27415-09-4

Basic information

• Product Name: o-succinylbenzoic acid
• Synonyms: o-succinylbenzoic acid;2-(3-carboxypropanoyl)benzoic acid;O-succinylbenzoate
• CAS NO: 27415-09-4
• Molecular Formula: C₁₁H₁₀O₅
• Molecular Weight: 222.1941
• Mol File: 27415-09-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 486.5°Cat760mmHg
• Flash Point: 262.1°C
• Appearance: /
• Density: 1.378g/cm³
• Vapor Pressure: 2.82E-10mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: o-succinylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: o-succinylbenzoic acid(27415-09-4)
• EPA Substance Registry System: o-succinylbenzoic acid(27415-09-4)

Safety Data

• Hazardous Substances Data: 27415-09-4(Hazardous Substances Data)

Usage

General Description

O-succinylbenzoic acid is a chemical compound that belongs to the class of benzoic acids and derivatives. It is an intermediate in the biosynthesis of menaquinone, which is an essential component of the electron transport chain in bacteria. O-succinylbenzoic acid is produced through the condensation of o-succinylbenzoyl-CoA with malonyl-CoA, in a reaction catalyzed by o-succinylbenzoyl-CoA synthetase. o-succinylbenzoic acid is an important precursor for the synthesis of menaquinone, which plays a crucial role in the respiratory electron transport chain of bacteria. Menaquinone is essential for the growth and survival of many bacterial species, making o-succinylbenzoic acid an important intermediate in bacterial metabolism.

InChI:InChI=1/C11H10O5/c12-9(5-6-10(13)14)7-3-1-2-4-8(7)11(15)16/h1-4H,5-6H2,(H,13,14)(H,15,16)

Synthetic route

spiro<(2-oxo-tetrahydrofuran)-5,3'-(1'-oxo-benzofuran)> (54103-04-7) → 4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4)

Conditions	Yield
With water
With alkali

6,7-dihydro-5H-benzocyclohepten-5-one (52092-30-5) → 4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4)

Conditions	Yield
With dichloromethane Ozonolyse;

C32H44N7O20P3S (97226-61-4) → 4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4)

Conditions	Yield
With alkali

spiro<(2-oxo-tetrahydrofuran)-5,3'-(1'-oxo-benzofuran)> (54103-04-7) + water (7732-18-5) → 4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4)

spiro<(2-oxo-tetrahydrofuran)-5,3'-(1'-oxo-benzofuran)> (54103-04-7) + alkali → 4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4)

6-hydroxy-2-succinyl-2,4-cyclohexadiene-1-carboxylic acid → 4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4) + succinylbenzene (2051-95-8)

Conditions	Yield
With phosphate buffer; o-succinylbenzoate synthase at 25℃; pH=8.0; Kinetics; Enzyme kinetics;

C11H11(2)HO6 → 4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4) + succinylbenzene (2051-95-8)

Conditions	Yield
With phosphate buffer; o-succinylbenzoate synthase at 25℃; pH=8.0; Kinetics; Enzyme kinetics;

phthalic anhydride (85-44-9) + activated aluminium → 4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate / 240 - 250 °C / man kocht das Reaktionsprodukt mit Wasser aus 2: alkali View Scheme

diazomethane (186581-53-3, 908094-01-9) + 4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4) → 4-(2-methoxycarbonyl-phenyl)-4-oxo-butyric acid methyl ester (54103-08-1)

4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4) → 4-(2-carboxyphenyl)-4-hydroxybutanoic acid (77939-88-9)

Conditions	Yield
With sodium tetrahydroborate In ethanol; water for 0.25h; Ambient temperature;	47 mg

4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4) + coenzyme A (900498-43-3) → spiro<(2-oxo-tetrahydrofuran)-5,3'-(1'-oxo-benzofuran)> (54103-04-7) + C32H44N7O20P3S (97226-61-4)

Conditions	Yield
With extract from mycobacterium phlei; ATP; magnesium chloride at 30℃; for 0.5h;
With extract from galium molluga; ATP; magnesium chloride at 30℃; for 0.5h;
With extract from mycobacterium phlei; ATP; magnesium chloride at 30℃; for 0.5h;

4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4) + coenzyme A (900498-43-3) → C32H44N7O20P3S (97226-61-4) + C32H44N7O20P3S (72471-59-1)

Conditions	Yield
With 1,1'-carbonyldiimidazole Multistep reaction;

4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4) + 1,1'-carbonyldiimidazole (530-62-1) → 4-[2-(Imidazole-1-carbonyl)-phenyl]-4-oxo-butyric acid (97204-49-4) + 2-(4-Imidazol-1-yl-4-oxo-butyryl)-benzoic acid (97204-50-7)

4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4) + 1,1'-carbonyldiimidazole (530-62-1) → 1-[2-(Imidazole-1-carbonyl)-phenyl]-4-imidazol-1-yl-butane-1,4-dione (97204-51-8)

4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4) → 4-(2'-[methoxycarbonyl]phenyl)-4-oxobutanoic acid (113432-82-9)

4-(2'-carboxyphenyl)-4-oxobutanoic acid (27415-09-4) → C32H44N7O20P3S (72471-59-1)

Conditions	Yield
Multi-step reaction with 2 steps 2: 1,1'-carbonyldiimidazole View Scheme

Upstream product

• 85-44-9 phthalic anhydride 
• 54103-04-7 spiro<(2-oxo-tetrahydrofuran)-5,3'-(1'-oxo-benzofuran)> 
• 7732-18-5 water 
• 97226-61-4 C₃₂H₄₄N₇O₂₀P₃S 
• 52092-30-5 6,7-dihydro-5H-benzocyclohepten-5-one 

Downstream Products

• 54103-08-1 4-(2-methoxycarbonyl-phenyl)-4-oxo-butyric acid methyl ester 
• 77939-88-9 4-(2-carboxyphenyl)-4-hydroxybutanoic acid 
• 54103-04-7 spiro<(2-oxo-tetrahydrofuran)-5,3'-(1'-oxo-benzofuran)> 
• 97226-61-4 C₃₂H₄₄N₇O₂₀P₃S 
• 72471-59-1 C₃₂H₄₄N₇O₂₀P₃S 
• 97204-49-4 4-[2-(Imidazole-1-carbonyl)-phenyl]-4-oxo-butyric acid 
• 97204-50-7 2-(4-Imidazol-1-yl-4-oxo-butyryl)-benzoic acid 
• 97204-51-8 1-[2-(Imidazole-1-carbonyl)-phenyl]-4-imidazol-1-yl-butane-1,4-dione 
• 113432-82-9 4-(2'-[methoxycarbonyl]phenyl)-4-oxobutanoic acid 

Relevant articles and documents

The lesser burden borne by o-succinylbenzoate synthase: An easy reaction involving a carboxylate carbon acid [1]

-