α- Ketoglutaric acid

α- Ketoglutaric acid（ α- Ketoglutaric acid)

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α- ketone Glutaric acid （ α- Ketoglutaric acid), chemical formula C five H six O 5， Two bands of glutaric acid Keto group One of its derivatives, white fine Crystallinity Powder. Its salts are important biological compounds.

α- Ketoglutarate participates in organism Tricarboxylic acid cycle , an intermediate metabolite of the tricarboxylic acid cycle, participates in the synthesis and energy metabolism of amino acids, vitamins and organic acids. It can be used as a dietary supplement and has a broad application prospect.

Chinese name: α- Ketoglutaric acid
Foreign name: α- Ketoglutaric acid
chemical formula: C five H six O five
molecular weight: one hundred and forty-six point zero two one five
CAS login number: 328-50-7

EINECS login number: 206-330-3
Melting point: 113.5 ℃
Boiling point: 345.62 ℃
Water solubility: Easily soluble in water
Appearance: White fine crystalline powder
Flash point: 177.02 ℃

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five Molecular structure data
six security information

brief introduction

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α- ketone Glutaric acid (English: α- Ketoglutaric acid) are two types of glutaric acid Keto group One of the derivatives of α Type. β- Ketoglutarate is only the position of ketone group is different, and it is not commonly used) white fine Crystallinity Powder. Melting point 113.5 ℃. It is easily soluble in water, alcohol, and very difficult to dissolve in ether. After long storage, it turns pale grayish yellow and is easy to deliquescence.^[1]

Of this substance anion ， α- Ketoglutarate is an important biological compound. It is glutamic acid Deamination Of Keto acid And is an intermediate product of the tricarboxylic acid cycle.^[2]

Preparation method

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1. Apply 225 g Oxalosuccinic acid Mix triethyl ester with 600 mL concentrated hydrochloric acid, and place the solution. Distill and concentrate to 140 ℃, and the residue is cooled and crystallized to obtain α- Ketoglutarate 110-112 g, yield 92-93%。

2. Preparation method:

Oxalyl Succinic acid three ethyl ester (3) : Installed on Agitator In the reaction bottle of reflux condenser, add Anhydrous ethanol 360 mL, add clean metal in batches sodium 23 g（1.0 mol ）After addition, heat and reflow to make the reaction of metal sodium complete. Convert to distillation unit ethanol Steamed out continuously Dropwise addition toluene , remove ethanol until internal temperature reaches 105 ℃, cool to room temperature, add anhydrous Ether 650 mL， Diethyl oxalate 146 g (1 mol), added with stirring Diethyl succinate (2) 174 g (1.0 mol) at room temperature for 12 h. Add 500mL of water under mixing to separate Organic layer , the organic layer is extracted with 150 mL water, and the water layer is merged, Concentrated hydrochloric acid Acidify and precipitate oily substances. Separate the oil layer and extract the water layer with ether for three times. Consolidated organic layer, Magnesium sulfate anhydrous dry. The yellow oily compound (3) was 235~250 g in 86%~91% yield from the recovery of ether. a- carbonyl Glutaric acid (1): add 225 g (0.82 mol) of the above compound (3), 330 mL of concentrated hydrochloric acid, and 660 mL of water into a reaction flask equipped with an agitator and reflux condenser, heat and reflux for 4 hours under stirring, Vacuum concentration To dry (60~70 ℃), add Nitroethane 200 mL, dissolved by heating Thermal filtration ， filter cake Wash with hot nitroethane. Combine nitroethane solution, and stir at 0~10 ℃ for 5 h. Suction filtration at 90 ℃ Vacuum drying 4 h, compound (1) 88 ～ 99 g was obtained in 73% ～ 83% yield.^[6]

function

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Tricarboxylic acid cycle

α- Ketoglutarate is an important component of microbial tricarboxylic acid cycle Metabolic intermediate , is to connect intracellular carbon- Nitrogen metabolism The key node of, the position in the loop is at Isocitrate After and Succinyl coenzyme A Before. In this part, Compensatory reaction Can be accessed from glutamate Of Transamination produce α- Ketoglutarate to supplement the middle Metabolites By Glutamate dehydrogenase This can also be achieved by acting on glutamic acid.^[2]

Generate amino acids

Glutamate in glutamine Synthase Glutamine can be produced under the action of ATP To produce glutamyl phosphate ； This one Intermediate product Be treated as Nucleophile Ammonia attack, thus forming glutamine and inorganic phosphoric acid 。^[3]

Dietary supplements

α- Ketoglutarate is sold as a dietary supplement, Trade name Is A KG Or a-KG, sold to fitness enthusiasts or Bodybuilding The salesperson claimed that this substance could improve the performance at the peak of training. The seller claims that this is based on "research shows that too much ammonia can be combined into α- Ketoglutarate is removed to reduce Ammonia poisoning Many problems ". However, it shows that α- Ketoglutarate can reduce ammonia poisoning. Effective research is only used for existing research Hemodialysis Patients.^[4]

alias^[5]	2-ketoglutaric acid
MeSH	alpha-ketoglutaric+acid
melting point	one hundred and thirteen point five
Solubility (tetrahydrofuran, ethanol, methanol)	Tetrahydrofuran: 2.33 M, ethanol: 1.94 M, methanol: 3.75 M
InChIKey：	KPGXRSRHYNQIFN-UHFFFAOYSA-N
Unless otherwise specified, all data are from general conditions (25 ℃, 100 kPa).

3D (2 sheets)

purpose

1. It is mainly used as an ingredient of sports nutrition drinks.

2. Organic intermediate, Biochemical reagent , measurement liver function Reagent kit for.

3. Reduce the body loss of postoperative patients and long-term patients.

4. In the brain as Tyrosine And glutamate precursors. （ α- Ketoglutarate can pass Transamination Glutamic acid production)

5、 α- Ketoglutaric acid（ α- Ketoglutaric acid also has anti cyanide effect. The test shows that Sodium nitrite 、 Sodium thiosulfate Compatible use can improve the cyanide resistance convulsions effect.