Propyl gallate appears as fine white to creamy-white crystalline powder. Odorless or with a faint odor. Melting point 150°C. Insoluble in water. Slightly bitter taste.
Propyl gallate was quickly metabolized and excreted when administered orally to rats and rabbits. ...When fed to rats, most of the propyl gallate was passed in the feces as the original ester. The urinary components detected were the original ester and gallic acid, and these were excreted completely within 24 hours. When administered orally to rabbits, 79 percent of the administered dose of propyl gallate was excreted in the urine, 72 percent as 4-methoxygallic acid glucuronide and 6.7 percent as unconjugated phenolic compounds. Minor metabolites included pyrogallol (free and conjugated) and free 4-methoxy gallic acid.
In rats, /SRP: some/ of an oral dose of propyl gallate is absorbed in the GI tract. In vivo, the gallate esters are hydrolized to gallic acid and free alcohol. Free alcohol is metabolized through the Krebs cycle, and most of the gallic acid is converted into 4-O-methyl gallic acid. Free gallic acid or a conjugated derivative of 4-O-methyl gallic acid is excreted in the urine. Significant amounts of unchanged esters are excreted in the feces of rats. In pigs, the metabolism is similar to rats.
The available evidence indicates that the gallate esters are hydrolyzed in the body to gallic acid. Most of the gallic acid is converted into 4-O-methyl gallic acid. Free gallic acid or a conjugated derivative of 4-O-methyl gallic acid is excreted in the urine. Conjugation of the 4-O-methyl gallic acid with glucuronic acid was demonstrated ... .
In vitro incubations with propyl, octyl and dodecyl gallate were performed using homogenates of liver, mucosa of the small intestine, and contents of caecum/colon as a source of intestinal microflora. The various homogenates were incubated at 37 °C with the individual gallate esters. At various time points up to 24 hr, samples were taken and analyzed by HPLC. ... All test substances were extensively metabolized by the homogenate of the intestinal mucosa. ... Furthermore, the caecum and colon contents also showed a high metabolic capacity, especially towards propyl gallate. The amt of gallic acid detected in the incubations was always much smaller than the total decrease of the amt of ester. It seems likely that apart from hydrolysis of the ester bond, other biotransformation routes ... are of major importance for all three gallate esters.
IDENTIFICATION AND USE: Propyl gallate is white to creamy-white crystalline powder. It is used as an antioxidant for foods and cosmetics; especially fats, oils, emulsions, and waxes. It is used in transformer oils and as a stabilizer for synthetic vitamin A. It is also used as experimental medication. HUMAN EXPOSURE AND TOXICITY: Statistically significant increase in propyl gallate-positive rates on patch testing over the last decade have been reported. Propyl gallate produced contact dermatitis in 5 of 10 patients. Patients applied 20% in 70% ethyl alcohol to forearm daily for 24 days. 5 patients complained of pruritus and erythema. Propyl gallate was investigated in vitro at concentration of 0.5, 5.0 and 50 ug/mL employing WI-38 human embryonic lung cells for anaphase abnormalities. Propyl gallate was not mutagenic. ANIMAL STUDIES: In a 4-week oral toxicity study, rats ingested 0%, 0.1%, 0.5%, or 2.5% propyl gallate in feed. In rats ingesting the highest dose, a decrease in weight gain of more than 10%, dirty tails, thickening of the stomach wall, necrosis, and ulceration of the stomach mucosa, a moderate to severe granulomatous inflammatory response in the submucosa and muscular wall of the stomach, anemia, hyperplastic tubuli in the outer medulla of the kidneys, and increased activity of several microsomal and cytoplasmic drug-metabolizing enzymes in the liver were observed. Increased activity of hepatic drug metabolizing enzymes was also noted in rats treated with 0.5% propyl gallate. No effects were noted in those ingesting 0.1%. Guinea pigs fed 0.02% propyl gallate in the diet for 14 months and dogs fed 0.01% for a year showed no signs of toxicity. Administration to rats of 2.5% propyl gallate in the diet caused maternal toxicity and slight retardation of fetal development, but no teratogenic effects. In dose levels up to 250 mg/kg/day, propyl gallate had no effects on organogenesis in rabbits. At a concentration of 0-0.1 mg/plate, propyl gallate was mutagenic in S. typhimurium strain TA102, in the presence, but not the absence, of metabolic activation. An intraperitoneal injection of 900 mg/kg propyl gallate caused a positive result in a mouse micronucleus test. Propyl gallate was found to be negative when tested for mutagenicity using the Salmonella/microsome preincubation assay with 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of metabolic activation. ECOTOXICITY STUDIES: The toxic effects of propyl gallate on aquatic organisms were investigated, using five model systems from four trophic levels. The most sensitive system was the hepatoma fish cell line PLHC-1 according to total protein content, with an EC(50) of 10 uM and a NOAEL of 1 uM at 72 hours, followed by the immobilization of Daphnia magna, the inhibition of bioluminescence of Vibrio fischeri, the salmonid fish cell line RTG-2 and the inhibition of the growth of Chlorella vulgaris.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌物分类
对人类不具有致癌性（未被国际癌症研究机构IARC列名）。
No indication of carcinogenicity to humans (not listed by IARC).
来源:Toxin and Toxin Target Database (T3DB)
毒理性
副作用
神经毒素 - 其他中枢神经系统神经毒素
Neurotoxin - Other CNS neurotoxin
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
The antioxidant propyl gallate (PG) induced lipid peroxidation in combination with non-toxic Cu(II) concentrations in human fibroblasts. This was measured by the thiobarbituric acid assay (TBA assay) and by detection of accumulating fluorescent products after a 1-hr treatment of cells with CuCl2/PG at concentrations higher than 0.125 mM. PG alone led to a significant reduction of thiobarbituric acid-reactive substances (TBARS) demonstrating its antioxidative properties. Time course studies of lipid peroxidation by PG/Cu(II) showed that formation of TBARS was preceded by a lag phase of 60 min. Thereafter, the TBARS value increased rapidly for 1 hr and then reached a constant maximum or slightly decreased. The induction of lipid peroxidation by PG/Cu(II) is probably due to the formation of reactive species like reactive oxygen species (ROS), Cu(I) and semiquinone radicals which are able to participate in initiation and propagation of lipid peroxidation. Combination effects of PG/Cu(II) were demonstrated also on inhibition of membrane-bound succinate dehydrogenase. Cytosolic esterases were affected only slightly. The greater susceptibility of membrane-bound enzymes is in accordance with the lipid peroxidation-inducing effects of PG/Cu(II).
来源:Hazardous Substances Data Bank (HSDB)
毒理性
相互作用
我们研究了抗氧化剂对40株白念珠菌临床分离株的抗真菌活性的影响。咪唑与PG联合使用，其MIC值较单独使用咪唑低10-150倍。这种增强活性的最佳条件是pH 6.2-8.0，真菌细胞浓度低于3 x 10(5)个/mL。咪唑与PG之间的相互作用机制尚不清楚，但可能与PG对P-450细胞色素的影响有关。
We looked at the in vitro effect of an antioxidant, propyl gallate (PG), on the antifungal activity of miconazole sulphosalicylate, econazole sulphosalicylate and ketoconazole against 40 clinical isolates of Candida albicans. The combination of imidazole and PG gave MIC values 10-150 times lower than those of imidazole alone. The optimal conditions for this enhanced activity were pH 6.2-8.0 and a fungal cell concentration lower than 3 x 10(5) cells/mL. The mechanism of the interaction between imidazole and PG is not known but may be as a result of an effect of PG on the P-450 cytochrome. ...
Propyl gallate was quickly metabolized and excreted when administered orally to rats and rabbits. ...When fed to rats, most of the propyl gallate was passed in the feces as the original ester. The urinary components detected were the original ester and gallic acid, and these were excreted completely within 24 hours. When administered orally to rabbits, 79 percent of the administered dose of propyl gallate was excreted in the urine, 72 percent as 4-methoxygallic acid glucuronide and 6.7 percent as unconjugated phenolic compounds. Minor metabolites included pyrogallol (free and conjugated) and free 4-methoxy gallic acid.
In rats, /SRP: some/ of an oral dose of propyl gallate is absorbed in the GI tract. In vivo, the gallate esters are hydrolized to gallic acid and free alcohol. Free alcohol is metabolized through the Krebs cycle, and most of the gallic acid is converted into 4-O-methyl gallic acid. Free gallic acid or a conjugated derivative of 4-O-methyl gallic acid is excreted in the urine. Significant amounts of unchanged esters are excreted in the feces of rats.
Synthesis and Retrostructural Analysis of Libraries of AB3 and Constitutional Isomeric AB2 Phenylpropyl Ether-Based Supramolecular Dendrimers
摘要：
We report the synthesis of methyl esters of 3-(4-hydroxyphenyl)propionic, 3-(3,4-dihydroxyphenyl)propionic, 3-(3,5-dihydroxyphenyl)propionic, and 3-(3,4,5-trihydroxyphenyl)propionic acids and their use in a convergent iterative strategy to prepare up to four generations of three libraries, one of 3,4,5- and two of constitutional isomeric 3,4- and 35-substituted 3-phenylpropyl dendrons. Each library contains 3-[3,4,5-tris(dodecyl-1-oxy)phenyl]propyl-, 3-[3,4-bis(dodecyl-1-oxy)phenyl]propyl-, 3,4-bis[3-(4-dodecyl-1-oxyphenyl)propyl-1-oxy]phenyl-1-propyl-, and 3-13,4,5-tris[3-(4-dodecyl-1-oxyphenyl)propyl-1-oxy]phenyllpropyI ether first-generation clendrons on their periphery and -CO2CH3, -COOH, and -CH2OH groups at their apex. Regardless of their generation number and their periphery, internal, and apex structures, these dendrons self-assemble into supramolecular dendrimers that self-organize into all periodic and quasi-periodic assemblies encountered previously and in several unencountered with architecturally related benzyl ether-based supramolecular dendrimers. A variety of porous columnar lattices that were previously obtained only from clendritic dipepticles and hollow supramolecular spheres were also discovered from these building blocks. The more flexible and less compact 3-phenylpropyl ether repeat units are stable under acidic conditions, facilitate a simpler synthetic strategy, provide faster dynamics of self-assembly into higher-order supramolecular structures of larger dimensions, exhibit lower transition temperatures than the corresponding benzyl ether homologues, and demonstrate the generality of the self-assembly concept based on amphiphilic dendrons.
Synthesis of propyl gallate from tannic acid catalyzed by tannase from Aspergillus oryzae: Process optimization of transesterification in anhydrous media
摘要：
Improving the catalytic capability of enzyme is an important challenge of biocatalysis in organic medium. Optimization of organic reaction system and reaction mode can elevate the catalytic ability. In order to enhance the catalytic efficiency of tannase-catalyzed transesterification from tannic acid, process parameters of the reaction and reaction mode were optimized further to improve the conversion rate of substrate. The result showed that with hexane as solvent, a conversion rate of substrate, 75%, was achieved at 40 degrees C in 20 mL reaction mixture composed of 0.75% water and 7.5% n-propanol, and that semicontinuous catalysis was the most favorable for production of propyl gallate, its average production rate was 2.5-fold that of batch catalysis. By SCC, a noted computative conversion rate of approximate, 90%, was obtained. Thus, it is expected that this study may present an efficient and ecofriendly method for industrial production of PG. (C) 2012 Elsevier B.V. All rights reserved.
[EN] SUBSTITUTED N-HETEROCYCLIC CARBOXAMIDES AS ACID CERAMIDASE INHIBITORS AND THEIR USE AS MEDICAMENTS<br/>[FR] CARBOXAMIDES N-HÉTÉROCYCLIQUES SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE LA CÉRAMIDASE ACIDE ET LEUR UTILISATION EN TANT QUE MÉDICAMENTS
申请人：BIAL BIOTECH INVEST INC
公开号：WO2021055627A1
公开（公告）日：2021-03-25
The invention provides substituted N-heterocyclic carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat a medical disorder, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.
[EN] COMPOUNDS AND THEIR USE AS BACE INHIBITORS<br/>[FR] COMPOSÉS ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE BACE
申请人：ASTRAZENECA AB
公开号：WO2016055858A1
公开（公告）日：2016-04-14
The present application relates to compounds of formula (I), (la), or (lb) and their pharmaceutical compositions/preparations. This application further relates to methods of treating or preventing Αβ-related pathologies such as Down's syndrome, β- amyloid angiopathy such as but not limited to cerebral amyloid angiopathy or hereditary cerebral hemorrhage, disorders associated with cognitive impairment such as but not limited to MCI ("mild cognitive impairment"), Alzheimer's disease, memory loss, attention deficit symptoms associated with Alzheimer's disease, neurodegeneration associated with diseases such as Alzheimer's disease or dementia, including dementia of mixed vascular and degenerative origin, pre-senile dementia, senile dementia and dementia associated with Parkinson's disease.
[EN] COMPOUNDS AS MODULATORS OF TIGIT SIGNALLING PATHWAY<br/>[FR] COMPOSÉS MODULATEURS DE LA VOIE DE SIGNALISATION DE TIGIT
申请人：AURIGENE DISCOVERY TECH LTD
公开号：WO2018047139A1
公开（公告）日：2018-03-15
The present invention relates to compound of formula (I) as therapeutic agents to modulate the TIGIT signalling pathway. The invention also encompasses the use of the compound of formula (I) or a stereoisomer thereof or a pharmaceutically acceptable salt thereof for the treatment of diseases or disorders mediated by TIGIT.
[EN] PREPARATION AND USES OF REACTIVE OXYGEN SPECIES SCAVENGER DERIVATIVES<br/>[FR] PRÉPARATION ET UTILISATIONS DE DÉRIVÉS PIÉGEURS D'ESPÈCES RÉACTIVES DE L'OXYGÈNE
申请人：XW LAB INC
公开号：WO2019033330A1
公开（公告）日：2019-02-21
Compounds of Formula (I) a or (I) b: including certain quinone derivatives, and the corresponding pharmaceutical compositions, which may serve to modulate ferroptosis in a subject. Also disclosed herein are the preparations of these compounds and pharmaceutical compositions and their potential uses in the manufacture of a medicament in reducing reactive oxygen species (ROS) in a cell and for preventing, treating, ameliorating certain related disorder or a disease.
Melanocortin-4 receptor binding compounds and methods of use thereof
申请人：Millennium Pharmaceuticals, Inc.
公开号：US20040082779A1
公开（公告）日：2004-04-29
Provided are MC4-R binding compounds of the formula XVII:
1
wherein L
2
is a linker group, and P
1
, P
2
, P
3
, P
4
, Z
1
, Z
2
, Z
3
, Z
4
, Z
5
, t, s, and R are as described in the specification. Methods of using the compounds to treat MC4-R associated disorders, such as disorders associated with weight loss, are also provided.
