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328-50-7
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328-50-7
2-Ketoglutaric acid, also known as α-ketoglutaric acid (also called 2-oxoglutaric acid, α-ketoglutaric acid, 2-oxopentanedioic acid, oxoglutaric acid, AKG), has the chemical formula C5H6O5, a molecular weight of 146.10, CAS number 328-50-7, EINECS 206-330-3, UNII 8ID597Z82X, and InChIKey KPGXRSRHYNQIFN-UHFFFAOYSA-N. It is an α-keto dicarboxylic acid containing one ketone group (C=O) and two carboxyl groups (-COOH). It belongs to the keto acid class of organic compounds and is a key intermediate in the tricarboxylic acid (TCA) cycle and a normal metabolite in the human body (listed in HMDB). It is an important biochemical and nutritional chemical: a white crystalline powder or crystal with a melting point of approximately 115°C (decomposes), readily soluble in water, ethanol, and methanol; its aqueous solution is acidic and hygroscopic. Due to its properties as a TCA cycle intermediate, an amino acid transamination hub, α-keto acid reactivity, and a dicarboxylic acid taste, α-ketoglutaric acid is widely used in nutrition, food, cosmetics, and scientific research: in nutrition and health foods, it is a sports nutrition supplement (CK-AKG, AAKG); in food, it is an approved flavoring and fragrance ingredient; in biotechnology and diagnostics, it is a cell culture medium component and a substrate for transaminase detection; in cosmetics, it is an anti-aging active ingredient; and in scientific research, it is a metabolomics standard.
3-Basic identification information : Chemical formula C5H6O5; Molecular weight 146.10; CAS number 328-50-7; EINECS 206-330-3; UNII 8ID597Z82X; InChIKey KPGXRSRHYNQIFN-UHFFFAOYSA-N; IUPAC name 2-oxopentanedioic acid; ChEBI 30915; ChEMBL 1686; INN name Oxoglurate (Oxogluric Acid); Synonyms: α-ketoglutaric acid, 2-oxoglutaric acid, 2-oxoglutaric acid, alpha-ketoglutaric acid, 2-oxoglutaric acid, oxoglutaric acid, AKG, etc.
Structurally , α-ketoglutarate consists of a ketone group attached to the 2 position of the glutarate backbone and a carboxyl group attached to the 1 and 5 positions. The α-ketone group and the adjacent carboxyl group form an α-keto acid structure, which has high reactivity. It is a product of isocitrate oxidation and decarboxylation in the TCA cycle and is also a keto acid acceptor for the transamination of glutamate.
Physically , α-ketoglutaric acid is a white crystalline powder or crystal with a melting point of about 115℃ (which decomposes simultaneously). It is readily soluble in water, ethanol, and methanol, and slightly soluble in ether and benzene. Its aqueous solution is acidic (dicarboxylic acid) and hygroscopic. When heated above its melting point, it decomposes to release gases such as carbon dioxide. It is relatively stable at room temperature, but its aqueous solution may slowly change color if left to stand for a long time.
Chemically , α-ketoglutarate is an α-keto dicarboxylic acid: the α-keto group (carbonyl group) is electrophilic and can undergo reductive amination, transamination, esterification, condensation and other reactions; under the catalysis of transaminases, it interconverts with glutamate (α-ketoglutarate + amino acid ↔ glutamate + α-keto acid), serving as a hub for amino transfer in the body; its carboxyl group can be esterified and formed into salts (such as arginine salts and creatine salts used in nutritional supplements); it participates in cellular energy metabolism as an intermediate in the TCA cycle; it also has the ability to chelate metal ions and scavenge reactive oxygen species; the two carboxyl groups endow it with a synergistic flavor profile of sourness and umami.
Why does α-ketoglutarate play these roles in various fields such as nutrition, food, cosmetics, and scientific research? Its mechanism of action mainly includes the following:
Metabolic intermediate mechanism : α-ketoglutarate is a key intermediate in the tricarboxylic acid cycle and participates in cellular energy metabolism; at the same time, it is the hub of the glutamate-α-ketoglutarate transamination system, connecting carbon metabolism and nitrogen metabolism. Supplementing α-ketoglutarate can provide intermediate substrates for energy supply and amino acid synthesis, which is the physiological basis for its nutritional supplementation.
Mechanism of α-keto acid reactivity : The strong electrophilicity of the α-keto group makes it easy to undergo reductive amination, condensation and derivatization reactions, which are key precursors for the chemical synthesis of amino acids (such as glutamic acid and glutamine), and this is the basis for their use as fine chemical intermediates.
The synergistic mechanism of sourness and flavor : The two carboxyl groups and the α-keto acid structure endow α-ketoglutaric acid with sourness and produce a synergistic effect with umami substances. It can be used as a food flavoring and flavoring ingredient to adjust the sourness and flavor layers.
Chelation and antioxidant mechanism : The α-keto acid structure can chelate with metal ions and scavenge reactive oxygen free radicals, protecting cells from oxidative damage. This is the active basis for its anti-aging supplementation and cosmetic skin care applications.
Corresponding products: Creatine alpha-ketoglutarate (CK-AKG), Arginine alpha-ketoglutarate (AAKG), pre-workout supplements, mass gainer formulas, sports recovery drinks, strength training nutrition products, and raw materials for fitness nutrition formulas, etc.
Why it can be used for this purpose: α-Ketoglutarate participates in the TCA cycle and amino acid metabolism, provides intermediate substrates for muscle energy metabolism, and after forming salts with creatine, arginine, etc., it has the nutritional effects of both components. As a sports nutrition supplement, it supports energy supply, strength training performance and exercise recovery, and is a common raw material in the fields of bodybuilding and sports nutrition.
Corresponding products: α-ketoglutarate dietary supplements , energy support tablets, oral powders, health food raw materials, etc.
Why it can be used for this purpose: Alpha-ketoglutarate, as an intermediate in the TCA cycle and an endogenous metabolite, is a popular ingredient in health supplements, and its market application continues to grow with increasing research.
Corresponding products: complete nutritional formula foods , recovery nutritional powders, amino acid metabolism support formulas, nutritional supplements, etc.
Why it can be used for this purpose: α-ketoglutarate, as an amino acid transamination hub, can participate in maintaining the balance of amino acid metabolism in the body and is an amino acid metabolism support component in foods for special medical purposes.
Corresponding products: food flavoring formulations, flavor-enhancing ingredients, acidity regulators, compound seasoning components, beverage flavoring ingredients, baking flavoring agents, meat flavoring additives, food ingredients, etc.
Why it can be used for this purpose: α-Ketoglutarate is a flavoring and flavoring ingredient approved for use in food. Its synergistic properties of acidity and umami can regulate the acidity of food and enhance the flavor profile. It is used as a food flavoring and flavoring ingredient in beverage, condiment, and processed food formulations.
Corresponding products: glutamic acid intermediates, glutamine synthesis raw materials, amino acid production intermediates, etc.
Why it can be used for this purpose: The α-keto acid structure of α-ketoglutarate can be converted into amino acids such as glutamic acid and glutamine through reductive amination and transamination reactions, which are important precursor raw materials for the amino acid industry.
Corresponding products: anti-aging serums, repair creams, antioxidant skincare formulas, cellular energy skincare ingredients, eye care products, firming and lifting products, functional skincare ingredients, etc.
Why it can be used for this purpose: Alpha-ketoglutarate has the ability to chelate and scavenge reactive oxygen species, which can reduce oxidative damage and support the energy supply of skin cells. It is used as an active ingredient in anti-aging and repair cosmetics and in skin care formulas such as serums and creams.
Corresponding products: High performance liquid chromatography standards, metabolomics standards, gas chromatography standards, biochemical research reagents, metabolite detection standard substances, research synthesis raw materials, analytical grade reagents, etc.
Why it can be used for this purpose: α-Ketoglutarate is an endogenous metabolite and a marker molecule of the TCA cycle in the human body. Its high-purity standard is used for qualitative and quantitative analysis of keto acid content in metabolomics, biological samples and food, and is also a commonly used scientific research reagent in metabolic and biochemical research.
α-Ketoglutaric acid (2-Ketoglutaric acid, CAS 328-50-7) is a dicarboxylic acid containing an α-keto group. Its core functions include being a TCA cycle intermediate, a key component for amino acid transamination, and exhibiting α-keto acid reactivity and synergistic effects with acidity. It is used across nutrition, food, cosmetics, and scientific research: in nutrition and health foods, it is a core ingredient in sports nutrition supplements; in food, it is a flavoring and aromatic ingredient; in biotechnology and diagnostics, it is a component of cell culture media and a substrate for transaminase detection; in cosmetics, it is an anti-aging active ingredient; and in scientific research, it is a metabolomics standard. Understanding its α-keto acid structure and its pivotal role in metabolism explains why it can perform energy metabolism , synthesize amino acids, support metabolic regulation, and modulate flavor—this is precisely why it is used across nutrition, food, cosmetics, and scientific research.
