γ-Octalactone

γ-Octalactone
Names
Preferred IUPAC name
5-Butyloxolan-2-one
Other names
2(3H)-Furanone, 5-butyldihydro-; 4-Octanolide; 5-Butyldihydro-2(3H)-furanone; (R/S)-γ-octalactone; 5-Butyldihydrofuran-2(3H)-one; 4-Hydroxyoctanoic acid lactone; γ-Octanolactone; γ-Octalactone; Octan-4-olide; Octanoic acid 4-hydroxy-γ-lactone; γ-Octanolide; γ-Butyl-γ-butyrolactone; γ-Butylbutyrolactone; 4-Butyl-γ-butyrolactone; 5-Butyltetrahydro-2-furanone; γ-n-Butyl-γ-butyrolactone; Octanoic acid, γ lactone; Octanolide-1,4; 2(3H)-Furanone, dihydro-5-butyl-; 4-Hydroxyoctanoic acid, γ-lactone; NSC 24270; Octanoic acid, 4-hydroxy-, lactone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.917
EC Number
  • 203-208-1
UNII
  • InChI=1S/C8H14O2/c1-2-3-4-7-5-6-8(9)10-7/h7H,2-6H2,1H3
    Key: IPBFYZQJXZJBFQ-UHFFFAOYSA-N
  • CCCCC1CCC(=O)O1
Properties
C8H14O2
Molar mass 142.198 g·mol−1
Appearance colorless solid
Density 0.9703 g/cm³
Melting point 91[1] °C (196 °F; 364 K)
Boiling point 234 °C (453 °F; 507 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

γ-Octalactone is an organic compound with the chemical formula C8H14O2. It is classified as lactone and used as an fragrance It has a coconut flavor.[2]


Preparation and occurrence

γ-Octalactone is prepared from crotonic acid and pentanal.[2]

It is a component of urban aerosols[3] as well as some liquors.[4]

References

  1. ^ National Institute of Standards and Technology. "gamma-Octalactone". webbook.nist.gov. Retrieved 2017-09-07.
  2. ^ a b Panten, Johannes; Surburg, Horst (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–45. doi:10.1002/14356007.t11_t02. ISBN 978-3-527-30673-2.
  3. ^ Rogge, Wolfgang F.; Hildemann, Lynn M.; Mazurek, Monica A.; Cass, Glen R.; Simoneit, Bernd R. T. (1991). "Sources of fine organic aerosol. 1. Charbroilers and meat cooking operations". Environmental Science & Technology. 25 (6): 1112–1125. Bibcode:1991EnST...25.1112R. doi:10.1021/es00018a015.
  4. ^ Fan, Wenlai; Qian, Michael C. (2006). "Characterization of Aroma Compounds of Chinese "Wuliangye" and "Jiannanchun" Liquors by Aroma Extract Dilution Analysis". Journal of Agricultural and Food Chemistry. 54 (7): 2695–2704. doi:10.1021/jf052635t. PMID 16569063.