LILIAL
what is lilial?
Synthetic Ingredient For Perfumery Overview
Lilial ® (Givaudan) [ CAS 80-54-6 for the racemic mixture ] (a trade name for lily aldehyde, also known as Lysmeral (BASF) \ Lysmal) 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 aldehyde.
Like most aldehydes, lilial is not long term stable and tends to slowly oxidize on storage.
Lilial is commonly produced and sold as a racemic mixture; however, testing has indicated that the different enantiomers of the compound do not contribute equally to its odor. The (R)-enantiomer has a strong floral odor, reminiscent of cyclamen or lily of the valley; whereas the (S)-enantiomer possesses no strong odor [2].
Structurally, 2-(4-tert-butylbenzyl)propionaldehyde is derived from bourgeonal and has an additional methyl group at the C-2 atom. The molecule has a chiral structure with a stereogenic center and thus occur in two enantiomeric variants, an (R)- and an (S)-isomer. The two enantiomers smell slightly different: the (R)-isomer smells rather aldehydic-chemical while the (S)-isomer smells rather flowery-oily [3].
Profile
📂 CAS N° 80-54-6
⚖️ MW — 204.31 g/mol
📝 Odor Type — Muguet (Lily of the Valley) + Aldehydic
📈 Odor Strength — High
👃🏼 Odor Profile — Floral, sweet, aldehydic, muguet, soapy, clean, fresh, watery, transparent, clean, more synthetic (compared to other muguet odorants), plastic, aldehydic (F. Ciccolo at Scentspiracy, 2021)
Arctander says: Sweet, yet refreshing and intensely floral green odor of considerable radiance, although at the same time quite tenacious. There are notes resembling Hydroxycitronellal, and other notes recalling Cyclamen aldehyde. (No wonder. Look at the chemical structure).
⚗️ Uses — It is widely used in soap perfumes and many cosmetic perfumes. An excellent floralizer in itself, it also blends well with other floral materials, as well as with the musks and woody notes. It is far more versatile than Cyclamen aldehyde, or one can say that it is much more difficult to “’overdose” Lilial than it is to overdose Cyclamal. Yet, Lilial gives floral effects at lower concentration than Hydroxycitronellal, a fact that almost compensates for the cost difference. A conventional material in Lily, Lilac, Muguet, Orange blossom, Magnolia, Sweet Pea, Frangipani, it is also used in Chypres, Orientals, wood complexes and musky bases, as weIl as in modem fantasy soap perfumes, etc. ( S. Arctander, 1969)
Lilial has, in the comparatively short time it has existed, grown to become one of the truly “large-volume”’ fragrance chemicals, with an estimated annual production of well in excess of 100 tons, counting Lilial, Bamca, Bucinal and other brands.
Production
Lysmeral is produced at BASF through a double anodic oxidation of 4-tert-butyl toluene on >10,000 ton per year scale [4].
Lilial Safety
The Scientific Committee on Consumer Safety (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".
It can sometimes act as an allergen and may cause contact dermatitis in susceptible individuals.
Author’s opinion on this document: In the end, after 68 pages of data, the answer to the question is lilial safe? is: No but yes, we don’t know yet.
Sad but true.
Sources and informations
Fulvio Ciccolo, 2021
Bartschat, Dietmar; Bürner, Susanne; Mosandl, A.; Bats, Jan W. (1997). "Stereoisomeric flavour compounds LXXVI: direct enantioseparation, structure elucidation and structure-function relationship of 4-tert-butyl-α-methyldihydrocinnamaldehyde". Zeitschrift für Lebensmitteluntersuchung und -Forschung A. 205 (1): 76–79. doi:10.1007/s002170050127. ISSN 1431-4649. S2CID 97399242.
The Lilials. In: leffingwell.com. John C. Leffingwell, abgerufen am 9. Mai 2018 (englisch).
Möhle, S.; Zirbes, M.; Rodrigo, E.; Gieshoff, T.; Wiebe, A.; Waldvogel, S. R. Modern Electrochemical Aspects for the Synthesis of Value-Added Organic Products. Angew. Chem., Int. Ed. 2018, 57, 6018−6041
Perfume and flavor chemicals, S. Arctander, Denmark 1969.