trans-3-Methyl-4-decanolide

trans-3-Methyl-4-decanolide is a chemical compound with formula C
11
H
20
O
2
, found in clary sage,[1] in the juice of the blood orange, and in the extract of mandarin peel.[2] It is a lactone with coconut-like odor.[2]

trans-3-Methyl-4-decanolide

(4R,5S)-trans-3-Methyl-4-decanolide

(4S,5R)-trans-3-Methyl-4-decanolide
Names
IUPAC names
(4R,5S)-5-Hexyl-4-methyldihydrofuran-2(3H)-one
(4S,5R)-5-Hexyl-4-methyldihydrofuran-2(3H)-one
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C11H20O2/c1-3-4-5-6-7-10-9(2)8-11(12)13-10/h9-10H,3-8H2,1-2H3/t9-,10+/m0/s1 checkY
    Key: XNRLAEXLQFIKEY-VHSXEESVSA-N checkY
  • (4R,5S): InChI=1S/C11H20O2/c1-3-4-5-6-7-10-9(2)8-11(12)13-10/h9-10H,3-8H2,1-2H3/t9-,10+/m1/s1
    Key: XNRLAEXLQFIKEY-ZJUUUORDSA-N
  • (4R,5S): C[C@H]1[C@H](CCCCCC)OC(C1)=O
  • (4S,5R): C[C@@H]1[C@@H](CCCCCC)OC(C1)=O
Properties
C11H20O2
Molar mass 184.279 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

The cis isomer is found in an African orchid.[2][3]

See also edit

References edit

  1. ^ B. Maurer and A. Mauser (1983), New constituents of clary sage oil. IXth Int. Congr. Essent. Oils, Book 3, pages 69-76
  2. ^ a b c Regula Naef and Alain Velluz (2005). "Identification of trans-3-Methyl-4-Decanolide in Blood Orange Juice and Mandarin Peel". Journal of Essential Oil Research.
  3. ^ R. Kaiser (1993), The Scent of Orchids,page 191. Elsevier