AURANTIOL Chemical Properties

Boiling point:

445.7±45.0 °C(Predicted)

Density 

1.01±0.1 g/cm3(Predicted)

Flash point:

97℃

solubility 

Almost insoluble in water, soluble in alcohol and oils, poorly soluble in Propylene glycol.

form 

Intensely yellow, viscous to very viscous liquid

pka

15.31±0.29(Predicted)

Odor

at 50.00 % in dipropylene glycol. floral lily orange blossom sweet

Odor Type

floral

LogP

5.417 (est)

EPA Substance Registry System

Benzoic acid, 2-[(7-hydroxy-3,7-dimethyloctylidene)amino]-, methyl ester (89-43-0)

Safety Information

Toxicity

The acute oral LD₅₀ value in rats was reported as > 5 g/kg (Moreno, 1973). The acute dermal LD₅₀ value in rabbits was reported as > 2 g/kg (Moreno, 1973).

AURANTIOL Usage And Synthesis

Chemical Properties

Viscous, colorless, or faintly yellow liquid; sweet lily-type odor.Soluble in alcohol (50%), fixed oils; slightly soluble in water, glycerol, and mineral oil. Combustible.

Occurrence

Has apparently not been reported to occur in nature.

Uses

hydroxycitronellal is used to mask odor.

Uses

Perfumery (fixative, muguet odor), flavoring, soap and cosmetic fragrances.

Application

This Schiff-s base Aurantiol is the most widely used of all Schiff's bases known in perfumery. Its low cost and considerable strength, its tenacity and versatility are virtues that make the product applicable in fragrances of all price levels and for numerous purposes. Obviously and almost inevitably used in Orange blossom, Neroli and related heavy florals, it finds use in smaller amounts in countless other fragrant types: Citrus blends, Ambres, and Orientals. Chyprcs, etc. It forms the steady undertone in many such sweet florals, in Honeysuckle, Frangipanni, Magnolia, exotic florals, etc. In the Citrus Cologne types, it has the ability to appear even in the initial notes, besides being a fixative. Used for nearly 50 years, it has been brought "back to life" several times, e. g., when the fruity-musky perfume was fashionable (and still is, to a certain degree), that perfume had a solid undertone of this type of material, backed up by Ethylene brassylate and Undecanolide in unusually high proportions. This base has a perceptible effect in a perfume oil at concentrations beginning well below 1%, but is often used at a much higher level.

Preparation

By hydration of citronellal (Bedoukian, 1967).

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 108, 1974 DOI: 10.1021/jo00915a028

Trade name

Aurantiol Pure (Givaudan).

AURANTIOL(89-43-0)Related Product Information

• Methyl anthranilate
• Citronellal
• Aurantiol (methyl anthranilate and hydroxycitronellal schiff base)
• AURANTIOL