Lilial

Lilial
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, BMHCA, p-BMHCA;
Identifiers
CAS Number	80-54-6 (Racemic) ; 75166-31-3 (2R) ; 75166-30-2 (2S) ;
3D model (JSmol)	Interactive image;
ChemSpider	1266494 (2R); 1363748 (2S); 199342;
ECHA InfoCard	100.001.173
EC Number	201-289-8;
PubChem CID	1549660 (2R); 1715213 (2S); 228987;
RTECS number	MW4895000;
UNII	T7540GJV69 (Racemic) ; 14X71K3AMT (2R) ; WP1PPC4R9G (2S) ;
UN number	3082
CompTox Dashboard (EPA)	DTXSID9026500 ;
	InChI 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;
	SMILES CC(CC1=CC=C(C=C1)C(C)(C)C)C=O;
Properties
Chemical formula	C14H20O
Molar mass	204.313 g·mol−1
Appearance	Clear viscous liquid
Density	0.94 g/cm3
Melting point	−20 °C (−4 °F; 253 K)
Boiling point	275 °C (527 °F; 548 K)
Solubility in water	0.045 g/L at 20 °C
log P	4.36
Pharmacology
Routes of; administration	Topical
Related compounds
Related aldehydes	Bourgeonal; Isobutyraldehyde; Hexyl cinnamaldehyde; 2-Methylundecanal
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Lilial (a trade name for lily aldehyde, also known as lysmeral or lilestralis) is an organic compound with the formula (CH₃)₃CC₆H₄CH₂CH(CH₃)CHO. It is an aromatic aldehyde, naturally occurring in crow-dipper and tomato plants.^[2] It was once produced synthetically in a multi-ton scale for use as a perfume in cosmetic preparations and laundry powders, often under the name butylphenyl methylpropional. It has been largely banned after being found to be harmful to fertility.^[3]

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.

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.^[4]

Like most aldehydes, lilial tends to 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".^[5] The toxicity of Lilial is attributed to its degradation product tert-butylbenzoic acid.^[3]

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.^[6]

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,^[7] 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.^[3]

References

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.
↑ "Lilial".
1 2 3 Armanino, N., Charpentier, J., Flachsmann, F., Goeke, A., Liniger, M., Kraft, P. (14 September 2020). "What's Hot, What's Not: The Trends of the Past 20 Years in the Chemistry of Odorants". Angewandte Chemie International Edition. 59 (38): 16310–16344. doi:10.1002/anie.202005719.
↑ 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.
↑ 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.
↑ "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
↑ "Купить духи Salvador Dali Laguna — цена туалетной воды, фото, отзывы, описание аромата". Salvador Dali (in Russian). Retrieved 2025-03-12.

[HaefligerJeckelmann2010-1] 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".

[ACIE-3] 1 2 3 Armanino, N., Charpentier, J., Flachsmann, F., Goeke, A., Liniger, M., Kraft, P. (14 September 2020). "What's Hot, What's Not: The Trends of the Past 20 Years in the Chemistry of Odorants". Angewandte Chemie International Edition. 59 (38): 16310–16344. doi:10.1002/anie.202005719.

[BartschatBürner1997-4] 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.

[5] 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.

[6] "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

[7] "Купить духи Salvador Dali Laguna — цена туалетной воды, фото, отзывы, описание аромата". Salvador Dali (in Russian). Retrieved 2025-03-12.

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Lilial

Synthesis

Properties

Safety

See also

References