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2-isobutyl-3-methoxypyrazine

Chemical Structure

General Material Information

Preferred name 2-isobutyl-3-methoxypyrazine
Trivial Name 2-Isobutyl-3-methoxypyrazine
Short Description 2-methoxy-3-isobutylpyrazine
Formula C9 H14 N2 O
CAS Number 24683-00-9
FEMA Number 3132
Flavis Number 14.043
ECHA Number 246-402-1
FDA UNII S327O0T12O
Nikkaji Number J126.472I
MDL MFCD00006128
COE Number 11338
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 792 2-isobutyl-3-methoxypyrazine
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 24683-00-9 ; 2-ISOBUTYL-3-METHOXYPYRAZINE
Synonyms
  • iso butyl methoxypyrazine
  • 2-iso butyl-2-methoxypyrazine
  • 3-iso butyl-2-methoxypyrazine
  • 2-iso butyl-3-methoxy pyrazine
  • galbanum pyrazine
  • 2-methoxy 3 iso butyl pyrazine
  • 2 methoxy 3 isobutylpyrazine (2-isobutyl-3-methoxypyrazine)
  • 2-methoxy 3-isobutyl pyrazine
  • 3-methoxy-2-isobutylpyrazine
  • 2-methoxy-3-(2-methyl propyl) pyrazine
  • 2-methoxy-3-(2-methylpropyl)pyrazine
  • 2-methoxy-3-isobutyl pyrazine
  • 2-methoxy-3-isobutyl pyrazine 1% DPG
  • 2-methoxy-3-isobutylpyrazine
  • 2-methoxy-3(6)-isobutyl pyrazine
  • 2-2-methyl propyl-3-methoxypyrazine
  • pyrazine, 2-isobutyl-3-methoxy-
  • pyrazine, 2-methoxy-3-(2-methylpropyl)-
  • pyrazine, 2-methoxy-3-isobutyl
  • 2-methoxy-3-(2-methylpropyl)pyrazine
  • 2-Methoxy-3-isobutylpyrazine
  • 3-Isobutyl-2-methoxypyrazine
  • 3-Methoxy-2-isobutylpyrazine
  • 3-(2-Methylpropyl)-2-methoxypyrazine

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

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Literature & References

2-methoxy-3-(2-methylpropyl)pyrazine
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:24683-00-9
Pubchem (cid):32594
Pubchem (sid):134994257
Flavornet:24683-00-9
Pherobase:View
Publications by PubMed
Key aroma compounds in roasted in-shell peanuts.
Comparison of the key aroma compounds in organically grown, raw West-African peanuts (Arachis hypogaea) and in ground, pan-roasted meal produced thereof.
Growth behavior of off-flavor-forming microorganisms in apple juice.
Odor thresholds of microbially induced off-flavor compounds in apple juice.
Effect of cultivar and storage time on the volatile flavor components of baked potato.
Characteristic aroma components of British Farmhouse Cheddar cheese.
Solid-phase microextraction method development for headspace analysis of volatile flavor compounds.
Electrochemical detection of the 2-isobutyl-3-methoxypyrazine model odorant based on odorant-binding proteins: The proof of concept.
Dynamics of odorant binding to thin aqueous films of rat-OBP3.
Identification of a specific olfactory receptor for 2-isobutyl-3-methoxypyrazine.
Selectable one-dimensional or two-dimensional gas chromatography-olfactometry/mass spectrometry with preparative fraction collection for analysis of ultra-trace amounts of odor compounds.
A systematic study on spatial and seasonal patterns of eight taste and odor compounds with relation to various biotic and abiotic parameters in Gonghu Bay of Lake Taihu, China.
Following in their footprints: cuticular hydrocarbons as overwintering aggregation site markers in Hippodamia convergens.
Simultaneous determination of ten taste and odor compounds in drinking water by solid-phase microextraction combined with gas chromatography-mass spectrometry.
A methyltransferase essential for the methoxypyrazine-derived flavour of wine.
The role of semiochemicals in short-range location of aggregation sites in Adalia bipunctata (Coleoptera, Coccinellidae).
Defensive allomones function as aggregation pheromones in diapausing Ladybird Beetles, Hippodamia convergens.
Genetic analysis of the biosynthesis of 2-methoxy-3-isobutylpyrazine, a major grape-derived aroma compound impacting wine quality.
Detection and quantification of natural contaminants of wine by gas chromatography-differential ion mobility spectrometry (GC-DMS).
Key aroma compounds in roasted in-shell peanuts.
Behavior of 3-isobutyl-2-hydroxypyrazine (IBHP), a key intermediate in 3-isobutyl-2-methoxypyrazine (IBMP) metabolism, in ripening wine grapes.
Classification of grape berries according to diameter and total soluble solids to study the effect of light and temperature on methoxypyrazine, glutathione, and hydroxycinnamate evolution during ripening of Sauvignon blanc (Vitis vinifera L.).
Fruit ripening in Vitis vinifera: light intensity before and not during ripening determines the concentration of 2-methoxy-3-isobutylpyrazine in Cabernet Sauvignon berries.
Occurrence of dissolved and particle-bound taste and odor compounds in Swiss lake waters.
Accurate analysis of trace earthy-musty odorants in water by headspace solid phase microextraction gas chromatography-mass spectrometry.
The effect of pyrazine odor on body weight and the weight of various organs in chicks (Gallus gallus domesticus).
Simultaneous determination of eight common odors in natural water body using automatic purge and trap coupled to gas chromatography with mass spectrometry.
Purification and characterization of two odorant-binding proteins from nasal tissue of rabbit and pig.
Development of a mixed-mode solid phase extraction method and further gas chromatography mass spectrometry for the analysis of 3-alkyl-2-methoxypyrazines in wine.
2-Methoxy-3-isobutylpyrazine in grape berries and its dependence on genotype.
Effect of enzyme activity and frozen storage on jalapeño pepper volatiles by selected ion flow tube-mass spectrometry.
Time-resolved fluorescence spectroscopy and molecular dynamics simulations point out the effects of pressure on the stability and dynamics of the porcine odorant-binding protein.
Long-timescale molecular-dynamics simulations of the major urinary protein provide atomistic interpretations of the unusual thermodynamics of ligand binding.
Identification of alkyl-methoxypyrazines as the malodorous compounds in water supplies from Northwest Spain.
Automated trace determination of earthy-musty odorous compounds in water samples by on-line purge-and-trap-gas chromatography-mass spectrometry.
Why has porcine VEG protein unusually high stability and suppressed binding ability?
Three odorant-binding proteins from rabbit nasal mucosa.
Multiple types and forms of odorant-binding proteins in the Old-World porcupine Hystrix cristata.
Ligand-binding properties and structural characterization of a novel rat odorant-binding protein variant.
Odorant-binding proteins of the mouse.
Purification and characterisation of an odorant-binding protein from cow nasal tissue.
Survey of 3-alkyl-2-methoxypyrazine content of South African Sauvignon blanc wines using a novel LC-APCI-MS/MS method.
Rapid measurement of 3-alkyl-2-methoxypyrazine content of winegrapes to predict levels in resultant wines.
Volatile composition of Catharanthus roseus (L.) G. Don using solid-phase microextraction and gas chromatography/mass spectrometry.
Structural basis of the broad specificity of a general odorant-binding protein from honeybee.
Odor thresholds of microbially induced off-flavor compounds in apple juice.
The molecular basis for wine grape quality--a volatile subject.
Van der Waals interactions dominate ligand-protein association in a protein binding site occluded from solvent water.
Removal of earthy-musty odorants in drinking water by powdered activated carbon.
Effect of cultivar and storage time on the volatile flavor components of baked potato.
The determination of six taste and odour compounds in water using Ambersorb 572 and high resolution mass spectrometry.
Odorant and pheromone binding by aphrodisin, a hamster aphrodisiac protein.
Complexes of porcine odorant binding protein with odorant molecules belonging to different chemical classes.
Quantitative determination of 2-methoxy-3-isobutylpyrazine in red wines and grapes of Bordeaux using a stable isotope dilution assay.
Membrane receptor for odour-binding proteins.
Odorant-sensitive adenylate cyclase: rapid, potent activation and desensitization in primary olfactory neuronal cultures.
Activation by odorants of a multistate cation channel from olfactory cilia.
The odorant-sensitive adenylate cyclase of olfactory receptor cells. Differential stimulation by distinct classes of odorants.
Isolation and characterization of an olfactory receptor protein for odorant pyrazines.
A survey of seasonal temperatures and vineyard altitude influences on 2-methoxy-3-isobutylpyrazine, C13-norisoprenoids, and the sensory profile of Brazilian Cabernet Sauvignon wines.
Determination of characteristic odorants from Harmonia axyridis beetles using in vivo solid-phase microextraction and multidimensional gas chromatography-mass spectrometry-olfactometry.
Evidence of chemical exchange in recombinant Major Urinary Protein and quenching thereof upon pheromone binding.
Influence of vine training and sunlight exposure on the 3-alkyl-2-methoxypyrazines content in musts and wines from the Vitis vinifera variety cabernet sauvignon.
Thermodynamics of binding of 2-methoxy-3-isopropylpyrazine and 2-methoxy-3-isobutylpyrazine to the major urinary protein.
Absolute configuration of 2-sec-butyl-4,5-dihydrothiazole in male mouse urine.
Characteristic aroma components of British Farmhouse Cheddar cheese.
Solid-phase microextraction method development for headspace analysis of volatile flavor compounds.
Similar increases in extracellular lactic acid in the limbic system during epileptic and/or olfactory stimulation.
Conformational stability and binding properties of porcine odorant binding protein.
Subtypes of odorant-binding proteins--heterologous expression and ligand binding.
Lipocalins of boar salivary glands binding odours and pheromones.
Isolation of two odorant-binding proteins from mouse nasal tissue.
Ligand binding characteristics of homologous rat and mouse urinary proteins and pyrazine-binding protein of calf.
Ultrastructural characteristics of sustentacular cells in control and odorant-treated olfactory mucosae of the salamander.
Odorant stimulation of secretory and neural processes in the salamander olfactory mucosa.
Immunocytochemical localization of pyrazine-binding protein in bovine nasal mucosa.
Occurrence of a pyrazine binding protein in the nasal mucosa of some vertebrates.

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):HMDB31860
FooDB:FDB008544
YMDB (Yeast Metabolome Database):YMDB01586
Export Tariff Code:2933.99.9701
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 166.22378540039
Specific gravity @ 25 °C
Pounds per Gallon 8.259 to 8.342
Refractive Index 1.489 to 1.497 @ 20 °C
Boiling Point 214 to 215°C @ 760 mm Hg
Vapor Pressure 0.273 mmHg @ 25 °C
Vapor Density 5.7
Flash Point TCC Value 80 °C TCC
logP (o/w) 2.547 est
Shelf life 24 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
water, 229.6 mg/L @ 25 °C (est) Yes
Stability
stable in most media Unspecified

Organoleptic Properties

Odor Type: Green
pea green pea, pepper bell pepper, green, galbanum
General comment At 0.10 % in dipropylene glycol. green pea green bell pepper green pea galbanum
Flavor Type: Green
green, pepper bell pepper, pea green pea, galbanum
General comment Green bell pepper green pea galbanum
Used at very low levels in green vegetable flavours: 0.0005-0.05ppm, and in galbanum substitutes. Green pea, green bell-pepper-like

Occurrences

Safety Information

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 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:
gavage-mouse LD50 2000 mg/kg
(Quest International, 1983a)

gavage-rat LD50 > 4000 mg/kg
(Roure Inc., 1974)

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-isobutyl-3-methoxypyrazine usage levels up to:
0.1000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 1.60 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 1.00 (μg/capita/day)
Structure Class: II
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: 4
Click here to view publication 4
average usual ppmaverage maximum ppm
baked goods: -0.05000
beverages(nonalcoholic): -0.05000
beverages(alcoholic): --
breakfast cereal: -0.05000
cheese: --
chewing gum: -0.05000
condiments / relishes: -0.05000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -0.05000
fruit ices: -0.05000
gelatins / puddings: -0.05000
granulated sugar: --
gravies: -0.05000
hard candy: -0.05000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: -0.05000
milk products: -0.05000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: -0.05000
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) on a request from the Commission related to Flavouring Group Evaluation 17 (FGE.17): Pyrazine derivatives from chemical group 24 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

Flavouring Group Evaluation 50 (FGE.50): Consideration of pyrazine derivatives evaluated by JECFA (57th meeting) structurally related to pyrazine derivatives evaluated by EFSA in FGE.17 (2005) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 17, Revision 1 (FGE.17Rev1): Pyrazine derivatives from chemical group 24 - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) [1]
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 17, Revision 2 (FGE.17Rev2): Pyrazine derivatives from chemical group 24
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 50, Revision 1 (FGE.50Rev1): Consideration of pyrazine derivatives evaluated by JECFA (57th meeting) structurally related to pyrazine derivatives evaluated by EFSA in FGE.17Rev2 (2010)
View page or View pdf

Safety and efficacy of pyrazine derivatives including saturated ones belonging to chemical group 24 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):24683-00-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :32594
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-methoxy-3-(2-methylpropyl)pyrazine
Chemidplus:0024683009