67-07-2

Basic information

• Product Name: Creatine phosphate
• Synonyms: n-phosphocreatine;n-(phosphonoamidino)-sarcosine;CREATINE PHOSPHATE;n-[imino(phosphonoamino)methyl]-n-methyl-glycin;N-(N1-(dihydroxyphosphinyl)amidino)sarcosine;phosphocreatine;PhosphoCreatineSodiumC4H8N3Na2O5P;Creatine phosphoric acid
• CAS NO: 67-07-2
• Molecular Formula: C₄H₁₀N₃O₅P
• Molecular Weight: 211.11
• EINECS: 200-643-9
• Mol File: 67-07-2.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 520.3 °C at 760 mmHg
• Flash Point: 268.5 °C
• Appearance: Off-White Solid
• Density: 1.83 g/cm ³
• Vapor Pressure: 3.19E-12mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Water
• PKA: pKa 4.7± 0.01(H2O,t =25)(Approximate)
• Stability: Hygroscopic
• CAS DataBase Reference: Creatine phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: Creatine phosphate(67-07-2)
• EPA Substance Registry System: Creatine phosphate(67-07-2)

Safety Data

• Hazardous Substances Data: 67-07-2(Hazardous Substances Data)

Usage

Uses

Phosphocreatine used in the synthesis of hydroxypatite nanorod/nanosheets. Phosphocreatine is used in the treatment of heart and brain ischemia.

Enzyme inhibitor

This phosphagen (FW = 211.11 g/mol; CAS 67-07-2; 922-32-7 for disodium salt), known almost as commonly as creatine phosphate, is the primary cytosolic phosphoryl donor for the resynthesis of MgATP from MgADP through the action of creatine kinase in vertebrates and some invertebrates. While abundant in skeletal and cardiac muscle (40-60 mM), nonmuscle cells contain 3-5 mM, and some fungi (e.g., Candida) have intermediate levels of this metabolite. Note: The reported inhibitory action by creatine kinase is often due to impurities (e.g., the inhibition of 5’- nucleotidase is due to an impurity in the commercial phosphocreatine). The reported inhibition of AMP deaminase is due mainly to the presence of pyrophosphate. Phosphocreatine is a hygroscopic solid and very soluble in water. Unstable in acid, all is hydrolyzed after one minute at 100°C in 1.0 M HCl, and half is hydrolyzed in 4 min at 25°C in 0.5 M HCl. Molybdate and certain buffers reportedly accelerate hydrolysis. Hydrolysis is slow under slightly alkaline conditions (e.g., pH 7.8). Nevertheless, solutions should always be freshly prepared and stored frozen. Target(s): adenylate cyclase; AMP deaminase; glutamine synthetase; H+-extrusion by plasma membrane ATPase; NADH peroxidase; phosphofructokinase; and thiamin-phosphate diphosphorylase.

InChI:InChI=1/C4H10N3O5P/c1-7(2-3(8)9)4(5)6-13(10,11)12/h2H2,1H3,(H,8,9)(H4,5,6,10,11,12)

Synthetic route

diphenyl phosphate creatine → Phosphocreatine (67-07-2)

Conditions	Yield
With methanol; platinum Hydrogenation;

N-(diphenoxyphosphoryl-carbamimidoyl)-N-methyl-glycine benzyl ester (114134-66-6) → Phosphocreatine (67-07-2)

Conditions	Yield
With methanol; platinum Hydrogenation;

phosphoenolpyruvic acid (138-08-9) + Creatinine (57-00-1) → Phosphocreatine (67-07-2)

Conditions	Yield
in Gegenwart von Adenosintriphosphat und Extrakten aus verschiedenen tierischen Geweben.Geschwindigkeit der Bildung.;

Creatinine (57-00-1) → Phosphocreatine (67-07-2)

Conditions	Yield
With sodium hydroxide; trichlorophosphate at 0℃;
Edukt 2:anorganisches Phosphat.Geschwindigkeit der Bildung in Kaninchen- und Froschmuskeln;
With mercaptoethyl alcohol; methoxycarbonyl phosphate; ATP; magnesium chloride In water at 15℃; acetate kinase, creatine kinase; pH 9.0;	15 g

1-methyl-4-nitrosobenzene (623-11-0) + Creatinine (57-00-1) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → Phosphocreatine (67-07-2)

Conditions	Yield
at 0℃;

Phosphocreatine (67-07-2) + C18H20N2O4S → C22H28N5O8PS

Conditions	Yield
Stage #1: Phosphocreatine With dmap; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 0℃; for 6h; Stage #2: C18H20N2O4S In dimethyl sulfoxide at 25℃; Darkness;	60%

Phosphocreatine (67-07-2) + copper hydroxide (20427-59-2) → [Cu(phosphocreatine)(H2O)] (1103403-34-4)

Conditions	Yield
In water the 1:1 suspn. of Cu(OH)2 and phosphocreatine in water was stirred for 6h at 30°C; the solvent was slowly filtered, the suspn. was mixed again for 4 h at 15°C, reduced, -10°C, dried over H2SO4, ppt. was dried at 47°C for 4 h, 5:2 water-ether, kept in a vessel with CaCl2; elem. anal.;	47%

Phosphocreatine (67-07-2) → Creatinine (60-27-5)

Conditions	Yield
With hydrogenchloride
With 2,4,6-Trinitrophenol

Phosphocreatine (67-07-2) → creatinine (60-27-5)

Conditions	Yield
beim Erhitzen von Calcium-kreatinphosphat;

Phosphocreatine (67-07-2) → Creatinine (57-00-1)

Phosphocreatine (67-07-2) + 5'-adenosine monophosphate (61-19-8) → ATP (56-65-5)

Conditions	Yield
With creatine-kinase beim Behandeln mit einem Enzym-Praeparat aus Escherichia coli;

Phosphocreatine (67-07-2) + water (7732-18-5) → creatinine (60-27-5)

Conditions	Yield
at 38℃; Geschwindigkeit der Hydrolyse und der Umwandlung beim pH 6.0 bis 7.5;
at 37℃; Geschwindigkeit der Hydrolyse und der Umwandlung beim pH 1 bis 8;

Phosphocreatine (67-07-2) + acid → creatinine (60-27-5)

Conditions	Yield
neben der Hydrolyse;

Phosphocreatine (67-07-2) + HCl(gas) → creatinine (60-27-5) + 5-phosphono-3-methyl-hydantoic acid

Conditions	Yield
at 103℃;

Phosphocreatine (67-07-2) → Disodium phosphocreatine

Conditions	Yield
With sodium hydroxide In water for 3h; Time;	860 g

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 57-00-1 Creatinine 
• 10025-87-3 trichlorophosphate 
• 138-08-9 phosphoenolpyruvic acid 
• 114134-66-6 N-(diphenoxyphosphoryl-carbamimidoyl)-N-methyl-glycine benzyl ester 
• 959586-48-2 C₁₄H₂₆N₃O₉P 

Downstream Products

• 60-27-5 creatinine 
• 57-00-1 Creatinine 
• 60-27-5 Creatinine 
• 56-65-5 ATP 

Relevant articles and documents

Synthesis technology of creatine phosphate sodium

The invention provides a synthesis technology of creatine phosphate sodium. The technology comprises the following steps: reacting creatine monohydrate with phosphoric acid in ethanol to obtain ethanol-insoluble creatine phosphate; and carrying out a refluxing reaction on the creatine phosphate in an ethyl acetate solvent with 4-dimethylpyridine (DMAP) as a creatine phosphorylation reaction catalyst and dicyclohexylcarbodiimide (DCC) as a reaction dehydrant to obtain phosphorylated creatine, carrying out alkaline hydrolysis on the phosphorylated creatine in an aqueous solution of sodium hydroxide, filtering the obtained alkaline hydrolysis product, and adding ethanol to the obtained filtrate to obtain the creatine phosphate sodium. The whole technology is a normal-temperature and normal-pressure technology basically, and has the advantages of low energy consumption and high single-step reaction yield. Water-insoluble 1,3-dicyclohexylurea (DCU) completely formed by the DCC dehydrant in the alkaline hydrolysis workshop section can be filtered out, and the ethanol is directly added to the aqueous solution to precipitate a high-quality creatine phosphate disodium salt. The ethyl acetate and anhydrous ethanol used in the technology can be recycled. The discharge capacity of wastewater in the whole technology is small.

Carotenoid ester analogs or derivatives for controlling C-reactive protein levels

A method of controlling (e.g., influencing or affecting) C-reactive protein levels in a subject may include administering to the subject an effective amount of a pharmaceutically acceptable formulation. The pharmaceutically acceptable formulation may include a synthetic analog or derivative of a carotenoid. The subject may be administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include a cyclic ring including at least one substituent. In some embodiments, a cyclic ring of a carotenoid analog or derivative may include at least one substituent. The substituent may be coupled to the cyclic ring with an ester functionality.