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2-tridecanone

Chemical Structure

General Material Information

Preferred name 2-tridecanone
Trivial Name 2-Tridecanone
Short Description methyl undecyl ketone
Formula C13 H26 O
CAS Number 593-08-8
FEMA Number 3388
Flavis Number 7.103
ECHA Number 209-784-0
FDA UNII 5Q35VHX26K
Nikkaji Number J94.924H
Beilstein Number 1757402
MDL MFCD00008968
COE Number 11194
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 298 2-tridecanone
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 593-08-8 ; 2-TRIDECANONE
Synonyms
  • hendecyl methyl ketone
  • hexadecylmethyl ketone
  • ketone, methyl undecyl
  • methyl N-undecyl ketone
  • methyl undecyl ketone
  • methyl undecyl ketone, natural
  • tridecan-2-one
  • 2-tridecanone natural
  • tridecanone-2
  • NSC 14763

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

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Literature & References

tridecan-2-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:593-08-8
Pubchem (cid):11622
Pubchem (sid):134977844
Pherobase:View
Publications by US Patents
3,952,024 - Furfurylthioacetone
Certain 2,5-dimethyl-3-thiopyrazines
Publications by PubMed
North American Invasion of the Tawny Crazy Ant (Nylanderia fulva) Is Enabled by Pheromonal Synergism from Two Separate Glands.
Insecticidal Constituents of Essential Oil Derived from Zanthoxylum armatum against Two Stored-Product Insects.
Repellency and oviposition deterrence of wild tomato leaf extracts to spider mites, Tetranychus urticae Koch.
Chemical composition and larvicidal activity of Zanthoxylum armatum against diamondback moth, Plutella xylostella.
Odorant-binding proteins display high affinities for behavioral attractants and repellents in the natural predator Chrysopa pallens.
Larvicidal activity of the essential oil from Tetradium glabrifolium fruits and its constituents against Aedes albopictus.
A transferrin gene associated with development and 2-tridecanone tolerance in Helicoverpa armigera.
Cytochrome P450s from the fall armyworm (Spodoptera frugiperda): responses to plant allelochemicals and pesticides.
Identification of the 2-tridecanone responsive region in the promoter of cytochrome P450 CYP6B6 of the cotton bollworm, Helicoverpa armigera (Lepidoptera: Noctuidae).
A facile synthesis of 5,5-dideutero-4-dimethyl(phenyl)silyl-6-undecyl-tetrahydropyran-2-one as a deuterium labeled synthon for (-)-tetrahydrolipstatin and (+)-δ-hexadecanolide.
Wild tomato leaf extracts for spider mite and cowpea aphid control.
Structure elucidation and characterization of microbial 2-tridecyl sophorosides (biosurfactants).
Characterization of novel single-variety oxygenated sesquiterpenoid hop oil fractions via headspace solid-phase microextraction and gas chromatography-mass spectrometry/olfactometry.
Defensive chemicals of tawny crazy ants, Nylanderia fulva (Hymenoptera: Formicidae) and their toxicity to red imported fire ants, Solenopsis invicta (Hymenoptera: Formicidae).
Antioxidant and antimicrobial properties of the essential oil and extracts of Zanthoxylum alatum grown in north-western Himalaya.
2-undecanone and 2-tridecanone in field-grown onion.
The potential impact of washing machines on laundry malodour generation.
Molecular cloning and recombinant expression of cytochrome P450 CYP6B6 from Helicoverpa armigera in Escherichia coli.
Synthesis of methyl ketones by metabolically engineered Escherichia coli.
Metathesis-mediated synthesis of (R)-10-methyl-2-tridecanone, the southern corn rootworm pheromone.
Engineering of bacterial methyl ketone synthesis for biofuels.
2-undecanone rich leaf essential oil from Zanthoxylum armatum.
Synthesis and antimicrobial activity of long-chain 3,4-Epoxy-2-alkanones.
First report of the repellency of 2-tridecanone against ticks.
Enzymatic functions of wild tomato methylketone synthases 1 and 2.
HPLC assay for characterizing alpha-cyano-3-phenoxybenzyl pyrethroids hydrolytic metabolism by Helicoverpa armigera (Hubner) based on the quantitative analysis of 3-phenoxybenzoic acid.
Multiple biochemical and morphological factors underlie the production of methylketones in tomato trichomes.
Chemical composition and antimicrobial activity of the essential oils of leaves, roots and bark of Glossocalyx staudtii.
Mandibular gland secretions of meliponine worker bees: further evidence for their role in interspecific and intraspecific defence and aggression and against their role in food source signalling.
Repellency property of long chain aliphatic methyl ketones against Anopheles gambiae s.s.
A cut-off in ocular chemesthesis from vapors of homologous alkylbenzenes and 2-ketones as revealed by concentration-detection functions.
Insecticidal activity of 2-tridecanone against the cowpea weevil Callosobruchus maculatus (Coleoptera: Bruchidae).
Seasonal variation in volatile compound profiles of preen gland secretions of the dark-eyed junco (Junco hyemalis).
Chemical boundaries for detection of eye irritation in humans from homologous vapors.
Natural products: repellency and toxicity of wild tomato leaf extracts to the two-spotted spider mite, Tetranychus urticae Koch.
Chemical profiles of scent gland secretions in the cyphophthalmid opilionid harvestmen, Siro duricorius and S. exilis.
Natural products: seasonal variation in trichome counts and contents in Lycopersicum hirsutum f. glabratum.
Test of the Binding Threshold Hypothesis for olfactory receptors: explanation of the differential binding of ketones to the mouse and human orthologs of olfactory receptor 912-93.
Persistence of 2-tridecanone on the leaves of seven vegetables.
Janus kinase 3: a novel target for selective transplant immunosupression.
Responses of female orange wheat Blossom midge, Sitodiplosis mosellana, to wheat panicle volatiles.
Identification of the female-produced sex pheromone of the scarab beetle, Hoplia equina.
Seasonal variation in the essential oil of Pilocarpus microphyllus Stapf.
Resistance to 2-tridecanone in Tetranychus urticae: effects of induced resistance, cross-resistance and heritability.
Production and quantification of methyl ketones in wild tomato accessions.
Inducible P450s of the CYP9 family from larval Manduca sexta midgut.
Accumulation and turnover of 2-tridecanone in Tetranychus urticae and its consequences for resistance of wild and cultivated tomatoes.
Volatile compounds from Escherichia coli O157:H7 and their absorption by strawberry fruit.
Electroantennogram and oviposition bioassay responses of Culex quinquefasciatus and Culex tarsalis (Diptera: Culicidae) to chemicals in odors from Bermuda grass infusions.
A fatty acid alpha-ketol, a product of the plant lipoxygenase pathway, is oxidized to 3(Z)-dodecendioic acid by a bacterial monooxygenase.
Volatile ketones from interdigital glands of black-tailed deer,Odocileus hemionus columbianus.
Expression of cytochrome P450 genes of the CYP4 family in midgut and fat body of the tobacco hornworm, Manduca sexta.
Glutathione S-transferases from larval Manduca sexta midgut: sequence of two cDNAs and enzyme induction.
Ketone EC50 values in the Microtox test.
Fatty acid elongation in the biosynthesis of (Z)-10-heptadecen-2-one and 2-tridecanone in ejaculatory bulb microsomes of Drosophila buzzatii.
Influence of life history differences of two tachinid parasitoids ofHelicoverpa zea (Boddie) (Lepidoptera: Noctuidae) on their interactions with glandular trichome/methyl ketone-based insect resistance in tomato.
(Z)-10-Heptadecen-2-one and other 2-ketones in the aggregation pheromone blend ofDrosophila martensis, D. buzzatii, andD. serido.
Mandibular gland secretions of the male beewolvesPhilanthus crabroniformis, P. barbatus, andP. pulcher (Hymenoptera: Sphecidae).
Mortality and inhibition ofHelicoverpa zea Egg parasitism rates byTrichogramma in relation to trichome/methyl ketone-mediated insect resistance ofLycopersicon hirsutum f. glabratum, accession PI 134417.
Behavioral response ofTrichogramma pretiosum riley andTelenomus sphingis (Ashmead) to trichome/methyl ketone mediated resistance in tomato.
Chemistry of mandibular and Dufour's gland secretions of ants in genusMyrmecocystus.
Toxicity of allelochemicals from wild insect-resistant tomatoLycopersicon hirsutum f.glabratum toCampoletis sonorensis, a parasitoid ofHeliothis zea.
Inhibition ofCampoletis sonorensis parasitism ofHeliothis zea and of parasitoid development by 2-tridecanone-mediated insect resistance of wild tomato.
Activity of volatile compounds in glandular trichomes ofLycopersicon species against two insect herbivores.
Ester and ketone components of aggregation pheromone ofDrosophila hydei (Diptera: Drosophilidae).
[Produktion von 2-Tridecanon durch verschiedene Kultur- und Wildtomatenpflanzen (Lycopersicon spp.).]
Identification of a female-produced sex pheromone from the southern corn rootworm,Diabrotica undecimpunctata howardi Barber.
Toxicity studies of analogs of 2-tridecanone, a naturally occurring toxicant from a wild tomato.
Effect of day length and light intensity on 2-tridecanone levels and resistance inLycopersicon hirsutum f.glabratum toManduca sexta.
Soldier-specific chemicals of the termiteCurvitermes strictinasus Mathews (Isoptera, Nasutitermitinae).
2-Tridecanone: A Naturally Occurring Insecticide from the Wild Tomato Lycopersicon hirsutum f.glabratum.
Resistance plasmids in Pseudomonas cepacia 4G9.
A novel ketone monooxygenase from Pseudomonas cepacia. Purification and properties.
Source of oxygen in the conversion of 2-tridecanone to undecyl acetate by Pseudomonas cepacia and Nocardia sp.
Purification and properties of undecyl acetate esterase from Pseudomonas cepacia grown on 2-tridecanone.
Specificity and induction of undecyl acetate esterase from Pseudomonas cepacia grown on 2-tridecanone.
Oxidative degradation of methyl ketones. II. Chemical pathway for degradation of 2-tridecanone by Pseudomonas multivorans and Pseudomonas aeruginosa.
Bacterial oxidation of 2-tridecanone to 1-undecanol.

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):HMDB34148
FooDB:FDB012424
Export Tariff Code:2914.19.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 198.34942626953
Specific gravity @ 25 °C
Pounds per Gallon
Melting Point 29 to 31°C @ 760 mm Hg
Vapor Pressure 0.016 mmHg @ 25 °C
Flash Point TCC Value 107.22 °C TCC
logP (o/w) 5.053 est
Solubility
alcohol Yes
dipropylene glycol Yes
water, 4.53 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Waxy
fatty, waxy, dairy, milky, coconut, nutty, herbal, earthy, mushroom, chicken fat
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity > 8 hour(s) at 100.00 %
General comment At 10.00 % in dipropylene glycol. fatty waxy dairy milky coconut nutty herbal earthy
Mosciano, Gerard P&F 23, No. 1, 33, (1998) Fatty, waxy, mushroom, coconut and earthy with a mild chicken fat nuance
Flavor Type: Fatty
fatty, earthy, dairy, ketonic, cheesy
General comment Fatty
Mosciano, Gerard P&F 23, No. 1, 33, (1998) At 10.00 ppm. Fatty and earthy with a fatty mouthfeel and with a dairy, ketonic and cheesy nuance
Fatty, waxy notes for a variety of dairy flavors, especially milk. May also be useful for milky notes in coconut. Fatty, waxy
2-TRIDECANONE brings typical fatty profile with slightly spicy character and dairy, ketonic and cheesy nuances. It works nicely in cheese, butter, nut, meat and tropical fruit flavors. Powerful fatty, milky and herbaceous notes

Occurrences

Potential Uses

Applications
Odor purposes Butter, Coconut, Fungus, Herbal, Orris, Pineapple
Flavoring purposes Bacon, Cheese, Chicken, Dairy, Fat, Fruit tropical fruit, Milk, Nut
Cosmetic purposes Perfuming agents

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)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
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 2-tridecanone usage levels up to:
0.5000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 62.00 (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: 6
Click here to view publication 6
average usual ppmaverage maximum ppm
baked goods: -5.00000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: -3.00000
fish products: --
frozen dairy: -3.00000
fruit ices: -3.00000
gelatins / puddings: -3.00000
granulated sugar: --
gravies: --
hard candy: -3.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: -3.00000
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):593-08-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :11622
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
tridecan-2-one
Chemidplus:0000593088
EPA/NOAA CAMEO:hazardous materials