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trimethyl amine oxide
trimethylamine oxide

Sponsors

Name:N,N-dimethylmethanamine oxide
CAS Number: 1184-78-7Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:214-675-6
FDA UNII:FLD0K1SJ1A
Nikkaji Web:J7.304K
Beilstein Number:1734787
MDL:MFCD00002048
CoE Number:10494
XlogP3-AA:-0.30 (est)
Molecular Weight:75.11093000
Formula:C3 H9 N O
NMR Predictor:Predict (works with chrome or firefox)
Category:flavoring agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
JECFA Food Flavoring:1614 trimethylamine oxide
FLAVIS Number:11.025 (Old)
DG SANTE Food Flavourings:11.025 trimethylamine oxide
FEMA Number:4245 trimethylamine oxide
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm: TRIMETHYLAMINE OXIDE
 
Physical Properties:
Appearance:colorless to yellow solid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 213.00 °C. @ 760.00 mm Hg
Flash Point:> 212.00 °F. TCC ( > 100.00 °C. )
logP (o/w): -2.570
Soluble in:
 alcohol
 water
 water, 5.592e+005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor Strength:none
Odor Description:at 100.00 %. odorless
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Santa Cruz Biotechnology
For experimental / research use only.
Trimethylamine N-oxide
Sigma-Aldrich: Aldrich
For experimental / research use only.
Trimethylamine N-oxide 98%
TCI AMERICA
For experimental / research use only.
Trimethylamine N-Oxide Anhydrous >95.0%(T)
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
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.
 
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: flavoring agents
Recommendation for trimethyl amine oxide usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 2.30 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.09 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 340 (μg/person/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
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: 22
 average usual ppmaverage maximum ppm
baked goods: 2.0000010.00000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: 0.200001.00000
cheese: 0.400002.00000
chewing gum: --
condiments / relishes: 0.100000.50000
confectionery froastings: 1.000005.00000
egg products: --
fats / oils: 0.100000.50000
fish products: 0.200001.00000
frozen dairy: 0.400002.00000
fruit ices: 0.400002.00000
gelatins / puddings: --
granulated sugar: --
gravies: 0.100000.50000
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: 0.200001.00000
milk products: 0.400002.00000
nut products: --
other grains: 0.200001.00000
poultry: 0.200001.00000
processed fruits: 0.400002.00000
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 0.100000.50000
snack foods: 1.000005.00000
soft candy: --
soups: 0.100000.50000
sugar substitutes: --
sweet sauces: --
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 0.400002.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 0.100000.50000
Edible ices, including sherbet and sorbet (03.0): 0.400002.00000
Processed fruit (04.1): 0.400002.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 1.000005.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 0.200001.00000
Bakery wares (07.0): 2.0000010.00000
Meat and meat products, including poultry and game (08.0): 0.200001.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 0.200001.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 0.100000.50000
Foodstuffs intended for particular nutritional uses (13.0): 0.200001.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): --
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 1.000005.00000
Ready-to-eat savouries (15.0): 1.000005.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 0.200001.00000
 
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):

Flavouring Group Evaluation 86, (FGE.86)[1] - Consideration of aliphatic and aromatic amines and amides evaluated by JECFA (65th meeting) - Scientific Opinion of the Panel on Food Additives - Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 86, Revision 1 (FGE.86Rev1): Consideration of aliphatic and aromatic amines and amides evaluated by JECFA (65th meeting)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 86, Revision 2 (FGE.86Rev2): Consideration of aliphatic and arylalkyl amines and amides evaluated by JECFA (65th meeting)
View page or View pdf

EPI System: View
Cancer Citations:Search
Toxicology Citations:Search
Env. Mutagen Info. Center:Search
NLM Developmental and Reproductive Toxicity:Search
EPA Substance Registry Services (TSCA):1184-78-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :1145
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
N,N-dimethylmethanamine oxide
Chemidplus:0001184787
 
References:
 N,N-dimethylmethanamine oxide
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:1184-78-7
Pubchem (cid):1145
Pubchem (sid):134980467
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS):View
CHEBI:View
Metabolomics Database:Search
UM BBD:Search
KEGG (GenomeNet):C01104
HMDB (The Human Metabolome Database):HMDB00925
FooDB:FDB010413
Export Tariff Code:2921.11.0000
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
FLcereal
FLcheese
FLdairy
FLfish
 fruit
FLmeat
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 amine oxide, trimethyl-
N,N-dimethyl methanamine N-oxide
N,N-dimethylmethanamine N-oxide
N,N-dimethylmethanamine oxide
 methanamine, N,N-dimethyl-, N-oxide
 methanamine,N,N-dimethyl-, N-oxide
 TMA-oxide
 TMANO
 trimethyl amine N-oxide
 trimethyl oxamine
 trimethyl oxidoazanium
 trimethylamine N-oxide
 trimethylamine N-oxide anhydrous
 trimethylamine oxide
 trimethylamine-N-oxide
 trimethylamine, N-oxide
 

Articles:

Info:aliphatic and aromatic amines and amides derivatives
US Patents:3,981,311 - Aromatic compositions
PubMed:Pyridoxine supplementation does not alter in vivo kinetics of one-carbon metabolism but modifies patterns of one-carbon and tryptophan metabolites in vitamin B-6-insufficient oral contraceptive users.
US Patents:Process for the preparation of a diketone derivative
PubMed:Targeted plasma metabolome response to variations in dietary glycemic load in a randomized, controlled, crossover feeding trial in healthy adults.
PubMed:Neonatal environment exerts a sustained influence on the development of the intestinal microbiota and metabolic phenotype.
PubMed:Concomitant osmotic and chaotropicity-induced stresses in Aspergillus wentii: compatible solutes determine the biotic window.
PubMed:Maternal Choline Status, but Not Fetal Genotype, Influences Cord Plasma Choline Metabolite Concentrations.
PubMed:Determination of trimethylamine-N-oxide in combination with l-carnitine and γ-butyrobetaine in human plasma by UPLC/MS/MS.
PubMed:Kinetics of protein and textural changes in Atlantic salmon under frozen storage.
PubMed:Fish oil ameliorates trimethylamine N-oxide-exacerbated glucose intolerance in high-fat diet-fed mice.
PubMed:Oral L-carnitine supplementation increases trimethylamine-N-oxide but reduces markers of vascular injury in hemodialysis patients.
PubMed:Food, immunity, and the microbiome.
PubMed:Mammalian-microbial cometabolism of L-carnitine in the context of atherosclerosis.
PubMed:The gut microbiome and the brain.
PubMed:Metabolomic pattern analysis after mediterranean diet intervention in a nondiabetic population: a 1- and 3-year follow-up in the PREDIMED study.
PubMed:Risks and benefits of carnitine supplementation in diabetes.
PubMed:Discovery of systematic responses and potential biomarkers induced by ochratoxin A using metabolomics.
PubMed:The influence of chronic L-carnitine supplementation on the formation of preneoplastic and atherosclerotic lesions in the colon and aorta of male F344 rats.
PubMed:Alteration of gut bacteria and metabolomes after glucaro-1,4-lactone treatment contributes to the prevention of hypercholesterolemia.
PubMed:It takes two to tango: two TatA paralogues and two redox enzyme-specific chaperones are involved in the localization of twin-arginine translocase substrates in Campylobacter jejuni.
PubMed:Combined subchronic toxicity of dichlorvos with malathion or pirimicarb in mice liver and serum: a metabonomic study.
PubMed:Dietary trimethylamine N-oxide exacerbates impaired glucose tolerance in mice fed a high fat diet.
PubMed:Strategy of metabolic phenotype modulation in Portunus trituberculatus exposed to low salinity.
PubMed:Halorubrum halophilum sp. nov., an extremely halophilic archaeon isolated from a salt-fermented seafood.
PubMed:Aerial exposure to the bacterial volatile compound trimethylamine modifies antibiotic resistance of physically separated bacteria by raising culture medium pH.
PubMed:Thermodynamic analysis of osmolyte effect on thermal stability of ribonuclease A in terms of water activity.
PubMed:Effects of temperature on microbial succession and metabolite change during saeu-jeot fermentation.
PubMed:Pattern recognition analysis for hepatotoxicity induced by acetaminophen using plasma and urinary 1H NMR-based metabolomics in humans.
PubMed:Impact of geographical region on urinary metabolomic and plasma fatty acid profiles in subjects with the metabolic syndrome across Europe: the LIPGENE study.
PubMed:ESR studies on the thermal decomposition of trimethylamine oxide to formaldehyde and dimethylamine in jumbo squid (Dosidicus gigas) extract.
PubMed:Metabolomic analysis of amino acid metabolism in colitic rats supplemented with lactosucrose.
PubMed:Transient massive trimethylaminuria associated with food protein-induced enterocolitis syndrome.
PubMed:Metabolomic analysis reveals extended metabolic consequences of marginal vitamin B-6 deficiency in healthy human subjects.
PubMed:Studies of single-walled carbon nanotubes-induced hepatotoxicity by NMR-based metabonomics of rat blood plasma and liver extracts.
PubMed:1H-HRMAS NMR study of cold smoked Atlantic salmon (Salmo salar) treated with E-beam.
PubMed:Metabolic influence of acute cyadox exposure on Kunming mice.
PubMed:Effects of thermal processing and various chemical substances on formaldehyde and dimethylamine formation in squid Dosidicus gigas.
PubMed:Dynamic metabolic response of mice to acute mequindox exposure.
PubMed:Use of mass spectrometry fingerprinting to identify urinary metabolites after consumption of specific foods.
PubMed:Alcohol oxidase- and formaldehyde dehydrogenase-based enzymatic methods for formaldehyde assay in fish food products.
PubMed:Nuclear magnetic resonance (NMR)-based metabolomic studies on urine and serum biochemical profiles after chronic cysteamine supplementation in rats.
PubMed:The osmolyte trimethylamine N-oxide (TMAO) increases the proteolytic activity of botulinum neurotoxin light chains A, B, and E: implications for enhancing analytical assay sensitivity.
PubMed:Occurrence and role of lactic acid bacteria in seafood products.
PubMed:Quantitative PCR method for evaluating freshness of whiting (Merlangius merlangus) and plaice (Pleuronectes platessa).
PubMed:Changes of metabolic profiles in urine after oral administration of quercetin in rats.
PubMed:Bonitos with low content of malodorous trimethylamine as palliative care for self-reported Japanese trimethylaminuria subjects.
PubMed:Potential of human saliva for nuclear magnetic resonance-based metabolomics and for health-related biomarker identification.
PubMed:Export of methyl parathion hydrolase to the periplasm by the twin-arginine translocation pathway in Escherichia coli.
PubMed:Alishewanella jeotgali sp. nov., isolated from traditional fermented food, and emended description of the genus Alishewanella.
PubMed:Simultaneous determination of dimethylamine, trimethylamine and trimethylamine-n-oxide in aquatic products extracts by ion chromatography with non-suppressed conductivity detection.
PubMed:Trimethylamine oxide, dimethylamine, trimethylamine and formaldehyde levels in main traded fish species in Hong Kong.
PubMed:1H NMR metabonomics can differentiate the early atherogenic effect of dairy products in hyperlipidemic hamsters.
PubMed:Role of Campylobacter jejuni respiratory oxidases and reductases in host colonization.
PubMed:DNA induces folding in alpha-synuclein: understanding the mechanism using chaperone property of osmolytes.
PubMed:Susceptibility of human metabolic phenotypes to dietary modulation.
PubMed:Accurate quantification of dimethylamine (DMA) in human urine by gas chromatography-mass spectrometry as pentafluorobenzamide derivative: evaluation of the relationship between DMA and its precursor asymmetric dimethylarginine (ADMA) in health and disease.
PubMed:Enhancement of polyunsaturated fatty acid production by Tn5 transposon in Shewanella baltica.
PubMed:The dogfish shark (Squalus acanthias) increases both hepatic and extrahepatic ornithine urea cycle enzyme activities for nitrogen conservation after feeding.
PubMed:A spectrum of molecular variation in a cohort of Italian families with trimethylaminuria: identification of three novel mutations of the FM03 gene.
PubMed:Purification and characterization of trimethylamine-N-oxide demethylase from jumbo squid (Dosidicus gigas).
PubMed:Accumulation of trimethylamine and trimethylamine-N-oxide in end-stage renal disease patients undergoing haemodialysis.
PubMed:Identification of Shewanella baltica as the most important H2S-producing species during iced storage of Danish marine fish.
PubMed:Bioactive compounds in cod (Gadus morhua) products and suitability of 1H NMR metabolite profiling for classification of the products using multivariate data analyses.
PubMed:Trimethylamine: metabolic, pharmacokinetic and safety aspects.
PubMed:Freshwater to seawater acclimation of juvenile bull sharks (Carcharhinus leucas): plasma osmolytes and Na+/K+-ATPase activity in gill, rectal gland, kidney and intestine.
PubMed:Metabonomics, dietary influences and cultural differences: a 1H NMR-based study of urine samples obtained from healthy British and Swedish subjects.
PubMed:The passage of trimethylamine across rat and human skin.
PubMed:Quantitative relationship between trimethylamine oxide aldolase activity and formaldehyde accumulation in white muscle from gadiform fish during frozen storage.
PubMed:Dogmas and controversies in the handling of nitrogenous wastes: the effect of feeding and fasting on the excretion of ammonia, urea and other nitrogenous waste products in rainbow trout.
PubMed:Partial purification and characterization of trimethylamine-N-oxide demethylase from lizardfish kidney.
PubMed:Pharmacokinetics of trimethylamine in rats, including the effects of a synthetic diet.
PubMed:Development and characterization of a flavoring agent from oyster cooker effluent.
PubMed:Shelf-life extension of cod fillets with an acetate buffer spray prior to packaging under modified atmospheres.
PubMed:Denitrobacterium detoxificans gen. nov., sp. nov., a ruminal bacterium that respires on nitrocompounds.
PubMed:Dietary precursors of trimethylamine in man: a pilot study.
PubMed:Dimethylamine formation in the rat from various related amine precursors.
PubMed:The sensitivity of Escherichia coli O157 to some antimicrobials by conventional and conductance assays.
PubMed:Denaturation of fish proteins during frozen storage: role of formaldehyde.
PubMed:Dimethylamine formation in man.
PubMed:Hepatotoxicity and hepatocarcinogenicity in rats fed squid with or without exogenous nitrite.
PubMed:Evaluation of the bacteriological quality of seafood.
PubMed:Inhibition of the electron transport system in Staphylococcus aureus by trimethylamine-N-oxide.
PubMed:A microbial biosensor for trimethylamine using Pseudomonas aminovorans cells.
PubMed:In vitro studies on interactions of iron salts and complexes with food-stuffs and medicaments.
PubMed:The bacteriology of fresh and spoiling Lake Victorian Nile perch (Lates niloticus).
PubMed:Detection of salmonellas in animal feeds by electrical conductance.
PubMed:Potentiation of ferrous sulphate and ascorbate on the microbial transformation of endogenous trimethylamine N-oxide to trimethylamine and dimethylamine in squid extracts.
PubMed:Growth and activity of Shewanella putrefaciens isolated from spoiling fish.
PubMed:Formation of aliphatic amine precursors of N-nitrosodimethylamine after oral administration of choline and choline analogues in the rat.
PubMed:A conductance medium to distinguish between Salmonella and Citrobacter spp.
PubMed:Detection of salmonellas in confectionery products by conductance.
PubMed:A modified conductance medium for the detection of Salmonella spp.
PubMed:Food-borne amines and amides as potential precursors of endogenous carcinogens.
PubMed:Thermal conversion of trimethylamine-N-oxide to trimethylamine and dimethylamine in squids.
PubMed:Rapid and automated detection of salmonella by electrical measurements.
PubMed:[Quality changes in iced shrimps (Pandalus borealis). III. Indole and pH in shrimps caught in the Barents Sea compared with shrimps caught in the Far East (author's transl)].
PubMed:[Quality changes in iced shrimps (Pandalus borealis). II Changes in the contents of trimethylamine oxide and volatile nitrogen bases during automatic boiling and peeling (author's transl)].
PubMed:[Quality changes in iced shrimps (Pandalus borealis). I. Changes in the contents of trimethylamine oxide and volatile nitrogen bases and bacteria in raw shrimps after different storage periods compared with organoleptic examinations (author's transl)].
PubMed:Protein changes in frozen fish.
PubMed:Trimethylamine oxide reduction by Salmonella.
PubMed:Studies on the allergy-like food poisoning associated with putrefaction of marine products. IV. Effect of trimethylamine and trimethylamine oxide added to histamine or saurine upon their own physiological action.
 
Notes:
used in manufacture of quaternary ammonium cpds; insect attractant; warming agent for gas; oxidant. Trimethylamine N-oxide (TMAO) is an oxidation product of trimethylamine and a common metabolite in animals and humans. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood. TMAO is an osmolyte that the body will use to counter-act the effects of increased concentrations of urea (due to kidney failure) and can be used as a biomarker for kidney problems. Fish odor syndrome or trimethylaminuria is a defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3) causing incomplete breakdown of trimethylamine from choline-containing food into trimethylamine oxide. Trimethylamine then builds up and is released in the person's sweat, urine, and breath, giving off a strong fishy odor.; Trimethylamine N-oxide, also known by several other names and acronyms, is the organic compound with the formula (CH3)3NO. This colorless solid is usually encountered as the dihydrate. It is an oxidation product of trimethylamine and a common metabolite in animals. It is an osmolyte found in saltwater fish, sharks and rays, molluscs, and crustaceans. Along with free amino acids, it reduces the 3% salinity of seawater to about 1% of dissolved solids inside cells. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood.; Trimethylaminuria is a defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3),, causing incomplete breakdown of trimethylamine from choline-containing food into trimethylamine oxide. Trimethylamine then builds up and is released in the person's sweat, urine, and breath, giving off a strong fishy odor.
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