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词条 Lilial
释义

  1. Synthesis

  2. Properties

  3. Safety

  4. See also

  5. References

{{Chembox
| ImageFile = Lilial.svg
| IUPACName = 3-(4-tert-Butylphenyl)-2-methylpropanal
| OtherNames = {{unbulleted list|4-tert-Butyl-α-methyl-benzenepropanal | 4-tert-Butyl-α-methyl-hydrocinnamaldehyde | Butylphenyl methylpropional}}
|Section1={{Chembox Identifiers
| CASNo = 80-54-6
| CASNo_Comment = (Racemic)
| CASNo1 = 75166-31-3
| CASNo1_Comment = (2R)
| CASNo2 = 75166-30-2
| CASNo2_Comment = (2S)
| PubChem = 1549660
| PubChem_Comment = (2R)
| PubChem1 = 1715213
| PubChem1_Comment = (2S)
| PubChem2 = 228987
| ChemSpiderID = 1266494
| ChemSpiderID_Comment = (2R)
| ChemSpiderID1 = 1363748
| ChemSpiderID1_Comment = (2S)
| ChemSpiderID2 = 199342
| EINECS = 201-289-8
| UNNumber = 3082
| RTECS = MW4895000
| SMILES = CC(CC1=CC=C(C=C1)C(C)(C)C)C=O
| 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
| InChIKey = SDQFDHOLCGWZPU-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=14 | H=20 | O=1
| Appearance = Clear viscous liquid
| Density = 0.94 g/ml
| MeltingPtC = -20
| BoilingPtC = 275
| BoilingPt_ref = [1]
| Solubility =0.045 g/l at 20 °C
| LogP = 4.36 [1]
}}
|Section3={{Chembox Pharmacology
| AdminRoutes = Topical}}
|Section4={{Chembox Related
| OtherFunction_label = aldehydes
| OtherFunction = Bourgeonal
Isobutyraldehyde
Hexyl cinnamaldehyde
2-Methylundecanal
}}
}}

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]

{{clear-left}}

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.

See also

  • Helional
  • Bourgeonal

References

1. ^{{cite journal|last1=Haefliger|first1=Olivier P.|last2=Jeckelmann|first2=Nicolas|last3=Ouali|first3=Lahoussine|last4=León|first4=Géraldine|title=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|journal=Analytical Chemistry|volume=82|issue=2|year=2010|pages=729–737|issn=0003-2700|doi=10.1021/ac902460d|pmid=20025230}}
2. ^{{cite journal|last1=Bartschat|first1=Dietmar|last2=Bürner|first2=Susanne|last3=Mosandl|first3=A.|last4=Bats|first4=Jan W.|title=Stereoisomeric flavour compounds LXXVI: direct enantioseparation, structure elucidation and structure-function relationship of 4-tert-butyl-α-methyldihydrocinnamaldehyde|journal=Zeitschrift für Lebensmitteluntersuchung und -Forschung A|volume=205|issue=1|year=1997|pages=76–79|issn=1431-4649|doi=10.1007/s002170050127}}

3 : Aldehydes|Perfume ingredients|Tert-butyl compounds

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