6259-76-3

Basic information

• Product Name: Hexyl salicylate
• Synonyms: HEXYL 2-HYDROXYBENZOATE;HEXYL SALICYLATE;HEXYL SALICYLATE, N-;SALICYLIC ACID N-HEXYL ESTER;O-HYDROXYBENZOIC ACID N-HEXYL ESTER;N-HEXYL-2-HYDROXYBENZOATE;N-HEXYL ORTHO HYDROXY BENZOATE;N-HEXYL SALICYLATE
• CAS NO: 6259-76-3
• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 222.28
• EINECS: 228-408-6
• Product Categories: Used in variety of cosmetic and soap essences.;Food Additive
• Mol File: 6259-76-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 290 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.04 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000491mmHg at 25°C
• Refractive Index: n20/D 1.505(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.17±0.30(Predicted)
• Water Solubility: 0.28g/L(37 oC)
• BRN: 2453103
• CAS DataBase Reference: Hexyl salicylate(CAS DataBase Reference)
• NIST Chemistry Reference: Hexyl salicylate(6259-76-3)
• EPA Substance Registry System: Hexyl salicylate(6259-76-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3082 9 / PGIII
• WGK Germany: 2
• RTECS: DH2207000
• Hazardous Substances Data: 6259-76-3(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 6259-76-3 differently. You can refer to the following data:
1. Colorless and transparent oil liquid
2. Hexyl Salicylate has been reported in carnation flower absolute . It is a colorless liquid with a green, floral, spicy odor, reminiscent of azaleas. It is used for blossom and herbal notes in perfumes, for example, in soaps, personal hygiene products, and detergents.

Occurrence

Has apparently not been reported to occur in nature.

Uses

Hexyl salicylate may be 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 may also be used as a standard fragrance material for the quantification of the analyte in wastewater treatment plants using gas chromatography-mass spectrometry (GC?MS).

Preparation

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

General Description

Hexyl salicylate belongs to the class of flavor & fragrance standards, for use in food, beverage and cosmetic industry. These standards are widely used to add taste and/or smell to products without aroma, to mask unpleasant odors and to maintain stability of original flavor.

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

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

Downstream Products

• 90-01-7 salicylic alcohol 

Relevant articles and documents

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.

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.

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