113-24-6 Usage
Description
Sodium pyruvate is the sodium salt of pyruvate. It is frequently supplemented to the cell culture medium to act as a source of energy since it is a key intermediate during the production of the high-energy ATP molecules inside cells. For example, it can be used as a carbon source for bacteria. It may also protect cell against hydrogen peroxide, an oxidant to scavenger oxygen radicals. It is an important metabolic intermediate in many essential metabolic pathways such as carbohydrate metabolism. For example, it is converted into acetyl coenzyme A and enters into the TCA cycle (Kreb’s cycle) in organisms. It is also involved in the amino acid metabolism in organisms.
Chemical Properties
White to slightly yellow crystalline powder. soluble in water, very slightly soluble in ethanol.
Uses
Different sources of media describe the Uses of 113-24-6 differently. You can refer to the following data:
1. Intermediate in sugar metabolism and in enzymatic carbohydrate degradation (alcoholic fermentation) where it is converted to acetaldehyde and CO2 by carboxylase. In muscle, Pyruvic acid (derived from
glycogen) is reduced to lactic acid during exertion, which is reoxidized and partially retransformed to glycogen during rest. The liver can convert Pyruvic acid to alanine by amination.
A diagnostic
agent for Parkinson disease
2. Sodium pyruvate is used in cell culture media as an additional source of energy. It acts as an antioxidant and finds protective effects against oxygen radicals. It serves as an intermediate in many metabolic pathways such as sugar metabolism. It is converted into acetyl coenzyme A and enters the trichloroacetic acid cycle. In addition, it is involved with amino acid metabolism and initiates the Kreb's cycle. It plays an important role as a free radical scavenger.
Application
Sodium pyruvate has been used:To prepare Bull Tyrode′s albumin-lactate-pyruvate diluent.In pyruvate tolerance test.To prepare oligodendrocyte culture medium.
Preparation
The preparation of sodium pyruvate is as follows:Synthesis of pyruvate, a salt of a compound of formula (II) by ozonolysis of methacrylic acid, a compound of formula (II) A solution of methacrylic acid obtained in Example la or lb (15.31 g, 178 mmol) in dichloromethane/methanol (5 % methanol, 50 ml) was cooled to -78?0C and a stream of ozone was passed through until the solution turned blue. Dimethylsulfide (12.41 g, 200 mmol) was added and the mixture was allowed to reach room temperature. Excess dimethylsulfide was removed by passing a stream of nitrogen through the reaction mixture. The reaction mixture was evaporated in vacuo at 30?0C. To the residue was added water (100 ml) and then slowly added a solution of aq. NaOH (IM, 178 ml). The mixture was concentrated and left for crystallisation at 4 °C. The white crystalline material obtained was filtered and washed with acetone (3x100 ml). Yield: 14.50 g (92 %). Purity: 95 %.
Biological Functions
Sodium pyruvate (α-Ketopropionic acid sodium salt; 2-Oxopropanoic acid sodium salt;Pyruvic acid sodium; C3H3NaO3) as an important endogenous small molecules participates various tissue and organ metabolism processes that is the final product of glycolysis and the starting substrate for the tricarboxylic acid (TCA) cycle, and possesses antioxidant and scavenging free radical effects, thus widely using as buffer, excipient and antioxidant in medicine, diagnostic reagent and medical device.
Sodium pyruvate is an endogenous antioxidant and reactive oxygen radical scavenger. In this process, H2O2 or other reactive oxygen radicals are scavenged by sodium pyruvate by a nonenzymatic reaction or an oxidative dephosphorylation, and produce acetate, water and carbon dioxide. Thus, sodium pyruvate can suppress renal cellular injury induced by H2O2, such as lipid peroxidation of rat kidney homogenate, and cytosolic 51Cr release (a marker of cellular injury) from renal epithelial cells induced by H2O2. Thus, sodium pyruvate as effect antioxidant has potential in the clinical medication. Moreover, as effect antioxidant, sodium pyruvate is also as additives used in a vast range of foods and toiletries.
General Description
Sodium pyruvate (SP) is a simplest keto-acid. It crystallizes as very thin plates and belongs to the monoclinic system. Its utility in Knoevenagel condensation carried out in an aqueous medium has been examined. The standard molar enthalpy of formation and molar enthalpy of dissolution of SP at infinite dilution have been obtained. Its efficacy in treating mitochondrial DNA depletion syndromes has been investigated.
Flammability and Explosibility
Notclassified
Biochem/physiol Actions
Sodium pyruvate is known to be an effective therapeutic target for type II citrullinaemia which is characterized by hyperammonaemia. In vivo studies proves that sodium pyruvate has protective function against hemorrhagic shock by preventing lipid peroxidation, NAD+ reduction and cleavage of poly(ADP-ribose) polymerases. Sodium pyruvate is also known to possess anti-inflammatory action and might show improvement in chronic lung disorder.
storage
Sterile filtered commercial solutions of sodium pyruvate are stable up to 24 months, when stored at 2-8 °C.Pyruvic acid polymerizes and decomposes upon standing. It is advised to keep containers tightly sealed.
References
https://en.wikipedia.org/wiki/Sodium_pyruvate
Taidi, Behnam, et al. "Effect of carbon source and concentration on the molecular mass of poly (3-hydroxybutyrate) produced by Methylobacterium extorquens and Alcaligenes eutrophus." Applied microbiology and biotechnology 40.6 (1994): 786-790.
https://www.alfa.com/zh-cn/catalog/A11148/
http://bio.lonza.com/uploads/tx_mwaxmarketingmaterial/Lonza_BenchGuides_Sodium_Pyruvate_Solution_100mM.pdf
Check Digit Verification of cas no
The CAS Registry Mumber 113-24-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 3 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 113-24:
(5*1)+(4*1)+(3*3)+(2*2)+(1*4)=26
26 % 10 = 6
So 113-24-6 is a valid CAS Registry Number.
InChI:InChI=1/C3H4O3.Na/c1-2(4)3(5)6;/h1H3,(H,5,6);/q;+1/p-1
113-24-6Relevant articles and documents
Chemical transformations of the condensation products of pyridoxal with L-α-alanine and D-α-alanine
Pishchugin,Tuleberdiev
, p. 117 - 120 (2009)
The kinetics and mechanism of the reactions of pyridoxal with L- and D-α-alanine were studied. Under comparable conditions, the condensation of L- and D-α-alanines with pyridoxal includes three kinetically different steps. The first fast step is addition
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Price,Levintow
, p. 22 (1952)
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Alcohol oxidation catalysed by Ru(VI) in the presence of alkaline hexacyanoferrate(III)
Poblete, Francisco J.,Corrochano, Pablo
, p. 1088 - 1092 (2010)
The oxidation of sodium lactate, 2-methyl-2,4-pentanediol, 2,4-butanediol, 2-butanol and 2-propanol upon treatment with alkaline hexacyanoferrate(III) using a Ru(VI) catalyst is highly effective for the oxidation of alcohols by Fe(CN)63-. The reaction mechanism proposed involves the oxidation of the alcohol by the catalyst, a process that occurs through the formation of a substrate-catalyst complex. The decomposition of this complex yields Ru(IV) and a carbocation (owing to a hydride transfer from the α-C-H bond of the alcohol to the oxoligand of ruthenium). The role of the co-oxidant, hexacyanoferrate(III), is to regenerate the catalyst. In the oxidation reactions, the rate constants for complex decomposition and catalyst regeneration have been determined and a comparative study of the structure versus reactivity has been carried out. Copyright
Preparation method of sodium pyruvate
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Paragraph 0033-0122, (2018/07/30)
The invention relates to the field of preparation of sodium pyruvate, in particular to a preparation method of sodium pyruvate. The preparation method comprises the following steps that ethyl lactateis subjected to an oxidizing reaction under existing of a catalyst, and sodium pyruvate is obtained after hydrolyzation and neutralization are conducted, wherein the catalyst is one or more of 2,2,6,6-tetramethylpiperidine oxide, 9-azabicyclo[3.3.1]nonane-N-oxy-compound, 9-azabicyclo[3.3.1]nonane-3-ene-N-oxy-compound, 4,2,2,6,6-tetrametylpiperidine oxide and 4-amino-2,2,6,6-tetrametylpiperidine oxide. Compared with the existing commonly used bromine, the prepared method of sodium pyruvate improves the reaction rate of oxidization, and in the oxidization reaction process, the reaction is more steady and safer. In addition, a by-product, namely yellow oily matter is reduced, and post-treatment is easier as well.
Rational design of stereoselectivity in the class II pyruvate aldolase BphI
Baker, Perrin,Seah, Stephen Y. K.
scheme or table, p. 507 - 513 (2012/03/07)
BphI, a pyruvate-specific class II aldolase, catalyzes the reversible carbon-carbon bond formation of 4-hydroxy-2-oxoacids up to eight carbons in length. During the aldol addition catalyzed by BphI, the S-configured stereogenic center at C4 is created via attack of a pyruvate enolate intermediate on the si face of the aldehyde carbonyl of acetaldehyde to form 4(S)-hydroxy-2-oxopentanoate. Replacement of a Leu-87 residue within the active site of the enzyme with polar asparagine and bulky tryptophan led to enzymes with no detectable aldolase activity. These variants retained decarboxylase activity for the smaller oxaloacetate substrate, which is not inhibited by excess 4-hydroxy-2-oxopentanoate, confirming the results from molecular modeling that Leu-87 interacts with the C4-methyl of 4(S)-hydroxy-2-oxoacids. Double variants L87N;Y290F and L87W;Y290F were constructed to enable the binding of 4(R)-hydroxy-2-oxoacids by relieving the steric hindrance between the 5-methyl group of these compounds and the hydroxyl substituent on the phenyl ring of Tyr-290. The resultant enzymes were shown to exclusively utilize only 4(R)- and not 4(S)-hydroxy-2-oxopentanoate as the substrate. Polarimetric analysis confirmed that the double variants are able to synthesize 4-hydroxy-2-oxoacids up to eight carbons in length, which were the opposite stereoisomer compared to those produced by the wild-type enzyme. Overall the kcat/K m values for pyruvate and aldehydes in the aldol addition reactions were affected 10-fold in the double variants relative to the wild-type enzyme. Thus, stereocomplementary class II pyruvate aldolases are now available to create chiral 4-hydroxy-2-oxoacid skeletons as synthons for organic reactions.