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Lilial

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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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.173 Edit this at Wikidata
EC Number
  • 201-289-8
RTECS number
  • MW4895000
UN number 3082
  • 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
C14H20O
Molar mass 204.313 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

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).

Lilial (a trade name for lily aldehyde) 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. ^ 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.
  2. ^ 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.
  3. ^ 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.


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