449174-50-9Relevant academic research and scientific papers
CARBONOTHIOATES AS FLAVOURS AND FRAGRANCES
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Page/Page column 5, (2010/11/03)
Provided are new O-alkyl S-hydroxyalkyl carbonothioates and O-alkyl S-alkoxyalkyl carbonothioates of formula (I) where R1-R4 are as defined in the claims, their manufacture and their use as flavour and fragrance. Also provided are flavour and fragrance compositions comprising said substance and at least one further flavour ingredient.
1-Methoxyhexane-3-thiol, a powerful odorant of clary sage (Salvia sclarea L.)
Van De Waal, Matthijs,Niclass, Yvan,Snowden, Roger L.,Bernardinelli, Geerald,Escher, Sina
, p. 1246 - 1260 (2007/10/03)
The peculiar and highly diffusive odor signal of flowering clary-sage plants (Salvia sclarea L.) was identified to derive from trace amounts of 1 -methoxyhexane-3-thiol (1) by mass-spectrometry analysis and confirmed by comparison with synthetic racemic thiol (±)-1. The enantiomers (S)- and (R)-1 were prepared by enantioselective synthesis, and the absolute configuration of (S)-1 was fully corroborated by X-ray-diffraction analysis of the crystalline thioester (1′S,1S)-2. Compound (S)-1 is one of the most powerful odorants known, with a detection threshold of 0.04·10-3 ng/l air, and is, with its herbaceous-green, alliaceous, and perspiration profile, key to the fragrance of clary-sage flowers and of the freshly distilled essential oil. As a consequence of its unique odor, 1 was also suspected to be part of the volatiles of a Ruta species where it was subsequently identified together with its homologue, 1-methoxyheptane-3-thiol (3), 1-methoxy-4-methylpentane-3-thiol (4), and the known 4-methoxy-2-methylbutane-2-thiol (5). The syntheses of (±)-3 and (±)-4 as well as of the enantiomer (R)-4 are described. In both natural fractions, the ratio (S)-1/(R)-1 was slightly in favor of the (S)-enantiomer. Natural 4 has (R)-configuration.
1-methoxy-3-hexanethiol and its S-acetyl derivative as perfuming and flavoring ingredients
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, (2008/06/13)
A compound of formula wherein R represents a hydrogen atom or an acetyl group, is useful in perfumery and in the field of flavors. The compound of formula (I) confer an odor and flavor effect extremely powerful of the clary-sage type, even when used in small amounts.
Substituent-Directed Alkyl Addition Reactions of Epoxides. 1. Applications to the Synthesis of 3-Hydroxy-4-methylalkanoic Acids
Flippin, Lee A.,Brown, Peter A.,Jalali-Araghi, Keyvan
, p. 3588 - 3596 (2007/10/02)
The addition reactions of 3,4-epoxy-1-alkanol derivatives were studied using Li(CH3)2Cu (ether, 0 deg C) and 2:1 (CH3)3Al-n-BuLi or 2:1 (C2H5)3Al-n-BuLi (hexane, 0 deg C).In all cases Li(CH3)2Cu showed a small (2-3:1) preference for C(4) addition over C(3
