Isoamyl butyrate

Base Information

• Chemical Name: Isoamyl butyrate
• CAS No.: 106-27-4
• Molecular Formula: C9H18O2
• Molecular Weight: 158.241
• Hs Code.: 29156019
• European Community (EC) Number: 203-380-8
• NSC Number: 6548
• UNII: 505AFM77VU
• DSSTox Substance ID: DTXSID3042059
• Nikkaji Number: J3.243C
• Wikidata: Q49081089
• Metabolomics Workbench ID: 4219
• ChEMBL ID: CHEMBL3187370
• Mol file: 106-27-4.mol

Synonyms:3-Methylbutyl butanoate;Butanoic acid, 3-methylbutyl ester;FEMA No. 2060;Isoamyl butylate;Isoamyl-n-butyrate;Isopentyl alcohol, butyrate;Isoamyl butyrate (natural);Isoamyl butanoate;Isopentyl butyrate;3-Methylbutyl butyrate;Butyric acid, isopentyl ester;Iso-Amyl butyrate;Iso amyl butyrate 99%min;Natural Isoamyl Butyrate;Isoamyl butyrate nat.;Isoamyl n-Butyrate;Isoamyl butyrate/Nat.;

Chemical Property of Isoamyl butyrate

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 1.09mmHg at 25°C
• Melting Point: -73 °C
• Refractive Index: n20/D 1.411(lit.)
• Boiling Point: 176.486 °C at 760 mmHg
• Flash Point: 57.778 °C
• PSA: 26.30000
• Density: 0.874 g/cm³
• LogP: 2.37580
• Storage Temp.: Store below +30°C.
• Solubility.: 0.5g/l
• Water Solubility.: 184.7mg/L at 20℃
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 158.130679813
• Heavy Atom Count: 11
• Complexity: 108

Purity/Quality:

99% ^*data from raw suppliers

Isoamyl Butyrate >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCC(=O)OCCC(C)C
• Description: Isoamyl Butyrate is a chemical ester of butyrate. It is a kind of flavoring agent that widely used in the preparation of a variety of fruit juice flavor, such as apricots, bananas, pears, apples and other flavor. It is high-demand flavor and fragrance compounds widely used in the food, beverage, cosmetic, and pharmaceutical industries. It is also a kind of solvent for extracting natural spices and the solvent of acetate fiber. Its synthesis can be mediated by the lipase (from various sources) catalyzed esterfication of isoamyl alcohol and butyrate. Isoamyl butyrate has a strong, characteristic, fruity (pear-like) odor and a sweet, corresponding taste. Usually prepared by esterification of commercial isoamyl alcohols with butyric acid by heating in the presence of TwitchelFs reagent; or by fermentation from butyric acid and isoamyl alcohol.
• Uses: manufacture of artficial rum and fruit essences. Isoamyl Butyrate is a synthetic flavoring agent that is a stable, col- orless liquid of strong fruity odor. it is usually prepared by esterifica- tion of isoamyl alcohols with butyric acid. it is soluble in most fixed oils and mineral oil and is insoluble in glycerin and propylene gly- col. storage should be in glass, tin, or resin-lined containers. it is used in fruit flavors such as pineapple, raspberry, and strawberry and has application in dessert gels, puddings, and baked goods at 50–60 ppm.

Technology Process of Isoamyl butyrate

There total 6 articles about Isoamyl butyrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.9%

i-Amyl alcohol (123-51-3) + butyric acid (107-92-6) → isopentyl butanoate (106-27-4)

Guidance literature:

With Candida antarctica lipase B; at 50 ℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction;

DOI:10.1039/c2gc36081k

Reference yield:

i-Amyl alcohol (123-51-3) + vinyl n-butyrate (123-20-6,24991-31-9) → isopentyl butanoate (106-27-4)

Guidance literature:

With immobilized Burkholderia cepacia lipase; In toluene; at 44 ℃; for 3h; Reagent/catalyst; Kinetics; Green chemistry; Enzymatic reaction;

DOI:10.1021/jp5093493

Reference yield:

i-Amyl alcohol (123-51-3) + butanoic acid ethyl ester (105-54-4) → isopentyl butanoate (106-27-4)

Guidance literature:

With recombinant acyltransferase from Mycobacterium smegmatis; In aq. phosphate buffer; at 25 ℃; for 24h; pH=8; Concentration; Green chemistry; Enzymatic reaction;

DOI:10.1021/acs.jafc.9b01790

upstream raw materials:

butanoic acid anhydride

isoamylmagnesium chloride

i-Amyl alcohol

butyryl-sulfuric acid

Downstream raw materials:

1-phenyl-hex-1-yn-3-one

i-Amyl alcohol

butyric acid

3-Methyl-1-butene

Refernces

• 1、 Anschau, Andreia,Aragao, Vitor C.,Porciuncula, Barbara D.A.,Kalil, Susana J.,Burkert, Carlos A.V.,Burkert, Janaina F.M.. "Enzymatic synthesis optimization of isoamyl butyrate". . p. 2148 - 2156. Retrieved 2011.
• 2、 Wang, Song,Chang, Qian-Qian,Shawgi, Nazar,Li, San-Xi,Zhang, Lin-Nan. "Synthesis of butyrate using a heterogeneous catalyst based on polyvinylpolypyrrolidone". . p. 538 - 544. Retrieved 2016/03/05.
• 3、 Badgujar, Kirtikumar C.,Bhanage, Bhalchandra M.. "Solvent stability study with thermodynamic analysis and superior biocatalytic activity of Burkholderia cepacia lipase immobilized on biocompatible hybrid matrix of poly(vinyl alcohol) and hypromellose". . p. 14808 - 14819. Retrieved 2015/02/19.