air. First submitted to olfactory evaluation in June
1946, the similarity of Lilialb ( 3) with hydroxycitronellal ( 1) and cyclamen aldehyde ( 2) that were found
potent enough, did not generate any interest from
the evaluating perfumers. That’s how one of the most
important and successful odorants in the history of
perfumery got rated “sans intérêt olfactive apprécia-ble” (translation: “without any noticeable olfactory
benefit”) at first (F- 2).
Yet, the Lilial history shows that olfactory
performance prevails in the end, and Carpenter
kept insisting on re-evaluations. After 10 years, he
convinced the perfumers, and the Lilial patent was
filed in June, 1956.6 Since then, Lilial experienced a
triumphal success in perfumery, making it for quite a
while the most important Givaudan product in terms
of volume and value.
Moreover, Julian Dorsky and William M. Easter,
Jr., of Givaudan also synthesized the nor-derivative
4 of Lilial ( 3), which was initially introduced into
perfumery as Isolilial ( 4). 7 Although being more
diffusive, Isolilial is with a threshold of 0.4 ng/L
air comparable in strength to Lilial ( 3). When the
patent expired, the former Quest began to produce
and market Isolilial as Bourgeonalc ( 4). Being
promoted mainly in functional perfumery for its
stability in aggressive media, such as antiperspirants,
Bourgeonal ( 4) gained good fame in the late 1990’s.
However, compared to Lilial ( 3) with its universal
application range, the volumes of Bourgeonal ( 4)
remained generally over 50 times smaller.
The next milestone was the hydroxyaldehyde
Lyrald ( 5) which Robert W. Teegarden and Leonard
Steinbach of IFF discovered in 1960.8 Lyral ( 5)
possesses an odor threshold of 0.1 ng/L air, and due
to its long lastingness became a huge success in
perfumery, especially in fine fragrances, up to the
point where its massive usage led to sensitization
issues becoming one of the most abundant fragrance
allergens. It has to be labeled on the package as
“hydroxyisohexyl 3-cycohexene carboxaldehyde”
(HICC) and the SCCS recommended in 2011 to
discontinue the use of Lyral ( 5). 9
Installing the g,d-unsaturated linear aldehyde
motif of Bourgeonal ( 4) on the dicylopentadiene
dimer skeleton as an inexpensive bulky group then
led Harmannus Boelens and colleagues in Naarden
to discover Dupicale ( 6). 10 With an odor threshold
bLilial is a registered tradename of Givaudan. c,eBourgeonal and Dupical are registered tradenames of Givaudan.
d Lyral is a registereted tradename of IFF.