Helional (from
heliotropin, from which is it commonly derived) is a chemical compound used as a perfume in soap and laundry detergent. Chemically it is an
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 ...
with a
hydrocinnamaldehyde
Hydrocinnamaldehyde is the organic compound with the formula C6H5CH2CH2CHO. It is produced by the hydrogenation of cinnamaldehyde
Cinnamaldehyde is an organic compound with the formula(C9H8O) C6H5CH=CHCHO. Occurring naturally as predominantly the ...
motif; a structural element which is present in a number of other important commercial fragrances and odorants.
Synthesis
Several synthetic routes exist but the most common is a crossed-
aldol condensation
An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration to ...
between
piperonal
Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors.Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe a ...
(heliotropin) and
propanal
Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is the 3-carbon aldehyde. It is a colourless, flammable liquid with a slightly fruity odour. It is produced on a large scale industrially.
Production
Propionalde ...
followed by selective
hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a Catalysis, catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or S ...
of the intermediate alkene. This produces a
racemic
In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. ...
product.
See also
*
Cyclamen aldehyde
Cyclamen aldehyde is a fragrance molecule which has been used in soaps, detergents, lotions, and perfumes since the 1920s. It was granted generally recognized as safe (GRAS) status by Flavor and Extract Manufacturers Association (FEMA) in 1965 an ...
*
Lilial
Lilial (a trade name for lily aldehyde, also known as lysmeral) is a chemical compound commonly used as a perfume in cosmetic preparations and laundry powders, often under the name ''butylphenyl methylpropional''. It is a synthetic aromatic aldeh ...
*
Hexyl cinnamaldehyde
Hexyl cinnamaldehyde (hexyl cinnamal) is a common additive in the perfume and cosmetic industry as aroma substance. It is found naturally in the essential oil of chamomile. It is a pale yellow to yellow liquid to solid, which is nearly insoluble ...
References
Benzodioxoles
Aldehydes
Perfume ingredients
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