6259-76-3

Usage

Uses

Used in Analytical Chemistry:
Hexyl salicylate is used as an internal standard for the determination of allergenic ester, benzyl salicylate in propolis specimens using gas chromatography-mass spectrometry (GC-MS), high-performance liquid chromatography (HPLC), and ultraviolet-visible (UV-Vis) spectrophotometry. It helps to improve the accuracy and precision of the analysis by providing a reference point for comparison.
Used in Wastewater Treatment:
Hexyl salicylate is used as a standard fragrance material for the quantification of the analyte in wastewater treatment plants using gas chromatography-mass spectrometry (GC-MS). This application aids in monitoring and controlling the levels of fragrance compounds in wastewater, ensuring effective treatment and environmental safety.

Preparation

By methyl salicylate exchange with n-hexanol using a sodium methoxylate catalyst.

Flammability and Explosibility

Nonflammable

Metabolism

Because of the widespread medicinal use of salicyclic acid and its derivatives, there is an extensive literature on the metabolism and excretion of these compounds. Most esters of salicyclic acid hydrolyse to salicylic acid in the body, but this occurs more readily with the lower esters, little of the amyl ester being split. A large proportion of salicylic acid is excreted unchanged by most species; salicyluric acid, gentisic acid, and salicylglucuronides are also known to be excreted (Williams. 1959). Salicylic acid has been found to be teratogenic to rats (Koshakji. 1972).

InChI:InChI=1/C13H18O3/c1-2-3-4-7-10-16-13(15)11-8-5-6-9-12(11)14/h5-6,8-9,14H,2-4,7,10H2,1H3

Synthetic route

salicylic acid (69-72-7) + hexan-1-ol (111-27-3) → salicylic acid hexyl ester (6259-76-3)

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 20h; Inert atmosphere;	40%
With dmap; dicyclohexyl-carbodiimide In dichloromethane
With N-propanesulfonic acid pyridinium hydrogen sulfate at 105℃; for 0.333333h; Microwave irradiation;
With 1-methyl-3-(4-sulfobutyl)-1H-imidazol-3-ium hydrogensulfate at 130℃; for 2h; Reagent/catalyst;

1-bromo-hexane (111-25-1) + salicylic acid (69-72-7) → salicylic acid hexyl ester (6259-76-3)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl acetamide at 90℃; for 0.5h;

hexyl 2-benzyloxybenzoate (1330047-14-7) → salicylic acid hexyl ester (6259-76-3)

Conditions	Yield
With hydrogen; acetic acid; palladium hydroxide - carbon In ethyl acetate for 12h;	95 mg

C14H27N2OPol + salicylic acid (69-72-7) → salicylic acid hexyl ester (6259-76-3)

Conditions	Yield
In acetonitrile at 150℃; for 0.0833333h; Microwave irradiation; solid phase reaction;

C13H28N2O (123196-37-2) + salicylic acid (69-72-7) → 1,3-diisopropylurea (4128-37-4) + salicylic acid hexyl ester (6259-76-3)

Conditions	Yield
In acetonitrile at 120℃; for 0.0833333h; Microwave irradiation;

salicylaldehyde (90-02-8) + hexan-1-ol (111-27-3) → salicylic acid hexyl ester (6259-76-3)

Conditions	Yield
With cation-exchange resin 001x7 modified with Ce(SO4)2 at 94.84℃; under 760.051 Torr; for 12h;

salicylic acid hexyl ester (6259-76-3) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2-hexoxycarbonylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Conditions	Yield
With 1-Methylpyrrolidine; potassium carbonate at 75℃; for 2h; Molecular sieve;	78%

salicylic acid hexyl ester (6259-76-3) + acryloyl chloride (814-68-6) → hexyl 2-(acryloyloxy)benzoate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h;	71%

salicylic acid hexyl ester (6259-76-3) + acetyl chloride (75-36-5) → hexyl acetylsalicylate

Conditions	Yield
With triethylamine In dichloromethane at 40℃; for 20h; Inert atmosphere;	66%

salicylic acid hexyl ester (6259-76-3) → salicylic alcohol (90-01-7)

Conditions	Yield
With sodium tetrahydroborate; cetyltrimethylammonim bromide In water; acetonitrile at 20℃;	84 % Chromat.

salicylic acid hexyl ester (6259-76-3) + terbium(III) nitrate + triethylamine (121-44-8) → C6H16N(1+)*16C25H33O3(1-)*8HO(1-)*2O(2-)*9Tb(3+)

Conditions	Yield
In methanol at 20℃; for 0.5h;

salicylic acid hexyl ester (6259-76-3) → n-hexyl O-(3-dimethylaminopropyl)salicylate

Conditions	Yield
In hexan-1-ol

terbium(III) nitrate hexahydrate + salicylic acid hexyl ester (6259-76-3) → hexadeca(hexylsalicylate)deca(.mu-hydroxo)nonaterbium(III) nitrate

Conditions	Yield
With triethylamine In methanol salicylate dissolved, amine added at 40°C, Tb compd. in methanol added dropwise, stirred for 20 min; elem. anal.;

Upstream product

• 1330047-14-7 hexyl 2-benzyloxybenzoate 
• 90-02-8 salicylaldehyde 
• 111-27-3 hexan-1-ol 
• 123196-37-2 C₁₃H₂₈N₂O 
• 69-72-7 salicylic acid 
• 111-25-1 1-bromo-hexane 

Downstream Products

• 90-01-7 salicylic alcohol 

Relevant academic research and scientific papers

Synthesis, computational evaluation and pharmacological assessment of acetylsalicylic esters as anti-inflammatory agents

A convenient approach to the synthesis of alkyl esters of aspirin (ASA-OR) has been developed. The synthesis of ASA-OR has been realized in two steps: (1) direct esterification of salicylic acid with alcohols in the presence of dicyclohexylcarbodiimide to give alkyl salicylates (SAL-OR); (2) acetylation of SAL-OR with acetyl chloride to yield ASA-OR. Molecular mechanics simulations, performed to calculate the kinetic radii of several ASA-OR, indicated that the pentyl and hexyl acetylsalicylates possess the best properties to cross cell membranes. The in vitro biological tests demonstrate their anti-inflammatory activity, superimposable to that of aspirin. The results of our study suggest that ASA-OR may be used as anti-inflammatory drugs for topical application.

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

Six Bronsted acidic ionic liquids (BAILs) composed of [HSO 4] were prepared, characterized, and used as catalysts of low dosage in the synthesis of isoamyl salicylate. The effects of various parameters such as the kind of BAILs, temperature, catalyst loading, and molar ratio of the reactants on the conversion of salicylic acid were also examined in detail. The results suggested that the catalytic performances of BAILs were of close relevance to their Hammett acidities. The SO3H-functionalized BAILs 1-(4-sulfonic acid) butyl-3-methylimidazolium hydrogen sulfate ([BSmim][HSO 4]) and N-(4-sulfonic acid) butyl triethylammonium hydrogen sulfate ([BSEt3N][HSO4]) of strong acidities exhibited excellently catalytic activities and selectivities in the esterification of salicylic acid with isoamyl alcohol. The fully optimized geometries of [BSmim][HSO4] and [BSEt3N][HSO4] further manifest that their strong acidities are derived from the strong interactions between the anion with the sulfonic acid group. In addition, it was found that [BSmim][HSO4] could be also recovered easily and used repetitively at least six times without obvious decline in activity and quantity.

Esterification of salicylic acid using Ce4+ modified cation-exchange resin as catalyst

The esterification of salicylic acid with methanol was carried out over a series of Ce4+ modified cation-exchange resins. The effect of different reaction conditions was studied on the conversion of salicylic acid, and the optimal reaction parameters were obtained. The experimental results indicated that Ce(SO4)2/001×7 was an effective catalyst for the synthesis of methyl salicylate. The conversion of salicylic acid could reach 93.3% while its selectivity was more than 99.0%. SEM-EDS and TG-DSC analysis were employed to characterize the structure and property of the catalyst. Besides, the catalytic performance of Ce(SO4) 2/001×7 in the esterification of salicylic acid with different alcohols was compared. The reusability of Ce(SO4)2/ 001×7 was also studied by using salicylic acid and methanol as model substrates. The mechanism was proposed for the esterification of salicylic acid with methanol over Ce4+ modified cation-exchange resins.

LILIAN SURROGATE

Due to toxicological concerns, it may be desirable to replace the fragrance compound lilial with less problematic compounds without losing the creative power and quality regarding perfumes. The present invention addresses this need by using selected oxazolidines described herein.

Microwave-accelerated esterification of salicylic acid using Br?nsted acidic ionic liquids as catalysts

A variety of Br?nsted acidic ionic liquids were screened as catalysts for the esterification of salicylic acid. The experimental results indicated that SO3H-functionalized ionic liquids with HSO4- performed high catalytic activity under microwave irradiation, and the yields can reach 91.9-93.6%. Furthermore, ionic liquids can be easily separated by simple decantation and have a fair reusability. The Br?nsted acidity-catalytic activity relationships were also investigated and the results showed that the activity of the acidic ionic liquids is in excellent agreement with their acidity order. Crown Copyright

Microwave-assisted ester formation using O-alkylisoureas: A convenient method for the synthesis of esters with inversion of configuration

(Chemical Equation Presented) The formation of carboxylic esters via reaction of carboxylic acids with O-alkylisoureas proceeds in excellent yields with very short reaction times when conducted in a monomode microwave synthesizer. Efficient processes were

Design and evaluation of anacardic acid derivatives as anticavity agents

On the basis of antibacterial anacardic acids, 6-pentadecenylsalicylic acids, isolated from the cashew apple, Anacardium occidentale L. (Anacardiaceae), a series of 6-alk(en)ylsalicylic acids were synthesized and tested for their antibacterial activity against Streptococcus mutans ATCC 25175. Among them, 6-(4′,8′-dimethylnonyl)salicylic acid was found to exhibit the most potent antibacterial activity against this cariogenic bacterium with the minimum inhibition concentration (MIC) of 0.78 μg/ml.

Efficient and simple NaBH4 reduction of esters at cationic micellar surface

(Chemical Equation Presented) A simple, efficacious, and biocompatible methodology for reducing esters with sodium borohydride at an aqueous cationic micellar surface under ambient conditions has been developed. The present method holds promise for future use in selective functional group reduction and stereocontrolled alcohol synthesis.

PERFUME COMPOSITION

A perfume composition contains specified ketones, salicylates and alcohols/acetates/propionates. Use of such a perfume composition inhibits development of human body malodour. The combination of specified materials makes it possible to avoid inclusion of individual components with powerful, unacceptable odours. The perfume composition may be used in various products notably in a fabric conditioning product used during the rinsing or tumble drying of fabrics after washing to soften the fabrics.

Perfume compositions

A perfume composition contains at least 50% by weight of materials which fall into five categories defined by structure, and molecular weight. Amounts of material within each category fall within specified ranges of percentage of the whole composition. Two categories, ethers and salicylates, must be present. At least two of the remaining three categories, which are alcohols, acetate/propionate esters and methyl aryl ketones, must also be present. The compositions enable good levels of deodorant activity to be achieved along with consumer-acceptable fragrance.