Cis-3-Methyl-4-octanolide
Encyclopedia
cis-3-Methyl-4-octanolide, also called cis-β-methyl-γ-octalactone or 5-butyldihydro-4-methylfuran-2(3H)-one, is a chemical compound
of the lactone
family with formula . It exists in two optical isomers: 3R,4R ("+") and 3S,4S ("-").
The 3S,4S isomer, commonly known as whisky lactone or quercus lactone is an important ingredient in the aroma of whiskey (where it was first identified by Suomalainen and Nykänen in 1970),and other alcoholic beverage
s that have been aged in oak barrel
s. It is sometimes added to the liquor as a flavoring agent. It has a coconut
, celery
or fresh wood aroma, that can be detected by humans at the concentration of 1 μg
/L
in air. A mixture of the cis and trans isomers is repellent
for mosquito
s and flies.
The 3S,4S isomer is extracted by the alcoholic beverage from some precursor substances in the oak wood. It can be synthesized from a cyclopentane
derivative.
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
of the lactone
Lactone
In chemistry, a lactone is a cyclic ester which can be seen as the condensation product of an alcohol group -OH and a carboxylic acid group -COOH in the same molecule...
family with formula . It exists in two optical isomers: 3R,4R ("+") and 3S,4S ("-").
The 3S,4S isomer, commonly known as whisky lactone or quercus lactone is an important ingredient in the aroma of whiskey (where it was first identified by Suomalainen and Nykänen in 1970),and other alcoholic beverage
Alcoholic beverage
An alcoholic beverage is a drink containing ethanol, commonly known as alcohol. Alcoholic beverages are divided into three general classes: beers, wines, and spirits. They are legally consumed in most countries, and over 100 countries have laws regulating their production, sale, and consumption...
s that have been aged in oak barrel
Barrel
A barrel or cask is a hollow cylindrical container, traditionally made of vertical wooden staves and bound by wooden or metal hoops. Traditionally, the barrel was a standard size of measure referring to a set capacity or weight of a given commodity. A small barrel is called a keg.For example, a...
s. It is sometimes added to the liquor as a flavoring agent. It has a coconut
Coconut
The coconut palm, Cocos nucifera, is a member of the family Arecaceae . It is the only accepted species in the genus Cocos. The term coconut can refer to the entire coconut palm, the seed, or the fruit, which is not a botanical nut. The spelling cocoanut is an old-fashioned form of the word...
, celery
Celery
Apium graveolens is a plant species in the family Apiaceae commonly known as celery or celeriac , depending on whether the petioles or roots are eaten: celery refers to the former and celeriac to the latter. Apium graveolens grows to 1 m tall...
or fresh wood aroma, that can be detected by humans at the concentration of 1 μg
Microgram
In the metric system, a microgram is a unit of mass equal to one millionth of a gram , or 1/1000 of a milligram. It is one of the smallest units of mass commonly used...
/L
Litér
- External links :*...
in air. A mixture of the cis and trans isomers is repellent
Insect repellent
An insect repellent is a substance applied to skin, clothing, or other surfaces which discourages insects from landing or climbing on that surface. There are also insect repellent products available based on sound production, particularly ultrasound...
for mosquito
Mosquito
Mosquitoes are members of a family of nematocerid flies: the Culicidae . The word Mosquito is from the Spanish and Portuguese for little fly...
s and flies.
The 3S,4S isomer is extracted by the alcoholic beverage from some precursor substances in the oak wood. It can be synthesized from a cyclopentane
Cyclopentane
Cyclopentane is a highly flammable alicyclic hydrocarbon with chemical formula 510 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and below the plane. It occurs as a colorless liquid with a petrol-like odor. Its melting point is −94 °C...
derivative.
See also
- trans-3-Methyl-4-octanolideTrans-3-Methyl-4-octanolidetrans-3-Methyl-4-octanolide, also called trans-β-methyl-γ-octalactone is a chemical compound of the lactone family with formula . It exists in two stereoisomers: and ....
, a stereoisomer also found in oak-aged beverages.