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2-Oxoglutaric acid

2-Oxoglutaric acid structure

CAS No:
328-50-7
Formula:
C5H6O5
Chemical Name:
2-Oxoglutaric acid
Synonyms:
Pentanedioic acid,2-oxo-;Glutaric acid,2-oxo-;2-Oxopentanedioic acid;α-keto-Glutaric acid;α-Oxoglutaric acid;2-Oxoglutaric acid;2-Oxo-1,5-pentanedioic acid;2-Ketoglutaric acid;α-Ketoglutaric acid;α-Oxopentanedioic acid;NSC 17391;27175-99-1
Categories:
Cosmetic Ingredient > Deodorant

Description

2-Ketoglutaric acid is an intermediate compound of the Krebs cycle and is also connected to glutamic acid and glutamine metabolisms through the transamination reactions.

Solid|white to pale yellow crystalline powder

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 derives from a glutaric acid. It is a conjugate acid of a 2-oxoglutarate(1-).|Oxogluric acid (α-Ketoglutarate) is not approved for any indication in the world but is an investigational drug in the United States. In the United States a phase I clinical trial is investigating whether oxogluric acid precursors found in nutritional supplements can benefit patients with the metabolic disorder propionic acidemia. Oxogluric acid is sold as a dietary supplement to athletes to improve their performance by helping to remove excess ammonia, but it is not officially approved for this indication and only experimental studies have shown a reduction in ammonia by oxogluric acid in hemodialysis patients. Physiologically, oxogluric acid acts in the Krebs cycle as an intermediate, is involved in transamination reactions during the metabolism of amino acids, forms glutamic acid by combining with ammonia, and reduces nitrogen by combining with it as well. Several experimental studies have also shown that administration of oxogluric acid helped attenuate the decreased synthesis of muscle protein that is often seen post-surgery.|A family of compounds containing an oxo group with the general structure of 1,5-pentanedioic acid. (From Lehninger, Principles of Biochemistry, 1982, p442)

2-Oxoglutaric acid Basic Attributes

Molecular Weight：

146.1

Exact Mass：

146.10

BRN：

1705689

EC Number：

206-330-3

UNII：

8ID597Z82X

NSC Number：

17391

DSSTox ID：

DTXSID5033179

HScode：

29183000

Characteristics

PSA：

91.7

XLogP3：

-0.9

Appearance：

White to slightly yellow Crystalline Powder

Density：

1.64 g/cm³

Melting Point：

115.5 °C

Boiling Point：

345.6°C at 760 mmHg

Flash Point：

177.0±19.7 °C

Refractive Index：

1.494

Water Solubility：

soluble in water, methanol and dimethyl sulfoxide.H2O: soluble 0.1g/mL, clear, colorless

Storage Conditions：

2-8°C

Collision Cross Section：

124.43 Å² [M-H]- [CCS Type: DT, Method: stepped-field]|120.9 Å² [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|125.2 Å² [M-H]-

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

37/38-41-36/37/38-23/24/25

safety instructions：

26-39-45-36/37/39

Marks：

Xi,T

Precautionary statement(s)：

P280-P305 + P351 + P338 + P310

Hazard Statements：

H318

GHS Classification：

|Danger|H315 (53.71%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 176 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

α-α-Ketoglutarate is not approved for any indication in the world but is an investigational drug in the United States. The potential indications for α-Ketoglutarate are in patients with the metabolic disorder propionic acidemia and in trauma patients with muscle loss.

Pharmacology：

All 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.

MeSH Entry Terms：

2 Ketoglutarate

2-Oxoglutaric acid Use and Manufacturing

Methods of Manufacturing

225 g of triethyl oxalosuccinate was mixed with 600 ml of concentrated hydrochloric acid, and the solution was left. Distilled and concentrated to 140 ℃, the residue was cooled and crystallized to obtain 110-112g of α-ketoglutaric acid, the yield was 92-93%.

Uses

A derivative of glutaric acid.

Manufacturing Info：

Pentanedioic acid, 2-oxo-, sodium salt (1:?): INACTIVE|Pentanedioic acid, 2-oxo-: ACTIVE

Use Classification：

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Deodorant

Food Additive Classes：

Flavoring Agents

Computed Properties

Molecular Weight:146.10
XLogP3:-0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:146.02152329
Monoisotopic Mass:146.02152329
Topological Polar Surface Area:91.7
Heavy Atom Count:10
Complexity:171
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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