
Fatty aldehydes are
aliphatic
In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated (in which all ...
, long-chain
aldehyde
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...
s which may be mono- or
polyunsaturated. The fatty aldehydes include compounds such as
octanal
Octanal is the organic compound, an aldehyde, with the chemical formula CH3(CH2)6CHO. A colorless fragrant liquid with a fruit-like odor, it occurs naturally in citrus oils. It is used commercially as a component in perfumes and in flavor produ ...
,
nonanal
Nonanal is an organic compound with the chemical formula . It is one of several isomers, all are colorless oil. The nonanals are classified as aldehydes. The linear nonanal is produced commercially by the hydroformylation of 1-octene. It is ...
,
decanal
Decanal is an organic compound with the chemical formula . A colorless oil, it is classified as an aldehyde.
Occurrence
Decanal occurs naturally in citrus, along with octanal, citral, and sinensal, in buckwheat,
and in coriander essential oil ...
or
dodecanal. The nomenclature is derived from the nomenclature of the
alkane
In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in whi ...
s, the ending ''-al'' is added to indicate the aldehyde group.
Occurrence
Fatty aldehydes are a natural component of many
natural ingredients such as the
essential oil
An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the ...
s of various citrus fruits.
Decanal
Decanal is an organic compound with the chemical formula . A colorless oil, it is classified as an aldehyde.
Occurrence
Decanal occurs naturally in citrus, along with octanal, citral, and sinensal, in buckwheat,
and in coriander essential oil ...
, for example, is a component of orange peel. The
pheromone cocktails of various insect pheromones contain fatty aldehydes. Fat aldehydes were also detected in the
heart muscle of mammals.
Preparation
Fatty aldehydes can be prepared by
dehydrogenation
In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At ...
of
fatty alcohol
Fatty alcohols (or long-chain alcohols) are usually high-molecular mass, straight-chain primary alcohols, but can also range from as few as 4–6 carbon atoms to as many as 22–26, derived from natural fats and oils. The precise chain length vari ...
s on copper-zinc
catalysts
Catalysis () is the increase in reaction rate, rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst ...
. By the
hydroformylation
In organic chemistry, hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes () from alkenes (). This chemical reaction entails the net addition of a formyl group () and a hydrogen ...
of
alkene
In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins.
The Internationa ...
s, fatty aldehydes are produced on a large industrial scale.
Use
A large proportion of the fatty aldehydes prepared by
hydroformylation
In organic chemistry, hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes () from alkenes (). This chemical reaction entails the net addition of a formyl group () and a hydrogen ...
is directly processed further to
fatty alcohol
Fatty alcohols (or long-chain alcohols) are usually high-molecular mass, straight-chain primary alcohols, but can also range from as few as 4–6 carbon atoms to as many as 22–26, derived from natural fats and oils. The precise chain length vari ...
s. Many fatty aldehydes find use as a
fragrance
An aroma compound, also known as an odorant, aroma, fragrance, flavoring or flavor, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficien ...
in perfume production. An example is
2-methylundecanal which is the typical odor component of
Chanel No. 5.
[{{cite web, title=Chemistry in its element - 2-Methylundecanal, url=http://www.rsc.org/chemistryworld/podcast/CIIEcompounds/transcripts/2-methylundecanal.asp, url-status=dead, accessdate=2014-06-20, archiveurl=https://web.archive.org/web/20140528084048/http://www.rsc.org/chemistryworld/podcast/CIIEcompounds/transcripts/2-methylundecanal.asp, archivedate=2014-05-28, language=German] Decanal
Decanal is an organic compound with the chemical formula . A colorless oil, it is classified as an aldehyde.
Occurrence
Decanal occurs naturally in citrus, along with octanal, citral, and sinensal, in buckwheat,
and in coriander essential oil ...
, whose sweet, flowery odor reminiscents of orange peels, is used, among other things, as a
flavoring agent
A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive that is used to improve the taste or Sense of smell, smell of food. It changes the perceptual impression of food as determined primarily by the chem ...
in the
food industry
The food industry is a complex, global network of diverse businesses that supplies most of the food consumed by the world's population. The food industry today has become highly diversified, with manufacturing ranging from small, traditional, ...
and as a perfume in the
perfume industry.
See also
*
Fatty acid
In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...
*
Fatty alcohol
Fatty alcohols (or long-chain alcohols) are usually high-molecular mass, straight-chain primary alcohols, but can also range from as few as 4–6 carbon atoms to as many as 22–26, derived from natural fats and oils. The precise chain length vari ...
References
Fatty aldehydes
Sweet-smelling chemicals