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, like hexane, or ...

, long-chain

aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...

s which may be mono- or

polyunsaturated In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food. The term often refers specifically to triglycerides (triple es ...

. 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, also called nonanaldehyde, pelargonaldehyde or Aldehyde C-9, is an aldehyde. A colourless, oily liquid, nonanal is a component of perfumes. Although it occurs in several natural oils, it is produced commercially by hydroformylation of 1 ...

decanal Decanal is an organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of ...

dodecanal Dodecanal, also known as lauraldehyde or dodecyl aldehyde, is an organic compound with the chemical formula CH3(CH2)10CHO. This colourless liquid is a component of many fragrances. It occurs naturally in citrus oils, but commercial samples are us ...

. 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 which ...

s, the ending ''-al'' is added to indicate the aldehyde group.

Occurrence

Fatty aldehydes are a natural component of many

natural ingredients A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical syn ...

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 o ...

s of various citrus fruits.

Decanal Decanal is an organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of ...

, 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 Cardiac muscle (also called heart muscle, myocardium, cardiomyocytes and cardiac myocytes) is one of three types of vertebrate muscle tissues, with the other two being skeletal muscle and smooth muscle. It is an involuntary, striated muscle tha ...

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 ...

fatty alcohol Fatty alcohols (or long-chain alcohols) are usually high-molecular-weight, straight-chain primary alcohols, but can also range from as few as 4–6 carbons to as many as 22–26, derived from natural fats and oils. The precise chain length varies ...

s on copper-zinc

catalysts Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

. By the

hydroformylation 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 (CHO) and a hydrogen atom to a carbon-carbon d ...

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...

s, fatty aldehydes are produced on a large industrial scale.

Use

A large proportion of the fatty aldehydes prepared by

is directly processed further to

s. Many fatty aldehydes find use as a

fragrance An aroma compound, also known as an odorant, aroma, fragrance or flavoring, 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 sufficiently vol ...

in perfume production. An example is

2-methylundecanal 2-Methylundecanal is an organic compound that is found naturally in kumquat peel oil. This compound smells herbaceous, orange, and ambergris-like. At high dilution it has a flavor similar to honey and nuts. It is a colorless or pale yellow liquid ...

which is the typical odor component of

Chanel No. 5 Chanel No. 5 was the first perfume launched by French couturier Gabrielle "Coco" Chanel in 1921. The scent formula for the fragrance was compounded by French-Russian chemist and perfumer Ernest Beaux. The design of its bottle has been an impo ...

.{{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

, 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 used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of the gustat ...

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, traditiona ...

and as a perfume in the

perfume industry Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. The ...

References

Fatty aldehydes Sweet-smelling chemicals

Occurrence

Preparation

Use

See also

References