Hydroxymethylpentylcyclohexenecarboxaldehyde is a synthetic

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 ...

known by the trade names Lyral, Kovanol, Mugonal, Landolal. It is found in some

soap Soap is a salt of a fatty acid used in a variety of cleansing and lubricating products. In a domestic setting, soaps are surfactants usually used for washing, bathing, and other types of housekeeping. In industrial settings, soaps are use ...

eau de toilette Eau de toilette (, meaning "grooming water") is a lightly scented perfume. It is also referred to as aromatic waters and has a high alcohol content. It is usually applied directly to the skin after bathing or shaving. It is traditionally composed ...

aftershave Aftershave is a product applied to skin after shaving. Traditionally it is an Alcohol (chemistry), alcohol-based liquid (splash), but it can be a lotion, gel, or even a paste (rheology), paste. It often contains an antiseptic agent such as de ...

s and

deodorant A deodorant is a substance applied to the body to prevent or mask body odor due to bacterial breakdown of perspiration or vaginal secretions, for example in the armpits, groin, or feet. A subclass of deodorants, called antiperspirants, prevents s ...

Synthesis

Typical synthesis starts from

myrcene Myrcene, or β-myrcene, is a monoterpene. A colorless oil, it occurs widely in essential oils. It is produced mainly semi-synthetically from '' Myrcia'', from which it gets its name. It is an intermediate in the production of several fragrances. � ...

and involves a

Diels–Alder reaction In organic chemistry, the Diels–Alder reaction is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene derivative. It is the prototypical example of a peric ...

with

acrolein Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a piercing, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fa ...

to produce the cyclohexenecarbaldehyde group, this species is marketed as a fragrance in its own right, most commonly under the name 'myrac aldehyde'. Acid-catalyzed hydration of this completes the synthesis by forming the tertiary alcohol.

Safety

Lyral is known to act as a skin allergen and is listed as such in EU Directive 76/768/EEC. It is commonly tested for in patients undergoing patch testing.

References

{{Reflist Perfume ingredients Aldehydes Tertiary alcohols Cyclohexenes