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Characteristics of some synthetic terpenoids with a grapefruit odour discovered by serendipity
Author(s) -
Bonikowski Radosław,
Świtakowska Paulina,
Jabłońska Aneta,
Kula Józef,
Sienkiewicz Monika,
Gabrysiak Justyna,
Kajrukszto Krzysztof
Publication year - 2014
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.3217
Subject(s) - chemistry , terpenoid , acetal , organic chemistry , serendipity , citronellal , terpene , stereochemistry , catalysis , philosophy , epistemology
This work presents odour characteristics of a newly synthesized family of seven terpenoid alcohols with citrusy grapefruit odours. The alcohols were prepared from citronellal that was subjected to a two‐ or three‐step reaction sequence to deliver secondary or tertiary alcohols. Two other compounds with an acetal structure (containing 18 and 19 carbon atoms) with the same odour type and very high tenacity were synthesized from (+)‐3‐carene. The most olfactorily potent compounds were 5,9‐dimethyldec‐8‐en‐2‐ol 10 and 2‐carene derivative acetal 25. Copyright © 2014 John Wiley & Sons, Ltd.