Lilial

Last updated
Lilial
Lilial.svg
Names
IUPAC name
3-(4-tert-Butylphenyl)-2-methylpropanal
Other names
  • 4-tert-Butyl-α-methyl-benzenepropanal
  • 4-tert-Butyl-α-methyl-hydrocinnamaldehyde
  • Butylphenyl methylpropional
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.173 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-289-8
PubChem CID
RTECS number
  • MW4895000
UNII
UN number 3082
  • InChI=1S/C14H20O/c1-11(10-15)9-12-5-7-13(8-6-12)14(2,3)4/h5-8,10-11H,9H2,1-4H3
    Key: SDQFDHOLCGWZPU-UHFFFAOYSA-N
  • CC(CC1=CC=C(C=C1)C(C)(C)C)C=O
Properties
C14H20O
Molar mass 204.313 g·mol−1
AppearanceClear viscous liquid
Density 0.94 g/cm3
Melting point −20 °C (−4 °F; 253 K)
Boiling point 275 °C (527 °F; 548 K) [1]
0.045 g/L at 20 °C
log P 4.36 [1]
Pharmacology
Topical
Related compounds
Related aldehydes
 Bourgeonal

Isobutyraldehyde
Hexyl cinnamaldehyde
2-Methylundecanal

Contents

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lilial (a trade name for lily aldehyde, also known as lysmeral or lilestralis) is a chemical compound commonly used as a perfume in cosmetic preparations and laundry powders, often under the name butylphenyl methylpropional. It is an aromatic aldehyde, naturally occurring in crow-dipper and tomato plants, [2] and produced synthetically in large scale. It was banned for use in cosmetics by the EU in March 2022 after being found to be harmful to fertility.

It is also used as an intermediate in the synthesis of agrochemicals such as fenpropimorph and fenpropidin.

Synthesis

Lilial is produced by the mixed aldol coupling of 4-tert-butylbenzaldehyde (typically as it's methanol acetal) and propionaldehyde, followed by hydrogenation.

Lysmeral Industriell.svg

Properties

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. [3]

(R)-Lilial (top) and (S)-lilial 2-(4-tert-Butylbenzyl)propionaldehyd Formulae V.1.svg
(R)-Lilial (top) and (S)-lilial

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

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". [4]

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. [5]

It can sometimes act as an allergen and may cause contact dermatitis in susceptible individuals. Lilial was used in many perfumes (examples: Byredo Inflorescence, Salvador Dali Laguna [6] , Elizabeth Arden 5th Avenue, etc.) produced before 2022 as a synthetic substitute for the scent of lily of the valley. Due to the ban on the use of lilial, safe analogues are currently used in perfume production.

See also

References

  1. 1 2 Haefliger, Olivier P.; Jeckelmann, Nicolas; Ouali, Lahoussine; León, Géraldine (2010). "Real-Time Monitoring of Fragrance Release from Cotton Towels by Low Thermal Mass Gas Chromatography Using a Longitudinally Modulating Cryogenic System for Headspace Sampling and Injection". Analytical Chemistry. 82 (2): 729–737. doi:10.1021/ac902460d. ISSN   0003-2700. PMID   20025230.
  2. ↑ "Lilial".
  3. ↑ 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 Lebensmittel-Untersuchung und -Forschung A. 205 (1): 76–79. doi:10.1007/s002170050127. ISSN   1431-4649. S2CID   97399242.
  4. ↑ Scientific Committee on Consumer Safety (2019-05-10). "OPINION ON the safety of Butylphenyl methylpropional (p-BMHCA) in cosmetic products" (PDF). Retrieved 2020-05-28. On individual product basis, Butylphenyl methylpropional (p-BMHCA) (CAS 80-54-6) with alpha-tocopherol at 200 ppm, can be considered safe when used as fragrance ingredient in different cosmetic leave-on and rinse-off type products. However, considering the first-tier deterministic aggregate exposure, arising from the use of different product types together, Butylphenyl methylpropional at the proposed concentrations cannot be considered as safe.
  5. ↑ "COMMISSION REGULATION (EU) 2021/1902 OF 29 October 2021 amending Annexes II, III and V to Regulation (EC) No 1223/2009 of the European Parliament and of the Council as regards the use of cosmetic products of certain substances classified as carcinogenic, mutagenic or toxic for reproduction" . Retrieved 2022-01-03. CAS No. 80-54-6
  6. ↑ "Купить духи Salvador Dali Laguna — цена туалетной воды, фото, отзывы, описание аромата". Salvador Dali (in Russian). Retrieved 2025-03-12.
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