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geranyl acetone

Chemical Structure

General Material Information

Preferred name geranyl acetone
Trivial Name 6,10-Dimethyl-5,9-undecadien-2-one
Short Description 6,10-dimethyl-5,9-undecadien-2-one
Formula C13 H22 O
CAS Number 689-67-8
FEMA Number 3542
ECHA Number 211-711-2
FDA UNII Search
MDL MFCD00008910
xLogP3-AA 3.70 (est)
NMR Predictor External link
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 3796-70-1 ; GERANYL ACETONE
Synonyms
  • 6,10-dimethyl undeca-5,9-dien-2-one
  • 6,10-dimethyl-5,9-undecadien-2-one
  • 6,10-dimethyl-undeca-5,9-dien-2-one
  • 6,10-dimethylundeca-5,9-dien-2-one
  • 5,9-undecadien-2-one, 6,10-dimethyl-
  • 6,10-dimethylundeca-5,9-dien-2-one
  • 5,9-Undecadien-2-one, 6,10-dimethyl-
  • 5,9-Hendecadien-2-one, 6,10-dimethyl-
  • 6,10-Dimethyl-5,9-undecadien-2-one
  • 2,6-Dimethylundeca-2,6-dien-10-one
  • Dihydropseudoionone
  • 6,10-Dimethyl-5,9-undecadiene-2-one
  • NSC 406679
  • 6,10-Dimethyl-5,9-undec-2-one

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

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Literature & References

6,10-dimethylundeca-5,9-dien-2-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:689-67-8
Pubchem (cid):19633
Pubchem (sid):135050711
Pherobase:View
Publications by PubMed
Circadian Release of Male-Specific Components of the Greater Date Moth, Aphomia (Arenipses) Sabella, Using Sequential SPME/GC/MS Analysis.
Alterations in exhaled breath metabolite-mixtures in two rat models of lipopolysaccharide-induced lung injury.
Essential oils from the leaves of six medicinal plants of Nigeria.
Odorant-binding proteins and olfactory coding in the solitary bee Osmia cornuta.
Steps in the biosynthesis of fuscumol in the longhorn beetles Tetropium fuscum (F.) and Tetropium cinnamopterum Kirby.
Biosynthesis and site of production of sex pheromone components of the cerambycid beetle, Hedypathes betulinus.
Antitrypanosomal compounds from the essential oil and extracts of Keetia leucantha leaves with inhibitor activity on Trypanosoma brucei glyceraldehyde-3-phosphate dehydrogenase.
Towards an early warning system for Rhodesian sleeping sickness in savannah areas: man-like traps for tsetse flies.
Are the wild and laboratory insect populations different in semiochemical emission? The case of the medfly sex pheromone.
SVOC exposure indoors: fresh look at dermal pathways.
Chemical composition and in vitro cytotoxic, genotoxic effects of essential oil from Urtica dioica L.
Chemical composition of essential oils from leaves, stems, flower heads and roots of Conyza bonariensis L. from Tunisia.
Male-produced sex pheromone of the cerambycid beetle Hedypathes betulinus: chemical identification and biological activity.
Attractants for rice leaf bug, Trigonotylus caelestialium (Kirkaldy), are emitted from flowering rice panicles.
Evaluation of semiochemical toxicity to houseflies and stable flies (Diptera: Muscidae).
Constituents of the essential oil of Suregada zanzibariensis leaves are repellent to the mosquito, Anopheles gambiae s.s.
Changes in volatile aroma compounds of organic fragrant rice during storage under different conditions.
Leaf essential oil of Juniperus oxycedrus L. (Cupressaceae) harvested in northern Tunisia: composition and intra-specific variability.
Evaluation of semiochemical toxicity to Aedes aegypti, Ae. albopictus and Anopheles quadrimaculatus (Diptera: Culicidae).
Comparative analysis of essential oil components and antioxidant activity of extracts of Nelumbo nucifera from various areas of China.
Heterogeneous oxidation of squalene film by ozone under various indoor conditions.
Mice recognize recent urine scent marks by the molecular composition.
Ozone-initiated chemistry in an occupied simulated aircraft cabin.
Electrophysiological and behavioral responses of Ips subelongatus to semiochemicals from its hosts, non-hosts, and conspecifics in China.
Composition and antimicrobial activity of Equisetum arvense L. essential oil.
Carotenoid pigmentation affects the volatile composition of tomato and watermelon fruits, as revealed by comparative genetic analyses.
Stir bar sorptive extraction applied to volatile constituents evolution during Vitis vinifera ripening.
Electroantennographic and behavioral responses of the sphinx moth Manduca sexta to host plant headspace volatiles.
Olfactory receptors on the antennae of the malaria mosquito Anopheles gambiae are sensitive to ammonia and other sweat-borne components.
Inhibition of host-seeking response and olfactory responsiveness in Anopheles gambiae following blood feeding.
A non-toxic heat shock protein 70 inducer, geranyl-geranyl-acetone, restores the heat shock response in gastric mucosa of protein-malnourished rats.
Effects of geranyl-geranyl-acetone administration before heat shock preconditioning for conferring tolerance against ischemia-reperfusion injury in rat livers.
Chemicals in laboratory room air stimulate olfactory neurons of female Bombyx mori.
Geranyl-geranyl acetone: a novel stimulant of secretin release in the dog.
Identification of isoprenoid-type components in human expired air: a possible shunt pathway in sterol metabolism.
A comparative study of the exocrine products of cleptoparasitic bees (Holcopasites) and their hosts (Calliopsis) (Hymenoptera: Anthophoridae, Andrenidae).
[Effect of prostaglandin E2, cimetidine and geranyl-geranyl-acetone on rat gastric mucosal damage (author's transl)].

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
FDA Substances Added to Food (formerly EAFUS):View
CHEMBL:View
HMDB (The Human Metabolome Database):Search
FooDB:FDB021664
Export Tariff Code:2914.19.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 194.31753540039
Vapor Pressure 0.016 mmHg @ 25 °C
Flash Point TCC Value 100 °C TCC
logP (o/w) 3.834 est
Solubility
alcohol Yes
water, very slightly Yes
water, 8.867 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Floral
fresh, rose, leafy, floral, green, magnolia, aldehydic, fruity
Luebke, William tgsc, (1985) At 100.00 %. fresh rose leaf floral green magnolia aldehydic fruity
Flavor Type: Floral
floral, fruity, tropical, green, pear, apple, banana, citrus
Luebke, William tgsc, (1985) Floral fruity tropical green pear apple banana citrus

Occurrences

Potential Uses

Applications
Odor purposes Banana, Floral, Green, Jasmin, Magnolia, Mint, Passion fruit, Pear, Plum, Rose
Flavoring purposes Tea, Tomato, Tropical
Cosmetic purposes Perfuming agents

Safety Information

Safety information

European information :
Most important hazard(s):
Xi N - Irritant, Dangerous for the environment.
R 38 - Irritating to skin.
R 51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-mouse LD50 [sex: M,F] 8650 mg/kg
(Moreno, 1976b)

oral-rat LD50 [sex: M,F] > 6800 mg/kg
(Hoffman, 1978)

oral-rat LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 17, Pg. 787, 1979.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 17, Pg. 787, 1979.

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
Recommendation for geranyl acetone usage levels up to:
5.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 41.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 2.00 (μg/capita/day)
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 11
Click here to view publication 11
average usual ppmaverage maximum ppm
baked goods: -10.00000
beverages(nonalcoholic): -10.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -10.00000
fruit ices: --
gelatins / puddings: -10.00000
granulated sugar: --
gravies: --
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: -10.00000
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):689-67-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :19633
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
6,10-dimethylundeca-5,9-dien-2-one
Chemidplus:0000689678
RTECS:YQ1190000 for cas# 689-67-8