ChemicalBook--->CAS DataBase List--->89-43-0

89-43-0

89-43-0 Structure

89-43-0 Structure
IdentificationBack Directory
[Name]

AURANTIOL
[CAS]

89-43-0
[Synonyms]

AURALVA
AURANTIOL
AURANTION
AURANTIUM
201-908-1
Hydroxycitronellal
Hydroxycitronellal methyl anthranilate
METHYL ANTHRANILATE HYDROXY CITRONELLAL
HYDROXYCITRONELLYLIDENE METHYLANTHRANILATE
HYDROXYCITRONELLAL-METHYLANTHRANILATE SCHIFF'S BASE
METHYL N-3,7-DIMETHYL-7-HYDROXYOCTYLIDENEANTHRANILATE
Methyl-2-[(7-hydroxy-3,7-dimethyloctyliden)amino]benzoat
SCHIFF'S BASE-HYDROXYCITRONELLAL AND METHYL ANTHRANILATE
methyl 2-[(7-hydroxy-3,7-dimethyloctylidene)amino]benzoate
2-[(7-hydroxy-3,7-dimethyloctylidene)amino]-benzoicacimethylester
N-(7-HYDROXY-3 7-DIMETHYLOCTYLIDENE)ANTHRANILIC ACID METHYL ESTER
2-(3,7-Dimethyl-7-hydroxyoctylideneamino)benzoic acid methyl ester
2-[(7-Hydroxy-3,7-dimethyloctylidene)amino]benzoic acid methyl ester
Benzoicacid,2-[(7-hydroxy-3,7-dimethyloctylidene)amino]-,methylester
[EINECS(EC#)]

201-908-1
[Molecular Formula]

C18H27NO3
[MDL Number]

MFCD00021817
[MOL File]

89-43-0.mol
[Molecular Weight]

305.41
Chemical PropertiesBack Directory
[Appearance]

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.
[Boiling point ]

445.7±45.0 °C(Predicted)
[density ]

1.01±0.1 g/cm3(Predicted)
[Fp ]

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
[Cosmetics Ingredients Functions]

PERFUMING
[LogP]

5.417 (est)
[Uses]

Perfumery (fixative, muguet odor), flavoring, soap and cosmetic fragrances.
[EPA Substance Registry System]

Benzoic acid, 2-[(7-hydroxy-3,7-dimethyloctylidene) amino]-, methyl ester(89-43-0)
Hazard InformationBack Directory
[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.
[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).
Safety DataBack Directory
[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).
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