(4S,5S)-(-)-cis-Aerangis
lactone - the sole stereoisomer of Aerangis
lactone present in the scent of living, white
flowering orchids (Aerangis confusa). The
fragrance of the (4S,5S)-isomer was described by
Bartschat, et. al., to be typical for the
lactonic odour of A. confusa and A. kirkii, and
identical to the olfactory qualities of natural
Aerangis lactone.
Odour
threshold = 0.13 ng
cis-Aerangis
lactone (cis-4-methyl-5-decanolide) was
described by Kaiser in 1993 as the main odour
component of the African moth
orchids Aerangis confusa J. Stewart and
Aerangis kirkii (Rolfe) Schltr.
The cis
isomer was found to have a very pleasant and
surprising room-filling odor which on the one
hand is reminiscent of certain aspects of the
smell of the flower of the tuberose (Polianthes
tuberosa) and gardenia varieties and on the
other hand is reminiscent of caramel, condensed
milk and coconut, especially coconut
milk
Also known as
(4S,5S)-(-)-cis-4-methyl-5-decanolide or
(5S,6S)-(-)-cis-6-pentyl-5-methyltetrahydropyran-2-one
Ref:
Bartschat, D., Lehmann, D., Dietrich, A.,
Mosandl, A., Kaiser, R. (1995). Chiral compounds
of essential oils XIX: 4-Methyl-5-decanolide:
Chirospecific analysis, structure and properties
of the stereoisomers. Phytochem. Anal., 6,
130-134;
Kaiser,
R. The Scent of Orchids, Olfactory and Chemical
Investigations ; Editions Roche, F. Hoffmann La
Roche:AG Basel, 1993;
Kaiser,
R. 5-methyl-6-pentyl-tetrahydro-.alpha.-pyrone
and analogs, US Patent No. 5,248,792 (September
28, 1993); Elisabetta Brenna, Claudia Dei Negri,
Claudio Fuganti and Stefano Serra, Bakers
yeast-mediated approach to (-)-cis- and
(+)-trans-Aerangis lactones, Tetrahedron:
Asymmetry 12 (2001) 18711879.;
Elisabetta
Brenna, Claudio Fuganti and Stefano Serra,
"Enantioselective perception of chiral
odorants", Tetrahedron Asymmetry, 14 (1),
142,
2003; Wu,
Y.; Shen, X.; Tang, C.-J.; Chen, Z.-L.; Hu, Q.;
Shi, W.; Synthesis of Natural Fragrant Molecules
cis-3-Methyl-4-decanolide and Aerangis Lactone.
General Enantioselective Routes to
beta-gamma-cis-Disubstituted gamma-Lactones and
gamma-delta-cis-Disubstituted delta-Lactones, J.
Org. Chem., 2002, 67(11) 3802-3810.
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