4160-80-9

Basic information

• Product Name: Glutaric anhydride
• Synonyms: 4-phenyldihydro-2H-pyran-2,6(3H)-dione;4-phenyloxane-2,6-dione;4-phenyltetrahydropyran-2,6-dione
• CAS NO: 4160-80-9
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 114.09934
• Mol File: 4160-80-9.mol
• Article Data: 28

Chemical Properties

• Melting Point: 105.6°C
• Boiling Point: 285.69°C (rough estimate)
• Flash Point: 178.6°C
• Appearance: /
• Density: 1.1752 (rough estimate)
• Vapor Pressure: 1.55E-05mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• CAS DataBase Reference: Glutaric anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: Glutaric anhydride(4160-80-9)
• EPA Substance Registry System: Glutaric anhydride(4160-80-9)

Safety Data

• Hazardous Substances Data: 4160-80-9(Hazardous Substances Data)

Usage

General Description

Glutaric anhydride is a chemical compound with the molecular formula C5H6O3. It is a cyclic anhydride of glutaric acid, which is widely used in the production of polymers, resins, and plasticizers. Glutaric anhydride is a colorless, solid substance with a pungent odor and is highly reactive, especially towards water and alcohols. It is commonly employed as a chemical intermediate in the manufacturing of various industrial products, including pharmaceuticals, dyes, and agricultural chemicals. Additionally, it is utilized in the synthesis of certain adhesives and as a curing agent for epoxy resins. However, it is important to handle glutaric anhydride with care as it can be hazardous to human health and the environment if not properly managed.

InChI:InChI=1/C11H10O3/c12-10-6-9(7-11(13)14-10)8-4-2-1-3-5-8/h1-5,9H,6-7H2

Upstream product

• 68204-17-1 3-phenylbut-2-enoyl chloride 
• 704-80-3 (E)-3-phenyl-2-butenoic acid 
• 25631-82-7 4-phenyl-2H-pyran-2,6(3H)-dione 
• 13277-74-2 diethyl 2,4?diacetyl?3?phenylpentanedioate 
• 100-52-7 benzaldehyde 
• 463-51-4 Ketene 
• 6768-26-9 2-phenyl-1,1,3,3-tetraethoxycarbonylpropane 
• 4192-77-2 ethyl cinnamate 
• 5394-85-4 2-phenyl-propane-1,1,3-tricarboxylic acid triethyl ester 
• 4161-10-8 β-Phenyl-glutarsaeure-mono-(4-brom-phenyl)-ester 
• 4165-96-2 3-phenylglutaric acid 

Downstream Products

• 101105-63-9 5-oxo-3-phenyl-5-pyrrolidino-valeric acid 
• 102076-28-8 5-oxo-3-phenyl-5-piperidino-valeric acid 
• 1221962-35-1 4-(5-iodo-2-benzimidazolyl)-3-phenylbutanoic acid monohydrochloride 
• 1221962-09-9 4-(5,6-dichloro-2-benzimidazolyl)-3-phenylbutanoic acid hydrochloride 
• 1221962-08-8 7,8-dichloro-3-phenyl-3,4-dihydropyrido[1,2-a]benzimidazol-1(2H)-one 

Relevant articles and documents

Prochiral Recognition in the Reaction of 3-Substituted Glutaric Anhydrides with Chiral Secondary Alcohols

The scope of a previously-reported process for the desymmetrization 3-substituted glutaric anhydrides has been investigated.Thus, prochiral anhydrides 5-9 react with 1-(1'-naphthyl)ethanol (2) to give glutaric acid half-esters, which are esterified by treatment with diazomethane to obtaine the corresponding diesters 16-20.The degree of prochiral recognition is inversely related to the steric bulk of the stereodifferentiating group, which the series TBDMSO, Me, Et, Ph, i-Pr, and t-Bu giving ratios of 40:1, 16:1, 14:1, 8:1, 7:1, and 1:3, respectively.The absolute sense of the prochiral recognition was established by conversion of two of the diesters, 16a and 18a, into 3-substituted valerolactones (22a, 22c) of known absolute configuration.

Novel amide derivatives of 3-phenylglutaric acid as potent soluble epoxide hydrolase inhibitors

Abstract: Soluble epoxide hydrolase (sEH) enzyme plays an important role in the metabolism of endogenous chemical mediators, epoxyeicosatrienoic acids, which are involved in the regulation of blood pressure and inflammation. According to the pharmacophoric model suggested for sEH inhibitors, some new amide-based derivatives of 3-phenylglutaric acid were designed, synthesized and biologically evaluated. Docking study illustrated that the amide group as a primary pharmacophore had a suitable distance from the three amino acids of Tyr383, Tyr466 and Asp335 for effective hydrogen binding. Most of the compounds showed moderate to high sEH inhibitory activities in in vitro test in comparison with 12-(3-Adamantan-1-yl-ureido)-dodecanoic acid, as a potent urea-based sEH inhibitor. Compound 6o with phenethyl in R position exhibited the highest activity with IC50 value of 0.5?nM. Graphic abstract: In this study, some new amide-based derivatives of 3-phenylglutaric acid were designed, synthesized and biologically evaluated. Most of the synthesized compounds provided nanomolar range inhibition against sEH enzyme. The best observed IC50 value was 0.5?nM. Incorporating a carboxylic moiety into these structures by forming carboxylate salts would increase the solubility and improving physicochemical properties.[Figure not available: see fulltext.]

Carboxylative Cyclization of 2-Butenoates with Carbon Dioxide: Access to Glutaconic Anhydrides

Cyclic anhydrides are versatile synthons and functional comonomers. Herein, we reported an organic base-promoted carboxylative cyclization of 2-butenoates with carbon dioxide to produce important glutaconic anhydrides in good yields. This metal-free react

Synthesis and biological evaluation of pentanedioic acid derivatives as farnesyltransferase inhibitors

Structure-based virtual screening of a commercial library identified pentanedioic acid derivatives (6 and 13b) as a kind of novel scaffold farnesyltransferase inhibitors (FTIs). Chemical modifications of the lead compounds, biological assays and analysis of the structure-activity relationships (SAR) were conducted to discover more potent FTIs. Some of them displayed excellent inhibition against FTase, and among them, the most active compound 13n with an IC50 value of 0.0029 μM and SAR analysis might be helpful to the discovery of more potent FTIs. This journal is