Product Name

  • Name

    Sodium phenylpyruvate

  • EINECS 204-053-2
  • CAS No. 114-76-1
  • Article Data5
  • CAS DataBase
  • Density 1.257g/cm3
  • Solubility Soluble in water
  • Melting Point >300 °C(lit.)
  • Formula C9H8O3.Na
  • Boiling Point 299.1 °C at 760 mmHg
  • Molecular Weight 186.143
  • Flash Point 148.9 °C
  • Transport Information
  • Appearance White powder
  • Safety 22-24/25-36-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 114-76-1 (Sodium phenylpyruvate)
  • Hazard Symbols IrritantXi
  • Synonyms Benzenepropanoicacid, a-oxo-, sodium salt (9CI);Pyruvicacid, phenyl-, sodium salt (8CI);Phenylpyroracemic acid sodium salt;Phenylpyruvic acid sodium salt;Sodium 3-phenyl-2-oxopropionate;b-Phenylpyruvic acid sodium salt;Sodium b-phenylpyruvate;
  • PSA 57.20000
  • LogP -0.45190

Synthetic route

(Z)-5'-benzylidenecyclohexanespiro-2'-(1',3'-dioxolan)-4'-one
93831-17-5

(Z)-5'-benzylidenecyclohexanespiro-2'-(1',3'-dioxolan)-4'-one

A

cyclohexanone
108-94-1

cyclohexanone

B

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water for 18h; Ambient temperature;A n/a
B 89%
5-benzylidenehydantoin
3775-01-7, 74805-60-0, 109754-06-5

5-benzylidenehydantoin

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Conditions
ConditionsYield
With sodium hydroxide In water at 140℃; for 3h; Hydrolysis;77%
L-phenylalanine
63-91-2

L-phenylalanine

sodium pyruvate
113-24-6

sodium pyruvate

A

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

B

rac-Ala-OH
302-72-7

rac-Ala-OH

Conditions
ConditionsYield
With acetate buffer; N(1+)C5His2C16; PL(1+)2C16; copper(II) perchlorate In water at 30℃; for 48h; Kinetics; var. catalysts;A n/a
B 27%
...Expand
L-phenylalanine
63-91-2

L-phenylalanine

α-ketoglutarate monosodium salt
22202-68-2

α-ketoglutarate monosodium salt

A

Glutamic acid
617-65-2

Glutamic acid

B

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Conditions
ConditionsYield
With acetate buffer; N(1+)C5His2C16; PL(1+)2C16; copper(II) perchlorate In water at 30℃; for 48h; Kinetics;
...Expand
(Z)-4-benzylidene-2-methyl-5(4H)-oxazolone
38879-46-8

(Z)-4-benzylidene-2-methyl-5(4H)-oxazolone

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Conditions
ConditionsYield
With hydrogenchloride; sodium methylate In methanol for 3h; Product distribution; Mechanism;
benzaldehyde
100-52-7

benzaldehyde

HI, I2

HI, I2

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / sodium acetate / acetic acid / 5 h / Heating
2: 77 percent / NaOH / H2O / 3 h / 140 °C
View Scheme
5-benzylidenehydantoin
3775-01-7

5-benzylidenehydantoin

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Conditions
ConditionsYield
With sodium hydroxide In propan-1-ol; water at 125 - 130℃; under 2250.23 Torr; Temperature; Pressure; Inert atmosphere;
cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

dichloromethane
75-09-2

dichloromethane

tris[(6-methyl-2-pyridyl)methyl]amine
25599-08-0

tris[(6-methyl-2-pyridyl)methyl]amine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

[{(6Me3TPA)CoII}2(PP)](BPh4)2

[{(6Me3TPA)CoII}2(PP)](BPh4)2

Conditions
ConditionsYield
In methanol at 20℃; for 5h;95%
...Expand
sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

<15N>-L-phenylalanine
29700-34-3

<15N>-L-phenylalanine

Conditions
ConditionsYield
With formate dehydrogenase; 1,4-dihydronicotinamide adenine dinucleotide; 15N-ammonium formate; phenylalanine dehydrogenase; diothiothreitol Ambient temperature; TRIS, pH=6.5-7.0, 0.1M HCl;92%
sodium tetrachloropalladate(II)

sodium tetrachloropalladate(II)

N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Pd{O2CC(CH2C6H5)N(OCH3)}2
154070-59-4

Pd{O2CC(CH2C6H5)N(OCH3)}2

Conditions
ConditionsYield
With NaOH In water N2; soln. of sodium-α-oxocarboxylate and O-alkylhydroxylamine stirred at room temp. for 10-24 h; soln. of Na2PdCl4 added slowly;; washed with cold water; dried in high vacuum;; recrystd. from EtOH/H2O; elem. anal.;;90%
...Expand
methanol
67-56-1

methanol

p-hydroxybenzoic acid hydrazone

p-hydroxybenzoic acid hydrazone

dibenzyltin(IV) dichloride
3002-01-5

dibenzyltin(IV) dichloride

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

C31H30N2O5Sn

C31H30N2O5Sn

Conditions
ConditionsYield
at 45 - 65℃; for 15h; Time; Inert atmosphere;89.9%
...Expand
di(n-butyl)tin oxide
818-08-6

di(n-butyl)tin oxide

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

p-toluic hydrazide
3619-22-5

p-toluic hydrazide

2-carbonyl-3-phenylpropionic acid p-methylbenzoylhydrazone bis-n-butyltin complex

2-carbonyl-3-phenylpropionic acid p-methylbenzoylhydrazone bis-n-butyltin complex

Conditions
ConditionsYield
In methanol at 45 - 65℃; for 24h; Time; Inert atmosphere;88.8%
...Expand
methanol
67-56-1

methanol

4-methoxybenzoic acid hydrazide
3290-99-1

4-methoxybenzoic acid hydrazide

di(n-butyl)tin oxide
818-08-6

di(n-butyl)tin oxide

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

C52H72N4O10Sn2

C52H72N4O10Sn2

Conditions
ConditionsYield
at 45 - 65℃; for 8h; Inert atmosphere;88.5%
...Expand
di(n-butyl)tin oxide
818-08-6

di(n-butyl)tin oxide

2-Hydroxybenzoylhydrazine
936-02-7

2-Hydroxybenzoylhydrazine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Sn(4+)*C16H12N2O4(2-)*2C4H9(1-)

Sn(4+)*C16H12N2O4(2-)*2C4H9(1-)

Conditions
ConditionsYield
In methanol at 45 - 65℃; for 5h; Inert atmosphere;85.5%
...Expand
sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

methyl iodide
74-88-4

methyl iodide

sodium 2-oxo-3-phenylbutanoate
125116-72-5

sodium 2-oxo-3-phenylbutanoate

Conditions
ConditionsYield
With sodium hydroxide In methanol; diethyl ether85%
methanol
67-56-1

methanol

diphenyltin(IV) dichloride
1135-99-5

diphenyltin(IV) dichloride

4-hydroxybenzoic acid hydrazide
5351-23-5

4-hydroxybenzoic acid hydrazide

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

C58H52N4O10Sn2

C58H52N4O10Sn2

Conditions
ConditionsYield
at 45 - 65℃; for 5h; Inert atmosphere;84.5%
...Expand
4-tert-butylbenzoic acid hydrazide
43100-38-5

4-tert-butylbenzoic acid hydrazide

dibenzyltin dichloride
70335-32-9

dibenzyltin dichloride

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

C70H76N4O8Sn2

C70H76N4O8Sn2

Conditions
ConditionsYield
In methanol at 50 - 65℃; for 20h; Concentration; Inert atmosphere;82.8%
...Expand
sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

D-phenyllactic acid
828-01-3, 7326-19-4, 20312-36-1, 156-05-8

D-phenyllactic acid

Conditions
ConditionsYield
With phosphate buffer; D-glucose; 2-hydroxyethanethiol; sodium chloride; formate dehydrogenase; 1,4-dihydronicotinamide adenine dinucleotide; benzoylformate reductase; bovine serum albumin; yeast alcohol dehydrogenase In ethanol; water; toluene at 30℃; for 48h;80%
With hydrogenchloride; Candida boidinii formate dehydrogenase; ethylenediaminetetraacetic acid; Staphylococcus epidermis D-lactate dehydrogenase; NAD; ammonium formate; 2-hydroxyethanethiol In water for 24h; pH=7; Enzymatic reaction; enantioselective reaction;
potassium 3-phenyl-5-methylhydrido-trispyrazol-1-ylborate

potassium 3-phenyl-5-methylhydrido-trispyrazol-1-ylborate

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

iron(II) chloride

iron(II) chloride

[(hydrotris(3-phenyl-5-methylpyrazolyl)borate)FeII(phenylpyruvate)]

[(hydrotris(3-phenyl-5-methylpyrazolyl)borate)FeII(phenylpyruvate)]

Conditions
ConditionsYield
Stage #1: potassium hydrotris(3-phenyl-5-methyl-pyrazol-1-yl)borate; iron(II) chloride In dichloromethane for 1h;
Stage #2: sodium phenylphyruvate In methanol; dichloromethane for 8h;		80%
...Expand
sodium tetrachloropalladate(II)

sodium tetrachloropalladate(II)

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

rac-methylbenzylamine
618-36-0

rac-methylbenzylamine

Pd{O2CC(CH2C6H5)N(CH(CH3)C6H5)}2
154070-66-3

Pd{O2CC(CH2C6H5)N(CH(CH3)C6H5)}2

Conditions
ConditionsYield
In methanol N2;α-oxocarboxylate and amine in MeOH stirred at room temp.; Na2PdCl4 added; stirred at room temp. for 1 h;; evapd.; stirred in hexane; crystd.; washed with hexane and water; dried in high vacuo; elem. anal.;;79%
...Expand
ethanol
64-17-5

ethanol

dibenzyltin(IV) dichloride
3002-01-5

dibenzyltin(IV) dichloride

2-Hydroxybenzoylhydrazine
936-02-7

2-Hydroxybenzoylhydrazine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

2-carbonyl-3-phenylpropionic acid salicyloyl hydrazone dibenzyltin complex

2-carbonyl-3-phenylpropionic acid salicyloyl hydrazone dibenzyltin complex

Conditions
ConditionsYield
at 45 - 65℃; for 15h; Concentration; Inert atmosphere;78.6%
...Expand
methanol
67-56-1

methanol

dibenzyltin(IV) dichloride
3002-01-5

dibenzyltin(IV) dichloride

benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

C62H60N4O8Sn2

C62H60N4O8Sn2

Conditions
ConditionsYield
at 45 - 65℃; for 15h; Concentration;78.2%
...Expand
sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

tris[(2-pyridylmethyl)amine]
16858-01-8

tris[(2-pyridylmethyl)amine]

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

cobalt(II) perchlorate hexahydrate

cobalt(II) perchlorate hexahydrate

[(TPA)CoII(PPH)](BPh4)
1418284-81-7

[(TPA)CoII(PPH)](BPh4)

Conditions
ConditionsYield
In methanol at 20℃; for 5h;78%
...Expand
methanol
67-56-1

methanol

di-p-methylbenzyltin(IV) dichloride

di-p-methylbenzyltin(IV) dichloride

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

p-toluic hydrazide
3619-22-5

p-toluic hydrazide

C68H74N4O8Sn2

C68H74N4O8Sn2

Conditions
ConditionsYield
at 50 - 65℃; for 5h; Time;77.9%
...Expand
methanol
67-56-1

methanol

dibenzyltin(IV) dichloride
3002-01-5

dibenzyltin(IV) dichloride

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

p-toluic hydrazide
3619-22-5

p-toluic hydrazide

C64H64N4O8Sn2

C64H64N4O8Sn2

Conditions
ConditionsYield
at 50 - 65℃; for 20h; Concentration; Inert atmosphere;77.8%
...Expand
iron(II) perchlorate hexahydrate

iron(II) perchlorate hexahydrate

dichloromethane
75-09-2

dichloromethane

sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

tris[(6-methyl-2-pyridyl)methyl]amine
25599-08-0

tris[(6-methyl-2-pyridyl)methyl]amine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

[(tris(6-methyl-2-pyridylmethyl)amine)2Fe2(phenypyruvate enolato)](BPh4)2 * 0.5(dichloromethane)

[(tris(6-methyl-2-pyridylmethyl)amine)2Fe2(phenypyruvate enolato)](BPh4)2 * 0.5(dichloromethane)

Conditions
ConditionsYield
In methanol ligands and Fe salt in MeOH stirred under Ar for 2 h; pptd. with a MeOH soln. of NaBPh4, filtered, washed (MeOH), dried; elem.anal.;76%
...Expand
diphenyltin(IV) dichloride
1135-99-5

diphenyltin(IV) dichloride

2-Hydroxybenzoylhydrazine
936-02-7

2-Hydroxybenzoylhydrazine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

2-oxo-3-phenylpropionic acid salicyloylhydrazone diphenyltin

2-oxo-3-phenylpropionic acid salicyloylhydrazone diphenyltin

Conditions
ConditionsYield
In methanol at 45 - 65℃; for 8h; Concentration;75.8%
...Expand
N-phenylethylhydroxylamine
3217-93-4

N-phenylethylhydroxylamine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

N-phenethyl-2-phenylacetamide
5460-60-6

N-phenethyl-2-phenylacetamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 15h; Product distribution / selectivity;75%
methanol
67-56-1

methanol

di-p-methylbenzyltin(IV) dichloride

di-p-methylbenzyltin(IV) dichloride

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

N-amino-(4-nitrophenyl)carboxamide
636-97-5

N-amino-(4-nitrophenyl)carboxamide

C66H66N6O12Sn2

C66H66N6O12Sn2

Conditions
ConditionsYield
at 50 - 65℃; for 20h; Inert atmosphere;74.5%
...Expand
bis(2,4-dichlorobenzyl)tin dichloride
849144-53-2

bis(2,4-dichlorobenzyl)tin dichloride

2-Hydroxybenzoylhydrazine
936-02-7

2-Hydroxybenzoylhydrazine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

2-oxo-3-phenylpropionic acid salicyloyl hydrazone bis(2,4-dichlorobenzyl)tin

2-oxo-3-phenylpropionic acid salicyloyl hydrazone bis(2,4-dichlorobenzyl)tin

Conditions
ConditionsYield
In ethanol at 45 - 65℃; for 22h; Concentration; Time; Inert atmosphere;74.3%
...Expand
sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

L-3-phenyllactic acid
20312-36-1

L-3-phenyllactic acid

Conditions
ConditionsYield
With fructose 1,6-bisphosphate trisodium; nicotinamide adenine dinucleotide red. form; piperazine*HCl buffer; sodium formate; diothiothreitol In water lyophilized formate dehydrogenase, mutant lactate dehydrogenase from Bacillus stearothermophilus (BSLDH), pH=6.0;70%
With Fructose 1,6-bisphosphate; piperazine*HCl buffer; sodium formate; nicotinamide adenine dinucleotide; diothiothreitol pH 6.0, lyophilized formate dehydrogenase, lactate dehydrogenase from Bacillus stearothermophilus (BSLDH Q102R/C97G);65%
With fructose 1,6-bisphosphate trisodium; lyophilized formate dehydrogenase; mutant lactate dehydrogenase; nicotinamide adenine dinucleotide red. form; sodium formate; piperazine hydrochloride; diothiothreitol In water at 25℃; Rate constant; other 2-keto acids; other enzymes; stereospecific enzymatic reduction;
di(para-chlorobenzyl)tin(IV) dichloride

di(para-chlorobenzyl)tin(IV) dichloride

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

p-toluic hydrazide
3619-22-5

p-toluic hydrazide

C62H48Cl8N4O6Sn2

C62H48Cl8N4O6Sn2

Conditions
ConditionsYield
In methanol at 45 - 65℃; for 5h; Time; Inert atmosphere;68.5%
...Expand
sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

methyl iodide
74-88-4

methyl iodide

3-methyl-2-oxo-3-phenylbutanoic acid
91133-59-4

3-methyl-2-oxo-3-phenylbutanoic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol68%
With sodium hydroxide In tetrahydrofuran65%
With sodium hydroxide42%
sodium tetrachloropalladate(II)

sodium tetrachloropalladate(II)

(S)-2-methylbutylamine
34985-37-0

(S)-2-methylbutylamine

sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

Pd{O2CC(CH2Ph)N(S-CH2CH(CH3)CH2CH3)}2

Pd{O2CC(CH2Ph)N(S-CH2CH(CH3)CH2CH3)}2

Conditions
ConditionsYield
In methanol N2;α-oxocarboxylate and amine in MeOH stirred at room temp.; Na2PdCl4 added; stirred at room temp. for 1 h;; evapd.; stirred in hexane; crystd.; washed with hexane and water; dried in high vacuo; elem. anal.;;68%
...Expand
sodium phenylphyruvate
114-76-1

sodium phenylphyruvate

6,7-diamino-8-chloroquinoline
261764-97-0

6,7-diamino-8-chloroquinoline

3-benzyl-5-chloropyrido[2,3-g]quinoxalin-2(1H)-one
1037303-28-8

3-benzyl-5-chloropyrido[2,3-g]quinoxalin-2(1H)-one

Conditions
ConditionsYield
Stage #1: sodium phenylphyruvate; 6,7-diamino-8-chloroquinoline With sulfuric acid In water at 60℃; for 1h;
Stage #2: With sodium hydroxide In water		66%
With sulfuric acid In water; N,N-dimethyl-formamide at 60℃; for 1h;

Sodium phenylpyruvate Specification

The Benzenepropanoic acid, a-oxo-, sodium salt (1:1) with CAS registry number of 114-76-1 is also known as Sodium phenylpyruvate. The IUPAC name is Sodium 2-oxo-3-phenylpropanoic acid. Its EINECS registry number is 204-053-2. In addition, the formula is C9H8O3.Na and the molecular weight is 187.14. This chemical is a white powder that may cause inflammation to the skin or other mucous membranes.

Physical properties about Benzenepropanoic acid, a-oxo-, sodium salt (1:1) are: (1)ACD/LogP: 0.54; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.3; (4)ACD/LogD (pH 7.4): -3.18; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Flash Point: 148.9 °C; (13)Enthalpy of Vaporization: 56.92 kJ/mol; (14)Boiling Point: 299.1 °C at 760 mmHg; (15)Vapour Pressure: 0.000546 mmHg at 25 °C.

Preparation of Benzenepropanoic acid, a-oxo-, sodium salt (1:1): it is prepared by hydrolysis reaction of 5-benzylidene-imidazolidine-2,4-dione. The reaction needs reagent NaOH and solvent H2O at the temperature of 140 °C for 3 hours. The yield is about 77%.

Benzenepropanoic acid, a-oxo-, sodium salt (1:1) is prepared by hydrolysis reaction of 5-benzylidene-imidazolidine-2,4-dione.

Uses of Benzenepropanoic acid, a-oxo-, sodium salt (1:1): it is used to produce L-phenylalanine. The reaction occurs with reagents (R)-15-amino-methyl-14-hydroxy-5,5-dimethyl-2,8-dithia<9>(2,5)pyridinophane, Zn(ClO4)*6H2O and solvent methanol with other condition of ambient temperature for 24 hours. The yield is about 60%.

Benzenepropanoic acid, a-oxo-, sodium salt (1:1) is used to produce L-phenylalanine.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing. Do not breathe dust and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC=C(C=C1)CC(=O)C(=O)O.[Na+]
2. InChI: InChI=1S/C9H8O3.Na/c10-8(9(11)12)6-7-4-2-1-3-5-7;/h1-5H,6H2,(H,11,12);/q;+1
3. InChIKey: MQGYVGKMCRDEAF-UHFFFAOYSA-N

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