Isoamyl+acetate


 * Isoamyl acetate **, also known as ** isopentyl acetate ** , is an [|organic compound] that is the [|ester] formed from [|isoamyl alcohol] and [|acetic acid] . It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isoamyl acetate has a strong odor (similar to [|Juicy Fruit] , a foam banana sweet or a [|pear drop] ) which is also described as similar to both [|banana] and [|pear] . ** Banana oil ** is a term that is applied either to pure isoamyl acetate or to flavorings that are mixtures of isoamyl acetate, [|amyl acetate] , and other flavors.

Production
Isoamyl acetate is prepared by the acid catalyzed reaction ( [|Fischer esterification] ) between [|isoamyl alcohol] and glacial [|acetic acid] as shown in the reaction equation below. Typically, [|sulfuric acid] is used as the [|catalyst]. Alternately, an acidic ion exchange resin can be used as the catalyst.



Applications
Isoamyl acetate is used to confer banana flavor in foods. //Pear oil// commonly refers to a solution of isoamyl acetate in [|ethanol] that is used as an artificial flavor.

It is also used as a solvent for some varnishes and nitrocellulose lacquers, as well as being a honey bee [|pheromone] and can be used to attract large groups of honeybees to a small area, a reason it is released during a sting to signal other bees to sting the same target. This is used by honey bee's and killer wasps in the Yosemite region of California. As a solvent and carrier for materials such as nitrocellulose, it was extensively used in the aircraft industry for stiffening and wind-proofing fabric flying surfaces, where it and its derivatives were generally known as 'dope'. Now that most aircraft are all-metal, such use is now limited to model aircraft, where it is still popularly used for strengthening tissue coverings and balsa wood.

Because of its intense, pleasant odor and its low toxicity, isoamyl acetate is used to test the effectiveness of [|respirators] or [|gas masks].

Occurrence in nature
Banana oil is made naturally by the [|banana] plant; it is also produced synthetically.

Isoamyl acetate is released by a [|honey bee] 's [|sting] apparatus where it serves as a [|pheromone] beacon to attract other bees and provoke them to sting.
 * ~ Isoamyl acetate ||
 * [[image:http://upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Isoamyl_acetate.svg/200px-Isoamyl_acetate.svg.png width="200" height="88" link="http://en.wikipedia.org/wiki/File:Isoamyl_acetate.svg"]] ||
 * [[image:http://upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Isoamyl-acetate-3D-balls.png/200px-Isoamyl-acetate-3D-balls.png width="200" height="101" link="http://en.wikipedia.org/wiki/File:Isoamyl-acetate-3D-balls.png"]] ||
 * [|IUPAC name] [|[hide]] 3-methylbut-1-yl ethanoate ||
 * Other names [|[hide]] isopentyl acetate

banana oil

isopentyl ethanoate

pear essence

3-methylbutyl acetate

3-methylbutyl ethanoate || [|[show]]  || [|[show]]  ||  3  1   0  ||
 * ~ Identifiers ||
 * [|CAS number] || [|123-92-2]  [[image:http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png width="7" height="7" caption="Yes"]] ||
 * [|ChemSpider] || [|29016]  [[image:http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png width="7" height="7" caption="Yes"]] ||
 * [|UNII] || [|Z135787824]  [[image:http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png width="7" height="7" caption="Yes"]] ||
 * [|KEGG] || [|C12296]  [[image:http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png width="7" height="7" caption="Yes"]] ||
 * [|ChEBI] || [|CHEBI:31725]  [[image:http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png width="7" height="7" caption="Yes"]] ||
 * [|ChEMBL] || [|CHEMBL42013]  [[image:http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png width="7" height="7" caption="Yes"]] ||
 * [|Jmol] -3D images || [|Image 1] ||
 * [|SMILES]
 * [|InChI]
 * ~ Properties ||
 * [|Molecular formula] || C7H14O2 ||
 * [|Molar mass] || 130.19 g/mol ||
 * [|Density] || 0.876 g/cm3 ||
 * [|Melting point] || −78 °C, 195 K, -108 °F ||
 * [|Boiling point] || 142 °C, 415 K, 288 °F ||
 * ~ Hazards ||
 * [|NFPA 704] || [[image:http://upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/75px-NFPA_704.svg.png width="75" height="75" caption="NFPA 704.svg" link="http://en.wikipedia.org/wiki/File:NFPA_704.svg"]]
 * [|Flash point] || 25 °C ||
 * ** ISOAMYL ACETATE ** ||
 * PRODUCT IDENTIFICATION ||
 * CAS NO. || 123-92-2 || [[image:http://www.chemicalland21.com/specialtychem/perchem/123-92-2.gif width="60" height="143" caption="ISO-AMYL ACETATE"]]  ||
 * EINECS NO. || 204-662-3 ||^  ||
 * FORMULA || CH3COOCH2CH2CH(CH3)2 ||^  ||
 * MOL WT. || 130.19 ||^  ||
 * H.S. CODE || 2930.90 ||^  ||
 * DERIVATION ||  ||^   ||
 * CLASSIFICATION ||  ||^   ||
 * TOXICITY || Oral rat LD50: 16,600 mg/kg ||^  ||
 * SYNONYMS |||| Isopentyl Acetate; -methyl-1-butanol acetate; Banana Oil; ||
 * Acetato De Isoamilo; 3-Methylbutyl acetate; amyl acetate ester; 3 3-Methyl-1-Butyl Acetate; acetic acid 3-methyl butyl ester; isopentyl ester acetic acid; isopentyl alcohol, acetate; pear oil; Beta-methyl butyl acetate; ||
 * PHYSICAL AND CHEMICAL PROPERTIES ||
 * PHYSICAL STATE |||| clear, colorless liquid with a banana-like odor ||
 * MELTING POINT |||| -78 C ||
 * BOILING POINT |||| 142 C ||
 * SPECIFIC GRAVITY |||| 0.868 **-** 0.878 ||
 * SOLUBILITY IN WATER |||| Slightly (Soluble well in Ethyl Butyrate**;** Isoamyl Butyrate) ||
 * pH ||||  ||
 * VAPOR DENSITY |||| 4.5 ||
 * REFRACTIVE INDEX |||| 1.400 **-** 1.404 ||
 * NFPA RATINGS |||| Health: 1 Flammability: 3 Reactivity: 0 ||
 * FLASH POINT ||||  ||
 * STABILITY |||| Stable under ordinary conditions ||
 * APPLICATIONS ||
 * Acetate is the ester that an organic group replaces a hydrogen atom in -OH group of acetic acid through reaction (typically condensation) with alcohols. Condensation is the reaction in which two molecules having -OH groups are joined with eliminating a water molecule from their -OH groups.They are produced by esterification reaction from acetic acid and the corresponding alcohol in the presence of strong acids like sulfuric acid. This reaction is reversible and acetate can be hydrolyzed back into alcohol and acetic acid in the presence of strong bases or strong acid, especially at elevated temperature. The term acetate is also for the salt that one or more of the hydrogen atoms of acetic acid are replaced by one or more cations of the base, resulting in a compound containing the negative organic ion of CH3COO-. Lower acetate is a non-polar to weak polar aprotic solvent which have some solubility portion in water. Its miscibility with water gets higher at elevated temperature. Higher acetates have a low solubility in water and used as extraction solvents for fine chemicals particularly for certain antibiotics. Organic acetates are good solvents for a broad range of resins as they are miscible with almost all common organic liquids. Due to their powerful solvency, high volatility and mild odor, acetates are widely used as solvents for paints, coatings, adhesives, cellulose, plastics, fats, wood stains. Additionally ether acetates series are also widely used as solvents. This surfactant-like structure provides the compatibility between water and a number of organic solvents, and the ability to couple unlike phases. The main products include ethyleneglycol monoethyl ether acetate, ethyleneglycol monobutyl ether acetate, and propyleneglycol monomethyl ether acetate. Aromatic acetates such as benzyl acetate are also useful solvent. Benzyl acetate has jasmine like odor. Isoamyl acetate has a similar smell to both banana and pear. Acetates have characteristic fruity odor. They are used as component of perfumes and flavorings. They are used as chemical intermediate to manufacture pharmaceuticals, synthetic flavorings, cleaners, and other organic compounds. || ** Acetate ** || **FORMULA** || ** CAS RN ** || ** B.P C ** ||
 * Methyl acetate || CH3COOCH3 || 79-20-9 || 57 - 58 ||
 * Ethyl acetate || CH3COOC2H5 || 141-78-6 || 76.5 - 77.5 ||
 * Propyl acetate || CH3COOCH2CH2CH3 || 109-60-4 || 101 - 102 ||
 * Isopropyl acetate || CH3COOCH(CH3)2 || 108-21-4 || 89 ||
 * Butyl acetate || CH3COO(CH2)3CH3 || 123-86-4 || 124 - 126 ||
 * isobutyl acetate || CH3COOCH2CH(CH3)2 || 110-19-0 || 115 - 117 ||
 * Amyl acetate || CH3COO(CH2)4CH3 || 628-63-7 || 149 ||
 * Isoamyl acetate || CH3COOCH2CH2CH(CH3)2 || 123-92-2 || 142 ||
 * Hexyl acetate || CH3COO(CH2)5CH3 || 142-92-7 || 170 - 172 ||
 * Heptyl acetate || CH3COO(CH2)6CH3 || 112-06-1 || 192 - 193 ||
 * Octyl acetate || CH3COO(CH2)7CH3 || 112-14-1 || 205 - 211 ||
 * Nonanyl acetate || CH3COO(CH2)8CH3 || 143-13-5 || 212 ||
 * Decyl acetate || CH3COO(CH2)9CH3 || 112-17-4 || 272 ||
 * Undecyl acetate || CH3COO(CH2)10CH3 || 112-19-6 || 269 - 271 ||
 * Lauryl acetate || CH3COO(CH2)11CH3 || 112-66-3 || 265 ||
 * Tridecyl acetate || CH3COO(CH2)12CH3 || 1072-33-9 ||  ||
 * Myristyl acetate || CH3COO(CH2)13CH3 || 638-59-5 ||  ||
 * Pentadecyl acetate || CH3COO(CH2)14CH3 || 629-58-3 ||  ||
 * Cetyl acetate || CH3COO(CH2)15CH3 || 629-70-9 ||  ||
 * Heptadecyl acetate || CH3COO(CH2)16CH3 || 822-20-8 ||  ||
 * Stearyl acetate || CH3COO(CH2)17CH3 || 822-23-1 ||  ||
 * Behenyl acetate || CH3COO(CH2)21CH3 || 822-26-4 ||  ||
 * Hexacosyl acetate || C28H56O2 || 822-32-2 ||  ||
 * Triacontyl acetate || C32H64O2 || 41755-58-2 ||  ||
 * Benzyl acetate || CH3COOCH2C6H5 || 140-11-4 || 213 - 214 ||
 * Bornyl acetate || C12H20O2 || 76-49-3 || 228 - 231 ||
 * Isobornyl acetate || C12H20O2 || 125-12-2 || 229 - 233 ||
 * Cyclohexyl acetate || CH3COOC6H11 || 622-45-7 || 172 - 173 ||  ||
 * SALES SPECIFICATION ||
 * APPEARANCE |||| Clear liquid, free from suspended matter ||
 * PURITY |||| 99.0% min ||
 * ISO-AMYL ALCOHOL |||| 1.0% max ||
 * ACIDITY |||| 0.01% max (AS ACETIC ACID) ||
 * WATER (KF) |||| 0.1% max ||
 * RESIDUE ON IGNITION |||| 100ppm max ||
 * DISTILLATION RANGE |||| 135 - 145 C ||
 * COLOUR (HAZEN) |||| 20 max ||
 * TRANSPORTATION ||
 * PACKING |||| 180kgs in Drum ||
 * HAZARD CLASS |||| 3 ||
 * UN NO. |||| 1104 ||
 * OTHER INFORMATION ||