Menthyl acetate

Not to be confused with methyl acetate.
l-Menthyl acetate[1]
Names
IUPAC name
(1R,3R,4S)-p-Menthan-3-yl acetate
Systematic IUPAC name
(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl acetate
Other names
(1R)-(−)-Menthyl acetate

Ethanoic (1R,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carboxylate

Acetic (1R,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.018.252 Edit this at Wikidata
UNII
  • InChI=1S/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H3/t9-,11+,12-/m1/s1 ☒N
    Key: XHXUANMFYXWVNG-ADEWGFFLSA-N ☒N
  • InChI=1/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H3/t9-,11+,12-/m1/s1
    Key: XHXUANMFYXWVNG-ADEWGFFLBI
  • C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)C)C(C)C
Properties
C12H22O2
Molar mass 198.30 g/mol
Density 0.92 g/mL
Boiling point 229–230 °C (444–446 °F; 502–503 K)
Hazards
Flash point 77 °C (171 °F; 350 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Menthyl acetate is a natural monoterpene which contributes to the smell and flavor of peppermint. It is the acetate ester of menthol. Menthyl acetate constitutes 3–5% of the volatile oil of mentha piperita, contributing to its smell and flavour.[2][3]

References

  1. ^ L-Menthyl acetate at Sigma-Aldrich
  2. ^ PDR for Herbal Medicines, 4th Edition, Thomson Healthcare, page 640. ISBN 978-1-56363-678-3
  3. ^ Nature’s Treatment for Irritable Bowel Syndrome: Studies on the Isolation of (−)-Menthol from Peppermint Oil and Its Conversion to (−)-Menthyl Acetate Maeve Egan, Éilis Margaret Connors, Zeeshan Anwar, and John J. Walsh Journal of Chemical Education 2015 92 (10), 1736-1740 doi:10.1021/ed5007037