Lilial: Difference between revisions
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'''Lilial''' (a trade name for '''lily aldehyde''', also known as '''lysmeral''') is a [[chemical compound]] commonly used as a [[perfume]] in [[cosmetics|cosmetic preparations]] and laundry powders, often under the name ''butylphenyl methylpropional''. It is an [[Aromaticity|aromatic]] [[aldehyde]], naturally occurring in [[Pinellia ternata|crow-dipper]] and [[Solanum lycopersicum|tomato]] plants,<ref>{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Lilial | title=Lilial }}</ref> 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''' (a trade name for '''lily aldehyde''', also known as '''lysmeral''' or '''lilestralis''') is a [[chemical compound]] commonly used as a [[perfume]] in [[cosmetics|cosmetic preparations]] and laundry powders, often under the name ''butylphenyl methylpropional''. It is an [[Aromaticity|aromatic]] [[aldehyde]], naturally occurring in [[Pinellia ternata|crow-dipper]] and [[Solanum lycopersicum|tomato]] plants,<ref>{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Lilial | title=Lilial }}</ref> 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. |
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It is also used as an intermediate in the synthesis of agrochemicals such as [[fenpropimorph]]. |
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==Synthesis== |
==Synthesis== |
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Lilial is produced by the mixed aldol coupling of [[4-tert-butylbenzaldehyde]] (typically as it's methanol [[acetal]]) and [[propionaldehyde]], followed by [[hydrogenation]]. |
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Lilial is produced at [[BASF]] through a double anodic oxidation of 4-''tert''butyl-toluene on >10,000 ton per year scale.<ref>Möhle, S.; Zirbes, M.; Rodrigo, E.; Gieshoff, T.; Wiebe, A.; |
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Waldvogel, S. R. Modern Electrochemical Aspects for the Synthesis of Value-Added Organic Products. Angew. Chem., Int. Ed. 2018, 57, 6018−6041</ref> |
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:[[File:Lysmeral Industriell.svg|600px]] |
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==Properties== |
==Properties== |
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Latest revision as of 10:38, 23 December 2024
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| Names | |
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| IUPAC name
3-(4-tert-Butylphenyl)-2-methylpropanal
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Other names
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| Identifiers | |
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.001.173 |
| EC Number |
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PubChem CID
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| RTECS number |
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| UNII |
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| UN number | 3082 |
CompTox Dashboard (EPA)
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| Properties | |
| 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] |
| 0.045 g/L at 20 °C | |
| log P | 4.36 [1] |
| Pharmacology | |
| Topical | |
| Related compounds | |
Related aldehydes
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Bourgeonal |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.
Synthesis
[edit]Lilial is produced by the mixed aldol coupling of 4-tert-butylbenzaldehyde (typically as it's methanol acetal) and propionaldehyde, followed by hydrogenation.
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 cyclamen or lily of the valley; whereas the (S)-enantiomer possesses no strong odor.[3]
(R)-Lilial (top) and (S)-lilial
propionaldehyd_Formulae_V.1.svg)
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".[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.
See also
[edit]References
[edit]- ^ 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".
- ^ 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.
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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