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

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

Uses

Used in Pharmaceutical Industry:
O-succinylbenzoic acid is used as a pharmaceutical intermediate for the synthesis of menaquinone, which is essential for the growth and survival of many bacterial species. It plays a crucial role in the respiratory electron transport chain of bacteria, making it a vital component in bacterial metabolism.
Used in Biochemical Research:
O-succinylbenzoic acid is used as a research tool in biochemical studies to understand the biosynthesis of menaquinone and its role in the electron transport chain of bacteria. It helps researchers investigate the mechanisms of bacterial metabolism and the importance of menaquinone in various biological processes.
Used in Microbiology:
O-succinylbenzoic acid is used in microbiology to study the growth and survival of bacterial species that rely on menaquinone for their respiratory electron transport chain. It aids in understanding the metabolic pathways and the role of menaquinone in bacterial species.
Used in Drug Development:
O-succinylbenzoic acid can be used in the development of drugs targeting bacterial species that depend on menaquinone for their growth and survival. By inhibiting the synthesis of menaquinone or disrupting its function, it may be possible to develop new antimicrobial agents to combat bacterial infections.

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

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

Downstream Products

• 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 
• 72471-59-1 C₃₂H₄₄N₇O₂₀P₃S 
• 97226-61-4 C₃₂H₄₄N₇O₂₀P₃S 
• 54103-04-7 spiro<(2-oxo-tetrahydrofuran)-5,3'-(1'-oxo-benzofuran)> 
• 77939-88-9 4-(2-carboxyphenyl)-4-hydroxybutanoic acid 
• 54103-08-1 4-(2-methoxycarbonyl-phenyl)-4-oxo-butyric acid methyl ester 

Relevant articles and documents

4-(2'-CARBOXYPHENYL)-4-OXOBUTYRATE: PREPARATIVE ISOLATION FROM ANTHRAQUINONE PRODUCING CELL SUSPENSION CULTURES OF GALIUM MOLLUGO

4-(2'-carboxyphenyl)-4-oxobutyrate(o-succinylbenzoic acid) was isolated from anthraquinone producing plant cell suspension cultures of gallium mollugo.