Ljiljan
Lily of the valley (Convallaria majalis, muguet in French) is a plant whose scent must be recreated synthetically, because no natural aromatic extract can be produced from it. Hydroxycitronellal, an odorant used in perfumery, has a sweet floral, lily-like and green smell.
- Type
- Akord
- Olfactive family
- Cvetni
- Source
- Recreated synthetically; no natural aromatic extract can be produced from the plant
- Chemical class
- Aldehydes (hydroxycitronellal, bourgeonal, lilial)
Miris
Detaljno
Zanimljivosti
In vitro, bourgeonal acts as a chemo-attractant for human spermatozoa, activating an olfactory receptor called OR1D2. As of 2010, bourgeonal is the only known odor substance to which males have a higher average sensitivity than females.
Dobijanje i hemija
Način dobijanja
In laboratory studies, the volatiles that lily flowers emit are collected by headspace solid-phase microextraction, and the compounds that remain in petal tissue are extracted with organic solvents, both followed by gas chromatography-mass spectrometry. Of eight common solvents, dichloromethane was the most suitable for extracting the endogenous compounds from the petals of one lily cultivar. Lilial is produced by the mixed aldol coupling of 4-tert-butylbenzaldehyde (typically as its methanol acetal) and propionaldehyde, followed by hydrogenation. Industrial synthesis of bourgeonal involves a mixed aldol reaction of 4-tert-butylbenzaldehyde and acetaldehyde, followed by hydrogenation. Alternatively, bourgeonal may be produced by the Heck reaction of 1-bromo-4-tert-butylbenzene with 2-hydroxymethylpropene followed by isomerisation.
- Formula
- C₁₀H₂₀O₂ (hydroxycitronellal)
- CAS
- 107-75-5 (hydroxycitronellal)
- Botanički naziv
- Convallaria majalis (lily of the valley); Lilium candidum (Madonna lily, a true lily)
- Izgled
- Colourless liquid (hydroxycitronellal)
- Sinonimi
- muguet, lily of the valley
Restricted — IFRA Standard « Hydroxycitronellal » (Amendment 51)
- Tačka ključanja
- 241 °C at 760 mm Hg
- Relativna gustina
- 0.918-0.923
- Indeks prelamanja
- 1.447-1.450
- Nota
- Values are those of hydroxycitronellal.
U parfemima
Perfumes imitating lily of the valley sometimes carry its French name, muguet. Hydroxycitronellal was used to build the lily-of-the-valley scent in a classic 1956 fragrance; the European Chemicals Agency now considers it a skin sensitiser and its use has been restricted. Hydroxycitronellal is used as an ingredient in fragrances and is found in a wide variety of consumer products. It is found in soaps, shampoos, detergents, perfumes and household cleaning and maintenance products. Lilial was used in perfumes produced before 2022 as a synthetic substitute for the scent of lily of the valley. Because of the ban on lilial, safe analogues are currently used in perfume production. The Schiff base of hydroxycitronellal and methyl anthranilate is known as Aurantiol, which is extensively used in a large variety of floral notes such as orange-blossom, linden-blossom and tuberose.
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