Aurantiol
Aurantiol is the Schiff base of hydroxycitronellal and methyl anthranilate. It has an orange blossom and neroli character.
- Type
- Sirovina
- Olfactive family
- Cvetni
- Source
- Synthetic
- Chemical class
- Schiff base
Miris
Detaljno
Zanimljivosti
Schiff bases are named after the chemist Hugo Schiff, who discovered them. The reaction between methyl anthranilate and an aldehyde continues even after a perfume has been bottled, so older samples may show Schiff bases that were not present when the fragrance was originally formulated.
Dobijanje i hemija
Način dobijanja
When methyl anthranilate reacts with an aldehyde, water is released and a single, heavier compound is formed. Schiff bases can be synthesized from odorant aldehydes and primary amines through a condensation reaction. The Schiff base of hydroxycitronellal and methyl anthranilate can be prepared by direct condensation of the neat liquid reagents at 110 °C, without solvents or dehydrating agents. Of four methyl anthranilate Schiff bases made in one study, three gave their best yield with a 2:1 excess of the aldehyde, and one with a 2:1 excess of methyl anthranilate. Perfumers can also add methyl anthranilate as a separate ingredient alongside an aldehyde such as hydroxycitronellal, so that the Schiff base forms gradually inside the finished compound over weeks or months, in a process known as maceration.
- Formula
- C₁₈H₂₇NO₃
- CAS
- 89-43-0
- Izgled
- Pale yellow to amber viscous liquid
- Jačina mirisa
- Visok
- Sinonimi
- Hydroxycitronellal methyl anthranilate, Aurantium, Aurantine, Aurantion, Auralva, Hydroxycitronellylidene methyl anthranilate
No IFRA Standard for the material itself (51st Amendment)
U parfemima
Aurantiol is used extensively in a large variety of floral notes, such as orange-blossom, linden-blossom and tuberose. Schiff bases of methyl anthranilate with four aldehydes, hydroxycitronellal among them, may be applied as profragrances, which release the aldehyde and methyl anthranilate on hydrolysis.
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