Tag: M.W=200-250

Montanaro, Sara published the artcilePhotonucleophilic Addition of the ε-Amino Group of Lysine to a Triflusal Metabolite as a Mechanistic Key to Photoallergy Mediated by the Parent Drug, Related Products of alcohols-buliding-blocks, the publication is ChemMedChem (2009), 4(7), 1196-1202, database is CAplus and MEDLINE.

A mechanism for triflusal-induced photoallergy involving complexation of 2-hydroxy-4-trifluoromethylbenzoic acid with site I of human serum albumin and subsequent formation of a covalent adduct by photoreaction between a metabolite and a neighboring lysine residue is proposed. This is supported by the observed photobinding to poly-L-lysine. Thereby, a photoantigen is generated, which is a likely trigger of the immune response. The goal of the work presented herein is to gain deeper insight into the mol. basis of photoallergy mediated by triflusal through its active metabolite, 2-hydroxy-4-trifluoromethylbenzoic acid (HTB). For this purpose, the interaction between HTB and human serum albumin (HSA) was investigated by fluorescence and laser flash photolysis to monitor inclusion into the protein binding sites through variation in the excited-state properties. A remarkable lengthening of HTB triplet lifetime in the presence of HSA was observed The use of oleic acid as a displacement probe clearly suggests the preference for dark binding in site I. The mechanism of photobinding was studied by irradiation of HTB in the presence of amino acids, and, in the case of lysine, a photoadduct was detected that arises from nucleophilic attack by the ε-amino group to the trifluoromethyl substituent of HTB. Accordingly, photobinding of the metabolite to poly-L-lysine was also observed Overall, these results are consistent with a mechanism for triflusal photoallergy involving complexation of HTB to site I of HSA and subsequent formation of a covalent photoadduct with one neighboring lysine residue.

ChemMedChem published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Jia, Le published the artcileCleavage/cross-coupling strategy for converting β-O-4 linkage lignin model compounds into high valued benzyl amines via dual C-O bond cleavage, Safety of 2-Phenoxy-1-phenylpropane-1,3-diol, the publication is Chinese Chemical Letters (2022), 33(3), 1519-1523, database is CAplus.

Lignin is the most recalcitrant of the three components of lignocellulosic biomass. The strength and stability of the linkages have long been a great challenge for the degradation and valorization of lignin biomass to obtain bio-fuels and com. chems. Up to now, the selective cleavage of C-O linkages of lignin to afford chems. contains only C, H and O atoms. Authors’ group has developed a cleavage/cross-coupling strategy for converting 4-O-5 linkage lignin model compounds into high value-added compounds Herein, a palladium-catalyzed cleavage/cross-coupling of the β-O-4 lignin model compounds with amines via dual C-O bond cleavage for the preparation of benzyl amine compounds and phenols is presented.

Chinese Chemical Letters published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C15H16O3, Safety of 2-Phenoxy-1-phenylpropane-1,3-diol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Yang, Jie published the artcileStudy on ethylhexylglycerin and phenoxyethanol complex ligand, Recommanded Product: 3-((2-Ethylhexyl)oxy)propane-1,2-diol, the publication is Guangdong Huagong (2016), 43(2), 55-56, 58, database is CAplus.

The antimicrobial efficacy of Huake-CHLOR comprising ethylhexylglycerin and phenoxyethanol as cosmetic preservative was studied. The MIC of Huake-CHLOR with different ratio of ethylhexylglycerin and phenoxyethanol was measured. The best ratio between ethylhexylglycerin and phenoxyethanol was 1:9, so that the complex ligand at this ratio was named as Huake-CHLOR. The MIC of Huake-CHLOR on Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Candida albicans, and Aspergillus niger was presented. The skin cream challenge test and deep moisturizing essence test showed that Huake-CHLOR had good long-acting antibacterial and antifungal efficacy. The toxicol. test showed that Huake-CHLOR under normal concentration had no irritation and allergy to skin and eye. The results showed that Huake-CHLOR has good long-acting antibacterial and antifungal efficacy, and has no irritation and allergy to skin and eye.

Guangdong Huagong published new progress about 70445-33-9. 70445-33-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is 3-((2-Ethylhexyl)oxy)propane-1,2-diol, and the molecular formula is C15H12O6, Recommanded Product: 3-((2-Ethylhexyl)oxy)propane-1,2-diol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Park, Sung Min published the artcilePopulation pharmacokinetic and pharmacodynamic modeling of transformed binary effect data of triflusal in healthy Korean male volunteers: a randomized, open-label, multiple dose, crossover study, Computed Properties of 328-90-5, the publication is BMC Pharmacology and Toxicology (2014), 75/1-75/21, 21 pp., database is CAplus and MEDLINE.

Background Triflusal is a drug that inhibits platelet aggregation. In this study we investigated the dose-exposure- response relationship of a triflusal formulation by population pharmacokinetic (PK) and pharmacodynamic (PD) modeling of its main active metabolite, hydroxy-4-(trifluoromethyl) benzoic acid (HTB). Methods This study was a randomized, open-label, multiple-dose, two-period, two-treatment, comparative crossover design. All volunteers received a single oral loading dose of 900 mg of triflusal on Day 1, followed by a dose of 600 mg/day from Day 2 to 9. Using data from 34 healthy volunteers, 476 HTB plasma concentration data points and 340 platelet aggregation data points were used to construct PK and PD models resp. using NONMEM (version 6.2). As the PD endpoint was qual., we implemented binary anal. of ‘inhibition’ and ‘non-inhibition’ rather than using the actual value of the test. The final PK-PD model was evaluated using a visual predictive check (VPC) and bootstrap. Results The time-concentration profile of HTB over the entire dosing period was described by a one-compartment model with a first-order formation rate constant for HTB. Weight was selected as a covariate for clearance and volume of triflusal, resp. The structure and the population estimates for triflusal PK were as follows: oral clearance (CL/F) = 0.2 · (weight/71.65)0.845 L/h, oral volume of distribution (V/F) = 8.3 · (weight/71.65) L, and kf = 0.341 h-1. A sigmoid relationship between triflusal concentration and the probability of significant inhibition with shape factor was chosen as the final PD model. No time delay between concentration and response was identified. The final structure between predicted concentration (Cpred,ij γ) and the probability of inhibition of platelet aggregation (IPA) relationship was as follows: Probability of IPA = Cpred,ij19 / (84.9 μg/mL19 + Cpred,ij19). Thus, we concluded this relationship is more like quantal concentration-response relationship. The current dosing regimen was considered to be efficacious based on the EC50 estimate of 84.9 μg/mL obtained in this study. Conclusions A PK and binary probability PD model of triflusal was successfully developed for Korean healthy volunteers. The model may be used to further prediction inhibition of platelet aggregation by triflusal.

BMC Pharmacology and Toxicology published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Computed Properties of 328-90-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Shin, Seoungwoo published the artcileAnti-skin-aging activity of a standardized extract from Panax ginseng leaves in vitro and in human volunteer, Synthetic Route of 70445-33-9, the publication is Cosmetics (2017), 4(2), 18/1-18/12, database is CAplus.

Ginseng leaves contain high saponin composition and content, but are used less often than the root part. To develop a use for the leaves that exploits their properties, we studied ginseng leaves as the raw material of anti-aging cosmetics. This study highlights an assessment of the cellular activity and clin. efficacy of ginseng leaf extract, providing necessary information relevant to the development of new cosmetic products. Panax ginseng leaf purified extracts (PGLE) were shown to have high contents of Rb3 and Rb2. Rb3, the major chem. components of PGLE, promoted collagen synthesis though the activation of transforming growth factor-β (TGF-β) in human skin fibroblast cells. In addition, the possibility of PGLE as an anti-skin-aging agent has also been clin. validated. Our anal. of the crow’s feet wrinkle showed that there was a decrease in the depth of deep furrows in the region of interest (RI) treated with PGLE lotion over an eight-week period. Based on these results, we suggest the possibility that PGLE, having high levels of Rb3, be considered as an attractive, wrinkle-reducing candidate for topical application.

Cosmetics published new progress about 70445-33-9. 70445-33-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is 3-((2-Ethylhexyl)oxy)propane-1,2-diol, and the molecular formula is C15H14O, Synthetic Route of 70445-33-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Denton, Elliott H. published the artcileCatalytic Carbochlorocarbonylation of Unsaturated Hydrocarbons via C-COCl Bond Cleavage, Application of 2-Hydroxy-4-(trifluoromethyl)benzoic acid, the publication is Angewandte Chemie, International Edition (2021), 60(43), 23435-23443, database is CAplus and MEDLINE.

A palladium-catalyzed difunctionalisation of unsaturated C-C bonds with acid chlorides was reported. Formally, C-COCl bond of an acid chloride was cleaved and added, with complete atom economy, across either strained alkenes or a tethered alkyne to generate new acid chlorides I [Ar = Ph, 2-naphthyl, benzo[b]thiophen-2-yl, etc.]. The transformation does not require exogenous carbon monoxide, operated under mild conditions, showed a good functional group tolerance, and gave isolated products with excellent stereoselectivity. The intermol. reaction tolerated both aryl- and alkenyl-substituted acid chlorides and was successful when carboxylic acids were transformed to acid chloride in situ. The reaction also showed an example of temperature-dependent stereodivergence which, together with plausible mechanistic pathways, was investigated by DFT calculations Moreover, it was shown that benzofurans could be formed in an intramol. variant of reaction. Finally, derivatisation of products from intermol. reaction provided a highly stereoselective approach for synthesis of tetrasubstituted cyclopentanes.

Angewandte Chemie, International Edition published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Application of 2-Hydroxy-4-(trifluoromethyl)benzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Beilfuss, W. published the artcileA new concept to boost the preservative efficacy of phenoxyethanol, SDS of cas: 70445-33-9, the publication is SOFW Journal (2005), 131(11), 30,32-36, database is CAplus.

A new cosmetic preservative for leave-on products based on a combination of the active ingredient phenoxyethanol and the skin care additive and deodorant active ethylhexylglycerin is presented. Ethylhexylglycerin boosts the antimicrobial activity of phenoxyethanol. Properties, antimicrobial activity and a possible mechanism of action are discussed.

SOFW Journal published new progress about 70445-33-9. 70445-33-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is 3-((2-Ethylhexyl)oxy)propane-1,2-diol, and the molecular formula is C11H24O3, SDS of cas: 70445-33-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kim, Seung-Woo published the artcileRobust neuroprotective effects of 2-((2-oxopropanoyl)oxy)-4-(trifluoromethyl)benzoic acid (OPTBA), a HTB/pyruvate ester, in the postischemic rat brain, Synthetic Route of 328-90-5, the publication is Scientific Reports (2016), 31843, database is CAplus and MEDLINE.

Postischemic brain damage in stroke is proceded with complicated pathol. events, and so multimodal drug treatments may offer better therapeutic means for improving clin. outcomes. Here, we report robust neuroprotective effects of a novel compound, 2-((2-oxopropanoyl)oxy)-4-(trifluoromethyl)benzoic acid (OPTBA), a 2-hydroxy-4-trifluoromethyl benzoic acid (HTB, a metabolite of triflusal)-pyruvate ester. I.v. administration of OPTBA (5 mg/kg) 3 or 6 h after middle cerebral artery occlusion (MCAO) in Sprague-Dawley rats reduced infarct volumes to 38.5 ± 11.4% and 46.5 ± 15.3%, resp., of that of MCAO controls, and ameliorated motor impairment and neurol. deficits. Importantly, neuroprotective effects of OPTBA were far greater than those afforded by combined treatment of HTB and pyruvate. Furthermore, OPTBA suppressed microglial activation and proinflammatory cytokine inductions more effectively than HTB/pyruvate co-treatment in the postischemic brain and LPS-treated cortical slice cultures and also attenuated NMDA-induced neuronal death in hippocampal slice cultures. LC-MS anal. demonstrated that OPTBA was hydrolyzed to HTB and pyruvate with a t_1/2 of 38.6 min in blood and 7.2 and 2.4 h in cortex and striatum, resp., and HTB was maintained for more than 24 h both in blood and brain tissue. Together these results indicate OPTBA acts directly and via its hydrolysis products, thus acting as a multimodal neuroprotectant in the postischemic brain.

Scientific Reports published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Synthetic Route of 328-90-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ohmura, Toshimichi published the artcileIridium-Catalyzed C(sp³)-H Addition of Methyl Ethers across Intramolecular Carbon-Carbon Double Bonds Giving 2,3-Dihydrobenzofurans, Application of 2-Hydroxy-4-(trifluoromethyl)benzoic acid, the publication is Advanced Synthesis & Catalysis (2019), 361(19), 4448-4453, database is CAplus.

Intramol. addition of an O-Me C(sp³)-H bond across a carbon-carbon double bond occurs in the iridium-catalyzed reaction of Me 2-(propen-2-yl)phenyl ethers 2-MeC(=CH₂)-4-R-3-R¹-2-R²C₆HOMe (R = H, Me, Cl, t-Bu; R¹ = H, Me, MeO, CF₃; R² = H, Me, Ph, t-Bu, Br; R¹R² = CH=CH-CH=CH). The Ir/(S)-DTBM-SEGPHOS catalyst promotes the reaction efficiently in toluene at 110-135 °C to afford 3,3-dimethyl-2,3-dihydrobenzofurans I. Enantioselective C(sp³)-H addition is achieved in the reaction of Me 2-(1-siloxyethenyl)phenyl ethers 2-TBSOC(=CH₂)-4-R³-3-R⁴-2-R⁵C₆HOMe (R³ = H, Cl, t-Bu; R⁴ = H, MeO; R⁵ = H, Me, MeO, t-Bu, Cl; R⁴R⁵ = CH=CH-CH=CH), affording enantioenriched 3-hydroxy-2,3-dihydrobenzofuran derivatives II with up to 96% ee.

Advanced Synthesis & Catalysis published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Application of 2-Hydroxy-4-(trifluoromethyl)benzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ohmura, Toshimichi published the artcileIridium-Catalyzed C(sp³)-H Addition of Methyl Ethers across Intramolecular Carbon-Carbon Double Bonds Giving 2,3-Dihydrobenzofurans, Application of 2-Hydroxy-4-(trifluoromethyl)benzoic acid, the publication is Advanced Synthesis & Catalysis (2019), 361(19), 4448-4453, database is CAplus.

Intramol. addition of an O-Me C(sp³)-H bond across a carbon-carbon double bond occurs in the iridium-catalyzed reaction of Me 2-(propen-2-yl)phenyl ethers 2-MeC(=CH₂)-4-R-3-R¹-2-R²C₆HOMe (R = H, Me, Cl, t-Bu; R¹ = H, Me, MeO, CF₃; R² = H, Me, Ph, t-Bu, Br; R¹R² = CH=CH-CH=CH). The Ir/(S)-DTBM-SEGPHOS catalyst promotes the reaction efficiently in toluene at 110-135 °C to afford 3,3-dimethyl-2,3-dihydrobenzofurans I. Enantioselective C(sp³)-H addition is achieved in the reaction of Me 2-(1-siloxyethenyl)phenyl ethers 2-TBSOC(=CH₂)-4-R³-3-R⁴-2-R⁵C₆HOMe (R³ = H, Cl, t-Bu; R⁴ = H, MeO; R⁵ = H, Me, MeO, t-Bu, Cl; R⁴R⁵ = CH=CH-CH=CH), affording enantioenriched 3-hydroxy-2,3-dihydrobenzofuran derivatives II with up to 96% ee.

Advanced Synthesis & Catalysis published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Application of 2-Hydroxy-4-(trifluoromethyl)benzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts