305-72-6

Basic information

• Product Name: Disodium 2-oxoglutarate dihydrate
• Synonyms: 2-oxo-pentanedioicacidisodiumsalt;DISODIUM 2-KETOGLUTARATE;DISODIUM 2-OXOGLUTARATE;ALPHA-KETOGLUTARIC ACID, SESQUISODIUM SALT;ALPHA-KETOGLUTARATE DISODIUM;ALPHA-KETOGLUTARIC ACID DISODIUM SALT;2-KETOGLUTARIC ACID DISODIUM SALT;2-KETOGLUTARIC ACID SODIUM SALT
• CAS NO: 305-72-6
• Molecular Formula: C₅H₄O₅*2Na
• Molecular Weight: 226.09
• EINECS: 206-167-8
• Product Categories: Building Blocks;Carbonyl Compounds;Carboxylic Acid Salts;Chemical Synthesis;Organic Building Blocks;metabolite
• Mol File: 305-72-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 345.6 °C at 760 mmHg
• Flash Point: 177 °C
• Appearance: White/Crystalline Powder or Granules
• Density: 1.499g/cm3
• Vapor Pressure: 0.02Pa at 20-50℃
• Storage Temp.: 2-8°C
• Water Solubility: soluble
• Sensitive: Hygroscopic
• BRN: 5658566
• CAS DataBase Reference: Disodium 2-oxoglutarate dihydrate(CAS DataBase Reference)
• NIST Chemistry Reference: Disodium 2-oxoglutarate dihydrate(305-72-6)
• EPA Substance Registry System: Disodium 2-oxoglutarate dihydrate(305-72-6)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 22-24/25-45-36/37/39-26
• WGK Germany: 3
• RTECS: SA0454700
• Hazardous Substances Data: 305-72-6(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 305-72-6 differently. You can refer to the following data:
1. Disodium 2-oxoglutarate dihydrate is suitable reagent used in a study to investigate the role of nitric oxide (NO) in mast cell physiology and biochemistry.
2. α-Ketoglutaric acid disodium salt dihydrate (2-Oxoglutaric acid disodium salt) may be used as starting reagent for the synthesis of deuteriated 2-oxo[3,3-2H2]glutarate disodium salt.

General Description

α-Ketoglutaric acid disodium salt dihydrate (2-Oxoglutaric acid disodium salt) is the hydrated disodium salt of 2-oxoglutaric acid.

Hazard

Moderately toxic by ingestion.

InChI:InChI=1/C5H6O5.Na/c6-3(5(9)10)1-2-4(7)8;/h1-2H2,(H,7,8)(H,9,10);

Synthetic route

2-oxoglutaric acid 1-ethyl ester (35818-60-1) → α-ketoglutaric acid disodium salt (305-72-6)

Conditions	Yield
With [D]-sodium hydroxide; water-d2 for 0.00416667h; pH=11;	>= 95 %Spectr.

α-ketoglutaric acid (328-50-7) → α-ketoglutaric acid disodium salt (305-72-6)

Conditions	Yield
With sodium hydroxide In water at 25 - 35℃; Reagent/catalyst; Large scale;

α-ketoglutaric acid disodium salt (305-72-6) → 2-oxo[3,3-2H]glutaric acid disodium salt

Conditions	Yield
With water-d2 at 80℃; for 3h; Substitution;	100%

α-ketoglutaric acid disodium salt (305-72-6) → calcium alpha-ketaglutarate (71686-01-6)

Conditions	Yield
With calcium chloride In water at 65 - 70℃; Large scale;	77%

triphenylsulfonium bromide (3353-89-7) + α-ketoglutaric acid disodium salt (305-72-6) → bis(triphenylsulfonium) 2-ketoglutaricacid

Conditions	Yield
In dichloromethane; water at 20℃;	75%
In dichloromethane; water

α-ketoglutaric acid disodium salt (305-72-6) + zinc(II) chloride (7646-85-7) → alpha-ketoglute zinc (293766-90-2)

Conditions	Yield
In water at 80 - 85℃; Large scale;	73%

1-chloro-4-nitroso-benzene (932-98-9) + α-ketoglutaric acid disodium salt (305-72-6) → 4-(4'-hydroxy-phenylamino)-4-oxo-butanoic acid (62558-67-2) + 4-amino-phenol (123-30-8) + 2-amino-5-chlorophenol (28443-50-7) + N-(4-chloro-2-hydroxyphenyl)succinamic acid (81576-13-8)

Conditions	Yield
With thiamine pyrophosphate; α-ketoglutarate dehydrogenase; magnesium chloride In water at 30℃; for 2h; 0.05M KH2PO4 buffer (pH 7.5); Further byproducts given. Yields of byproduct given;	A n/a B n/a C n/a D 2 mg

1-chloro-4-nitroso-benzene (932-98-9) + α-ketoglutaric acid disodium salt (305-72-6) → 4-(4'-hydroxy-phenylamino)-4-oxo-butanoic acid (62558-67-2) + 2-amino-5-chlorophenol (28443-50-7) + N-(4-chlorophenyl)succinohydroxamic acid (81576-12-7) + N-(4-chloro-2-hydroxyphenyl)succinamic acid (81576-13-8)

Conditions	Yield
With thiamine pyrophosphate; α-ketoglutarate dehydrogenase; magnesium chloride In water at 30℃; for 2h; 0.05M KH2PO4 buffer (pH 7.5); Further byproducts given. Yields of byproduct given;	A n/a B n/a C 1.5 mg D 2 mg

α-ketoglutaric acid disodium salt (305-72-6) → 2-hydroxyglutaric acid (2889-31-8)

Conditions	Yield
With hydrogenchloride; sodium tetrahydroborate for 0.0833333h; Reduction;

α-ketoglutaric acid disodium salt (305-72-6) → (S)-2-oxo[3-2H]glutaric acid disodium salt

Conditions	Yield
With isocitrate dehydrogenase; water-d2; NADPH at 37℃; for 2h; Substitution;

α-ketoglutaric acid disodium salt (305-72-6) → 2-oxo[3,3-3H2]glutaric acid disodium salt

Conditions	Yield
With tritium oxide Substitution; Heating;

α-ketoglutaric acid disodium salt (305-72-6) → (+/-)-diethyl 2-hydroxypentandioate (69134-53-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4; HCl / 0.08 h 2: NaHCO3 / aq. NaOH; acetonitrile / 20 °C / pH 7 - 8 View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → (3R)-2-hydroxy[3-2H]glutaric acid

Conditions	Yield
Multi-step reaction with 2 steps 1: D2O; isocitrate dehydrogenase; NADPH / 2 h / 37 °C 2: NaBH4; aq. HCl / 0.08 h View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → (3S)-2-hydroxy[3-2H]glutaric acid

Conditions	Yield
Multi-step reaction with 2 steps 1: D2O; isocitrate dehydrogenase; NADPH / 2 h / 37 °C 2: NaBH4; aq. HCl / 0.08 h View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → 2-hydroxy[3,3-2H2]glutaric acid

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / D2O / 3 h / 80 °C 2: NaBH4; HCl / 0.08 h View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → (3S)-2-methylidene[3,3-2H2]glutaric acid

Conditions	Yield
Multi-step reaction with 7 steps 1: 100 percent / D2O / 3 h / 80 °C 2: NaBH4; HCl / 0.08 h 3: 86 percent / TsOH / 48 h / Heating 4: pyridine / CH2Cl2 / 0.5 h / -5 °C 5: 2.9 mmol / CH2Cl2 / 20 °C 6: 92 percent / NaOEt / ethanol 7: 65 percent / aq. NaOH / methanol / 16 h / 20 °C View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → (R)-2-hydroxy[3-2H,3-3H]glutaric acid

Conditions	Yield
Multi-step reaction with 3 steps 1: T2O / Heating 2: D2O; isocitrate dehydrogenase 3: NaBH4; aq. HCl View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → (S)-2-hydroxy[3-2H,3-3H]glutaric acid

Conditions	Yield
Multi-step reaction with 3 steps 1: 100 percent / D2O / 3 h / 80 °C 2: T2O; isocitrate dehydrogenase 3: NaBH4; aq. HCl View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → diethyl 2-hydroxy[3,3-2H2]glutarate

Conditions	Yield
Multi-step reaction with 3 steps 1: 100 percent / D2O / 3 h / 80 °C 2: NaBH4; HCl / 0.08 h 3: 86 percent / TsOH / 48 h / Heating View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → diethyl 2-methylidene[3,3-2H2]glutarate

Conditions	Yield
Multi-step reaction with 6 steps 1: 100 percent / D2O / 3 h / 80 °C 2: NaBH4; HCl / 0.08 h 3: 86 percent / TsOH / 48 h / Heating 4: pyridine / CH2Cl2 / 0.5 h / -5 °C 5: 2.9 mmol / CH2Cl2 / 20 °C 6: 92 percent / NaOEt / ethanol View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → 2-trifluoromethanesulfonyloxy-pentanedioic acid diethyl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: NaBH4; HCl / 0.08 h 2: NaHCO3 / aq. NaOH; acetonitrile / 20 °C / pH 7 - 8 3: pyridine / CH2Cl2 / -5 °C View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → C10H13(2)H2F3O7S

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / D2O / 3 h / 80 °C 2: NaBH4; HCl / 0.08 h 3: 86 percent / TsOH / 48 h / Heating 4: pyridine / CH2Cl2 / 0.5 h / -5 °C View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → (R)-2-oxo[3-2H]glutaric acid disodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / D2O / 3 h / 80 °C 2: D2O; isocitrate dehydrogenase; NADPH / 2 h / 37 °C View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → (R)-2-oxo[3-2H,3-3H]glutaric acid disodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: T2O / Heating 2: D2O; isocitrate dehydrogenase View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → (3S)-2-oxo[3-2H,3-3H]glutaric acid disodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / D2O / 3 h / 80 °C 2: T2O; isocitrate dehydrogenase View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → [1,3-bis(ethoxycarbonyl)propyl]triphenylphosphonium triflate

Conditions	Yield
Multi-step reaction with 4 steps 1: NaBH4; HCl / 0.08 h 2: NaHCO3 / aq. NaOH; acetonitrile / 20 °C / pH 7 - 8 3: pyridine / CH2Cl2 / -5 °C 4: CH2Cl2 / 20 °C View Scheme

α-ketoglutaric acid disodium salt (305-72-6) → [1,3-bis(ethoxycarbonyl)[2,2-2H2]propyl]triphenylphosphonium triflate

Conditions	Yield
Multi-step reaction with 5 steps 1: 100 percent / D2O / 3 h / 80 °C 2: NaBH4; HCl / 0.08 h 3: 86 percent / TsOH / 48 h / Heating 4: pyridine / CH2Cl2 / 0.5 h / -5 °C 5: 2.9 mmol / CH2Cl2 / 20 °C View Scheme

α-ketoglutaric acid disodium salt (305-72-6) + 1-bromomethyl-4-nitro-benzene (100-11-8) → 2-oxo-glutaric acid 1-p-nitrobenzyl ester (108049-92-9)

Conditions	Yield
In N-methyl-acetamide

α-ketoglutaric acid disodium salt (305-72-6) → sodium succinate (150-90-3)

Conditions	Yield
With hydrogenchloride; iron(II) ammonium sulfate; pseudomonas sp.AK1 γ-butyrobetaine hydroxylase; potassium chloride; γ-butyrobetaine hydrochloride In water-d2 pH=7.5; Kinetics; Reagent/catalyst; Enzymatic reaction;

α-ketoglutaric acid disodium salt (305-72-6) → glutamic acid sodium salt (142-47-2, 149-65-5, 15383-53-6, 16079-50-8, 16177-21-2, 16690-92-9, 21932-17-2, 26247-79-0, 28223-73-6, 30617-64-2, 30811-79-1, 32221-81-1, 32342-59-9, 56-86-0)

Conditions	Yield
With ammonium sulfate; [(pentamethylcyclopentadienyl)Rh(2,2’-bipyridyl)H2O]2+; L-glutamic dehydrogenase from bovine liver; β-nicotinamide adenine dinucleotide In aq. phosphate buffer pH=7.5; Catalytic behavior; Reagent/catalyst; Irradiation; Enzymatic reaction;

Upstream product

• 35818-60-1 2-oxoglutaric acid 1-ethyl ester 
• 328-50-7 α-ketoglutaric acid 

Downstream Products

• 62558-67-2 4-(4'-hydroxy-phenylamino)-4-oxo-butanoic acid 
• 123-30-8 4-amino-phenol 
• 28443-50-7 2-amino-5-chlorophenol 
• 81576-13-8 N-(4-chloro-2-hydroxyphenyl)succinamic acid 
• 81576-12-7 N-(4-chlorophenyl)succinohydroxamic acid 
• 108049-92-9 2-oxo-glutaric acid 1-p-nitrobenzyl ester 
• 142-47-2 glutamic acid sodium salt 
• 71686-01-6 calcium alpha-ketaglutarate 
• 150-90-3 sodium succinate 
• 2889-31-8 2-hydroxyglutaric acid 
• 69134-53-8 (+/-)-diethyl 2-hydroxypentandioate 

Relevant articles and documents

PROCESS OF MAKING CALCIUM ALPHA-KETOGLUTARATE

Methods and processes for preparing calcium salts of alpha-ketoglutarate are described herein.