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Effect of complex formation between 4-hexylresorcinol and ethyl myristate on release rate of 4-hexylresorcinol from petrolatum base.

The effect of ethyl myristate on the release rate of 4-hexylresorcinol from petrolatum base was studied at pH 7.4 and 37 degrees. 4-Hexylresorcinol was analyzed spectrophotometrically at 278 nm. The release rate of hexylresorcinol from the ointments was directly proportional to the square root of time and depended on the percentage of ethyl myristate in the ointment base. For 0, 0.5, 1, 3, and 5% of ethyl myristate, the release rates were 29.6, 35.4, 38.3, 55.7, and 70.0 micrograms/hr1/2/cm2, respectively. The solubility of hexylresorcinol in the petrolatum base was determined as a function of ethyl myristate using partitioning techniques. The enhancement in hexylresorcinol solubility was rationalized on the basis of 1:1 and 1:2 complexes between hexylresorcinol and ethyl myristate. The complexation constants of these complexes were estimated to be 10 M-1 and 206.1 M-2, respectively. The diffusion coefficient of hexylresorcinol in the petrolatum base was estimated to be 1.31 x 10(-8) cm2/sec.

Hexylresorcinol↗

NTP Toxicology and Carcinogenesis Studies of 4-Hexylresorcinol (CAS No. 136-77-6) in F344/N Rats and B6C3F1 Mice (Gavage Studies).

4-Hexylresorcinol, which is used as an anthelmintic and antiseptic, was nominated by the National Cancer Institute for study. Toxicology and carcinogenesis studies were conducted by administering 4-hexylresorcinol (greater than 99% pure) in corn oil by gavage to groups of F344/N rats and B6C3F1 mice of each sex for 16 days, 13 weeks, or 2 years. Sixteen-Day and Thirteen-Week Studies: In the 16-day studies, groups of five rats and five mice of each sex were administered 0, 31.3, 62.5, 125, 250, or 500 mg/kg 4-hexylresorcinol. Survival was not affected. Decreased body weights were seen in male rats that received 250 or 500 mg/kg 4-hexylresorcinol. No other effects were observed. In the 13-week studies, groups of 10 rats and 10 mice of each sex were administered 0, 62.5, 125, 250, 500, or 1,000 mg/kg of the chemical, 5 days per week. All rats and male mice and 9/10 female mice that received 1,000 mg/kg died before the end of the studies. Final mean body weights of male rats that received 250 or 500 mg/kg were 22% or 38% lower than that of the vehicle controls; final mean body weights of female rats that received 250 or 500 mg/kg were 16% or 9% lower. No compound-related gross or microscopic pathologic effects were observed in rats. No body weight effects were observed for mice. Mild to moderate nephropathy was dose related in male and female mice. Based on these results, 2-year toxicology and carcinogenesis studies of 4-hexylresorcinol were conducted by administering 0, 62.5, or 125 mg/kg to groups of 50 F344/N rats and 50 B6C3F1 mice of each sex, 5 days per week. Body Weight and Survival in the Two-Year Studies: Mean body weights of high dose male rats were 7%-11% lower than those of the vehicle controls throughout the study. Mean body weights of low dose male and dosed female rats were similar to those of the vehicle controls. The body weights of dosed male and dosed female mice were comparable to those of vehicle controls except during the last 16 weeks of the studies, when body weights were 6%-16% lower in the dosed groups. No significant differences in survival were observed between any groups of rats or mice of either sex (male rats: vehicle control, 30/50; low dose, 29/50; high dose, 33/50; female rats: 28/50; 32/50; 30/50; male mice: 36/50; 26/50; 30/50; female mice: 35/50; 32/50; 35/50). Nonneoplastic and Neoplastic Lesions in the Two-Year Studies: Two astrocytomas and an oligodendroglioma were observed in high dose male rats, a glioma was observed in one low dose male rat, and an oligodendroglioma was observed in one vehicle control male rat. These neoplasms were not considered to be related to 4-hexylresorcinol administration. Focal medullary hyperplasia of the adrenal gland was observed at increased incidences in dosed male mice (5/50; 16/50; 10/49). Pheochromocytomas in male mice occurred with a marginal upward trend (1/50; 2/50; 5/49). Historically, these neoplasms are observed in about 1% of corn oil vehicle control B6C3F1 male mice. The incidences of neoplasms of the harderian gland in male mice were slightly increased over those in the vehicle controls (adenomas or carcinomas, combined: 0/50; 4/50; 3/50). Decreases were observed in the incidences of mononuclear cell leukemia in dosed male (12/49; 7/50; 1/50) and female (16/50; 3/50; 2/50) rats, hepatocellular adenomas or carcinomas (combined) in dosed male mice (21/50; 9/50; 9/50), and circulatory system tumors in male (10/50; 4/50; 2/50) and female (6/50; 2/49; 0/50) mice. These decreased incidences of tumors in rats and mice are considered to be possibly related to 4-hexylresorcinol administration. The incidences and severity of nephropathy (male: 39/50; 43/50; 47/50; female: 7/50; 40/49; 47/50) and incidences of osteosclerosis (male: 5/50; 5/50; 15/50; female: 21/50; 25/49; 40/50) were increased in both dosed male and female mice and are considered to be related to chemical exposure. Genetic Toxicology: 4-Hexylresorcinol was not mutagenic for Salmonella typhimurium strains TA98, TA100, TA1535, or TA1537 with or without S9 metabolic activation. 4-Hexylre, TA1535, or TA1537 with or without S9 metabolic activation. 4-Hexylresorcinol induced forward mutations at the TK locus in mouse L5178Y cells in the presence of S9; no response was observed in the absence of metabolic activation. In cytogenetic assays with cultured Chinese hamster ovary (CHO) cells, 4-hexylresorcinol caused an increase in the frequency of sister chromatid exchanges (SCEs) in the absence of metabolic activation; no induction of SCEs was observed in the presence of S9. Chromosomal aberrations were not induced in CHO cells with or without metabolic activation. Data Audit: The data, documents, and pathology materials from the 2-year studies of 4-hexylresorcinol were audited at the NTP Archives. The audit findings show that the conduct of the studies is documented appropriately and support the data and results given in this Technical Report. Conclusions: Under the conditions of these 2-year gavage studies, there was no evidence of carcinogenic activity of 4-hexylresorcinol for male or female F344/N rats given doses of 62.5 or 125 mg/kg. There was equivocal evidence of carcinogenic activity of 4-hexylresorcinol for male B6C3F1 mice, as shown by marginally increased incidences of pheochromocytomas (and hyperplasia) of the adrenal medulla and of harderian gland neoplasms. There was no evidence of carcinogenic activity for female B6C3F1 mice given doses of 62.5 or 125 mg/kg 4-hexylresorcinol. Decreased incidences of three tumors types were considered related to 4-hexylresorcinol administration: mononuclear cell leukemia in male and female rats, hepatocellular neoplasms in male mice, and circulatory system tumors in male and female mice. Synonyms: 4-hexyl-1,3-benzenediol; 4-hexyl-1,3-dihydroxybenzene

Journal Article↗

Inhibitory effects of hexylresorcinol and dodecylresorcinol on mushroom (Agaricus bisporus) tyrosinase.

The effects of hexylresorcinol and dodecylresorcinol on the monophenolase and diphenolase activity of mushroom tyrosinase have been studied. The results show that hexylresorcinol and dodecylresorcinol can inhibit both monophenolase and diphenolase activity of the enzyme. The lag period of the enzyme was obviously lengthened, and the steady-state activity of the enzyme decreased sharply. Two microM of hexylresorcinol and dodecylresorcinol can lengthen the lag period from 98 s to 260 and 275 s, respectively. Both hexylresorcinol and dodecylresorcinol can lead to reversible inhibition of the enzyme. The IC50 values of hexylresorcinol and dodecylresorcinol were estimated as 1.24 and 1.15 microM for monophenolase and as 0.85 and 0.80 microM for diphenolase, respectively. A kinetic analysis shows that hexylresorcinol and dodecylresorcinol are competitive inhibitors. The apparent inhibition constant for hexylresorcinol and dodecylresorcinol binding with free enzyme has been determined to be 0.443 and 0.405 microM for diphenolase, respectively.

Agaricales↗

Effects of resveratrol and 4-hexylresorcinol on hydrogen peroxide-induced oxidative DNA damage in human lymphocytes.

The protective effects of resveratrol and 4-hexylresorcinol against oxidative DNA damage in human lymphocytes induced by hydrogen peroxide were investigated. Resveratrol and 4-hexylresorcinol showed no cytotoxicity to human lymphocytes at the tested concentration (10-100 microM). In addition, DNA damage in human lymphocytes induced by H2O2 was inhibited by resveratrol and 4-hexylresorcinol. Resveratrol and 4-hexylresorcinol at concentrations of 10-100 microM induced an increase in glutathione (GSH) levels in a concentration-dependent manner. Moreover, these two compounds also induced activity of glutathione peroxidase (GPX) and glutathione reductase (GR). The activity of glutathione-S-transferase (GST) in human lymphocytes was induced by resveratrol. Resveratrol and 4-hexylresorcinol inhibited the activity of catalase (CAT). These data indicate that the inhibition of resveratrol and 4-hexylresorcinol on oxidative DNA damage in human lymphocytes induced by H2O2 might be attributed to increase levels of GSH and modulation of antioxidant enzymes (GPX, GR and GST).

Antioxidants↗

[Determination of 4-hexylresorcinol residues in prawns and crabs].

A method for the determination of 4-hexylresorcinol residues in prawn and crab meat by HPLC was developed. 4-Hexylresorcinol in prawn and crab meats was extracted with methanol using a homogenizer. The extract was diluted 4 times with water, and the diluted solution was passed through a C18 cartridge. The cartridge was washed with water and methanol-water (4 : 6), and then 4-hexylresorcinol was eluted with acetonitrile-0.1% phosphoric acid (55 : 45). The eluate was separated on a Capcell Pak C18 MG column with a mobile phase of acetonitrile-0.1% phosphoric acid (6 : 4) and 4-hexylresorcinol was determined with a UV detector (210 nm). Recoveries of 4-hexylresorcinol from commercial prawn and crab meats spiked at 1.0 and 10 microg/g were 82.4-92.2 and 88.9-91.8%, respectively. The determination limit of 4-hexylresorcinol was 1.0 microg/g in the samples.

Animals↗

Generally recognized as safe (GRAS) evaluation of 4-hexylresorcinol for use as a processing aid for prevention of melanosis in shrimp.

4-Hexylresorcinol (C12H18O2) is proposed for use as a processing aid for prevention of melanosis ("black spot") in shrimp and as an alternative to the currently approved sulfites. A safety evaluation was conducted to affirm, based upon scientific procedures, the generally recognized as safe ("GRAS") status of 4-hexylresorcinol for proposed use. The GRAS safety evaluation compiled, reviewed, and analyzed data on the following areas: chemical identity, analytical methodology, historical and proposed uses, functionality, and safety. The publicly available safety data on 4-hexylresorcinol cover a broad range of potential toxicity concerns including acute and subacute toxicity, subchronic toxicity, carcinogenicity, mutagenicity, and allergenicity. These studies, along with the aforementioned data, demonstrate that 4-hexylresorcinol presents no risk of toxicity at the levels proposed for treatment of shrimp, and the use of 4-hexylresorcinol as a processing aid to prevent melanosis in shrimp is GRAS.

Animals↗

[Hexylresorcinol induces chromosome aberrations in mouse peripheral blood cells].

Hexylresorcinol has been demonstrated to induce chromosome aberrations in eukaryotic cells at doses of 0.5, 0.05, and 0.005 mg/g body weight. The metabolic transformation of hexylresorcinol in mice decreases its genotoxic effect. The mutagenic effect is retained for three days only after the administration of the highest dose of hexylresorcinol (0.5 mg/g); during the first two days, lower doses are also genotoxic. Therefore, hexylresorcinol doses lower than 0.5 mg/g body weight are metabolized within two days to the extent precluding the expression of the cytotoxic effect. After a single administration to mice, exogenous hexylresorcinol is transformed at a rate of 0.0025-0.025 mg/day.

Animals↗

Determination of 4-hexylresorcinol in crab meat.

A method is described for determining 4-hexylresorcinol in crab meat. 4-Hexylresorcinol is used to prevent melanosis in shrimp, and the same use has been proposed for crab meat. Because 4-hexylresorcinol may be added illegally to crab meat as a preservative, consumer protection requires that residues of the compound be monitored in crab meat. 4-Hexylresorcinol is extracted from crab meat with acetonitrile. After dilution with water, the extract is passed through a C18 solid-phase extraction column and 4-hexylresorcinol is eluted from the column with ethanol. The compound is determined by reversed-phase liquid chromatography with diode array detection at 206 nm. Limit of quantitation is 1.0 microgram/g. Mean recovery in the range 1-20 micrograms/g is 89%, with a relative standard deviation of 6.3.

Animals↗

Liquid chromatographic determination of the processing aid 4-hexylresorcinol in shrimp.

A rapid, sensitive, liquid chromatographic (LC) method has been developed for determination of residuals of the processing aid, 4-hexylresorcinol, on shrimp meat. An aqueous homogenate of shrimp meat is extracted with ethyl acetate followed by precolumn preparation on a silica Sep-Pak cartridge. LC determination is preformed with a Nova-Pak C18 column, with UV detection at 214 nm. Sensitivity was 0.006 micrograms, and recovery from shrimp meat samples of known 4-hexylresorcinol addition was 94%. Shrimp treated with 4-hexylresorcinol under the recommended dip protocol had mean residuals of 1.18 ppm, with a standard deviation of 0.13 ppm.

Animals↗

Determination of noscapine, hexylresorcinol and anethole in cough lozenges by liquid chromatography.

A liquid chromatographic method was developed for the simultaneous separation and determination of noscapine hydrochloride, hexylresorcinol and anethole in cough lozenges. Analysis was performed on a phenyl column with phosphate buffer- acetonitrile as mobile phase and the separated components were detected at 282 mm. Recoveries obtained for the analytes were of 94.6% for noscapine hydrochloride, 99.1% for hexylresorcinol and 96.3% for anethole. The values of the relative standard deviation were 0.8% for noscapine hydrochloride, 1.5% for hexylresorcinol and 1.1% for anethole. The analytical method was validated and a system suitability test was accomplished for the chromatographic method.

Anethole Trithione↗

Quantitative determination of hexylresorcinol in commercial antiseptic solution by high-pressure liquid chromatography.

High-pressure liquid chromatography was used with a 5-micron silica gel column to quantitate hexylresorcinol in a commercial antiseptic solution following extraction with methylene chloride. This method shows linearity to at least 0.025% hexylresorcinol. A mobile phase consisting of 63% heptane, 34% chloroform, and 5% methanol was used with a UV detector (254 nm) and a flow of 3 ml/min. No interfering substances were observed.

Anti-Infective Agents, Local↗

The treatment of Fasciolopsis buski infection in children: a comparison of thiabendazole, mebendazole, levamisole, pyrantel pamoate, hexylresorcinol and tetrachloroethylene.

Four relatively new broad spectrum anthelmintics (thiabendazole, mebendazole, levamisole and pyrantel pamoate) were compared with two older anthelmintics, (tetrachloroethylene and hexylresorcinol) to treat heavy Fasciolopis buski infections in 17 children aged 4-13 years in hospital. Tetrachloroethylene was the most effective drug in these 17 children and another 49. Large numbers of worms were expelled and faecal egg counts were markedly reduced (99%). The mean number of worms per child was 122 with a range of 7 to 818. All the other anthelmintics tested were ineffective; no worms or only a few were expelled after treatment. However, the oral administration of tetrachloroethylene and hexylresorcinol were associated with severe anaphylactic reactions which were prevented by prior treatment with antihistamines.

Adolescent↗

Influence of pH, benzoic acid, glutathione, EDTA, 4-hexylresorcinol, and sodium chloride on the pressure inactivation kinetics of mushroom polyphenol oxidase.

Pressure inactivation of mushroom PPO was studied for pH values ranging from 4 to 8, and the effect of some antibrowning agents on the pressure stability of mushroom PPO at pH 6.5 was evaluated. pH reduction below 6.5 resulted in a lowered inactivation threshold pressure and an increase of the absolute value of the activation volume (or a decrease of the z(p) value), the latter two parameters reflecting the pressure dependency of the inactivation rate constant. An increase in pH from 6.5 to 8, on the other hand, did only marginally affect the pressure stability of the enzyme. Mushroom PPO at pH 6.5 was markedly sensitized toward pressure by the presence of 2.5 mM 4-hexylresorcinol and slightly stabilized by the presence of 5 mM EDTA. The presence of 5 mM glutathione, sodium chloride, or benzoic acid caused no significant alteration of the enzyme pressure stability. Only in the presence of 4-hexylresorcinol, significant changes of the activation volume and z(p) value were noticed.

Agaricales↗

Exposure time and the effect of hexylresorcinol on bacterial aggregates.

The bactericidal effect of hexylresorcinol was assessed using bacterial aggregates. Increased drug concentration resulted in decreased survival of bacteria when the aggregates were exposed to hexylresorcinol for at least eight hours. This indicates that this drug may be effective against dental plaque only when available for long periods of time.

Actinomyces↗

[A comparative study of the inducing effect of homoserine lactone and hexylresorcinol on phenotypic dissociation in bacteria].

It has been shown that the phenotypic dissociation of Bacillus subtilis SK1 and S. typhimurium TA100 is induced by hexylresorcinol, an exogenous non-species-specific autoregulator of pleiotropic action, which is genotoxic for both pro- and eukaryotes. Nongenotoxic homoserine lactone, a chemical analogue of cell-density-responsive species-specific regulators, does not induce bacterial dissociation. The phage resistance of the S- and R-type variants of S. typhimurium TA100 induced by hexylresorcinol has been found to be the same as that of the S- and R-type salmonella variants obtained by the routine subculturing method.

4-Butyrolactone↗

Inhibition of some spontaneous tumors by 4-hexylresorcinol in F344/N rats and B6C3F1 mice.

4-Hexylresorcinol (4-HR) is used as an anthelmintic and antiseptic in human and veterinary medicine. Toxicology and carcinogenesis studies were conducted by administering 4-HR in corn oil by gavage at 0, 62.5, or 125 mg/kg to F344 rats and B6C3F1 mice of each sex for 2 years. The nonneoplastic lesions associated with 4-HR exposure were nephropathy and osteosclerosis in dosed male and female mice. The only evidence of neoplasia associated with 4-HR was marginally increased incidences of adrenal gland pheochromocytomas and harderian gland tumors in male mice. Decreases were observed in the incidences of mononuclear cell leukemia in dosed male and female rats, hepatocellular adenomas or carcinomas in dosed male mice, and circulatory system tumors in high-dose male and female mice. These negative tumor trends in rats and mice, along with an indication of reduced overall incidences of benign and malignant tumors in treated groups compared to controls, suggest that 4-HR may deserve further study as a possible antineoplastic agent.

Animals↗

4-Hexylresorcinol as inhibitor of shrimp melanosis: efficacy and residues studies; evaluation of possible toxic effect in a human intestinal in vitro model (Caco-2); preliminary safety assessment.

Studies were performed on the efficacy, residues and in vitro enterocyte toxicity of 4-hexylresorcinol (4-HR), which could be utilized as an inhibitor of shrimp melanosis (black spot). Mediterranean sea shrimp (Parapaeneus longirostris) were treated with solutions of 4-HR in sea-water, at three different concentrations, 25, 50 or 100 mg/kg of shrimp, to test its antioxidative property. As a comparison a group of shrimp was treated with sodium metabisulphite (1 g/kg), while another group was left untreated. 4-HR showed a marked ability to inhibit or slow down melanosis (black spot) in shrimp; the most effective concentration was 100 mg/kg within an optimum period of 7 days but with effects up to the tenth day. During the first 5 days, 4-HR residues in the edible part of the shrimp showed a fast decrease in all three groups, going from initial average values of 20 mg/kg at 0 time, to 0.9 in the group treated at 25 mg/kg; from 42 to 1.8 mg/kg in the group at 50 mg/kg and from 85 to 1.9 mg/kg in the group at 100 mg/kg. In vitro studies on enterocyte-like Caco-2 cells did not indicate any cytotoxic effect up to a concentration of 50 micrograms/ml. Moreover, no inhibition of protein synthesis was observed, which lends further support to the absence of significant damage to the intestinal mucosa induced by 4-HR. The available database on 4-HR pharmacology and toxicology is inadequate to determine even a provisional ADI. There is negative evidence of carcinogenesis and no significant untoward effects were observed in humans when it was used as an anthelmintic. However, it is not possible to determine a NOEL for non-genotoxic effects. 4-HR could become an interesting alternative to the use of sulphites to prevent black spot. However, a more complete database is needed to achieve a regulatory evaluation.

Animals↗

Review of the 4-hexylresorcinol procedure for acrolein analysis.

The purpose of this paper is to present laboratory results showing major problems with the 4-hexylresorcinol method used for acrolein analysis. A discrepancy in the analytical procedure described by ASTM and NIOSH gives rise to underestimation of acrolein levels based on the length of time the mixed reagents have been prepared prior to sampling. Underestimations by as much as 35% may occur due to the problems in the existing methodologies.

Acrolein↗