Lilial (a trade name for lily aldehyde, also known as lysmeral) is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

commonly used as a

perfume 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 ...

in cosmetic preparations and laundry powders, often under the name ''butylphenyl methylpropional''. It is a synthetic

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

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 gro ...

. It was banned for use in cosmetics by the EU in March 2022 after being found to be harmful to fertility.

Synthesis

Lilial is produced at

BASF BASF SE () is a German multinational chemical company and the largest chemical producer in the world. Its headquarters is located in Ludwigshafen, Germany. The BASF Group comprises subsidiaries and joint ventures in more than 80 countries ...

through a double anodic oxidation of 4-''tert''butyl-toluene on >10,000 ton per year scale.

Properties

Lilial is commonly produced and sold as a

racemic mixture 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. ...

; however, testing has indicated that the different

enantiomer In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical anti ...

s of the compound do not contribute equally to its odor. The (''R'')-enantiomer has a strong floral odor, reminiscent of

cyclamen ''Cyclamen'' ( or ) is a genus of 23 species of perennial flowering plants in the family Primulaceae. ''Cyclamen'' species are native to Europe and the Mediterranean Basin east to the Caucasus and Iran, with one species in Somalia. They g ...

or lily of the valley; whereas the (''S'')-enantiomer possesses no strong odor. : 2-(4-tert-Butylbenzyl)propionaldehyd Formulae V

Like most

aldehydes 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 ...

, lilial is not long term stable and tends to slowly oxidize on storage.

Safety

The

Scientific Committee on Consumer Safety The Scientific Committee on Consumer Safety (SCCS) is one of the independent scientific committees managed by the Directorate-General for Health and Consumer Protection of the European Commission, which provide scientific advice to the commission ...

(SCCS, scientific committee for consumer safety of the EU Commission) concluded in May 2019 that the use of lilial in both rinse-off and leave-on cosmetics "cannot be considered as safe". After animal studies found it to be toxic for reproduction, it was reclassified as a prohibited substance in the EU, and banned from use in cosmetics as of March 2022. It can sometimes act as an

allergen An allergen is a type of antigen that produces an abnormally vigorous immune response in which the immune system fights off a perceived threat that would otherwise be harmless to the body. Such reactions are called allergies. In technical t ...

and may cause

contact dermatitis Contact dermatitis is a type of acute or chronic inflammation of the skin caused by exposure to chemical or physical agents. Symptoms of contact dermatitis can include itchy or dry skin, a red rash, bumps, blisters, or swelling. These rashes are ...

in susceptible individuals.

References

{{Reflist Aldehydes Perfume ingredients Tert-butyl compounds

Synthesis

Properties

Safety

See also

References