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> Chemicals & Drugs > Organic Chemical > Benzoic Acid

Benzoic Acid

Benzoic acid is a widely used chemical compound with diverse applications in various industries.
It is a colorless, crystalline solid with the molecular formula C6H5COOH.
Benzoic acid is commonly used as a preservative in food, cosmetics, and pharmaceuticals due to its antimicrobial properties.
It is also an important intermediate in the production of other chemicals, such as dyes, plastics, and pharmaceuticals.
Benzoic acid has been studied extensively for its biological and medicinal properties, including its potential use as an analgesic, anti-inflammatory, and antifungal agent.
Researchers continue to explore new applications and optimize protocols for working with benzoic acid to enhance reproducibility and accuracy in their studies.

Most cited protocols related to «Benzoic Acid»

1
Solid Phase Extraction of Oxylipins
Cited 13 times
SPMs were extracted from plasma or serum samples and effluents from peritoneal dialysis (PD) using solid phase extraction (SPE) (Rund et al., 2017 (link)). In the first step a mixture of 20 deuterated IS (20 nM each, including 2H5-RvD1, 2H5-RvD2, 2H5-LXA4, 2H4-LTB4, and 2H4-9,10-DiHOME), antioxidant mixture (0.2 mg/mL BHT, 100 μM indomethacin, 100 μM soluble epoxide hydrolase inhibitor trans-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid (t-AUCB) in MeOH) were added to 500 μL of plasma/serum or 1,200 μL of PD exudates. Then 1,400 μL ice-cold MeOH (3,360 μL for PD exudates) were added for protein precipitation (at least 30 min at −80°C). Following centrifugation, the supernatant was evaporated under a gentle nitrogen stream to <50% MeOH, diluted with 0.1 M disodium hydrogen phosphate buffer (pH 5.5) and loaded onto the preconditioned SPE column (Bond Elut Certify II, 200 mg, 3 mL; Agilent, Waldbronn, Germany). Oxylipins were eluted with ethyl acetate/n-hexane (75/25, v/v) containing 1% acetic acid. After evaporation to dryness in a vacuum concentrator (30°C, 1 mbar, ca. 60 min; Christ, Osterode, Germany) sample extracts were reconstituted in 50 μL MeOH containing 40 nM 1-(1-(ethylsulfonyl)piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea as IS 2. Injection volume was 5 μL; for samples with low SPM content a second (10 μL) injection was used for SPM quantification.
Kutzner L., Rund K.M., Ostermann A.I., Hartung N.M., Galano J.M., Balas L., Durand T., Balzer M.S., David S, & Schebb N.H. (2019). Development of an Optimized LC-MS Method for the Detection of Specialized Pro-Resolving Mediators in Biological Samples. Frontiers in Pharmacology, 10, 169.
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Publication 2019
4-(4-(3-adamantan-1-ylureido)cyclohexyloxy)benzoic acid Acetic Acid Antioxidants Benzoic Acid Buffers Centrifugation Cold Temperature Epoxide hydrolase ethyl acetate Exudate Indomethacin Leukotriene B4 lipoxin A4 n-hexane Nitrogen Oxylipins Peritoneal Dialysis Plasma Proteins Serum sodium phosphate, dibasic Solid Phase Extraction Urea Vacuum
2
Quantifying Short-Chain Fatty Acids in Fecal Samples
Cited 12 times
Fecal SCFA content was determined by gas chromatography. Chromatographic
analysis was carried out using a Shimadzu GC14-A system with a flame ionization
detector (FID) (Shimadzu Corp, Kyoto, Japan). Fused silica capillary columns 30m
× 0.25 mm coated with 0.25um film thickness were used (Nukol™
for the volatile acids and SPB™-1000 for the nonvolatile acids (Supelco
Analytical, Bellefonte, PA). Nitrogen was used as the carrier gas. The oven
temperature was 170°C and the FID and injection port was set to
225°C. The injected sample volume was 2 µL and the run time for
each analysis was 10 minutes. The chromatograms and data integration was carried
out using a Shimadzu C-R5A Chromatopac. A volatile acid mix containing 10 mM of
acetic, propionic, isobutyric, butyric, isovaleric, valeric, isocaproic,
caproic, and heptanoic acids was used (Matreya, Pleasant Gap, PA). A
non-volatile acid mix containing 10 mM of pyruvic and lactic and 5 mM of
oxalacetic, oxalic, methy malonic, malonic, fumaric, and succinic was used
(Matreya, Pleasant Gap, PA). A standard stock solution containing 1%
2-methyl pentanoic acid (Sigma-Aldrich, St. Louis, MO) was prepared as an
internal standard control for the volatile acid extractions. A standard stock
solution containing 50 mM benzoic acid (Sigma-Aldrich, St. Louis, MO) was
prepared as an internal standard control for the non-volatile acid
extractions.
Samples were kept frozen at −80°C until analysis. The
samples were removed from the freezer and 1,200µL of water was added to
each thawed sample. The samples were vortexed for 1 minute until the material
was homogenized. The pH of the suspension was adjusted to 2–3 by adding
50 µL of 50% sulfuric acid. The acidified samples were kept at
room temperature for 5 minutes and vortexed briefly every minute. The samples
were centrifuged for 10 minutes at 5,000g. 500 µL of the clear
supernatant was transferred into two tubes for further processing. For the
volatile extraction 50 µL of the internal standard (1% 2-methyl
pentanoic acid solution) and 500 µL of ethyl ether anhydrous were added.
The tubes were vortexed for 30 seconds and then centrifuged at 5,000g for 10
minutes. 1 µL of the upper ether layer was injected into the
chromatogram for analysis. For the nonvolatile extraction 50 µL of the
internal standard (50 mM benzoic acid solution) and 500 µL of boron
trifluoride-methanol solution (Sigma-Aldrich St. Louis, MO) were added to each
tube. These tubes were incubated overnight at room temperature. 1 mL of water
and 500 µL of chloroform were added to each tube. The tubes were
vortexed for 30 seconds and then centrifuged at 5,000g for 10 minutes. 1
µL of the lower chloroform layer was injected into the chromatogram for
analysis. 500 µL of each standard mix was used and the extracts prepared
as described for the samples. The retention times and peak heights of the acids
in the standard mix were used as references for the sample unknowns. These acids
were identified by their specific retention times and the concentrations
determined and expressed as mM concentrations per gram of sample.
David L.A., Maurice C.F., Carmody R.N., Gootenberg D.B., Button J.E., Wolfe B.E., Ling A.V., Devlin A.S., Varma Y., Fischbach M.A., Biddinger S.B., Dutton R.J, & Turnbaugh P.J. (2013). Diet rapidly and reproducibly alters the human gut microbiome. Nature, 505(7484), 559-563.
Publication 2013
Acids Benzoic Acid Capillaries Chloroform Ethers Feces ferrous fumarate Freezing Gas Chromatography Heptanoic Acids Methanol Neoplasm Metastasis Nitrogen Retention (Psychology) Silicon Dioxide Sulfuric Acids valeric acid
3
Enzyme Kinetic Assay for Cocaine Hydrolysis
Cited 10 times
Initial in vitro screening of the enzyme activity against (−)-cocaine was carried out by using a single concentration (1 mM) of (−)-cocaine, assuming that KM << 1 mM such that the enzyme was always saturated by 1 mM (−)-cocaine and the maximum reaction velocity (Vmax) was reached for a given concentration [E] of the enzyme. Vmax = kcat[E]. The relative concentrations of the enzymes were determined by using an enzyme-linked immunosorbent assay (ELISA)26 (link),52 (link) described below. The ELISA buffers used in the present study are the same as those described in literature.26 (link),52 (link) Specifically, the coating buffer was 0.1 M sodium carbonate/bicarbonate buffer (pH 9.5). The washing buffer (PBS-T) was 0.01 M potassium phosphate monobasic/potassium phosphate monohydrate buffer (pH 7.5) containing 0.05% (vol/vol) Tween 20. The diluent buffer (EIA buffer) was potassium phosphate monobasic/potassium phosphate monohydrate buffer (pH 7.5) containing 0.9% sodium chloride and 0.1% bovine serum albumin (BSA).
To measure (−)-cocaine and benzoic acid, the product of the enzymatic (−)-cocaine hydrolysis, we used sensitive radiometric assays based on toluene extraction of [3H](−)-cocaine labeled on its benzene ring.24 (link) In brief, to initiate the enzymatic reaction, 100 nCi of [3H](−)-cocaine was mixed with 100 µl of enzyme solution. For Michaelis-Menten kinetic analysis, the enzymatic reactions proceeded at 37°C and pH 8 with varying concentrations of (−)-cocaine. The reactions were stopped by adding 200 µl of 0.05 M HCl, which neutralized the liberated benzoic acid while ensuring a positive charge on the residual (−)-cocaine. [3H]benzoic acid was extracted by 1 ml of toluene and measured by scintillation counting. Finally, the measured (−)-cocaine concentration-dependent radiometric data were analyzed in terms of the standard Michaelis-Menten kinetics so that the catalytic parameters were determined. The enzyme activity assays with [3H]ACh were similar to the assays with [3H](−)-cocaine. The primary difference was that the enzymatic reaction was stopped by addition of 200 µl of 0.2 M HCl containing 2 M NaCl and that the product was [3H]acetic acid for the ACh hydrolysis.
Zheng F., Xue L., Hou S., Liu J., Zhan M., Yang W, & Zhan C.G. (2014). A highly efficient cocaine detoxifying enzyme obtained by computational design. Nature communications, 5, 3457.
Publication 2014
Acetic Acid Benzene Benzoic Acid Bicarbonate, Sodium Bicarbonates Biological Assay Buffers Carbonates Catalysis Cocaine Enzyme-Linked Immunosorbent Assay enzyme activity Enzyme Assays Enzymes Hydrolysis Kinetics M-200 potassium phosphate potassium phosphate, monobasic Radiometry Serum Albumin, Bovine sodium carbonate Sodium Chloride Toluene Tween 20
4
NF54 P. falciparum Culture and Gametocyte Isolation
Cited 10 times

P. falciparum isolate NF54 [32] (link),[33] (link) was cultured using the automated tipper-table system of Ponnudurai et al [34] (link) as implemented in the CEPIA mosquito infection facility of Institut Pasteur. Briefly, a subculture of thawed NF54 stabilate was grown in 10 ml RPMI 1640 medium supplemented with 25 mM HEPES and L-glutamine, 10% heat-inactivated human serum, and sodium bicarbonate at 0.2% final concentration under a constant gas regime (5% CO2, 1% O2, 94% N2). Fresh anonymous erythrocytes obtained from blood banks were added to 7% final concentration. Fourteen days after initiating the subculture, gametocyte maturity was tested by exflagellation of microgametes, and parasitemia and numbers of mature male and female gametocytes were counted on Giemsa stained slides.
Ten ml of culture was centrifuged at 2000 rpm, and the cell pellet was resuspended in an equal volume of normal type AB human serum. The infected erythrocytes were added to fresh erythrocytes in AB human serum and were transferred to a membrane feeder warmed to 37°C. Mosquitoes were allowed to feed for 15 minutes, and only fully engorged females were used for further analysis. Bloodfed mosquitoes were maintained on 10% sucrose solution supplemented with 0.05% para-amino benzoic acid.
Mitri C., Jacques J.C., Thiery I., Riehle M.M., Xu J., Bischoff E., Morlais I., Nsango S.E., Vernick K.D, & Bourgouin C. (2009). Fine Pathogen Discrimination within the APL1 Gene Family Protects Anopheles gambiae against Human and Rodent Malaria Species. PLoS Pathogens, 5(9), e1000576.
Full text: Click here
Publication 2009
Amino Acids Benzoic Acid Bicarbonate, Sodium Cells Culicidae Erythrocytes Females Glutamine HEPES Homo sapiens Infection Males Parasitemia Serum Sucrose Tissue, Membrane
5
Enzyme Kinetic Assay for Cocaine Hydrolysis
Cited 9 times
Initial in vitro screening of the enzyme activity against (−)-cocaine was carried out by using a single concentration (1 mM) of (−)-cocaine, assuming that KM << 1 mM such that the enzyme was always saturated by 1 mM (−)-cocaine and the maximum reaction velocity (Vmax) was reached for a given concentration [E] of the enzyme. Vmax = kcat[E]. The relative concentrations of the enzymes were determined by using an enzyme-linked immunosorbent assay (ELISA)26 (link),52 (link) described below. The ELISA buffers used in the present study are the same as those described in literature.26 (link),52 (link) Specifically, the coating buffer was 0.1 M sodium carbonate/bicarbonate buffer (pH 9.5). The washing buffer (PBS-T) was 0.01 M potassium phosphate monobasic/potassium phosphate monohydrate buffer (pH 7.5) containing 0.05% (vol/vol) Tween 20. The diluent buffer (EIA buffer) was potassium phosphate monobasic/potassium phosphate monohydrate buffer (pH 7.5) containing 0.9% sodium chloride and 0.1% bovine serum albumin (BSA).
To measure (−)-cocaine and benzoic acid, the product of the enzymatic (−)-cocaine hydrolysis, we used sensitive radiometric assays based on toluene extraction of [3H](−)-cocaine labeled on its benzene ring.24 (link) In brief, to initiate the enzymatic reaction, 100 nCi of [3H](−)-cocaine was mixed with 100 µl of enzyme solution. For Michaelis-Menten kinetic analysis, the enzymatic reactions proceeded at 37°C and pH 8 with varying concentrations of (−)-cocaine. The reactions were stopped by adding 200 µl of 0.05 M HCl, which neutralized the liberated benzoic acid while ensuring a positive charge on the residual (−)-cocaine. [3H]benzoic acid was extracted by 1 ml of toluene and measured by scintillation counting. Finally, the measured (−)-cocaine concentration-dependent radiometric data were analyzed in terms of the standard Michaelis-Menten kinetics so that the catalytic parameters were determined. The enzyme activity assays with [3H]ACh were similar to the assays with [3H](−)-cocaine. The primary difference was that the enzymatic reaction was stopped by addition of 200 µl of 0.2 M HCl containing 2 M NaCl and that the product was [3H]acetic acid for the ACh hydrolysis.
Zheng F., Xue L., Hou S., Liu J., Zhan M., Yang W, & Zhan C.G. (2014). A highly efficient cocaine detoxifying enzyme obtained by computational design. Nature communications, 5, 3457.
Publication 2014
Acetic Acid Benzene Benzoic Acid Bicarbonate, Sodium Bicarbonates Biological Assay Buffers Carbonates Catalysis Cocaine Enzyme-Linked Immunosorbent Assay enzyme activity Enzyme Assays Enzymes Hydrolysis Kinetics M-200 potassium phosphate potassium phosphate, monobasic Radiometry Serum Albumin, Bovine sodium carbonate Sodium Chloride Toluene Tween 20

Most recents protocols related to «Benzoic Acid»

1
Optimizing FAAH Inhibitor Potency
Not available on PMC !

Example 37

To improve inhibition potency relative to FAAH, various portions of the t-TUCB molecule were modified to identify potential FAAH pharmacophores. The 4-trifluoromethoxy group on t-TUCB was modified to the unsubstituted ring (A-3), 4-fluorophenyl (A-2) or 4-chlorophenyl (A-26). Potency on both sEH and FAAH increased as the size and hydrophobicity of the para position substituent increased, with 4-trifluoromethoxy being the most potent on both enzymes. Substituting the aromatic ring for a cyclohexane (A-3) or adamantane (A-4) resulted in a complete loss in activity against FAAH. Results are summarized in Table 1 below.

TABLE 1
Modification of the 4-trifluoromethoxy group of t-TUCB
[Figure (not displayed)]
Stereo-IC50 (nM)
R2—N(R3)—L1—chemistryhsEHhFAAH
t-TUCB[Figure (not displayed)]
[Figure (not displayed)]
trans0.8140
A1-[Figure (not displayed)]
[Figure (not displayed)]
trans309,200
A-2[Figure (not displayed)]
[Figure (not displayed)]
trans184,600
A-26[Figure (not displayed)]
[Figure (not displayed)]
trans7380
A-3[Figure (not displayed)]
[Figure (not displayed)]
trans6>1,000
A-4[Figure (not displayed)]
[Figure (not displayed)]
trans3>10,000
A-10[Figure (not displayed)]
[Figure (not displayed)]
81,800

Next, the center portion of the molecule was modified to further investigate the specificity of t-TUCB on FAAH. Switching the cyclohexane linker to a cis conformation (A-5) resulted in a 20-fold loss of potency while removing the ring and replacing it with a butane chain (A-6) resulted in a completely inactive compound. While this suggests the compound must fit a relatively specific conformation in the active site to be active, we found the aromatic linker had essentially the same potency on FAAH (A-7). Although many potent urea-based FAAH inhibitors have a piperidine as the carbamoylating nitrogen, the modification to piperidine here reduced potency 13-fold. Results are summarized in Table 2 below.

TABLE 2
Modification of the central portion of t-TUCB
[Figure (not displayed)]
Stereo-IC50 (nM)
R2—N(R3)—L1—chemistryhsEHhFAAH
t-TUCB[Figure (not displayed)]
[Figure (not displayed)]
trans0.8140
A-5[Figure (not displayed)]
[Figure (not displayed)]
cis22,800
A-6[Figure (not displayed)]
[Figure (not displayed)]
15>10,000
A-7[Figure (not displayed)]
[Figure (not displayed)]
7170

Since none of the modifications at this point improved potency towards FAAH, we focused on the benzoic acid portion of the molecule as shown in Table 3. To determine the importance of the terminal acid, the corresponding aldehyde (A-20) and alcohol (A-24) in addition to the amide (A-19) and nitrile (A-11) were tested. While the amide had slightly improved potency, the more reduced forms of the acid (A-20 and A-24) and amide (A-11) had substantially less activity on FAAH. Converting the benzoic acid to a phenol (A-21) increased potency while the anisole (A-22) was completely inactive. Since the amide and acid appeared to be active, the amide bioisostere oxadiazole (A-25) was tested and had 38-fold less potency than the initial compound.

TABLE 3
Modification of the benzoic acid portion of t-TUCB
[Figure (not displayed)]
IC50 (nM)
R1hsEHhFAAH
t-TUCB[Figure (not displayed)]
0.8140
A-11[Figure (not displayed)]
5>10,000
A-19[Figure (not displayed)]
270
A-20[Figure (not displayed)]
41,100
A-24[Figure (not displayed)]
35,800
A-21[Figure (not displayed)]
2120
A-22[Figure (not displayed)]
3>10,000
A-25[Figure (not displayed)]
45,300

Since the substrates for FAAH tend to be relatively hydrophobic lipids, we speculated that conversion of the acid and primary amide to the corresponding esters or substituted amides would result in improved potency. The methyl ester (A-12) had 4-fold improved potency relative to the acid. Improving the bulk of the ester with an isopropyl group (A-13) results in a 11-fold loss in potency relative to the methyl ester. However, the similar potency of the benzyl ester (A-14) to the methyl ester demonstrates the bulk but not the size affects potency. Reversing the orientation of the ester (A-23) reduces the potency 3.4-fold. Relative to the primary amide, the methyl (A-18), ethanol (A-15) and glycyl (A-16) amides were all slightly less potent; however, the benzyl amide (A-27) was substantially less potent (16-fold). Generating the methyl ester of the glycyl amide (A-17) increased the potency 4-fold compared to the corresponding acid.

TABLE 4
Potency of ester and amide conjugates of t-TUCB
[Figure (not displayed)]
IC50 (nM)
R1hsEHhFAAH
t-TUCB[Figure (not displayed)]
0.8140
A-12[Figure (not displayed)]
735
A-13[Figure (not displayed)]
5400
A-14[Figure (not displayed)]
324
A-23[Figure (not displayed)]
4120
A-18[Figure (not displayed)]
2170
A-15[Figure (not displayed)]
2100
A-16[Figure (not displayed)]
2130
A-17[Figure (not displayed)]
330
A-27[Figure (not displayed)]
51,100

US11873288B2. Inhibitors for soluble epoxide hydrolase (sEH) and fatty acid amide hydrolase (FAAH) (2024-01-16). The Regents of the University of California [US]. Inventors: Bruce Hammock [US], Sean Kodani [US].
Full text: Click here
Patent 2024
Acids Adamantane Aldehydes Amides anisole Benzoic Acid Butanes Cyclohexane Dietary Fiber Enzymes Esters Ethanol inhibitors Lipids Nitriles Nitrogen Oxadiazoles Phenol piperidine Psychological Inhibition SOCS2 protein, human Urea
2
NMR and HPLC-MS Characterization of Organic Compound
Not available on PMC !

Example 26

1H-NMR (400 MHz, DMSO-d6): δ=12.88 (s, 1H), 9.02 (t, 1H), 8.92 (d, 1H), 8.38 (d, 2H), 8.25 (s, 1H), 8.10 (d, 1H), 7.98 (d, 1H), 7.92 (d, 2H), 7.83 (d, 2H), 7.71 (t, 1H), 7.38 (d, 2H), 7.27 (m, 2H), 7.15 (m, 2H), 7.04 (d, 1H), 4.54 (d, 2H).

HPLC-MS: Rt 2.15 m/z 519.2 (MH+)

US11872226B2. N-benzyl-2-phenoxybenzamide derivatives as prostaglandin E2 (PGE2) receptors modulators (2024-01-16). MEDIBIOFARMA, S.L. [ES]. Inventors: Julio Castro Palomino Laria [ES], Juan Camacho Gómez [ES], Rodolfo Rodríguez Iglesias [ES], Irene Velilla Martínez [ES].
Full text: Click here
Patent 2024
Benzoic Acid diphenyl High-Performance Liquid Chromatographies Sulfoxide, Dimethyl
3
Synthesis of 3-(7-Bromo-4-(1H-imidazol-1-yl)-8-methoxyquinolin-2-yl)benzoic Acid
Not available on PMC !

Example 20

[Figure (not displayed)]

Following step 1 in the preparation of I-49, tert-butyl 3-(7-bromo-4-chloro-8-methoxyquinolin-2-yl) benzoate was prepared from Intermediate 17.

Step 1: tert-Butyl 3-(7-bromo-4-(1H-imidazol-1-yl)-8-methoxyquinolin-2-yl)benzoate. To a mixture of tert-butyl 3-(7-bromo-4-chloro-8-methoxyquinolin-2-yl) benzoate (125 mg) and Cs2CO3 (136.8 mg) in DMF (2 mL) was added imidazole (96 mg). The suspended solution was stirred and heated at 130° C. over 2 h. Aqueous work-up with EtOAc and a column chromatography eluting with EtOAc/Hexane afforded the desired product tert-butyl 3-(7-bromo-4-(1H-imidazol-1-yl)-8-methoxyquinolin-2-yl) benzoate (120 mg) (MS: [M+1]+ 480).

Step 2: 3-(7-Bromo-4-(1H-imidazol-1-yl)-8-methoxyquinolin-2-yl)benzoic acid. To a solution of tert-butyl 3-(7-bromo-4-(1H-imidazol-1-yl)-8-methoxyquinolin-2-yl)benzoate (65 mg) in DCM (0.2 mL) and MeOH (0.2 mL) was added TFA (0.4 mL). The resultant solution was stirred over 5 h and concentrated to dryness. The resultant oily residue was suspended in water (0.5 mL) and lyophilized to afford the title compound 3-(7-bromo-4-(1H-imidazol-1-yl)-8-methoxyquinolin-2-yl) benzoic acid (60 mg) as light brown powder (MS: [M+1]+ 424).

US11873291B2. Quinoline cGAS antagonist compounds (2024-01-16). ImmuneSensor Therapeutics, Inc. [US], The Board of Regents of the University of Texas System [US]. Inventors: Jian Qiu [US], Qi Wei [US], Matt Tschantz [US], Heping Shi [US], Youtong Wu [US], Hulling Tan [US], Lijun Sun [US], Chuo Chen [US], Zhijian Chen [US].
Full text: Click here
Patent 2024
Anabolism Benzoate Benzoic Acid Chromatography Hexanes imidazole Light Oils Powder TERT protein, human
4
Synthesis of Fluorinated Monomers and Polymers
Not available on PMC !

Example 1

Monomer M-1 was prepared by mixing 2-(dimethylamino)ethyl methacrylate with pentafluorobenzoic acid in a molar ratio of 1:1. Similarly, Monomers M-2 to M-17 and cM-1 were prepared by mixing a nitrogen-containing monomer with a fluorinated carboxylic acid, fluorinated sulfonamide compound, fluorinated phenol compound, fluorinated β-diketone compound, or unsubstituted benzoic acid (for comparison).

[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
[2] Synthesis of Polymers

Fluorine-containing monomers FM-1 to FM-11 and PAG monomer PM-1 used in the synthesis of polymers have the structure shown below.

[Figure (not displayed)]
[Figure (not displayed)]

US11880136B2. Resist composition and patterning process (2024-01-23). Shin-Etsu Chemical Co., Ltd. [JP]. Inventors: Jun Hatakeyama [JP].
Full text: Click here
Patent 2024
Anabolism Benzoic Acid ethylmethacrylate Fluorine Molar Nitrous Acid pentafluorobenzoic acid Phenols Polymers Sulfonamides
5
Synthesis of 4-((Trans-4-aminocyclohexyl)oxy)benzamide
Not available on PMC !

Example 1

[Figure (not displayed)]

The starting material (4-((trans-4-aminocyclohexyl)oxy)benzoic acid) was prepared as previously described (Hwang et al, (2013) Bioorg. Med. Chem. Lett., 23:3732). To a solution of 4-((trans-4-aminocyclohexyl)oxy)benzoic acid (121 mg, 0.51 mmol) in dimethyl formamide (DMF, 10 mL) was added phenyl isocyanate (82 mg, 0.69 mmol). The reaction was allowed to stir overnight at which point ethyl acetate (EtOAc) and a solution of 1 M Na2CO3 was added and the aqueous layer was separated. A solution of 1 N HCl was added to the aqueous layer until pH=2 and the precipitates were filtered. The resulting product (103 mg, 0.29 mmol, 57%) was used without further purification. Melting point (MP)=241.2-252.9 (244.0)° C. 1H NMR (400 MHz, DMSO-d6) δ 12.60 (s, 1H), 8.29 (s, 1H), 7.87 (d, J=8.5 Hz, 2H), 7.37 (d, J=8.0 Hz, 2H), 7.21 (t, J=7.7 Hz, 2H), 7.02 (d, J=8.6 Hz, 2H), 6.87 (t, J=7.4 Hz, 1H), 6.13 (d, J=7.5 Hz, 1H), 4.49-4.41 (b, 1H), 3.57-3.50 (b, 1H), 2.05 (d, J=11.4 Hz, 2H), 1.94 (d, J=10.5 Hz, 2H), 1.49 (q, J=10.5 Hz, 2H), 1.36 (q, J=10.5 Hz, 2H).

US11873288B2. Inhibitors for soluble epoxide hydrolase (sEH) and fatty acid amide hydrolase (FAAH) (2024-01-16). The Regents of the University of California [US]. Inventors: Bruce Hammock [US], Sean Kodani [US].
Full text: Click here
Patent 2024
1H NMR Benzoic Acid Dimethylformamide ethyl acetate phenyl isocyanate Sulfoxide, Dimethyl

Top products related to «Benzoic Acid»

1
Benzoic acid by Merck Group
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Benzoic acid is a white, crystalline solid that is commonly used in the laboratory setting. It has the chemical formula C6H5COOH and is a carboxylic acid. Benzoic acid is a useful chemical compound that can be employed in various applications within the scientific and industrial realms.
2
Gallic acid by Merck Group
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Gallic acid is a naturally occurring organic compound that can be used as a laboratory reagent. It is a white to light tan crystalline solid with the chemical formula C6H2(OH)3COOH. Gallic acid is commonly used in various analytical and research applications.
3
Caffeic acid by Merck Group
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Caffeic acid is a phenolic compound commonly found in various plants. It serves as a laboratory standard for the identification and quantification of similar phenolic compounds using analytical techniques such as high-performance liquid chromatography (HPLC) and spectrophotometry.
4
Quercetin by Merck Group
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Quercetin is a natural compound found in various plants, including fruits and vegetables. It is a type of flavonoid with antioxidant properties. Quercetin is often used as a reference standard in analytical procedures and research applications.
5
Methanol by Merck Group
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Methanol is a clear, colorless, and flammable liquid that is widely used in various industrial and laboratory applications. It serves as a solvent, fuel, and chemical intermediate. Methanol has a simple chemical formula of CH3OH and a boiling point of 64.7°C. It is a versatile compound that is widely used in the production of other chemicals, as well as in the fuel industry.
6
P coumaric acid by Merck Group
Sourced in United States, Germany, Italy, Spain, France, China, Poland, United Kingdom, Sao Tome and Principe, Switzerland, Canada, Ireland, India, Australia, Japan, Macao, Portugal
P-coumaric acid is a naturally occurring phenolic compound that can be utilized as a reference standard or an analytical reagent in various laboratory settings. It is a white to off-white crystalline solid that is soluble in organic solvents. P-coumaric acid is commonly used as a standard in analytical techniques, such as high-performance liquid chromatography (HPLC) and spectrophotometric measurements, to quantify and characterize similar compounds in sample matrices.
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Vanillic acid by Merck Group
Sourced in United States, Germany, Italy, United Kingdom, Spain, China, France, Australia, Poland, India, Mexico, Singapore, Sao Tome and Principe, Canada
Vanillic acid is a chemical compound that is commonly used in laboratory settings. It is a white, crystalline solid with a characteristic vanilla-like odor. Vanillic acid is often used as a reference standard in analytical methods and as a precursor in the synthesis of other chemical compounds.
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Syringic acid by Merck Group
Sourced in United States, Germany, Italy, United Kingdom, China, Spain, Japan, France, Sao Tome and Principe, Poland, India, Australia
Syringic acid is a phenolic compound that can be used as a chemical reagent in laboratory research and analysis. It serves as a standard reference material for analytical techniques such as chromatography and spectroscopy. The specific core function of syringic acid is to act as a calibration and measurement standard for the quantification of similar phenolic compounds in various samples.
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Catechin by Merck Group
Sourced in United States, Germany, Italy, France, Australia, India, Spain, United Kingdom, China, Poland, Sao Tome and Principe, Japan, Portugal, Canada, Switzerland, Brazil, Malaysia, Singapore, Macao, Belgium, Ireland, Mexico, Hungary
Catechin is a natural polyphenolic compound found in various plants, including green tea. It functions as an antioxidant, with the ability to scavenge free radicals and protect cells from oxidative stress.
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Ferulic acid by Merck Group
Sourced in United States, Germany, Italy, United Kingdom, Spain, China, France, Poland, Australia, Ireland, Malaysia, Canada, India, Switzerland, Sao Tome and Principe, Japan, Brazil, Denmark
Ferulic acid is a phenolic compound that can be found in various plant sources, including rice, wheat, oats, and vegetables. It is commonly used as a lab equipment product for research and analysis purposes. Ferulic acid has antioxidant properties and can be used in a variety of applications, such as the study of plant-based compounds and their potential health benefits.

More about "Benzoic Acid"

Benzoic acid, a versatile chemical compound, is widely used in various industries due to its diverse applications.
Also known as benzenecarboxylic acid or C6H5COOH, this colorless, crystalline solid has gained attention for its antimicrobial properties, making it a common preservative in food, cosmetics, and pharmaceuticals.
Benzoic acid is an important intermediate in the production of other chemicals, including dyes, plastics, and pharmaceuticals.
Researchers have extensively studied its biological and medicinal properties, exploring its potential as an analgesic, anti-inflammatory, and antifungal agent.
Closely related compounds like Gallic acid, Caffeic acid, Quercetin, P-coumaric acid, Vanillic acid, Syringic acid, Catechin, and Ferulic acid share similar structural features and may exhibit overlapping functionalities with Benzoic acid.
Methanol, a commonly used solvent, is also of interest in the context of Benzoic acid research and applications.
To enhance reproducibility and accuracy in Benzoic acid studies, researchers can utilize tools like PubCompare.ai to locate optimized protocols from literature, preprints, and patents, while leveraging AI-driven comparisons to identify the best approaches.
By incorporating these insights, scientists can advance their understanding and unlock new applications for this versatile chemical compound.