 25℃)
• Flash Point: 118.1 °C
• PSA: 90.41000
• Density: 1.38 g/cm³
• LogP: -0.30370
• Storage Temp.: Store at RT.
• Solubility.: Water (Slightly, Heated)
• Water Solubility.: Soluble in water.
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 131.069476538
• Heavy Atom Count: 9
• Complexity: 134

Purity/Quality:

99%, ^*data from raw suppliers

Creatine, anhydrous ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: CN(CC(=O)O)C(=N)N
• Recent ClinicalTrials: Creatine Supplementation in Autism Spectrum Disorder
• Production method: 1. For taking lime nitrogen as raw materials for preparing creatine, there are three different process routes: Lime nitrogen has direct reaction with the aqueous solution of sodium sarcosine to generate creatine. Lime nitrogen is reacted with the methanol solution pre-saturated with dry hydrogen chloride gas to generate O-methylisourea hydrochloride which is further subject to reaction with sarcosine to generate creatine. Upon the condition of passing air, lime nitrogen was reacted with aqueous hydrochloric acid to generate chlorinated formamidine chloride which further reacts with sarcosine sodium to generate creatine. 2. Cyanamide is reacted with chloroacetic acid, methylamine to generate creatine monohydrate. 3. Take thiourea and dimethyl sulfate as raw materials to generate S-methylisothiourea sulfate which then have reaction with sarcosine, sodium sarcosine or potassium sarcosine to generate creatine. 4. Take urea and dimethyl sulfate as raw materials to generate O-methyl isourea sulfate which then reacts with sodium sarcosine to generate creatine monohydrate. Figure 1 The reaction formula for production of creatine Operation method: add 3.3 mol of urea and 6 mL 50% H2SO4 to a 500 mL four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser; heat to 40 ℃, add drop wise of 3 mol dimethyl sulfate under stirring for 3 h; during the addition of raw materials, the temperature should be maintained at less than 70 ℃; after the completion of adding the material, stir for 2h about 70 ℃, and cool to obtain 561.8 g of O-methyl isourea sulfate. Add 61.7 of 36% aqueous solution of sodium sarcosinate to a 500 mL four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser, use 30% HCl to adjust the pH to about 11.0, and then add drop wise at 20 ℃ of 50 g of O-methyl isourea sulfate within 2 h; during the process of adding, drop wise, use 25% NaOH solution to adjust the pH and maintain the pH at about 11.0, after the addition was complete, stirring was continued at 40 ℃ for 2 h, and then cool the mixture at 0 ~5℃ for 2h and filter out the formed colorless crystals. Use 2 × 15 mL of ice water to wash the filter cake to generate crude creatine monohydrate. Put the crude product into beaker, add water of 7 to 8 times the amount of crude product, heat to dissolve all the crude product, have liquid be subject to slow cooling at room temperature, crystallized, filter off the crystals, dry at a temperature below 50 ℃ to obtain the finished product of creatine monohydrate .
• Uses: 1. It can be used as the nutritional supplements for promoting the adaptation of skeletal muscle to strenuous exercise and fighting against the excessive fatigue for feeble individuals. 2. It can be used as the drugs for the treatment of heart disease and respiratory insufficiency. 3. It can be used for preparation of a pharmaceutical formulation containing human growth hormone. 4. It can be applied to compound health food with anti-aging and physical-power recovering effect. 5. It can be used as the reagents for biochemical research. Creatine is used for gyrate atrophy, McArdle's disease, muscular dystrophy, amyotrophic lateral sclerosis, and rheumatoid arthritis. It is used in congestive heart disease to improve exercise tolerance and to enhance athletic performance. Creatine is involved in the rapid production of ATP associated with creatine kinases in skeletal muscle tissue. Creatine may be used as a supplement to study its mechanism of action. It acts as a nutraceutical and a neuroprotective agent.

Technology Process of Creatine

There total 38 articles about Creatine 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: 86.0%

calcium cyanamide (156-62-7) + sodium sarcosinate (4316-73-8) → Creatinine (57-00-1)

Guidance literature:

With phosphoric acid; sulfuric acid;

Reference yield: 83.2%

sarcosine (107-97-1,25951-24-0) + Aminoiminomethanesulfinic acid (1758-73-2) → Creatinine (57-00-1)

Guidance literature:

With sodium hydroxide; at 20 ℃;

DOI:10.1055/s-2000-8201

Reference yield: 76.2%

CYANAMID (420-04-2) + sodium sarcosinate (4316-73-8) → Creatinine (57-00-1)

Guidance literature:

sodium sarcosinate; With hydrogenchloride; In water; pH=9.6; Cooling;

CYANAMID; In water; at 75 - 80 ℃; for 3.5h;

upstream raw materials:

Creatinine

creatinine

sarcosine

CYANAMID

Downstream raw materials:

creatinine

Phosphocreatine

oxalic acid

sarcosine

Refernces

• 1、 Shibuya. "-". . p. 339. Retrieved 1939.
• 2、 Kim, Jihoon,Oh, Jinyoung,Han, Min Su. "Versatile small molecule kinase assay through real-time, ratiometric fluorescence changes based on a pyrene-DPA-Zn2+complex". . p. 10375 - 10380. Retrieved 2021/03/23.
• 3、 -. "Synthetic method of creatine". Paragraph 0020. . Retrieved 2016/10/08.