Isoamyl Salicylate Research Articles

Update to RIFM fragrance ingredient safety assessment, isoamyl salicylate, CAS Registry Number 87-20-7

Update to RIFM fragrance ingredient safety assessment, isoamyl salicylate, CAS Registry Number 87-20-7

Use of in vitro ADME methods to identify suitable analogs of homosalate and octisalate for use in a read-across safety assessment.

Case studies are needed to demonstrate the use of human-relevant New Approach Methodologies in cosmetics ingredient safety assessments. For read-across assessments, it is crucial to compare the target chemical with the most appropriate analog; therefore, reliable analog selection should consider physicochemical properties, bioavailability, metabolism, as well as the bioactivity of potential analogs. To complement in vitro bioactivity assays, we evaluated the suitability of three potential analogs for the UV filters, homosalate and octisalate, according to their in vitro ADME properties. We describe how technical aspects of conducting assays for these highly lipophilic chemicals were addressed and interpreted. There were several properties that were common to all five chemicals: they all had similar stability in gastrointestinal fluids (in which no hydrolysis to salicylic occurred); were not substrates of the P-glycoprotein efflux transporter; were highly protein bound; and were hydrolyzed to salicylic acid (which was also a major metabolite). The main properties differentiating the chemicals were their permeability in Caco-2 cells, plasma stability, clearance in hepatic models, and the extent of hydrolysis to salicylic acid. Cyclohexyl salicylate, octisalate, and homosalate were identified suitable analogs for each other, whereas butyloctyl salicylate exhibited ADME properties that were markedly different, indicating it is unsuitable. Isoamyl salicylate can be a suitable analog with interpretation for octisalate. In conclusion, in vitro ADME properties of five chemicals were measured and used to pair target and potential analogs. This study demonstrates the importance of robust ADME data for the selection of analogs in a read-across safety assessment.

QSAR and Anticancer effect of Alkyl salicylate on Breast cancer T47D Cells Lines

Cancer is a major health concern in both developed and developing countries, second leading cause of mortality worldwide. Among the different types of cancer, breast cancer is the most common cancer found in females worldwide. Studies have shown that salicylic acid decreases cell viability and potentially used in cancer therapy. This research aim is to analyze the cytotoxicity effect of alkylated salicylic acid towards breast cancer cells T47D. Samples used are methyl salicylate, ethyl salicylate, butyl salicylate, isoamyl salicylate, and octyl salicylate. Thin layer chromatography was done to samples and MTT test was done against T47D cancer cells to obtain cancer cell growth and IC50 value. QSAR analysis were carried out to predict the theoretical activity of the alkylated salicylates. Based on MTT result, there was shown an increase of cytotoxicity effect with higher concentration. IC50 value of alkylated salicylic acid showed more significant cytotoxicity effect (p<0,05) when compared to IC50 value of salicylic acid, except octyl salicylate. This shows that addition of alkyl group enhances cytotoxicity effect of salicylic acid due to increase of affinity. The IC50 value of alkylated salicylic acid showed lower results compared to salicylic acid. The QSAR equation is Log (1/IC50) = -1236.21871 - 236.42806 *logP(o/w) -1186.53810 * AM1_LUMO +251.55826* mr ((n = 7 r = 0,94 RMSE = 4,08). The QSAR showed the descriptors which has effect towards inhibition activity of breast cancer cell line are log P, mr, and AM_1LUMO.

Chemical composition, antioxidant, anticholinesterase, antimicrobial and antibiofilm activities of essential oil and methanolic extract of Anthemis stiparum subsp. sabulicola (Pomel) Oberpr

Anthemis species are traditionally used to treat infectious and inflammatory processes, among others clinical disturbances. In the current study, the chemical composition, the total phenolic and flavonoid contents, the antioxidant, anticholinesterase, antimicrobial, and antibiofilm activities of Anthemis stiparum subsp. sabulicola aerial parts methanolic extract (As-ME) and essential oil (As-EO) were investigated. The chemical composition of As-EO was established by GC-MS and GC-FID. Total phenolic and flavonoid contents of As-ME were spectrophotometrically determined. Diphenyl-1-picrylhydrazyl (DPPH●) radical scavenging, cupric reducing antioxidant capacity (CUPRAC) and β-carotene bleaching assays were applied to evaluate the antioxidant potential. The anticholinesterase activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes were carried out spectrophotometrically. The antimicrobial activity was assessed by Minimal Inhibitory Concentration (MIC) using broth microdilution method against 7 ATCC® bacterial and one ATCC® yeast reference strains. The antibiofilm effect was determined quantifying the percentage of adhesion inhibition. GC-MS and GC-FID identified 72 compounds (99.02%), being As-EO predominantly constituted by germacrene D (11.13%), t-cadinol (11.01%), camphor (6.73%), spathulenol (6.50%) and isoamyl salicylate (6.45%). The total phenolic and flavonoid contents of As-ME were 13.6 ± 0.03 and 5.9 ± 0.04 pyrocatechol equivalents and quercetin equivalents, respectively. In β-carotene-linoleic acid assay, As-ME showed the best lipid peroxidation inhibition activity with an IC50 = 9.96 μg/mL followed by As-EO with an IC50 = 619.98 μg/mL. In contrast, in DPPH assay, As-ME and As-EO showed moderate to low activity with an IC50 = 92.69 μg/mL for As-ME and 917.69 μg/mL for As-EO. While in CUPRAC assay, As-EO and As-ME indicated a less to moderate reducing activity. As-ME inhibited AChE (IC50 = 490.46 μg/mL) and BChE (IC50 = 142.07 μg/mL), while As-EO was inactive against AChE and revealed a discreet inhibitory action against BChE (IC50 = 212.14 μg/mL). As-ME displayed better antimicrobial activity than As-EO, being active against Staphylococcus aureus (ATCC® 25923) and Bacillus subtilis (ATCC® 6633), with MIC of 1.56 mg/mL. An expressive fungal adhesion inhibition (80.02%) on Candida albicans (ATCC® 10239) was detected with As-ME at 6.25 mg/mL. These results showed that A. stiparum subsp. sabulicola is a natural source of active compounds with antibiotic and antibiofilm effects against S. aureus and B. subtilis, and C. albicans, respectively, and also presents antioxidant and anticholinesterase properties.

Scientific Opinion on the safety and efficacy of CRINA® Poultry Plus (benzoic acid, thymol, eugenol and piperine) as a feed additive for chickens for fattening, chickens reared for laying and minor poultry species for fattening and reared for laying

Crina® Poultry Plus is a preparation of benzoic acid, thymol, eugenol, piperine, benzyl salicylate, isoamyl salicylate and trans-anethole. In a previous opinion, the FEEDAP Panel could not conclude on the safety of the additive for chickens for fattening, the consumer or the environment, or on its efficacy. Based on the results from a new tolerance study, the FEEDAP Panel concluded that Crina® Poultry Plus is safe for chickens for fattening at the maximum recommended dose (300 mg/kg). This conclusion can be extended to chickens reared for laying and extrapolated to minor species for fattening/reared for laying with the same maximum dose. New data on the metabolism of eugenol and on residues of eugenol and piperine indicated that exposure of consumers to residues of these substances when consuming edible tissues from chickens for fattening receiving the additive would not be expected. Therefore, the use of Crina® Poultry Plus in chickens for fattening and minor poultry species for fattening is of no concern for consumers. The FEEDAP Panel concluded that the use of Crina® Poultry Plus in chickens for fattening, chickens reared for laying and minor species for fattening/reared for laying is of no concern for the environment. Three out of ten studies showed some beneficial effect on zootechnical parameters of Crina® Poultry Plus at a dose of 300 mg/kg complete feed. The Panel concluded that the additive has some potential to be efficacious in chickens for fattening at a dose of 300 mg/kg complete feed. This conclusion can be extended to chickens reared for laying and extrapolated to include the minor poultry species for fattening and reared for laying at the same dose.

SO3H-functionalized Brønsted acidic ionic liquids as efficient catalysts for the synthesis of isoamyl salicylate

Six Brønsted acidic ionic liquids (BAILs) composed of [HSO4] were prepared, characterized, and used as catalysts of low dosage in the synthesis of isoamyl salicylate.

Synthesis of isoamyl salicylate using a novel mesoporous titania superacid as a catalyst

Mesoporous titania was prepared by hydrothermal method and mesoporous titania solid superacid catalyst was prepared by wet impregnation method. The structure and property of the as-prepared catalysts were characterized by means of XRD, FT-IR and N2 physical adsorption. Isoamyl salicylate was synthesized by using concentrated sulfuric acid and solid superacid as catalyst, respectively. The effects of the molar ratio of raw material, the amount of catalyst, reaction time and reaction temperature on the yield of the product were systematically investigated. The results show that mesoporous titania solid superacid is a good catalyst for synthesizing isoamyl salicylate. The optimum conditions of isoamyl salicylate synthesized by using mesoporous titania solid superacid are the following: the molar ratio of salicylic acid to isoamyl alcohol is 1: 4, the quantity of catalyst is 1.6 g, the reaction time is 5 h, the reaction temperature is 130 °C and the yield can reach 94.6%.

A Smelling Trip into the Past: The Influence of Synthetic Materials on the History of Perfumery

Contemporary perfumery has its roots in the work of the past, and many of the perfumes from this time have long since disappeared. What follows is a short account of some of the most famous perfumes from the past which have been inspired by the novel synthetic materials of the time. These important creations include, 'Fougère Royale' by Houbigant (1884) containing coumarin (1), 'Jicky' by Guerlain (1889) containing vanillin (2) and linalool (3), 'Vera Violetta' by Roger & Gallet (1892) containing alpha- and beta-ionone (4 and 5, resp.), 'Trèfle Incarnat' by Piver (1898) containing isoamyl salicylate (6), 'La Rose Jacqueminot' of Coty (1904) containing Rhodinol (7), 'Après l'Ondée' by Guerlain (1906) containing para-anisaldehyde (8), 'Quelques Fleurs' by Houbigant (1912) containing hydroxycitronellal (9), 'N degrees 5' by Chanel (1921) containing the aldehydes C-10 (10), C-110 (11), and C-12 (12), 'Nuit De Noël' by Caron (1922) containing 6-isobutylquinoline (14), and 'Femme' by Rochas (1944) containing the so-called 'aldehyde C-14' (15, gamma-undecalactone). The Osmotheque, the International Conservatory of Perfumes, was launched in 1990 and is regarded as a primary source of knowledge for the history of perfumery. Its vocation is to compile an amazing collection of 1700 perfumes (400 of them almost forgotten fragrances)--jewels of perfumery.

Preparation of mesoporous titania solid superacid and its catalytic property

Mesoporous titania (TiO 2) was synthesized by hydrothermal method using cetyltrimethyl ammonium bromide (CTAB) as a template and using anhydrous ethanol and tetra- n-butyl titanate (TBOT) as raw materials. Mesoporous titania solid superacid and nanosized titania solid superacid catalysts were prepared by wet impregnation method. The structure and property of as-prepared samples were characterized by means of XRD, FT-IR and N 2 physical adsorption. The esterification of salicylic acid with isoamyl alcohol and the condensation of cyclohexanone with ethylene were used as model reactions to test the catalytic activities of the catalysts. On the other hand, the comparison of catalytic activities of the prepared solid superacid catalysts and the conventional liquid acid H 2SO 4 was also carried out under the same experimental conditions. The results show that the catalytic activities of the prepared solid superacid catalysts were higher than that of the conventional liquid acid H 2SO 4, and that the catalytic activity of mesoporous TiO 2 solid superacid is the highest among the three catalysts. Mesoporous TiO 2 solid superacid is a good catalyst for the synthesis of isoamyl salicylate or cyclohexanone ethylene ketal.

Short-term toxicity of isoamyl salicylate in rats

Isoamyl salicylate was given to groups of 15 male and 15 female rats at dietary concentrations of 0 (control), 50, 500 or 5000 ppm for 13 wk. There was a decrease in weight gain at the highest dietary level accompanied by a reduced food intake, but a paired-feeding study showed that this was due to the diet's unpalatability. The females given the highest dietary level drank more water than the controls and produced slightly greater volumes of more dilute urine. The relative kidney weight was increased in rats on the 500 and 5000 ppm levels without any histopathological changes. It is concluded that isoamyl salicylate was exerting a mildly nephrotoxic effect. The relative liver weight was increased at the highest level of feeding but there were no other effects attributable to treatment. The no-untoward-effect level from this study was 50 ppm of the diet, providing a mean intake of approximately 4·7 mg/kg/day.

Sphingidae 1 Collected in Blacklight Traps Baited with Isoamyl Salicylate

Collections of male tobacco horn worms, Manduca sexta (L.), in blacklight (BL) traps can be increased 10 or more times by baiting the traps with virgin female moths (Hoffman et al. 1966, Cantelo and Smith 1971). However. the rearing of these females is expensive and time consuming, and a synthetic female pheromone is not available. Therefore, we hoped to find a substitute material that could be used to increase collections. Isoamyl salicylate was chosen for evaluation because when it was used to bait relatively inefficient screen traps in Tennessee, it caught as many as 925 tobacco hornworms in a season. Also, 16 other species of sphingids were caught, but only Byles lineata (F.) and Xylophanes tersa (L.) were caught “in numbers” (Morgan and Lyon 1928). Moreover, at Oxford, N. C., collections in 12 similar-type traps (Stahl 1954) baited with isoamyl salicylate plus simulated jimson weed flowers averaged 112 M. sexta and 155 tomato hornworms, M. quinquemaculata (Haworth), each year from 1942 through 1953 with peak yearly collections of 414 M. sexta and 218 M. quinquemaculata . (However, in 1949, unbaited BL traps collected 15 × as many hornworm moths (both species) and in 1952–53 7–9× as many as the baited screen traps.)

Gas chromatography of?-valerolactam and?-valerolactone from reductive amination of butyl levulinate

Theγ-valerolactam andγ-valerolactone in the reductive amination products of butyl levulinate in water or alcoholic medium, after removing most of the light fractions, ammonia, and water or alcohol, have been determined by isothermal gas chromatography using phenylether or isoamyl salicylate as the internal standard. With the thermal conductivity detector, a column of 6 mm I. D., 2 m long copper tubing packed with 25% glycol adipate/chromosorb-W was used, with hydrogen as the carrier gas. The accuracy was ± 0.4% forγ-valerolactone and ± 0.5% forγ-valerolactam. Using the hydrogen flame ionization detector, a column of 3 mm I. D., 2 m long stainless steel tubing packed with 10% glycol adipate/chromosorb-W was used, with nitrogen as the carrier gas; the accuracies forγ-valerolactone andγ-valerolactam were ± 0.5% and ± 0.8% respectively.

Isoamyl Salicylate as an Attractant for Hornworm Moths1

Isoamyl Salicylate as an Attractant for Hornworm Moths1

Tartar Emetic as a Poison for the Tobacco Horn Worm Moths, a Preliminary Report

Tests of forty materials during several seasons in an effort to discover an efficient stomach poison for the tobacco hornworm moths, Phlegethontius sexta Joh. and P. quinquemaculata Haw., have revealed that a 5 per cent solution of tartar emetic is an effective and satisfactory poison when used in conjunction with isoamyl salicylate as an attractant. Large-scale field experiments have been conducted for three successive seasons with promising results. The latest type of moth feeder developed is illustrated.