Butyl acetates

Butyl acetates (also acetic acid butyl esters) are organic chemical compounds and comprise a group of four saturated carboxylic acid esters exhibiting structural isomerism. They are the esters formed from acetic acid and the four isomeric butanols. They share the molecular formula C6H12O2 and have a molar mass of 116.16 g/mol. sec-Butyl acetate is also chiral and exists as two enantiomeric forms. Consequently, a total of five isomers are possible. Butyl acetates occur naturally, for example in fruits, and are widely used industrially as solvents and flavorings.

Representatives and properties

Butyl acetates
Name Acetic acid n-butyl ester Acetic acid isobutyl ester Acetic acid sec-butyl ester Acetic acid tert-butyl ester
Other names n-butyl acetate iso-butyl acetate sec-butyl acetate (RS)-acetic acid sec-butyl ester tert-butyl acetate
Structural formula
(chiral)
CAS number Q411073 Q420657 Q421143 Q285657
PubChem CID 31272 from PubChem CID 8038 from PubChem CID 7758 from PubChem CID 10908 from PubChem
State liquid
Melting point -77 degrees Celsius[1] -98.9 degrees Celsius[2] -99 degrees Celsius[3]
Boiling point 127 °C[1] 118 °C[2] 112 °C[3] 97 °C[4]

Occurrence

n-Butyl acetate and iso-butyl acetate occur as flavor constituents in numerous fruits. In cultivated apple,[5] pears,[6] bananas,[7] plum[8], melon[9], and papaya[10], for example, both compounds are present.

Use

n-Butyl acetate and sec-butyl acetate are among the most important solvents used in coating processes,[11] while isobutyl acetate is employed to a lesser extent in this field.[12] n-Butyl acetate is one of the most important solvents for nail polish; isobutyl acetate is occasionally used for this purpose as well.[13] Three butyl acetates are used as flavoring agents and are generally authorized for use in food within the European Union: n-butyl acetate is approved under FL number 09.004,[14] isobutyl acetate under number 09.005[15], and sec-butyl acetate under number 09.323.[16]

References

  1. ^ a b Record of Essigsäure-n-butylester in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ a b Record of Essigsäureisobutylester in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ^ a b Record of sec-Butylacetat in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  4. ^ Record of tert-Butylacetat in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  5. ^ T. Lavilla, J. Puy, M. L. López, I. Recasens, M. Vendrell (1999-09-01), "Relationships between Volatile Production, Fruit Quality, and Sensory Evaluation in Granny Smith Apples Stored in Different Controlled-Atmosphere Treatments by Means of Multivariate Analysis", Journal of Agricultural and Food Chemistry, vol. 47, no. 9, pp. 3791–3803, doi:10.1021/jf990066h{{citation}}: CS1 maint: multiple names: authors list (link)
  6. ^ A. Rizzolo, C. Sodi, A. Polesello (January 1991), "Influence of ethylene removal on the volatile development in passa crassana pears stored in a controlled atmosphere", Food Chemistry, vol. 42, no. 3, pp. 275–285, doi:10.1016/0308-8146(91)90070-5{{citation}}: CS1 maint: multiple names: authors list (link)
  7. ^ "The banana ship, leader of the fruit ships – Soils in banana plantations in Côte d'Ivoire – Fruit crops in Israel", Fruits, vol. 65, no. 1, pp. A1–A2, January 2010, doi:10.1051/fruits/2010053
  8. ^ Jorge Antonio Pino, Clara Elizabeth Quijano (2012-01-31), "Study of the volatile compounds from plum (Prunus domestica L. cv. Horvin) and estimation of their contribution to the fruit aroma", Food Science and Technology, vol. 32, no. 1, pp. 76–83, doi:10.1590/S0101-20612012005000006
  9. ^ Moshe Shalit, Nurit Katzir, Yaakov Tadmor, Olga Larkov, Yosef Burger, Fernond Shalekhet, Elena Lastochkin, Uzi Ravid, Orit Amar, Menahem Edelstein, Zvi Karchi, Efraim Lewinsohn (2001-02-01), "Acetyl-CoA: Alcohol Acetyltransferase Activity and Aroma Formation in Ripening Melon Fruits", Journal of Agricultural and Food Chemistry, vol. 49, no. 2, pp. 794–799, doi:10.1021/jf001075p{{citation}}: CS1 maint: multiple names: authors list (link)
  10. ^ David B. Katague, Ernst R. Kirch (June 1965), "Chromatographic Analysis of the Volatile Components of Papaya Fruit", Journal of Pharmaceutical Sciences, vol. 54, no. 6, pp. 891–894, doi:10.1002/jps.2600540616
  11. ^ Song Gao, Shuwei Zhang, Xiang Che, Yiran Ma, Xi Chen, Yusen Duan, Qingyan Fu, Shanshan Wang, Bin Zhou, Chuanming Wei, Zheng Jiao (July 2022), "New understanding of source profiles: Example of the coating industry", Journal of Cleaner Production, vol. 357, p. 132025, doi:10.1016/j.jclepro.2022.132025{{citation}}: CS1 maint: multiple names: authors list (link)
  12. ^ RON L. STOUT (2000), "SOLVENTS IN TODAY'S COATINGS", Applied Polymer Science: 21st Century, Elsevier, pp. 527–543
  13. ^ Eeva-Liisa Sainio, Kerstin Engström, Maj-Len Henriks-Eckerman, Lasse Kanerva (October 1997), "Allergenic ingredients in nail polishes", Contact Dermatitis, vol. 37, no. 4, pp. 155–162, doi:10.1111/j.1600-0536.1997.tb00189.x{{citation}}: CS1 maint: multiple names: authors list (link)
  14. ^ "Butyl acetate". Food and Feed Information Portal Database | FIP. Retrieved 2023-10-19.
  15. ^ "Isobutyl acetate". Food and Feed Information Portal Database | FIP. Retrieved 2023-10-19.
  16. ^ "sec-Butyl acetate". Food and Feed Information Portal Database | FIP. Retrieved 2023-10-19.
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