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2-octanone

Chemical Structure

General Material Information

Preferred name 2-octanone
Trivial Name 2-Octanone
Short Description methyl hexyl ketone
Formula C8 H16 O
CAS Number 111-13-7
FEMA Number 2802
Flavis Number 7.019
ECHA Number 203-837-1
FDA UNII J2G84H29AF
Nikkaji Number J1.984D
Beilstein Number 0635843
MDL MFCD00009540
COE Number 153
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 288 2-octanone
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 111-13-7 ; 2-OCTANONE
Synonyms
  • hexyl methyl ketone
  • N- hexyl methyl ketone
  • ketone, hexyl methyl
  • laventerre
  • methyl hexyl cetone
  • methyl hexyl ketone
  • methyl hexyl ketone 90
  • methyl hexyl ketone, natural
  • methyl N-hexyl ketone
  • octan-2-one
  • 2-oxo octane
  • octane-2-one
  • 2-octanon
  • 2-octanone
  • 2-octanone natural
  • n-Hexyl methyl ketone
  • 2-Oxooctane
  • NSC 3712
  • NSC 5936

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

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Literature & References

octan-2-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:111-13-7
Pubchem (cid):8093
Pubchem (sid):134974863
Flavornet:111-13-7
Pherobase:View
Publications by US Patents
3,952,024 - Furfurylthioacetone
3,931,166 - Certain 2,5-dimethyl-3-thiopyrazines
Publications by PubMed
Binding of carbonyl flavours to canola, pea and wheat proteins using GC/MS approach.
Communication: Coordination structure of bromide ions associated with hexyltrimethylammonium cations at liquid/liquid interfaces under potentiostatic control as studied by total-reflection X-ray absorption fine structure.
Olfactory Sensitivity and Odor Structure-Activity Relationships for Aliphatic Ketones in CD-1 Mice.
Characterization of aroma compounds of Chinese famous liquors by gas chromatography-mass spectrometry and flash GC electronic-nose.
Brushed block copolymer micelles with pH-sensitive pendant groups for controlled drug delivery.
Mass and Ion Transport in Ketones and Ketone Electrolytes: Comparison with Acetate Systems.
Formation yields of C8 1,4-hydroxycarbonyls from OH + n-octane in the presence of NO.
Brain phospholipase C, diacylglycerol lipase and monoacylglycerol lipase are involved in (±)-epibatidine-induced activation of central adrenomedullary outflow in rats.
Analysis of quinolones by voltage-assisted liquid-phase microextraction combined with LC-MS.
Fragrance material review on methyl hexyl oxo cyclopentanone carboxylate.
Color, lipid oxidation, sensory quality, and aroma compounds of beef steaks displayed under different levels of oxygen in a modified atmosphere package.
Electromembrane extraction of peptides--fundamental studies on the supported liquid membrane.
Evaluation of parallel milliliter-scale stirred-tank bioreactors for the study of biphasic whole-cell biocatalysis with ionic liquids.
Evaluation of the use of Syzygium cumini fruit extract as an antioxidant additive in orange juice and its sensorial impact.
Controlling the facial selectivity of asymmetric [4+2] cyclo-additions: a concise synthesis of the cis-decalin core structure of superstolides A and B.
Thermodynamics and activity coefficients at infinite dilution measurements for organic solutes and water in the ionic liquid N-hexyl-3-methylpyridinium tosylate.
Comparison of volatile components in Chinese traditional pickled peppers using HS-SPME-GC-MS, GC-O and multivariate analysis.
Solvent free oxidation of primary alcohols and diols using thymine iron(III) catalyst.
Novel aspect of ketone action: β-hydroxybutyrate increases brain synthesis of kynurenic acid in vitro.
Isolation and characterization of 4-tert-butylphenol-utilizing Sphingobium fuliginis strains from Phragmites australis rhizosphere sediment.
Neurotoxicity of fungal volatile organic compounds in Drosophila melanogaster.
Prolonged stimulus exposure reveals prolonged neurobehavioral response patterns.
Hollow fiber-liquid-phase microextraction of fungicides from orange juices.
Asymmetric [4+2] cycloadditions employing 1,3-dienes derived from (R)-4-t-butyldimethyl-silyloxy-2-cyclohexen-1-one.
Purification and characterization of an anti-Prelog alcohol dehydrogenase from Oenococcus oeni that reduces 2-octanone to (R)-2-octanol.
Widespread occurrence of estrogenic UV-filters in aquatic ecosystems in Switzerland.
Ionic liquid based dispersive liquid-liquid microextraction for the extraction of pesticides from bananas.
Gas chromatography-olfactometry analysis of the volatile compounds of two commercial Irish beef meats.
Selective three-phase liquid phase microextraction of acidic compounds from foodstuff simulants.
Chemical characterization of territorial marking fluid of male Bengal tiger, Panthera tigris.
Templation of the excited-state chemistry of alpha-(n-alkyl) dibenzyl ketones: how guest packing within a nanoscale supramolecular capsule influences photochemistry.
Optimization of chlorophyllase-catalyzed hydrolysis of chlorophyll in monophasic organic solvent media.
Kinetic analysis of volatile formation in milk subjected to pressure-assisted thermal treatments.
Glial-cytokine-neuronal interactions underlying the mechanisms of persistent pain.
Purification, characterization, and gene cloning of glycerol dehydrogenase from Hansenula ofunaensis, and its expression for production of optically active diol.
Anti-prelog reduction of prochiral carbonyl compounds by Oenococcus oeni in a biphasic system.
Chemical boundaries for detection of eye irritation in humans from homologous vapors.
Dominant role for calpain in thromboxane-induced neuromicrovascular endothelial cytotoxicity.
Stability of immobilized soybean lipoxygenase in selected organic solvent media.
Stereoselective synthesis of c3-c12 dihydropyran portion of antitumor laulimalide using copper-catalyzed oxonium ylide formation-[2,3] shift.
1,4-hydroxycarbonyl products of the OH radical initiated reactions of C5-C8 n-alkanes in the presence of NO.
Bis{1-n-hexyl-3-methyl-4-[1-(phenylimino)propyl]-1H-pyrazol-5-olato}copper(II): a new copper(II) complex with a chelating alkylpyrazolone-based enamine.
Characterization of French and Spanish dry-cured hams: influence of the volatiles from the muscles and the subcutaneous fat quantified by SPME-GC.
Designing the "search pathway" in the development of a new class of highly efficient stereoselective hydrosilylation catalysts.
High-yield conversion of (R)-2-octanol from the corresponding racemate by stereoinversion using Candida rugosa.
Bimetallic isopropoxides M[Al(OC(3)H(i)(7))(4)](3) (M = Pr, Nd)--catalyzed reduction of 2-octanone and benzophenone.
Controlled production of Camembert-type cheeses. Part II. Changes in the concentration of the more volatile compounds.
Use of an ionic liquid in a two-phase system to improve an alcohol dehydrogenase catalysed reduction.
Expression of adhesion molecules by sphingosine 1-phosphate and histamine in endothelial cells.
Volatiles in a sausage surface model-influence of Penicillium nalgiovense, Pediococcus pentosaceus, ascorbate, nitrate and temperature.
An efficient direct alpha-alkylation of ketones with primary alcohols catalyzed by [Ir(cod)Cl]2/PPh3/KOH system without solvent.
Analysis of ketones by selected ion flow tube mass spectrometry.
Synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)- 6-hydroxy-3,5-dimethyl-2-octanone, the pheromone components of the bostrychid beetle, Dinoderus bifoveolatus.
Associative learning of complex odours in parasitoid host location.
Relationship between molecular structure, concentration and odor qualities of oxygenated aliphatic molecules.
Chlorpromazine inhibits the glucocorticoid receptor-mediated gene transcription in a calcium-dependent manner.
Aroma active components in aqueous kiwi fruit essence and kiwi fruit puree by GC-MS and multidimensional GC/GC-O.
Influence of lipid fraction, emulsifier fraction, and mean particle diameter of oil-in-water emulsions on the release of 20 aroma compounds.
Selective Oxidation of Vinyl Ethers and Silyl Enol Ethers with Hydrogen Peroxide Catalyzed by Peroxotungstophosphate.
An enantiospecific approach to tricyclic sesquiterpenes mayurone and thujopsenes.
Asymmetric reduction of ketones with catecholborane using 2,6-BODOL complexes of titanium(IV) as catalysts.
Interactions between artificial saliva and 20 aroma compounds in water and oil model systems.
Signalling mechanisms underlying the myogenic response in human subcutaneous resistance arteries.
Efficient oxidation of alcohols to carbonyl compounds with molecular oxygen catalyzed by N-hydroxyphthalimide combined with a Co species
Interactions between methyl ketones and beta-lactoglobulin: sensory analysis, headspace analysis, and mathematical modeling.
Blocking and the detection of odor components in blends.
Interactions of flavor compounds with pectic substances.
Oxidative cleavage of the octyl side chain of 1-(3,4-dichlorobenzyl)-5-octylbiguanide (OPB-2045) in rat and dog liver preparations.
Effect of aeration during cell growth on ketone reactions by immobilized yeast.
Interactions between aroma and edible films. 1. Permeability Of methylcellulose and low-density polyethylene films to methyl ketones.
Solvent-modified solid-phase microextraction for the determination of diazepam in human plasma samples by capillary gas chromatography.
An analysis of blocking in odorant mixtures: an increase but not a decrease in intensity of reinforcement produces unblocking.
Neighboring Group Participation in a Regio- and Stereoselective Chlorination of a Bicyclo[2.2.2]octanone.
Enhanced sensitivity to androstenone following regular exposure to pemenone.
Effects of solvation on partition and dimerization of benzoic acid in mixed solvent systems.
Ketone EC50 values in the Microtox test.
Structure, stereochemistry, and thermal isomerization of the male sex pheromone of the longhorn beetle Anaglyptus subfasciatus.
Immiscible organic solvent inactivation of urease, chymotrypsin, lipase, and ribonuclease: separation of dissolved solvent and interfacial effects.
Juvenile hormone esterase purified by affinity chromatography with 8-mercapto-1,1,1-trifluoro-2-octanone as a rationally designed ligand.
Sensory irritation and pulmonary irritation of n-methyl ketones: receptor activation mechanisms and relationships with threshold limit values.
Effect of some metallic cations and organic compounds on the O-hexyl O-2,5-dichlorophenyl phosphoramidate hydrolysing activity in hen plasma.
Competitive inhibition of lipolytic enzymes. VII. The interaction of pancreatic phospholipase A2 with micellar lipid/water interfaces of competitive inhibitors.
Electroantennogram response of alfalfa seed chalcid,Bruchophagus roddi (Hymenoptera: Eurytomidae) to host- and nonhost-plant volatiles.
Antidopaminergic effects of the stereoisomers of N-[(1-alkyl-2- pyrrolidinyl)methyl]-5-sulfamoylbenzamides and -2,3-dihydrobenzofuran-7-carboxamides.
Inhibition of cathepsin B and papain by peptidyl alpha-keto esters, alpha-keto amides, alpha-diketones, and alpha-keto acids.
Volatile methyl ketone seed-germination inhibitors fromAmaranthus palmeri S. Wats. Residues.
Experimental study on the enhancement of the neurotoxicity of methyl n-butyl ketone by non-neurotoxic aliphatic monoketones.
Neurophysiological studies on the relation between the structural properties and neurotoxicity of aliphatic hydrocarbon compounds in rats.
Volatile constituents of wolf (Canis lupus) urine as related to gender and season.
Further studies on ketone neurotoxicity and interactions.
[An experimental study on the neurotoxicity of 2-octanone and 2-hexanol, a metabolite of n-hexane].
Commercial-grade methyl heptyl ketone (5-methyl-2-octanone) neurotoxicity: contribution of 5-nonanone.
Gas-chromatographic resolution of enantiomeric secondary alcohols. Stereoselective reductive metabolism of ketones in rabbit-liver cytosol.
Cycloalkanones. 9. Comparison of analogues which inhibit cholesterol and fatty acid synthesis.
Cycloalkanones. 7. Hypocholesterolemic activity of aliphatic compounds related to 2,8-dibenzylcyclooctanone.

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
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB31294
FooDB:FDB003344
Export Tariff Code:2902.20.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Formulations/Preparations:
assay: 98% minimum

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 128.21472167969
Specific gravity @ 25 °C
Pounds per Gallon 6.782 to 6.798
Refractive Index 1.414 to 1.417 @ 20 °C
Melting Point -16 to -15°C @ 760 mm Hg
Boiling Point 173 to 175°C @ 760 mm Hg
Boiling Point 94 to 95°C @ 50 mm Hg
Acid Value 1 max KOH/g
Vapor Pressure 1.725 mmHg @ 25 °C
Vapor Density 4.4
Flash Point TCC Value 62.78 °C TCC
logP (o/w) 2.37
Solubility
alcohol Yes
water, 900 mg/L @ 20 °C (exp) Yes

Organoleptic Properties

Odor Type: Earthy
earthy, weedy, natural, woody, herbal, musty, ketonic, cheesy bleu cheese, cheesy parmesan cheese, dairy
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity > 4 hour(s) at 100.00 %
General comment At 10.00 % in dipropylene glycol. earthy weedy natural woody herbal
Mosciano, Gerard P&F 21, No. 1, 33, (1996) Musty, ketonic, bleu and parmesan cheese-like with earthy and dairy nuances
Flavor Type: Dairy
dairy, waxy, cheesy, woody, mushroom, yeasty
Mosciano, Gerard P&F 21, No. 1, 33, (1996) At 10.00 ppm. Dairy, waxy, cheese, woody, mushroom and yeast
Adds ketonic notes for a variety of cheese flavors, unroasted nuts especially hazelnut and cashews. Ketonic, fermented notes
General comment Cheesy, sharp, ketonic (waxy note)
2-OCTANONE adds nice fruity, blue and parmesan cheese-like notes with mushroom and dairy nuances to dairy, fruit and cooked meat flavors. Intense blue cheese, fruity, mushroom and green notes

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 21 - Harmful in contact with skin.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
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 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
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.
Human Experience:
4 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 > 5000 mg/kg
(Katz et al., 1980)

oral-mouse LD50 [sex: M] 3823 mg/kg
(Tanii et al., 1986)

oral-mouse LD50 3870 mg/kg
(Tanii et al., 1986)

intraperitoneal-mouse LD50 800 mg/kg
"Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4765, 1982.

oral-mouse LD50 3824 mg/kg
Toxicology Letters. Vol. 30, Pg. 13, 1986.

unreported-mouse LD50 1600 mg/kg
Journal of Medicinal Chemistry. Vol. 19, Pg. 1257, 1976.

intraperitoneal-rat LD50 800 mg/kg
"Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4765, 1982.

oral-rat LD50 3089 mg/kg
Kodak Company Reports. Vol. #901875

Dermal Toxicity:
skin-rabbit LD50 1337 mg/kg
Kodak Company Reports. Vol. #901875

Inhalation Toxicity:
inhalation-rat LC50 2132 ppm/6hours
KODAK*
#901875

inhalation-rat LC50 > 2132 ppm/6H
Kodak Company Reports. Vol. #901875

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 2-octanone usage levels up to:
4.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 93.00 (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: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: 0.400004.00000
beverages(nonalcoholic): 0.100001.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 0.200001.00000
fruit ices: 0.200001.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: 0.400004.00000
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: --
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...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 7 (FGE.07): Saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids from chemical group 5
View page or View pdf

Flavouring Group Evaluation 7, Revision 1 (FGE.07Rev1): Saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids from chemical group 5 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Scientific opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission
View page or View pdf

Flavouring Group Evaluation 7, Revision 2 (FGE.07Rev2) : Saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids from chemical group 5
View page or View pdf

Safety and efficacy of saturated and unsaturated aliphatic secondary alcohols, ketones and esters with esters containing secondary alcohols belonging to chemical group 5 when used as flavourings for all animal species
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):111-13-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :8093
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1224
WGK Germany:1
octan-2-one
Chemidplus:0000111137
RTECS:RH1484000 for cas# 111-13-7