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Pyruvic acid is a fundamental intermediate in protein and carbohydrate metabolism in the cell, playing a key role in cell metabolism and being involved in many catabolic and anabolic pathways, including glycolysis, gluconeogenesis, amino acid, and protein metabolism. It is a colorless to light yellow liquid with a sour, acetic odor and a pleasant, sour taste with a burning, somewhat sweet note. Pyruvic acid tends to darken and decompose unless kept free of minor contaminants and in tightly sealed containers.

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  • 127-17-3 Structure
  • Basic information

    1. Product Name: Pyruvic acid
    2. Synonyms: 2-oxo-propanoicaci;CH3COCOOH;Propanoic acid, 2-oxo-;Propanoicacid,2-oxo-;pyruvic;FEMA 2970;2-KETOPROPANOIC ACID;2-KETOPROPIONIC ACID
    3. CAS NO:127-17-3
    4. Molecular Formula: C3H4O3
    5. Molecular Weight: 88.06
    6. EINECS: 204-824-3
    7. Product Categories: PyruvicAcidSeries;Nutritional Supplements
    8. Mol File: 127-17-3.mol
    9. Article Data: 246
  • Chemical Properties

    1. Melting Point: 11-12 °C(lit.)
    2. Boiling Point: 165 °C(lit.)
    3. Flash Point: 183 °F
    4. Appearance: Clear colorless to light yellow or amber/Liquid
    5. Density: 1.272 g/mL at 20 °C
    6. Vapor Pressure: 0.968mmHg at 25°C
    7. Refractive Index: n20/D 1.428(lit.)
    8. Storage Temp.: 2-8°C
    9. Solubility: Miscible with chloroform and methanol.
    10. PKA: 2.39(at 25℃)
    11. Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases. Refrigerate.
    12. Merck: 14,8021
    13. BRN: 506211
    14. CAS DataBase Reference: Pyruvic acid(CAS DataBase Reference)
    15. NIST Chemistry Reference: Pyruvic acid(127-17-3)
    16. EPA Substance Registry System: Pyruvic acid(127-17-3)
  • Safety Data

    1. Hazard Codes: C
    2. Statements: 34
    3. Safety Statements: 26-36/37/39-45-25-27
    4. RIDADR: UN 3265 8/PG 2
    5. WGK Germany: 3
    6. RTECS: UZ0829800
    7. TSCA: Yes
    8. HazardClass: 8
    9. PackingGroup: II
    10. Hazardous Substances Data: 127-17-3(Hazardous Substances Data)

127-17-3 Usage

Uses

Used in Biochemical Research:
Pyruvic acid is used as a substrate for assaying activities of enzymes such as pyruvate dehydrogenase, pyruvate carboxylase, and pyruvate decarboxylase.
Used in Pharmaceutical Industry:
Pyruvic acid is used as an intermediate in sugar metabolism and enzymatic carbohydrate degradation, and as a diagnostic agent for Parkinson's disease.
Used in Food Industry:
Pyruvic acid is used as a component in culture broths and media, as a commercial red seaweed polysaccharide, and in the construction of amino acid alanine. It also supplies energy to living cells via the citric acid cycle (Krebs cycle) and is involved in the preparation of sialic acid.
Used in Cosmetics Industry:
Pyruvic acid is used as an alpha hydroxy acid, although it can be irritating and is considered difficult to work with due to its larger molecular size compared to other commonly used AHAs.
Used in Agriculture:
Pyruvic acid is employed to study the cultivation of soil bacteria as micro colonies using a soil substrate membrane system.
Used in Analytical Chemistry:
Pyruvic acid finds application in liquid chromatography and in the determination of organic acids in red wine.
Used in Flavor and Fragrance Industry:
Pyruvic acid is the key component formed during the hydrolysis of flavor-precursors in onion tissues, and its amount is used as a measure for onion pungency. It also has aroma characteristics of being acidic, sweet, caramellic, and sour.
Occurrence:
Pyruvic acid is isolated from cane sugar fermentation broth and a few plants, and is also found in peppermint, raw asparagus, leaves and stalk of celery, onion, rutabaga, milk, cream, buttermilk, wheaten bread, blue cheeses, cheddar cheese, cottage cheese, provolone cheese, yogurt, beef, Virginia tobacco, beer, white wine, botrytised wine, cocoa, and sake.

Antioxidant effect

Studies have shown that pyruvic acid can inhibit the oxidation of oxygen free radicals in mice, and as a hydrogen peroxide scavenger, it has the effect of preventing free radical damage, and it has been proved to be protective in cardiac reperfusion injury and acute renal failure. The body resists functional damage. Pyruvic acid can act as an antioxidant through two mechanisms: first, as an α-keto acid, pyruvic acid can directly inhibit hydrogen peroxide through a non-enzymatic decarbonation reaction; second, supplementation of pyruvic acid can enhance In the citric acid cycle, after the production of citric acid increases, the phosphofructokinase is inhibited, thereby entering the pentose phosphate bypass to generate reduced coenzyme II (NADPH), thereby indirectly increasing the ability of the glutathione (GSH) antioxidant system. Pyruvic acid can also increase the ratio of coenzyme I/reduced coenzyme I (NAD+/NADH) and promote the reaction of the tricarboxylic acid cycle.

Preparation

By distillation of tartaric acid in the presence of potassium acid sulfate as a dehydrating agent; from acetyl chloride and potassium cyanide to yield the nitrile, which is subsequently acid hydrolyzed to the acid; pyruvic acid must be rectified under vacuum.

Biochem/physiol Actions

Taste at 5 ppm

Purification Methods

Distil it twice, then fractionally crystallise it by partial freezing. [Beilstein 3 IV 1505.]

Check Digit Verification of cas no

The CAS Registry Mumber 127-17-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 7 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 127-17:
(5*1)+(4*2)+(3*7)+(2*1)+(1*7)=43
43 % 10 = 3
So 127-17-3 is a valid CAS Registry Number.
InChI:InChI=1/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)/p-1

127-17-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
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  • Alfa Aesar

  • (A13875)  Pyruvic acid, 98%   

  • 127-17-3

  • 100g

  • 587.0CNY

  • Detail
  • Alfa Aesar

  • (A13875)  Pyruvic acid, 98%   

  • 127-17-3

  • 500g

  • 1927.0CNY

  • Detail
  • Alfa Aesar

  • (A13875)  Pyruvic acid, 98%   

  • 127-17-3

  • 2500g

  • 6773.0CNY

  • Detail

127-17-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Pyruvic acid

1.2 Other means of identification

Product number -
Other names FEMA 2970

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:127-17-3 SDS

127-17-3Synthetic route

7,7,8,8-Tetramethyl-3-methylene-5-phenoxy-1,4,6,9-tetraoxa-5λ5-phospha-spiro[4.4]nonan-2-one
105930-58-3

7,7,8,8-Tetramethyl-3-methylene-5-phenoxy-1,4,6,9-tetraoxa-5λ5-phospha-spiro[4.4]nonan-2-one

A

2-hydroxy-4,4,5,5-tetramethyl<1,3,2>dioxaphospholane-2-oxide
13882-05-8

2-hydroxy-4,4,5,5-tetramethyl<1,3,2>dioxaphospholane-2-oxide

B

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

C

phenol
108-95-2

phenol

Conditions
ConditionsYield
With water In acetone at 20℃; for 24h;A 100%
B n/a
C n/a
α-Ethoxyacrylic acid
32821-76-4

α-Ethoxyacrylic acid

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With hydrogenchloride; water at 20℃; for 3 - 4h; Product distribution / selectivity;99%
With hydrogenchloride; water In tetrahydrofuran; Norlaudanosolin; acetone; pentane at 20℃; for 1h; Product distribution / selectivity;
LACTIC ACID
849585-22-4

LACTIC ACID

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With oxygen In water at 100℃; under 750.075 Torr; for 5h; Reagent/catalyst;95%
With dihydrogen peroxide; iron(II)
With lead anode; alkali Electrolysis;
D-Lactic acid
10326-41-7

D-Lactic acid

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With oxygen at 100℃; under 75.0075 Torr; for 8h; Temperature; Pressure; Autoclave;94.3%
With mutant 3-isopropylmalate dehydrogenase(Gly89-Gly-Leu90); nicotinamide adenine dinucleotide In water at 60℃; for 2h; pH=7.8; Enzyme kinetics;
With nicotinamide flucytosine dinucleotide at 25℃; pH=7.5; aq. buffer; Enzymatic reaction;
With D-lactate dehydrogenase of Planctomyces brasiliensis at 25℃; for 1h; pH=7; Concentration; pH-value; Reagent/catalyst; Temperature; Enzymatic reaction;
With D-lactate oxidase from Saccharomyces cerevisiae; oxygen; catalase In aq. buffer at 30℃; pH=7.4; Reagent/catalyst; Enzymatic reaction;
poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
Stage #1: poly(methacrylic acid) With ozone In methanol; dichloromethane at -78℃;
Stage #2: With dimethylsulfide In methanol; dichloromethane at -78 - 20℃;
90%
(3E)-4-morpholin-4-yl-pent-3-en-2-one
63913-42-8

(3E)-4-morpholin-4-yl-pent-3-en-2-one

A

4-acetylmorpholine
1696-20-4

4-acetylmorpholine

B

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

C

Acetic formic anhydride
2258-42-6

Acetic formic anhydride

Conditions
ConditionsYield
With ozone In dichloromethane at -70℃;A 86%
B 6%
C 6%
sodium pyruvate
113-24-6

sodium pyruvate

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With hydrogenchloride; water In acetonitrile at 0 - 20℃; for 3h; Product distribution / selectivity;83.1%
rac-Ala-OH
302-72-7

rac-Ala-OH

A

acetaldehyde
75-07-0

acetaldehyde

B

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

C

C3H5BrNO2(1-)

C3H5BrNO2(1-)

Conditions
ConditionsYield
With hypobromite In sodium hydroxide at 35℃; Kinetics; Mechanism;A 70%
B 25%
C n/a
C3H5BrNO2(1-)

C3H5BrNO2(1-)

A

acetaldehyde
75-07-0

acetaldehyde

B

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With hypobromite In sodium hydroxide at 35℃; Kinetics; Mechanism;A 70%
B 25%
rac-Ala-OH
302-72-7

rac-Ala-OH

A

acetaldehyde
75-07-0

acetaldehyde

B

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With bromine; perchlorate(1-) at 35℃; Rate constant; k2 = 50.0 x 10-7 s-1;A 70%
B 25%
propylene glycol
57-55-6

propylene glycol

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

C

hydroxy-2-propanone
116-09-6

hydroxy-2-propanone

Conditions
ConditionsYield
With 5% platinum on aluminium oxide In water at 40℃; for 6h; pH=10; pH-value; Time;A 70%
B 19%
C 11%
With 5% platinum on aluminium oxide In water at 40℃; for 6h; pH=10; Temperature; pH-value; Time;
hydroxy-2-propanone
116-09-6

hydroxy-2-propanone

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

acetic acid
64-19-7

acetic acid

C

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With oxygen In water at 119.84℃; under 15001.5 Torr; for 3h; Catalytic behavior; Kinetics; Temperature; Concentration; Reagent/catalyst; Autoclave;A 68.4%
B n/a
C n/a
With oxygen In water at 119.84℃; under 15001.5 Torr; for 3h; Autoclave;
With oxygen In water at 119.84℃; under 15001.5 Torr; for 3h; Autoclave;
carbon dioxide
124-38-9

carbon dioxide

acetaldehyde
75-07-0

acetaldehyde

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With Brewer's yeast pyruvate decarboxylase (EC 4.1.1.1); thiamine diphosphate In various solvent(s) at 25℃; for 1h; pH=11;61%
vitamin B1 2.) carbon dioxide pressure = 50 atm, DMF, Et3N, 20 deg C, 48 h; Yield given. Multistep reaction;
carbon dioxide
124-38-9

carbon dioxide

acetyl chloride
75-36-5

acetyl chloride

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide electrochemical synthesis with Pt cathod and Zn anod (3 mA/cm2);60%
hydroxy-2-propanone
116-09-6

hydroxy-2-propanone

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With 5% Pt/Al2O3; sodium hydroxide In water at 40℃; under 760.051 Torr; for 6h; pH=8; Kinetics; Reagent/catalyst; pH-value;A 60%
B n/a
With 5% Pt/Al2O3; MgO-Al2O3-800; oxygen In water at 40℃; for 6h; Reagent/catalyst; Time; Green chemistry;
propylene glycol
57-55-6

propylene glycol

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

carbon dioxide
124-38-9

carbon dioxide

C

acetic acid
64-19-7

acetic acid

D

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With oxygen; sodium hydroxide In water at 90℃; under 3750.38 Torr; for 2h; Reagent/catalyst; Inert atmosphere; Green chemistry;A 58%
B 18%
C 6%
D 13%
carbon dioxide
124-38-9

carbon dioxide

acetaldehyde
75-07-0

acetaldehyde

A

L-Lactic acid
79-33-4

L-Lactic acid

B

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With pyruvate decarboxylase; thiamine pyrophosphate; L-lactic dehydrogenase; 1,4-dihydronicotinamide adenine dinucleotide for 1h; pH=9.5; Enzymatic reaction;A 51%
B 14%
With pyruvate decarboxylase; thiamine pyrophosphate; L-lactic dehydrogenase; 1,4-dihydronicotinamide adenine dinucleotide for 1h; pH=10.5; Enzymatic reaction;A 27%
B 28%
2-methylenesuccinic acid
97-65-4

2-methylenesuccinic acid

A

propene
187737-37-7

propene

B

poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

C

2-methyllactic acid
594-61-6

2-methyllactic acid

D

carbon dioxide
124-38-9

carbon dioxide

E

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

F

acetone
67-64-1

acetone

Conditions
ConditionsYield
With barium hexa-aluminate In water at 250℃; under 15001.5 Torr; for 3h; Reagent/catalyst; Autoclave; Inert atmosphere;A n/a
B 50%
C n/a
D n/a
E n/a
F n/a
Propiolic acid
471-25-0

Propiolic acid

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With water; ruthenium trichloride at 80 - 100℃; for 12 - 36h; pH=1.3 - 2.0; Product distribution / selectivity;48%
With water; di[triaqua{2,6-di(phenylthiomethyl)pyridine}ruthenium(III)] tri-sulphate at 80℃; for 12h; pH=2.0; Product distribution / selectivity;38%
With water; iridium(III) chloride at 100℃; for 12h; pH=1.3; Product distribution / selectivity;29%
propylene glycol
57-55-6

propylene glycol

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With water; oxygen In water at 24.84℃; under 760.051 Torr; for 16h; Catalytic behavior; Time; Schlenk technique;A 47%
B 12%
With oxygen; sodium hydroxide at 60℃; under 2250.23 Torr; for 4h;
ethylene glycol
107-21-1

ethylene glycol

7,7,8,8-Tetramethyl-3-methylene-5-phenoxy-1,4,6,9-tetraoxa-5λ5-phospha-spiro[4.4]nonan-2-one
105930-58-3

7,7,8,8-Tetramethyl-3-methylene-5-phenoxy-1,4,6,9-tetraoxa-5λ5-phospha-spiro[4.4]nonan-2-one

A

2-(4,4,5,5-Tetramethyl-2-oxo-2λ5-[1,3,2]dioxaphospholan-2-yloxy)-ethanol
105900-05-8

2-(4,4,5,5-Tetramethyl-2-oxo-2λ5-[1,3,2]dioxaphospholan-2-yloxy)-ethanol

B

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
In chloroform-d1 at 20℃; for 48h;A 46%
B n/a
glycerol
56-81-5

glycerol

A

formic acid
64-18-6

formic acid

B

LACTIC ACID
849585-22-4

LACTIC ACID

C

acetic acid
64-19-7

acetic acid

D

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

E

acrylic acid
79-10-7

acrylic acid

F

2-oxopropanal
78-98-8

2-oxopropanal

Conditions
ConditionsYield
Stage #1: glycerol With sodium hydroxide; water at 300℃; for 1h; Compressed liquid(s);
Stage #2: With sulfuric acid In water Product distribution / selectivity;
A n/a
B 40%
C n/a
D n/a
E n/a
F n/a
rac-Ala-OH
302-72-7

rac-Ala-OH

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With potassiuim nitrosodisulfonate In water for 30h; Mechanism; Product distribution; pH 10.0; var. pH; other α-amino acids and α-hydroxy acids;37%
With sodium hydroxide; oxygen; copper
With air; iron (II)-dicarbonate; water
D-glucose
50-99-7

D-glucose

A

formic acid
64-18-6

formic acid

B

glycolic Acid
79-14-1

glycolic Acid

C

L-Lactic acid
79-33-4

L-Lactic acid

D

malonic acid
141-82-2

malonic acid

E

succinic acid
110-15-6

succinic acid

F

oxalic acid
144-62-7

oxalic acid

G

acetic acid
64-19-7

acetic acid

H

propionic acid
802294-64-0

propionic acid

I

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

J

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With sodium silicate; water at 300℃; under 64356.4 Torr; for 0.0166667h; Reagent/catalyst; Sealed tube;A n/a
B n/a
C 30%
D n/a
E n/a
F n/a
G n/a
H n/a
I n/a
J n/a
D-glucose
50-99-7

D-glucose

A

5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

B

formic acid
64-18-6

formic acid

C

L-Lactic acid
79-33-4

L-Lactic acid

D

succinic acid
110-15-6

succinic acid

E

oxalic acid
144-62-7

oxalic acid

F

acetic acid
64-19-7

acetic acid

G

propionic acid
802294-64-0

propionic acid

H

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

I

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With water at 300℃; under 64356.4 Torr; for 0.0166667h; Reagent/catalyst; Sealed tube;A n/a
B n/a
C 30%
D n/a
E n/a
F n/a
G n/a
H n/a
I n/a
citric acid
77-92-9

citric acid

A

Oxalacetic acid
328-42-7

Oxalacetic acid

B

L-Lactic acid
79-33-4

L-Lactic acid

C

D-Lactic acid
10326-41-7

D-Lactic acid

D

3-hydroxy-2-butanon
513-86-0, 52217-02-4

3-hydroxy-2-butanon

E

acetic acid
64-19-7

acetic acid

F

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With Leuconostoc mesenteroides at 30℃; for 1h; potassium phosphate buffer, pH 5.0; other conditions also investigated; several substrates investigated;A 0.66%
B 0.06%
C 1.77%
D 6.86%
E 15.5%
F 0.05%
citric acid
77-92-9

citric acid

A

Oxalacetic acid
328-42-7

Oxalacetic acid

B

L-Lactic acid
79-33-4

L-Lactic acid

C

D-Lactic acid
10326-41-7

D-Lactic acid

D

acetic acid
64-19-7

acetic acid

E

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

F

dimethylglyoxal
431-03-8

dimethylglyoxal

Conditions
ConditionsYield
With Leuconostoc mesenteroides at 30℃; for 1h; potassium phosphate buffer, pH 5.0; other conditions also investigated; several substrates investigated;A 0.66%
B 0.06%
C 1.77%
D 15.5%
E 0.05%
F 1.72%
piperidine
110-89-4

piperidine

2,3-dibromopropionic acid ethyl ester
3674-13-3

2,3-dibromopropionic acid ethyl ester

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

Conditions
ConditionsYield
With potassium hydrogensulfate; ethanol; water
glycolic Acid
79-14-1

glycolic Acid

L-Tartaric acid
87-69-4

L-Tartaric acid

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

acetaldehyde
75-07-0

acetaldehyde

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

3-hydroxy-2-butanon
513-86-0, 52217-02-4

3-hydroxy-2-butanon

Conditions
ConditionsYield
With sodium hydroxide; thiamine diphosphate chloride hydrochloride In methanol at 37℃; for 5.5h;100%
Vergaerung durch Essigbakterien;
durch Hefe; Ausbeute ist groesser,wenn zu der gaerenden Brenztraubensaeure-Loesung gleich nach Beginn der Gaerung noch Acetalehyd zugesetzt wird;
1,4-pyrazine
290-37-9

1,4-pyrazine

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

acetylpyrazine
22047-25-2

acetylpyrazine

Conditions
ConditionsYield
With NH4S2O8; silver nitrate; trifluoroacetic acid In dichloromethane; water at 40℃; for 2.5h;100%
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; sulfuric acid In dichloromethane; water at 40℃; Reagent/catalyst; Solvent; Minisci Aromatic Substitution;26%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

2-acetylpyridine-4-carbonitrile
37398-49-5

2-acetylpyridine-4-carbonitrile

Conditions
ConditionsYield
With NH4S2O8; sulfuric acid; silver nitrate In dichloromethane; water at 40℃; for 2.5h;100%
2,3-diethynylquinoxaline
91-19-0

2,3-diethynylquinoxaline

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

2-acetylquinoxaline
25594-62-1

2-acetylquinoxaline

Conditions
ConditionsYield
With ammonium peroxydisulfate; silver nitrate; trifluoroacetic acid In dichloromethane; water at 40℃;100%
With NH4S2O8; silver nitrate; trifluoroacetic acid In dichloromethane; water at 40℃; for 2.5h;94%
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; formic acid; dimethyl sulfoxide In dichloromethane; water at 40℃; Minisci Aromatic Substitution;67%
With nickel(II) acetylacetonate In dichloromethane; acetonitrile at 50℃; for 4h; Catalytic behavior; Electrochemical reaction;45%
With ammonium peroxydisulfate; sulfuric acid; silver nitrate In dichloromethane; water at 40℃; for 2.5h;42.9%
2-(3-methyl-2-butenyloxy)benzaldehyde
56074-73-8

2-(3-methyl-2-butenyloxy)benzaldehyde

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

4-<2-(3-Methyl-2-butenyloxy)phenyl>-2-oxo-3-butenoic acid
112881-83-1

4-<2-(3-Methyl-2-butenyloxy)phenyl>-2-oxo-3-butenoic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol Ambient temperature;100%
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

2,2-diethoxypropanoic acid
25741-02-0

2,2-diethoxypropanoic acid

Conditions
ConditionsYield
With sulfuric acid at 5 - 10℃; for 1h;100%
With sulfuric acid at 5 - 10℃; for 0.5h;
With sulfuric acid for 0.5h; Cooling with ice;
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

methoxybenzene
100-66-3

methoxybenzene

1,1-bis-(4-methoxyphenyl)ethylene
4356-69-8

1,1-bis-(4-methoxyphenyl)ethylene

Conditions
ConditionsYield
With methanesulfonic acid; phosphorus pentoxide for 24h; Ambient temperature;99%
calcium acetate hemihydrate

calcium acetate hemihydrate

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

calcium pyruvate semihydrate

calcium pyruvate semihydrate

Conditions
ConditionsYield
at 20℃; for 2.5h;99%
(S,E)-1-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pent-3-en-2-ol
1187335-22-3

(S,E)-1-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pent-3-en-2-ol

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

(S,E)-1-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pent-3-en-2-yl 2-oxopropanoate
1187335-28-9

(S,E)-1-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pent-3-en-2-yl 2-oxopropanoate

Conditions
ConditionsYield
With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine In benzene for 16h; Inert atmosphere;99%
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

β-naphthaldehyde
66-99-9

β-naphthaldehyde

(R)-1-hydroxy-1-(naphthalen-2-yl)propan-2-one

(R)-1-hydroxy-1-(naphthalen-2-yl)propan-2-one

Conditions
ConditionsYield
With cyclohexane-1,2-dione hydrolase In aq. buffer at 30℃; for 48h; pH=6.5; Enzymatic reaction;99%
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

edaravone
89-25-8

edaravone

C13H12N2O3

C13H12N2O3

Conditions
ConditionsYield
With zinc(II) chloride In acetic anhydride at 60℃; for 0.166667h; Temperature;98.4%
5-fluoro-1H-indole-2,3-dione
443-69-6

5-fluoro-1H-indole-2,3-dione

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

6-fluoroquinoline-2,4-dicarboxylic acid
220844-72-4

6-fluoroquinoline-2,4-dicarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide at 110℃; for 6h;98.15%
With sodium hydroxide at 110℃; for 4h;70%
With potassium hydroxide In water at 40℃; for 16h; Pfitzinger Quinoline Synthesis;65%
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

LACTIC ACID
849585-22-4

LACTIC ACID

Conditions
ConditionsYield
With [Ni(II)(N,N'-dimethyl-N,N'-bis(2-mercaptoethyl)-1,3-propanediamine)(μ-OH)(μ-H)Ru(II)(η6-C6Me6)]; hydrogen In water at 60℃; under 3750.38 Torr; for 4h; pH=8;98%
With formic acid; [Ir(III)Cp*(bpy)(OH2)](SO4) In water at 70℃; for 1h; pH=2.0;35%
Electrolysis;
L-histidine monohydrochloride
645-35-2

L-histidine monohydrochloride

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

(RS),(S)-histopine
25303-09-7

(RS),(S)-histopine

Conditions
ConditionsYield
With sodium hydroxide; sodium cyanoborohydride In water for 72h; Ambient temperature;98%
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

1,7-bis(hydroxymethyl)-4-methyl-2,4,6-triazatricyclo<5.1.1.02,6>nonane-3,5-dione
112422-49-8

1,7-bis(hydroxymethyl)-4-methyl-2,4,6-triazatricyclo<5.1.1.02,6>nonane-3,5-dione

1,7-bis((pyruvyloxy)methyl)-4-methyl-2,4,6-triazatricyclo<5.1.1.02,6>nonane-3,5-dione
112422-50-1

1,7-bis((pyruvyloxy)methyl)-4-methyl-2,4,6-triazatricyclo<5.1.1.02,6>nonane-3,5-dione

Conditions
ConditionsYield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane for 0.333333h;98%
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

2,2,2-trifluoroethanol
420-46-2

2,2,2-trifluoroethanol

Conditions
ConditionsYield
With sulfur tetrafluoride at 20℃; for 12h; steel autoclave;98%
N-methyl-2-chloroaniline
932-32-1

N-methyl-2-chloroaniline

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

N-methyl-1H-indole-2-carboxylic acid
16136-58-6

N-methyl-1H-indole-2-carboxylic acid

Conditions
ConditionsYield
With potassium phosphate; magnesium sulfate; acetic acid; bis(tri-t-butylphosphine)palladium(0) In N,N-dimethyl acetamide at 140℃; for 14h;98%
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

4-ethylbenzylaldehyde
4748-78-1

4-ethylbenzylaldehyde

(R)-1-(4-ethylphenyl)-1-hydroxypropan-2-one

(R)-1-(4-ethylphenyl)-1-hydroxypropan-2-one

Conditions
ConditionsYield
With cyclohexane-1,2-dione hydrolase In aq. buffer at 30℃; for 48h; pH=6.5; Enzymatic reaction;98%
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

C12H16O2

C12H16O2

Conditions
ConditionsYield
With cyclohexane-1,2-dione hydrolase In aq. buffer at 30℃; for 48h; pH=6.5; Enzymatic reaction;98%
4-tert-Butylbenzaldehyde
939-97-9

4-tert-Butylbenzaldehyde

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

(R)-1-(4-(tert-butyl)phenyl)-1-hydroxypropan-2-one

(R)-1-(4-(tert-butyl)phenyl)-1-hydroxypropan-2-one

Conditions
ConditionsYield
With cyclohexane-1,2-dione hydrolase In aq. buffer at 30℃; for 48h; pH=6.5; Enzymatic reaction;98%

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The present study describes the rapid microplate method to determine pyruvic acid content in different varieties of onions. Onion juice was treated with 2,4-dinitrophenylhydrazine to obtain hydrazone, which was further treated with potassium hydroxide to get stable colored complex. The stability...detailed

Oxidative dehydrogenation of lactic acid to Pyruvic acid (cas 127-17-3) over Pb-Pt bimetallic supported on carbon materials10/01/2019

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The purpose of this study is to assess some of the variables determining the aldol-like condensation of pyruvic acid (1), a peroxide scavenger, in aqueous solution to parapyruvic acid and higher oligomers. Its stability is compared to 3 other α-keto carboxylic acids, 2 with sterically hindered ...detailed

Does interfacial photochemistry play a role in the photolysis of Pyruvic acid (cas 127-17-3) in water?09/26/2019

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Biosynthesis of Pyruvic acid (cas 127-17-3) from glycerol-containing substrates and its regulation in the yeast Yarrowia lipolytica09/25/2019

The ability of different yeasts to synthesize pyruvic acid (PA) from glycerol-containing substrates has been studied. The selected strain Yarrowia lipolytica VKM Y-2378 synthesized PA with α-ketoglutaric acid (KGA) as a byproduct. The content of KGA greatly depended on cultivation conditions. T...detailed

Pyruvic acid (cas 127-17-3) prevents Cu2+/Zn2+-induced neurotoxicity by suppressing mitochondrial injury09/10/2019

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127-17-3Relevant articles and documents

Photocatalytic Conversion of Lactic Acid to Malic Acid through Pyruvic Acid in the Presence of Malic Enzyme and Semiconductor Photocatalysts

Inoue, Hiroshi,Yamachika, Mikio,Yoneyama, Hiroshi

, p. 2215 - 2220 (1992)

The photocatalytic fixation of CO2 in pyruvic acid to yield malic acid has been achieved in TiO2 microcrystal and CdS particle suspensions using malic enzyme as the catalyst, methyl viologen as the electron mediator and either 2-mercaptoethanol or lactic acid as the hole scavenger.The evaluation of the rate-determining step in the photocatalytic fixation reaction was made at the TiO2 microcrystal for the case of 2-mercaptoethanol as the hole scavenger.The use of lactic acid as the hole scavenger resulted in the selective photoproduction of pyruvic acid at the CdS photocatalyst, a fraction of which was then converted into malic acid by reductive CO2 fixation at the malic enzyme.However, it has been found that lactic acid causes a decrease in the catalytic activities of the enzyme, the degree depending on the relative concentrations of malic enzyme and lactic acid.

Oxidation of methylmalonic acid by cerium(IV). Evidence for parallel reaction pathways

Kvernberg, Per Olav,Hansen, Eddy W.,Pedersen, Bjorn,Rasmussen, Asbjorn,Ruoff, Peter

, p. 2327 - 2331 (1997)

The reaction between methylmalonic acid (MeMA) and Ce(IV) ion in 1 M sulfuric acid/D2SO4 has been studied by means of 1H- and 13C-NMR. When MeMA is in excess, acetic acid, hydroxymethylmalonic acid, and pyruvic acid are formed as stable end products. When Ce(IV) is in stoichiometric excess, acetic acid is the only product. Approximately 70-80% of the MeMA forms rapidly acetic acid with hydroxymethylmalonic acid and pyruvic acid as reactive intermediates. The remaining MeMA reacts along parallel pathways and forms two intermediates, which slowly convert to hydroxymethylmalonic acid and pyruvic acid, respectively.

Photooxidation of 2-Hydroxy Acids by Copper(II) Species in Aqueous Solution

Matsushima, Ryoka,Ichikawa, Yoshinori,Kuwabara, Katsuyuki

, p. 1902 - 1907 (1980)

Ultraviolet irradiation of aqueous lactic, glycolic, or 2-hydroxybutanoic acid in the presence of copper (II) leads to photoredox reaction to give corresponding α-keto acid, aldehyde with evolution of carbon dioxide, and the precipitate of copper (I).The mole ratio of the carbonyl products to the consumption of copper(II) is close to 0.5.Oxidative decarboxylation dominates at pH above 1 while the formation of α-keto acids favors at lower pH.The formation of α-keto acids is selectivity suppressed by the addition of free radical scavengers.Free radical oxidations of the acids with bromine atom or benzoyl radicals give exclusively α-keto acids.The reaction mechanism has been discussed.

Immobilization of thermotolerant intracellular enzymes on functionalized nanoporous activated carbon and application to degradation of an endocrine disruptor: kinetics, isotherm and thermodynamics studies

Saranya,Ranjitha,Sekaran

, p. 66239 - 66259 (2015)

A bacterium, Serratia marcescens capable of degrading the endocrine disruptor, 2-nitrophloroglucinol (NPG) was isolated from tannery wastewater contaminated soil. The mixed intracellular enzymes (MICE) produced from S. marcescens were extracted and characterized. The functionalized nanoporous activated carbon matrix (FNAC) was prepared to immobilize MICE. The optimum conditions for the immobilization of MICE on FNAC were found to be time, 2.5 h; pH, 7.0; temperature, 40°C; concentration of MICE, 4 mg; particle size of FNAC, 300 μm and mass of FNAC, 1 g. The FNAC materials before and after immobilization of MICE were characterized using scanning electron microscopy, Fourier transform-infrared spectrophotometry and an X-ray diffractometer. The thermal behaviour of the free and the immobilized MICE was studied using thermogravimetric analysis. The immobilization of MICE on FNAC obeyed the Freundlich model and the immobilization process followed a pseudo second order kinetic model. MICE-FNAC matrix was used to degrade NPG in aqueous solution. The degradation of NPG by MICE-FNAC was optimum at contact time, 3 h; pH, 7.0; temperature, 40°C; concentration of NPG, 20 μM and agitation speed, 70 rpm. The degradation of NPG was found to be enhanced in the presence of Zn2+, Cu2+, Ca2+ and V3+ ions. The degradation of NPG by MICE-FNAC was studied using UV-visible, fluorescence and FTIR spectroscopy. The degradation of NPG by MICE-FNAC was confirmed using HPLC, NMR and GC-MS spectroscopy.

Crystal structure of D-serine dehydratase from Escherichia coli

Urusova, Darya V.,Isupov, Michail N.,Antonyuk, Svetlana,Kachalova, Galina S.,Obmolova, Galina,Vagin, Alexei A.,Lebedev, Andrey A.,Burenkov, Gleb P.,Dauter, Zbigniew,Bartunik, Hans D.,Lamzin, Victor S.,Melik-Adamyan, William R.,Mueller, Thomas D.,Schnackerz, Klaus D.

, p. 422 - 432 (2012)

D-Serine dehydratase from Escherichia coli is a member of the β-family (fold-type II) of the pyridoxal 5′-phosphate-dependent enzymes, catalyzing the conversion of D-serine to pyruvate and ammonia. The crystal structure of monomeric D-serine dehydratase has been solved to 1.97 A-resolution for an orthorhombic data set by molecular replacement. In addition, the structure was refined in a monoclinic data set to 1.55 A resolution. The structure of DSD reveals a larger pyridoxal 5′-phosphate- binding domain and a smaller domain. The active site of DSD is very similar to those of the other members of the β-family. Lys118 forms the Schiff base to PLP, the cofactor phosphate group is liganded to a tetraglycine cluster Gly279-Gly283, and the 3-hydroxyl group of PLP is liganded to Asn170 and N1 to Thr424, respectively. In the closed conformation the movement of the small domain blocks the entrance to active site of DSD. The domain movement plays an important role in the formation of the substrate recognition site and the catalysis of the enzyme. Modeling of D-serine into the active site of DSD suggests that the hydroxyl group of D-serine is coordinated to the carboxyl group of Asp238. The carboxyl oxygen of D-serine is coordinated to the hydroxyl group of Ser167 and the amide group of Leu171 (O1), whereas the O2 of the carboxyl group of D-serine is hydrogen-bonded to the hydroxyl group of Ser167 and the amide group of Thr168. A catalytic mechanism very similar to that proposed for L-serine dehydratase is discussed.

Exploration of Transaminase Diversity for the Oxidative Conversion of Natural Amino Acids into 2-Ketoacids and High-Value Chemicals

Chen, Yanchun,Cui, Xuexian,Cui, Yinglu,Li, Chuijian,Li, Ruifeng,Li, Tao,Sun, Jinyuan,Wu, Bian,Zhu, Tong

, p. 7950 - 7957 (2020)

The use of 2-ketoacids is very common in feeds, food additives, and pharmaceuticals, and 2-ketoacids are valuable precursors for a plethora of chemically diverse compounds. Biocatalytic synthesis of 2-ketoacids starting from l-amino acids would be highly desirable because the substrates are readily available from biomass feedstock. Here, we report bioinformatic exploration of a series of aminotransferases (ATs) to achieve the desired conversion. Thermodynamic control was achieved by coupling an l-glutamate oxidation reaction in the cascade for the recycling of the amine acceptor. These enzymes were able to convert a majority of proteinogenic amino acids into the corresponding 2-ketoacids with high conversion (up to 99percent) and atom-efficiency. Furthermore, this enzyme cascade was extendable, and one-pot two-step processes were established for the synthesis of d-amino acids and N-methylated amino acids, achieving great overall conversion (up to 99percent) and high ee values (>99percent). These developed enzymatic methodologies offer convenient routes for utilizing amino acids as synthetic reagents.

Oxidation of lactic acid by water soluble (Colloidal) manganese dioxide

Khan, Zaheer,Raju,Akram, Mohd,Kabir-Ud-Din

, p. 359 - 366 (2004)

Spectrophotometric method has been used to characterize water-soluble colloidal manganese dioxide obtained by the redox reaction between sodium thiosulphate and potassium permanganate in neutral aqueous medium which shows a single peak in the visible region with λmax = 425 nm. The kinetics of the oxidation of lactic acid by colloidal manganese dioxide (oxidant) has been investigated spectrophotometrically under pseudo-first-order conditions of excess lactic acid. The rate of the noncatalytic reaction pathway was slow which increased with increasing lactic acid concentration. The reaction was first-order with respect to [oxidant] as well as [lactic acid]. In presence of manganase(II) and fluoride ions, the noncatalytic path disappeared completely while the oxidation rate of autocatalytic path increased and decreased, respectively with increasing [Mn(II)] and [F-]. A mechanistic scheme in conformity with the observed kinetics has been proposed with the rate-law: v = -d[MnO2]/dt = κ1κ2[MnO2] [H+][lactic acid]T/ ([H+] Ka)(κ_1 + ≤2)

Characterization of two isotypes of l-threonine dehydratase from Entamoeba histolytica

Husain, Afzal,Jeelani, Ghulam,Sato, Dan,Ali, Vahab,Nozaki, Tomoyoshi

, p. 100 - 104 (2010)

The genome sequence of the enteric protozoan parasite Entamoeba histolytica suggests that amino acid catabolism plays an important role in energy metabolism. In the present study, we described kinetic and regulatory properties of catabolic l-threonine and l-serine dehydratase (TD) from E. histolytica. TD catalyses the pyridoxal phosphate-dependent dehydrative deamination of l-threonine and l-serine to ammonia and keto acids (2-oxobutyrate and pyruvate, respectively). E. histolytica possesses two TD isotypes (EhTD1-2) showing 38% mutual identity, a calculated molecular mass of 45.0 or 46.5 kDa, and an isoelectric point of 6.68 or 5.88, respectively. Only EhTD1 showed l-threonine and l-serine dehydrative deaminating activities whereas EhTD2, in which the amino acid residues involved in the substrate and cofactor binding were not conserved, was devoid of these activities. The kcat/Km value of EhTD1 was >3 fold higher for l-threonine than l-serine. EhTD1 was inhibited by l-cysteine in a competitive manner with the Ki values of 1.1 mM and 2.2 mM for l-serine and l-threonine, respectively. EhTD1 was insensitive to the allosteric activation by AMP or CMP. Three major substitutions of EhTD1 likely attribute to the insensitivity. EhTD1 was also inhibited about 50% by 20 mM 2-oxobutyrate, pyruvate, and glyoxylate; the inhibition was not, however, reversed by AMP. Together, these data showed that EhTD1 possesses unique regulatory properties distinct from other organisms and may play an important role in energy metabolism via amino acid degradation in E. histolytica.

A Convenient Electrochemical Synthesis of α-Oxoacids

Pokhodenko, Vitaly D.,Koshechko, Vjacheslav G.,Titov, Vladimir E.,Lopushanskaja, Victorija A.

, p. 3277 - 3278 (1995)

The possibility of obtaining aliphatic and aromatic-α-oxoacids via the direct electrochemical carboxylation of acetyl and benzoyl chlorides has been shown for the first time.

Kinetics and mechanism of the oxidation of some α-hydroxy acids by 2,2′-bipyridinium chlorochromate

Kumbhat, Vinita,Sharma, Pradeep K.,Banerji, Kalyan K.

, p. 248 - 254 (2002)

The oxidation of glycolic, lactic, malic, and a few substituted mandelic acids by 2,2′-bipyridinium chlorochromate (BPCC) in dimethylsulphoxide leads to the formation of corresponding oxoacids. The reaction is first order each in BPCC and the hydroxy acids. The reaction is catalyzed by the hydrogen ions. The hydrogen ion dependence has the form: kobs = a + b [H+]. The oxidation of α-deuteriomandelic acid exhibited a substantial primary kinetic isotope effect (kH/kd = 5.29 at 303 K). Oxidation of p-methylmandelic acid was studied in 19 different organic solvents. The solvent effect has been analyzed by using Kamlet's and Swain's multiparametric equations. A mechanism involving a hydride ion transfer via a chromate ester is proposed.

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