2050-08-0

Basic information

• Product Name: Amyl salicylate
• Synonyms: amylesterkyselinysalicylove;Benzoic acid, 2-hydroxy-, pentyl ester;Benzoicacid,2-hydroxy-,pentylester;Pentyl-o-hydroxybenzoate;Salicylic acid, amyl ester;Salicylic acid, pentyl ester;salicylicacid,pentylester;salicylicacidpentylester
• CAS NO: 2050-08-0
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25
• EINECS: 218-080-2
• Mol File: 2050-08-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 270°C
• Flash Point: 113.3 °C
• Appearance: /
• Density: 1.056
• Vapor Pressure: 0.00144mmHg at 25°C
• Refractive Index: 1.512
• Storage Temp.: -20°C
• PKA: 8.16±0.30(Predicted)
• Water Solubility: 5.5mg/L at 20℃
• BRN: 2577253
• CAS DataBase Reference: Amyl salicylate(CAS DataBase Reference)
• NIST Chemistry Reference: Amyl salicylate(2050-08-0)
• EPA Substance Registry System: Amyl salicylate(2050-08-0)

Safety Data

• RIDADR: UN 3082 9 / PGIII
• RTECS: VO5425000
• Hazardous Substances Data: 2050-08-0(Hazardous Substances Data)

Usage

Occurrence

Apparently has not been reported to occur in nature.

Preparation

By esterification of salicylic acid with the isomeric amyl alcohols obtained from fusel oil and other sources.

Toxicity evaluation

The LD50 value iv in dogs was reported as 0.5-0.8 g/kg(Fassett, 1963).Human testing. A maximization test(Kligman, 1966) was carried out on 25 volunteers. The material was tested at a concentration of 10% in petrolatum and produced no reactions(Kligman, 1970).Aspirin-containing drugs will cause exacerbation in some patients with chronic urticaria. The action is probably due to the salicylate radical. It is suggested that aspirin acts in chronic urticaria by enhancing the effect of histamine in the skin(Moore- Robinson & Warin, 1967).

Metabolism

Most of the esters of salicylic acid are decomposed to salicylic acid in the body and excreted as such. Besides the unchanged acid, salicuric acid, genticic acid and salicyl glucuronide have been known to be excreted. The lower esters of salicylic acid decompose more readily than the higher esters and as a consequence, little of the amyl ester is split. The whole subject of salicylic esters is covered in an extensive literature by Gross & Greenberg(1948).

InChI:InChI=1/C12H16O3/c1-2-3-6-9-15-12(14)10-7-4-5-8-11(10)13/h4-5,7-8,13H,2-3,6,9H2,1H3

Synthetic route

pentan-1-ol (71-41-0) + salicylic acid (69-72-7) → 2-hydroxy-benzoic acid, pentyl ester (2050-08-0)

Conditions	Yield
With nano-SiO2-supported Preyssler heteropolyacid In dichloroethane at 80℃; for 0.05h; Microwave irradiation;	89%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 20h; Inert atmosphere;	40%
With sulfuric acid unter Entfernen des entstehenden Wassers;

pentan-1-ol (71-41-0) + salicylaldehyde (90-02-8) → 2-hydroxy-benzoic acid, pentyl ester (2050-08-0)

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

2-hydroxy-benzoic acid, pentyl ester (2050-08-0) + acetyl chloride (75-36-5) → pentyl acetylsalicylate

Conditions	Yield
With triethylamine In dichloromethane at 40℃; for 20h; Inert atmosphere;	45%

chlorure d'acide ethyl-2 butyrique (2736-40-5) + 2-hydroxy-benzoic acid, pentyl ester (2050-08-0) → 2-(2-ethyl-butyryloxy)-benzoic acid pentyl ester

Conditions	Yield
With pyridine; diethyl ether

2-hydroxy-benzoic acid, pentyl ester (2050-08-0) → silicic acid tetrakis-(2-pentyloxycarbonyl-phenyl ester)

Conditions	Yield
With tetrachlorosilane

2-hydroxy-benzoic acid, pentyl ester (2050-08-0) → n-amyl O-(3-dimethylaminopropyl)salicylate (79660-07-4)

Conditions	Yield
In pentan-1-ol

2-hydroxy-benzoic acid, pentyl ester (2050-08-0) → n-amyl O-(3-diethylaminopropyl)salicylate (79660-09-6)

Conditions	Yield
In pentan-1-ol

2-hydroxy-benzoic acid, pentyl ester (2050-08-0) → n-amyl O-(2-diisopropylaminoethyl)salicylate (79660-13-2)

Conditions	Yield
In pentan-1-ol

2-hydroxy-benzoic acid, pentyl ester (2050-08-0) → n-amyl O-(3-dimethylamino-2-methylpropyl)salicylate (79660-16-5)

Conditions	Yield
In pentan-1-ol

2-hydroxy-benzoic acid, pentyl ester (2050-08-0) → n-amyl O-(2-dimethylaminoethyl)salicylate (79660-17-6)

Conditions	Yield
In pentan-1-ol

2-hydroxy-benzoic acid, pentyl ester (2050-08-0) → n-amyl O-(2-diethylaminoethyl)salicylate (79660-18-7)

Conditions	Yield
In pentan-1-ol

tetrachlorosilane (10026-04-7, 53609-55-5) + 2-hydroxy-benzoic acid, pentyl ester (2050-08-0) → silicic acid tetrakis-(2-pentyloxycarbonyl-phenyl ester)

Upstream product

• 71-41-0 pentan-1-ol 
• 90-02-8 salicylaldehyde 
• 69-72-7 salicylic acid 

Downstream Products

• 79660-18-7 n-amyl O-(2-diethylaminoethyl)salicylate 
• 79660-17-6 n-amyl O-(2-dimethylaminoethyl)salicylate 
• 79660-16-5 n-amyl O-(3-dimethylamino-2-methylpropyl)salicylate 
• 79660-13-2 n-amyl O-(2-diisopropylaminoethyl)salicylate 
• 79660-09-6 n-amyl O-(3-diethylaminopropyl)salicylate 
• 79660-07-4 n-amyl O-(3-dimethylaminopropyl)salicylate 

Relevant articles and documents

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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.