110-45-2

Basic information

• Product Name: Isopentyl formate
• Synonyms: IsoaMyl forMate, Mixture of isoMers;Isopentyl forMate >=95.0%;AMYL FORMATE;3-METHYLBUTYL FORMATE;lsoamyl formate;ISOAMYL FORMATE;ISOPENTYL FORMATE;ISOPENTYL METHANOATE
• CAS NO: 110-45-2
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.16
• EINECS: 252-343-2
• Product Categories: C6 to C7;Carbonyl Compounds;Esters;Building Blocks;C6 to C7;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 110-45-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: -93°C
• Boiling Point: 123-124 °C(lit.)
• Flash Point: 86 °F
• Appearance: /
• Density: 0.859 g/mL at 25 °C(lit.)
• Vapor Pressure: 10 mm Hg ( 17.1 °C)
• Refractive Index: n20/D 1.397(lit.)
• Explosive Limit: 8%
• Merck: 14,5119
• BRN: 1739893
• CAS DataBase Reference: Isopentyl formate(CAS DataBase Reference)
• NIST Chemistry Reference: Isopentyl formate(110-45-2)
• EPA Substance Registry System: Isopentyl formate(110-45-2)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37
• Safety Statements: 24-2
• RIDADR: UN 1109 3/PG 3
• WGK Germany: 1
• RTECS: NT0185000
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 110-45-2(Hazardous Substances Data)

Usage

Description

Isopentyl formate, also known as isoamyl formate, is a synthetic flavoring agent characterized by its moderately stable, colorless to light yellow liquid with a pungent pear-plum odor. It has a fruity, characteristic odor suggestive of black currant and plum, along with a corresponding sweet taste. Isopentyl formate is soluble in most fixed oils, mineral oil, and propylene glycol, and is typically stored in glass or tin containers. It is prepared by reacting concentrated H2SO4 over a mixture of isoamyl alcohols and sodium formate.

Uses

Used in Flavor Industry:
Isopentyl formate is used as a flavoring agent for its fruity, characteristic odor and sweet taste. It is particularly utilized in the creation of fruit flavors such as pear, plum, and peach, finding application in dessert gels, puddings, candy, and ice cream at concentrations of 14–28 ppm.
Used in Artificial Fruit Syrups:
In the food and beverage industry, isopentyl formate is also employed in artificial fruit syrups to enhance the flavor and aroma of various products.
Taste Threshold Values:
At a concentration of 15 ppm, isopentyl formate exhibits taste characteristics described as sharp green, apple, and fruity, with additional winey and fatty notes.
Occurrence:
Isopentyl formate can be found naturally in a variety of fruits, vegetables, and other products, including apple, pineapple, strawberry, vinegar, Gruyere cheese, chicken fat, beer, cognac, rum, cider, port wine, tea, honey, avocado, plumcot, mango, quince, and sea buckthorn (Hippophae rhamnoides L.).
Chemical Properties:
As a colorless liquid with a fruity odor, isopentyl formate is partially soluble in water and fully soluble in alcohol and ether. It is also combustible, which should be taken into consideration when handling and storing the compound.

Preparation

By reacting concentrated H2SO4 over a mixture of isoamyl alcohols and sodium formate.

Hazard

Strong irritant.

Purification Methods

The colourless liquid ester is soluble in 300 volumes of H2O and is soluble in common organic solvents. It is purified by repeated distillation using an efficient column at atmospheric pressure. [Beilstein 2 H 22, 2 I 18, 2 II 31, 2 III 43, 2 IV 30.]

InChI:InChI=1/C6H12O2/c1-6(2)3-4-8-5-7/h5-6H,3-4H2,1-2H3

Upstream product

• 64-18-6 formic acid 
• 4396-03-6 chlorosulfurous acid isopentyl ester 
• 123-51-3 i-Amyl alcohol 
• 544-01-4 isopentyl ether 
• 19533-24-5 sodium isopentoxide 
• 141-53-7 sodium formate 
• 71-41-0 pentan-1-ol 
• 144-62-7 oxalic acid 
• 4396-02-5 boric acid triisopentyl ester 
• 122502-29-8 2-Hydroperoxy-1,1-bis-(3-methyl-butoxy)-propan-2-ol 
• 10028-15-6 ozone 
• 67-56-1 methanol 
• 109-94-4 formic acid ethyl ester 
• 121393-39-3 5,10,15,20-tetra(2,4,6-trimethylphenyl)porphyrinate rhodium(II) 

Downstream Products

• 5416-80-8 2-methyl-1H-indole-3-carbaldehyde 
• 1003-29-8 2-pyrrole aldehyde 
• 78052-01-4 hydroxymethylene-2 tetramethyl-3,3,5,5 cyclohexanone-1 
• 17130-63-1 2-hydroxymethylene-5α-cholestan-3-one 
• 872280-33-6 2,4-dimethyl-6-oxo-cyclohexanecarbaldehyde 
• 875250-15-0 6-isopropyl-3-methyl-2-oxo-cyclohexanecarbaldehyde 
• 53228-58-3 (3R)-6c-isopropyl-3r-methyl-2-oxo-cyclohexane-ξ-carbaldehyde 
• 123772-01-0 6-isopropenyl-3-methyl-2-oxo-cyclohex-3-enecarbaldehyde 
• 1194-91-8 3-methyl-2-oxo-cyclohexanecarbaldehyde 
• 1193-63-1 Cyclohexanone-2-carbaldehyde 
• 26706-86-5 5-methyl-2-oxo-cyclohexanecarbaldehyde 
• 603-48-5 tris[4-(dimethylamino)phenyl]methane 
• 2050-01-3 isobutyric acid isopentyl ester 
• 28745-06-4 3-methyl-6-isopropyl-2-oxymethylenecyclohexanone 

Relevant articles and documents

Efficient Enzymatic Preparation of Flavor Esters in Water

A straightforward biocatalytic method for the enzymatic preparation of different flavor esters starting from primary alcohols (e.g., isoamyl, n-hexyl, geranyl, cinnamyl, 2-phenethyl, and benzyl alcohols) and naturally available ethyl esters (e.g., formate, acetate, propionate, and butyrate) was developed. The biotransformations are catalyzed by an acyltransferase from Mycobacterium smegmatis (MsAcT) and proceeded with excellent yields (80-97%) and short reaction times (30-120 min), even when high substrate concentrations (up to 0.5 M) were used. This enzymatic strategy represents an efficient alternative to the application of lipases in organic solvents and a significant improvement compared with already known methods in terms of reduced use of organic solvents, paving the way to sustainable and efficient preparation of natural flavoring agents.

Deep eutectic solvent choline chloride·2CrCl3·6H2O: An efficient catalyst for esterification of formic and acetic acid at room temperature

A highly efficient and selective method for esterification of formic and acetic acid with alcohols has been achieved at room temperature, with the choline chloride (ChCl)/chromium(iii) chloride hexahydrate (CrCl3·6H2O) deep eutectic solvent as a catalyst. High yields and good selectivities of organic esters are obtained using DES [ChCl][CrCl3·6H2O]2 with the molar ratio 5:1 (carboxylic acids:alcohols) at room temperature in 24 h. The ease of recovery and reusability of DES with high catalytic activity makes this method efficient and practical.

Nickel-catalyzed hydrosilylation of CO2 in the Presence of Et3B for the synthesis of formic acid and related formates

The reaction of CO2 with Et3SiH catalyzed by the nickel complex [(dippe)Ni(μ-H)]2 (1) afforded the reduction products Et3SiOCH2OSiEt3 (12%), Et 3SiOCH3 (3%), and CO, which were characterized by standard spectroscopic methods. Part of the generated CO was found as the complex [(dippe)Ni(CO)]2 (2), which was characterized by single-crystal X-ray diffraction. When the same reaction was carried out in the presence of a Lewis acid, such as Et3B, the hydrosilylation of CO2 efficiently proceeded to give the silyl formate (Et3SiOC(O)H) in high yields (85-89%), at 80 C for 1 h. Further reactivity of the silyl formate to yield formic acid, formamides, and alkyl formates was also investigated.