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Lilial





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Lilial (a trade name for lily aldehyde, also known as lysmeral) is a chemical compound commonly used as a perfumeincosmetic 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.

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

  • 75166-31-3 (2R) checkY
  • 75166-30-2 (2S) checkY
  • 3D model (JSmol)

    ChemSpider
  • 1363748 (2S)
  • 199342
  • ECHA InfoCard 100.001.173 Edit this at Wikidata
    EC Number
    • 201-289-8

    PubChem CID

  • 1715213 (2S)
  • 228987
  • RTECS number
    • MW4895000
    UNII
  • 14X71K3AMT (2R) checkY
  • WP1PPC4R9G (2S) checkY
  • UN number 3082

    CompTox Dashboard (EPA)

    • 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

    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

    Synthesis

    edit

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

    Properties

    edit

    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 cyclamenorlily 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

    edit

    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

    edit

    References

    edit
    1. ^ a b 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".
  • ^ 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
  • ^ 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

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Lilial&oldid=1234766062"
     



    Last edited on 16 July 2024, at 01:29  





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    This page was last edited on 16 July 2024, at 01:29 (UTC).

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