Basic information
- CAS
328-50-7- Standard SMILES
O=C(O)CCC(=O)C(=O)O- InChIKey
KPGXRSRHYNQIFN-UHFFFAOYSA-N- Molecular formula
- C5H6O5
- Average molar mass
- 146.1 g/mol
- Monoisotopic mass
- 146.02152329
Overview
2-oxoglutaric acid is an oxo dicarboxylic acid that consists of glutaric acid bearing an oxo substituent at position 2. It is an intermediate metabolite in Krebs cycle. It has a role as a fundamental metabolite. It is functionally related to a glutaric acid. It is a conjugate acid of a 2-oxoglutarate(1-).
Names & identifiers
- Preferred name
- 2-Oxoglutaric Acid
- IUPAC
- 2-oxopentanedioic acid
- English name
- 2-oxopentanedioic acid
- Molecular formula
- C5H6O5
- Molecular weight
- 0
Names & synonyms
2-Oxopentanedioic acid328-50-72-oxoglutaric acidalpha-ketoglutaric acid2-oxoglutarateOxoglutaric acida-ketoglutaric acid2-Oxo-1,5-pentanedioic acidPentanedioic acid, 2-oxo-Alphaketoglutaric acidoxogluric acidGlutaric acid, 2-oxo-
Show more names
Glutaric acid, alpha ketoketoglutaric acidalpha ketoglutaric acidDTXSID5033179NSC-173918ID597Z82XA-KETOGLUTARICUM ACIDUMDTXCID3013179
Database identifiers
- CAS
328-50-7、34410-46-3- PubChem CID
- 51
- DTXSID
DTXSID5033179- ChEMBL
CHEMBL1686- ChEBI
CHEBI:30915- UNII
- 8ID597Z82X
- EC Number
- 206-330-3
- Nikkaji
- J11.847H
Properties
Computed structural properties
- XLogP
- -0.9
- Topological polar surface area
- 91.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 171
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Biochemical Research
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsDeodorant
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
541.5 mg/mL
soluble in water at >1000 g/l at 20�C and petrolatum at <100 g/kg at 20�C
(in ethanol)
Boiling Point323 °C
Melting Point115.5 °C
Physical Description
Solid; [Merck Index] White to off-white solid; [Acros Organics MSDS]
Solid
white to pale yellow crystalline powder
Collision Cross Section
124.43 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
120.9 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
121.1 Ų [M-H]-
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.4% (1 of 236) of reports.
Danger
H315 (40.3%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 236 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Pentanedioic acid, 2-oxo-
Status: Active Update: 28-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/21616
2-Oxoglutaric acid: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards Summary
Causes convulsions in acute intraperitoneal studies of mice; Causes other liver changes and multiple enzyme effects in 20-week intermittent oral studies of rats; [RTECS] Safe when used as a flavoring agent in food; [JECFA] An eye irritant that may cause corneal injury; [Acros Organics MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (40.3%)
Chemistry & industry
Pharmacology
PharmacodynamicsAll of the physiological roles of alpha-ketoglutarate have not been determined. What is known is that alpha-keotglutarate is involved in the Krebs cycle, transamination reactions, and promotes muscle synthesis.
Mechanism of Action
The exact mechanisms of action for α-Ketoglutarate have not yet been elucidated. Some of α-Ketoglutarate’s actions include acting in the Krebs cycle as an intermediate, transamination reactions during the metabolism of amino acids, forming glutamic acid by combining with ammonia, and reducing nitrogen by combining with it as well. Concerning α-Ketoglutarate’s actions with ammonia, it is proposed that α-Ketoglutarate can help patients with propionic academia who have high levels of ammonia and low levels of glutamine/glutamate in their blood. Because endogenous glutamate/glutamine is produced from α-Ketoglutarate, propionic acidemia patients have impaired production of α-Ketoglutarate and supplementation of α-Ketoglutarate should improve the condition of these patients. Several other experimental studies have also shown that administration of α-Ketoglutarate in parenteral nutrition given to post-operative patients helped attenuate the decreased synthesis of muscle protein that is often seen after a surgery. This decreased muscle synthesis is speculated to be due to too low α-Ketoglutarate levels.
Tissue LocationsPlacenta
Cellular LocationsEndoplasmic reticulum
Metabolite Pathways2-aminoadipic 2-oxoadipic aciduria
Uses & manufacturing
UsesPlays an important role in amino acid metabolism (transamination); [Merck Index] Involved in the Krebs cycle of intermediary metabolism; Has been used as a nutritional supplement; [ExPub: TERIS] Used as flavoring agent or adjuvant; [FDA]
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Cosmetics -> Deodorant
General Manufacturing InformationPentanedioic acid, 2-oxo-: ACTIVE
Additional notes
DefinitionChEBI: 2-oxoglutaric acid is an oxo dicarboxylic acid that consists of glutaric acid bearing an oxo substituent at position 2. It is an intermediate metabolite in Krebs cycle. It has a role as a fundamental metabolite. It is functionally related to a glutaric acid. It is a conjugate acid of a 2-oxoglutarate(1-).
Related reactions
74 records
Compound notes
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