GAMMA-KETOGLUTARIC ACID
2-Ketoglutaric acid
CAS: 328-50-7
Molecular Formula: C5H6O5
GAMMA-KETOGLUTARIC ACID - Names and Identifiers
GAMMA-KETOGLUTARIC ACID - Physico-chemical Properties
| Molecular Formula | C5H6O5 |
| Molar Mass | 146.1 |
| Density | 1.54g/cm3 |
| Melting Point | 113-115℃ |
| Boling Point | 320.7°C at 760 mmHg |
| Flash Point | 147.7°C |
| Solubility | Easily soluble in water, alcohol, acetone; extremely insoluble in ether |
| Vapor Presure | 6.5E-05mmHg at 25°C |
| Appearance | White fine crystalline powder. Long storage becomes light gray yellow |
| Storage Condition | 2-8℃ |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.544 |
| MDL | MFCD00004165 |
| Physical and Chemical Properties | Melting point 113-115°C |
| Use | Mainly as a component of sports nutrition drinks |
GAMMA-KETOGLUTARIC ACID - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R41 - Risk of serious damage to eyes |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
GAMMA-KETOGLUTARIC ACID - Upstream Downstream Industry
GAMMA-KETOGLUTARIC ACID - Reference
| Reference Show more | 1. Pei Ying, Sun Yubo, Huang Bin. Separation of α-ketoglutaric acid by aqueous two-phase extraction [J]. Food and Fermentation Industries 2018 044(012):150-154. 2. Pei Ying, Huang Bin. Aqueous two-phase extraction of α-ketoglutaric acid from fermentation broth [J]. Chemical engineering 2019 47(03):29-34. 3. Pei Ying, Sun Yubo, Huang Bin. Extraction of alpha-ketoglutarate from fermentation broth [J]. Journal of Xinyang Normal University (Natural Science Edition) 2018 v.31;No.132(03):123-126. 4. Zhou Lan, Hu Yueying, Chen Wenwen. Effects of black pepper extract on physiological metabolism of Bacillus subtilis [J]. Science and Technology of Food Industry, 2015, 36(023):148-151. 5. Zhou Lan, Hu Yueying, Chen Wenwen. Antibacterial mechanism of petroleum ether extracts from Black Pepper against Escherichia coli and Staphylococcus aureus [J]. Food Science and Technology, 2018(6). 6. Pei Fangyi Jiang Ming Ma rock, etc. Analysis of organic acid content in three strains of Saccharomyces cerevisiae during fermentation [J]. Food and machinery 2019(10). 7. Horse Rock, Jiang Ming, Liu Zhenyan, etc. Changes of organic acids and free amino acids during fermentation of Saccharomyces cerevisiae QY-1 [J]. China Brewing, 2019(10). 8. Peng Jiang, Sun Yancai, Cai Ying, etc. Study on urine metabolome of rats with Hepatotoxicity induced by Sophora flavescens ethanol extract based on Ultra performance liquid chromatography-high resolution mass spectrometry [J]. Journal of Anhui University of Traditional Chinese Medicine, 2018. 9. [IF = 3.575] Wei Hou et al."Propylselen inhibitors cancer cell growth by targeting glutamate dehydrogenase at the NADP binding site." Biochem Bioph Res Co. Jan 2019; 509:262 10. [IF = 9.423] Yi Li et al."Block of citrate export prevention TCA cycle fragmentation via Irg1 inactivation." Cell Rep. 2022 Feb;38:110391 11. [IF = 3.535] Ying Zhang et al."Screening prolyl hydroxylase domain 2 inhibitory activity of traditional Chinese medicine by CZE-UV."ELECTROPHORESIS. 2022 Apr 11 12. [IF=5.154] Ying Jiang et al."Isolation of a novel characterized Issatchenkia terricola from red raspberry fruits on the degradation of citric acid and enrichment of flavonoid and volatile profiles in fermented red raspberry juice."Food Science and Human Wellness. 202 |
GAMMA-KETOGLUTARIC ACID - Introduction
Long storage turns pale grayish yellow, easy to deliquesce.
Last Update：2022-10-16 17:24:38
GAMMA-KETOGLUTARIC ACID - Security information
| WGK Germany | 3 |
| TSCA | Yes |
| customs code | 29183000 |
Last Update：2024-04-10 22:29:15
GAMMA-KETOGLUTARIC ACID - Nature
| FEMA | 3891 | 2-OXOPENTANEDIOIC ACID |
| refractive index | 1.3920 (estimate) |
| storage conditions | 2-8°C |
| solubility | H2O: soluble0.1g/mL, clear, colorless |
| acidity coefficient (pKa) | 2.47(at 25℃) |
| morphology | Crystalline Powder |
| color | White to slightly yellow |
| Odor | Odorless |
| water solubility | Soluble in water, methanol and dimethyl sulfoxide. |
| Merck | 14,5303 |
| JECFA Number | 634 |
| BRN | 1705689 |
| InChIKey | KPGXRSRHYNQIFN-UHFFFAOYSA-N |
| NIST chemical information | 2-Oxopentanedioic acid(328-50-7) |
| EPA chemical information | Pentanedioic acid, 2-oxo- (328-50-7) |
Last Update：2024-04-10 22:29:15
GAMMA-KETOGLUTARIC ACID - Uses and synthesis methods
introduction
α-ketoglutaric acid is an important biomolecule, one of the important intermediate products in the tricarboxylic acid cycle, and a symbiotic substance in nitrogen transporter and molecular oxidation. It plays an important role in the metabolism of microbial cells and is also an important precursor for the synthesis of various amino acids and proteins.
application
It can be used as a nutritional enhancer, as an ingredient of sports nutritional drinks, organic intermediates, biochemical reagents and supporting reagents for liver function measurement, physical enhancement supplements, etc. In addition, α-ketoglutaric acid can prepare 1:1 and 2:1 L-arginine α-ketoglutaric acid for sports nutrition.
Preparation
The steps for synthesizing α-ketoglutarate by biological transformation are as follows:
(1) inoculate the bacteria ATCC36534 by the refrigerator in the fresh inclined medium and cultured in a constant temperature incubator at 25~30 ℃ for 24~36h to obtain the activated ATCC36534 strains of the yeast. The bevel medium is composed of glucose 10-20g/L, peptone 5-10g/L, yeast leaching powder 3-5g/L, agar 15-20g/L, solvent water, natural pH (measured 6.3-6.5), high-pressure steam sterilization at 121 ℃ for 15-20min.
(2) Use the inoculation ring to pick step (1) After activation and culture, the 2~3 rings of the slant bacteria ATCC36534 by the yeast of Markscruvies are inoculated into the seed medium. The inoculated seed medium was cultured at 25~30 ℃ and 200 ~ 250r /min for 20~24h to obtain seed solution with dry cell concentration of 5~7g/L. The composition of the seed culture medium is the same as the inclined culture medium in step (1) except that no agar is added. The loading amount in the triangular bottle is 20% to 40% of its volume. The triangular bottle is tied at 8 layers and sterilized at 121 ℃ for 15 to 20min.
(3) use the inoculation ring to pick the step (1) after activation and culture, the 3~5 rings of the slant bacteria ATCC36534 by Maxcroveromyces cerevisiae, or the seed liquid prepared in step (2), enter the conversion medium according to the volume percentage of 5% ~ 10%, and culture for 20~24h under the shaking conditions of 25~30 ℃ and 200 ~ 250r /min, the dry cell concentration was 6~10g/L, H2O2 with a final concentration of 10~50mmol/L, or methotrexate with a final concentration of 0.5~1.0 μmol/L, or both were added at the same time. L-glutamic acid with a final concentration of 20~50g/L was added. The triangular flask was cultured for 20~24h under the same conditions to obtain a synthetic culture solution with a concentration of α-ketoglutaric acid of 17.3~42.9g/L.
the composition of the conversion medium is: sucrose 50-100g/L, yeast leaching powder 10-20g/L,KH2PO4 3-5g/L,K2HPO4 5-6.5g/L,MgSO4 0.5-1.0g/L, solvent is tap water, pH is natural (measured 6.5), and the volume in the triangular bottle is 20%-40% of its volume. The triangular bottle was tied at 8 layers and sterilized at 121 ℃ for 15~20min.
(4) the synthetic culture solution prepared in step (3) is centrifuged to remove the bacteria by 3000-4000g and 5-10min to obtain supernatant a, activated carbon is added, activated carbon is filtered out after stirring for 30-60min, the filtrate is concentrated to 1/2-1/4 of the original volume under reduced pressure, the precipitate is removed by centrifugation again to obtain supernatant B, and α, slowly stirring and cooling to 4°C, standing for 8-12h, suction filtration to collect α-ketoglutaric acid crystals, vacuum drying at 45°C to obtain crystalline α-ketoglutaric acid; The volume of clear liquid A above the amount of activated carbon is 5-10g/L, and the volume of clear liquid B above the amount of α-ketoglutaric acid is 10-20g/L.
chemical properties
White fine crystalline powder. Melting point 113.5 ℃. Easily soluble in water, alcohol, extremely difficult to dissolve in ether, long-term storage becomes light grayish yellow, easy to deliquescence.
use
1. The substrate for the determination of amino-converting enzyme and dehydrogenase, the supporting reagent for the determination of liver function, and also used as an intermediate in organic synthesis.
2, mainly used as an ingredient in sports nutrition drinks
3, used as raw materials and food additives for medicines and health products
4. Analytical reagent for tryptophan; substrate for determination of amino converting enzyme and dehydrogenase; supporting reagent for determination of liver function
5. A derivative of valeric acid, which is an intermediate product of the KREB cycle catalyzed by glutamate dehydrogenase.
production method
mix 225g triethyl oxalosuccinate with 600ml concentrated hydrochloric acid and place the liquid. Distillate and concentrate to 140 ℃, and the residue is cooled and crystallized to obtain 110-112g of α-keto glutaric acid with a yield of 92-93%.
Last Update：2024-04-09 20:52:54
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View History
Raw Materials for GAMMA-KETOGLUTARIC ACID
Succinic acid
Pentanedioic acid, 2-oxo-, 1-ethyl ester
L-Glutamic acid, N-[(2S)-2-amino-2-carboxyethyl]-
3-Phenylpyruvic acid
SUCCINALDEHYDIC ACID
2,5-Furandicarboxylic acid
pyridoxal
L-Tyrosine
Pentanedioic acid, 2-oxo-, 1-ethyl ester
L-Glutamic acid, N-[(2S)-2-amino-2-carboxyethyl]-
3-Phenylpyruvic acid
SUCCINALDEHYDIC ACID
2,5-Furandicarboxylic acid
pyridoxal
L-Tyrosine
Downstream Products for GAMMA-KETOGLUTARIC ACID
L-GLUTAMIC-2,3,3,4,4-D5 ACID
ALPHA-KETOGLUTARIC ACID MONOSODIUM SALT
4-Carbethoxybutyrolactone,γ-Carboethoxy-γ-butyrolactone
6-Chloro-pyridazine-3-carboxylic acid ethyl ester
ALPHA-KETOGLUTARIC ACID MONOSODIUM SALT
4-Carbethoxybutyrolactone,γ-Carboethoxy-γ-butyrolactone
6-Chloro-pyridazine-3-carboxylic acid ethyl ester