Lilial

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
ChemSpider	1266494 (2R) 1363748 (2S) 199342
EC Number	201-289-8
Jmol interactive 3D	Image
PubChem	1549660 (2R) 1715213 (2S) 228987
RTECS number	MW4895000
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	204.31 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]
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) is a chemical compound commonly used as a perfume in cosmetic preparations and laundry powders where it often appears under the outdated systematic name of butylphenyl methylpropional.

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

• Helional
• Bourgeonal

References

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.
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.