Lilial
Names | |
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IUPAC name
3-(4-tert-Butylphenyl)-2-methylpropanal | |
Other names
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Identifiers | |
80-54-6 (Racemic) 75166-31-3 (2R) 75166-30-2 (2S) | |
3D model (Jmol) | Interactive image |
ChemSpider | 1266494 (2R) 1363748 (2S) 199342 |
ECHA InfoCard | 100.001.173 |
EC Number | 201-289-8 |
PubChem | 1549660 (2R) 1715213 (2S) 228987 |
RTECS number | MW4895000 |
UN number | 3082 |
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Properties | |
C14H20O | |
Molar mass | 204.31 g·mol−1 |
Appearance | clear viscous liquid |
Density | 0.94 g/ml |
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 |
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 a synthetic aromatic aldehyde.
Synthesis
Lilial may be prepared via a number of routes but is typically produced via a crossed-aldol condensation between para-tert-butylbenzaldehyde and propanal, followed by hydrogenation of the intermediate alkene. This produces a racemic product.
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.[2]
Like most aldehydes Lilial is not long term stable and tends to slowly oxidize on storage.
Safety
It can sometimes act as an allergen and may cause contact dermatitis in susceptible individuals.[3]
See also
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.
- ↑ 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.
- ↑ Schnuch A, Uter W, Geier J, Lessmann H, Frosch PJ (July 2007). "Sensitization to 26 fragrances to be labelled according to current European regulation. Results of the IVDK and review of the literature". Contact Dermatitis. 57 (1): 1–10. doi:10.1111/j.1600-0536.2007.01088.x. PMID 17577350.