Mercapto-alkanol flavor compounds
AssigneeGivaudan SA
InventorsGonzalo Acuna, Markus Gautschi, Frank Kumli, Joachim Schmid, Janos Zsindely
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Abstract
New diastereoisomer-enriched 3-mercapto-alkanols are disclosed. The compounds, namely 3-mercapto-2-methyl-butan-1-ol and/or 3-mercapto-3-methyl-hexan-1-ol, and the stereoisomers of each, are used to flavor products, such as foods and/or beverages. Methods for the preparation of both diastereoisomers of 3-mercapto-2-methyl-butan-1-ol are also disclosed.
Claims47
A 3-mercapto-2-methyl-butan-1-ol enriched in the diastereomer having the formula (u)-3-mercapto-2-methyl-butan-1-ol and enantiomers thereof
- relative to (l)-3-mercapto-2-methyl-butan-1-ol (formula IV) and enantiomers thereof
A 3-mercapto-2-methyl-butan-1-ol enriched in the diastereomer having the formula (l)-3-mercapto-2-methyl-butan-1-ol (formula IV) and enantiomers thereof
- relative to (u)-3-mercapto-2-methyl-butan-1-ol and enantiomers thereof
A flavor composition comprising
- (a) a (u)-3-mercapto-2-methyl-butan-1-ol diastereoisomer of 3-mercapto-2-methyl-butan-1-ol and enantiomers thereof,
- and
- (b) a (l)-3-mercapto-2-methyl-butan-1-ol (formula IV) diastereoisomer of 3-mercapto-2-methyl-butan-1-ol and enantiomers thereof,
- the composition enriched in the diastereoisomer and enantiomers in (a) in relation to (b), or the diastereoisomer and enantiomers in (b) in relation to (a).
A method of flavoring a product comprising
- adding to said product a flavor composition comprising
- (a) a (u)-3-mercapto-2-methyl-butan-1-ol (formula III) diastereoisomer of 3-mercapto-2-methyl-butan-1-ol and enantiomers thereof,
- and,
- (b) a (l)-3-mercapto-2-methyl-butan-1-ol (formula IV) a diastereoisomer of 3-mercapto-2-methyl-butan-1-ol and enantiomers thereof,
- the composition enriched in the diastereoisomer and enantiomers in (a) in relation to (b), or the diastereoisomer and enantiomers is (b) in relation to (a), in an amount effective to flavor the product.
A flavorant composition comprising (u)-3-mercapto-2-butan-1-ol
- enriched relative to (l)-3-mercapto-2-butan-1-ol (formula IV)
- having a meaty cooked vegetable taste and an odor threshold of 4 pg/l air.
A method of flavoring a food or beverage product comprising providing a composition selectively enriched at a ratio of at least greater than 3:1 in (u)-3-mercapto-2-butan-1-ol (formula III)
- relative to (l)-3-mercapto-2-butan-1-ol (formula IV)
- to the food or beverage product at a concentration in the range of about 0.1 ppb to about 100 ppb.
A flavorant composition comprising (l)-3-mercapto-2-butan-1-ol (formula IV)
- enriched relative to (u)-3-mercapto-2-butan-1-ol
- having a herbaceous onion-like leeky gassy taste and an odor threshold of 400 pg/l air.
A method of flavoring a food or beverage product comprising providing a composition selectively enriched at a ratio of at least greater than 10:1 in (l)-3-mercapto-2-butan-1-ol (formula IV)
- relative to (u)-3-mercapto-2-butan-1-ol
- to the food or beverage product at a concentration in the range of about 10 ppb to about 5 ppm.
A food or beverage product containing a flavor/aroma composition comprising a 3-mercapto-2-methyl-butan-1-ol enriched by a ratio of at least greater than 3:1 for the diastereomer having the formula (u)-3-mercapto-2-methyl-butan-1-ol (formula III) and enantiomers thereof
- relative to (l)-3-mercapto-2-methyl-butan-1-ol (formula IV)
- and enantiomers thereof.
A food or beverage product containing a flavor/aroma composition comprising a 3-mercapto-2-methyl-butan-1-ol enriched by a ratio of at least greater than 10:1 for the diastereomer having the formula (l)-3-mercapto-2-methyl-butan-1-ol (formula IV) and enantiomers thereof
- relative to (u)-3-mercapto-2-methyl-butan-1-ol (formula III)
- and enantiomers thereof.
Dependencies are inferred from the claim text.