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hydroxycitronellal / methyl anthranilate schiff's base

Chemical Structure

General Material Information

Preferred name hydroxycitronellal / methyl anthranilate schiff's base
Trivial Name Aurantiol
Short Description aurantiol (Givaudan)
Formula C18 H27 N O3
CAS Number 89-43-0
Deleted CAS Number 61792-01-6
ECHA Number 201-908-1
FDA UNII Search
Nikkaji Number J60.365A
MDL MFCD00021817
xLogP3-AA 3.30 (est)
Bio Activity Summary External link
NMR Predictor External link
Synonyms
  • anthranilic acid N-(7-hydroxy-3,7-dimethyl octylidene) methyl ester
  • anthranilic acid, N-(7-hydroxy-3,7-dimethyloctylidene)-, methyl ester
  • auralva (IFF)
  • aurantesin
  • aurantha
  • aurantia
  • aurantine
  • aurantiol (Givaudan)
  • aurantiol BJ
  • aurantiol pure
  • aurantion (Quest)
  • aurantium
  • benzoic acid, 2-((7-hydroxy-3,7-dimethyloctylidene)amino)-, methyl ester
  • benzoic acid, 2-[ (7-hydroxy-3, 7-dimethyloctylidene)amino]-, methyl ester
  • N-(7-hydroxy-3, 7-dimethyloctylidene)anthranilic acid methyl ester
  • hydroxycitronellylidene methyl anthranilate
  • methyl 2-((7-hydroxy-3,7-dimethyl octylidene)amino) benzoate
  • methyl 2-((7-hydroxy-3,7-dimethyl octylidene)amino)-1-benzene carboxylate
  • methyl 2-((7-hydroxy-3,7-dimethyloctylidene)amino)benzoate
  • methyl 2-[(7-hydroxy-3,7-dimethyloctylidene)amino]benzoate
  • methyl anthranilate / hydroxycitronellal schiff base
  • methyl anthranilate / hydroxycitronellal schiff's base
  • methyl N-3, 7-dimethyl-7-hydroxyoctylideneanthranilate
  • methyl N-3,7-dimethyl-7-hydroxyoctylideneanthranilate
  • methyl,N-3,7-dimethyl-7-hydroxyoctylidene anthranilate
  • orangeol
  • orantha-L-super
  • Benzoic acid, 2-[(7-hydroxy-3,7-dimethyloctylidene)amino]-, methyl ester
  • Aurantiol
  • Hydroxycitronellal methyl anthranilate
  • NSC 78483
  • Aurantion

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):Search
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 305.41778564453
Specific gravity @ 25 °C
Pounds per Gallon 8.501 to 8.548
Refractive Index 1.5036 to 1.5109 @ 20 °C
Vapor Pressure 0.004 mmHg @ 20 °C
Flash Point TCC Value 93.89 °C TCC
logP (o/w) 5.417 est
Shelf life 24 months (or longer if stored properly.)
Solubility
alcohol Yes
water, 3.603 mg/L @ 25 °C (est) Yes
paraffin oil No

Organoleptic Properties

Odor Type: Floral
floral, lily, orangeflower, sweet
Odor strength medium , recommend smelling in a 50.00 % solution or less
Substantivity 400 hour(s) at 100.00 %
Luebke, William tgsc, (1983) At 50.00 % in dipropylene glycol. floral lily orange blossom sweet
Aurantiol is perhaps the best known Schiff base and is extensively used in a large variety of floral notes such as orange-blossom, linden-blossom and tuberose. Used in citrus cologne types, it acts as an excellent fixative as well as exalting the top notes. It gives an oriental character when used in amber an chypre compositions and blends particularly well with macrocyclic musks. Floral, Orange flower, Linden-Blossom
General comment Neroli, orange, muguet and grape facets
Aurantiol is perhaps the best-known Schiff’s base (hydroxycitronellal / methyl anthranilate); extensively used in a large variety of floral notes such as orange-blossom, linden-blossom and tuberose. Used in citrus cologne types, it acts as an excellent fixative as well as exalting the top notes. It gives an oriental character when used in amber and chypre compositions and blends particularly well with macrocyclic musks. Sweet, floral-orange-blossom, linden-blossom, neroli and lily, amber

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Skin irritation (Category 2), H315
Eye irritation (Category 2A), H319
Specific target organ toxicity - single exposure (Category 3), Respiratory system, H335
Chronic aquatic toxicity (Category 2), H411
GHS Label elements, including precautionary statements
Pictogramexclamation-mark.jpgenvironment.jpg
Signal word Warning
Hazard statement(s)
H315 - Causes skin irritation
H319 - Causes serious eye irritation
H335 - May cause respiratory irritation
H411 - Toxic to aquatic life with long lasting effects
Precautionary statement(s)
P261 - Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 - Wash skin thouroughly after handling.
P271 - Use only outdoors or in a well-ventilated area.
P273 - Avoid release to the environment.
P280 - Wear protective gloves/protective clothing/eye protection/face protection.
P302 + P352 - IF ON SKIN: wash with plenty of soap and water.
P304 + P340 - IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305 + P351 + P338 - IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P312 - Call a POISON CENTER or doctor/physician if you feel unwell.
P332 + P313 - IF SKIN irritation occurs: Get medical advice/attention.
P337 + P313 - IF eye irritation persists: Get medical advice/attention.
P362 - Take off contaminated clothing and wash before reuse.
P391 - Collect spillage. Hazardous to the aquatic environment
P403 + P233 - Store in a well-ventilated place. Keep container tightly closed.
P405 - Store locked up.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Oral/Parenteral Toxicity:
oral-rat LD50 > 5000 mg/kg
Dispose of contents/ container to an approved waste disposal plant.

Dermal Toxicity:
skin-rabbit LD50 > 10000 mg/kg
Dispose of contents/ container to an approved waste disposal plant.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
IFRA Critical Effect:
Sensitization
IFRA fragrance material specification:
The IFRA Scientific Committee examined the physicochemical properties of Schiff bases and concluded that, based on the available information, these materials should be considered under contributions from other sources. By default, the stoichiometric presence of the aldehydes of the Schiff bases is taken into account assuming 100% dissociation. An indicative list of Schiff bases incorporating aldehydes covered by an IFRA Standard of restriction is reported at page 2. These Schiff bases must be taken into account for determination of the maximum use level of the respective aldehydes.
contains the following IFRA (Annex) restricted components: (non-analysis max. level reference only)
hydroxycitronellal Max. Found: 56.4 % and Reason: Sensitization
Recommendation for hydroxycitronellal / methyl anthranilate schiff's base usage levels up to:
8.0000 % in the fragrance concentrate.
Recommendation for hydroxycitronellal / methyl anthranilate schiff's base flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):89-43-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :98118
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
methyl 2-[(7-hydroxy-3,7-dimethyloctylidene)amino]benzoate
Chemidplus:0000089430