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

Identifiers

CAS Number

* 80-54-6 (Racemic) Y
* 75166-31-3 (2R) Y
* 75166-30-2 (2S) Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 1266494 (2R)
* 1363748 (2S)
* 199342

EC Number |

* 201-289-8

PubChem CID

* 1549660 (2R)
* 1715213 (2S)
* 228987

RTECS number |

* MW4895000

UNII |

* T7540GJV69 (Racemic) Y
* 14X71K3AMT (2R) Y
* WP1PPC4R9G (2S) Y

UN number | 3082

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)[1]

Solubility in water

| 0.045 g/L at 20 °C
log P | 4.36 [1]
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) 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.

## Contents

* 1 Synthesis
* 2 Properties
* 3 Safety
* 4 See also
* 5 References

## Synthesis

Lilial is produced at BASF through a double anodic oxidation of 4-tertbutyl-toluene on >10,000 ton per year scale.[3]

## 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]

(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".[5]

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.

## See also

* Helional
* Bourgeonal

## References

1. ↑ 1.0 1.1 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. ↑ https://pubchem.ncbi.nlm.nih.gov/compound/Lilial
3. ↑ 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
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 Lebensmitteluntersuchung und -Forschung A 205 (1): 76–79. doi:10.1007/s002170050127. ISSN 1431-4649.
5. ↑ Scientific Committee on Consumer Safety (2019-05-10). "OPINION ON the safety of Butylphenyl methylpropional (p-BMHCA) in cosmetic products" (in en). https://ec.europa.eu/health/sites/health/files/scientific_committees/consumer_safety/docs/sccs_o_213.pdf. "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". https://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32021R1902&from=EN. "CAS No. 80-54-6"

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*[CID]: Compound ID