2-isobutyl-3-methoxypyrazine
2-methoxy-3-isobutylpyrazine
Identification
| Name | 2-isobutyl-3-methoxypyrazine |
| IUPAC | 2-methoxy-3-(2-methylpropyl)pyrazine |
| CAS Number | 24683-00-9 |
| EINECS | 246-402-1 |
| FDA UNII | S327O0T12O |
| Molecular Formula | C9 H14 N2 O |
| Molecular Weight | 166.22378000 |
| MDL Number | MFCD00006128 |
| Nikkaji Number | J126.472I |
| CoE Number | 11338 |
| XlogP3 | 2.60 (est) |
Regulatory
| JECFA Food Flavoring | 792 2-isobutyl-3-methoxypyrazine |
| DG SANTE Food Flavourings | 14.043 2-isobutyl-3-methoxypyrazine |
| FEMA Number | 3132 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 24683-00-9 ; 2-ISOBUTYL-3-METHOXYPYRAZINE |
Physical Properties
| Appearance | colorless to pale yellow clear liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.99250 to 1.00250 @ 25.00 °C. |
| Pounds per Gallon - (est). | 8.259 to 8.342 |
| Refractive Index | 1.48900 to 1.49700 @ 20.00 °C. |
| Boiling Point | 214.00 to 215.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.273000 mmHg @ 25.00 °C. (est) |
| Vapor Density | 5.7 ( Air = 1 ) |
| Flash Point | 176.00 °F. TCC ( 80.00 °C. ) |
| logP (o/w) | 2.547 (est) |
| Shelf Life | 24.00 month(s) or longer if stored properly. |
| Storage | store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Soluble in | alcohol |
| Stability | stable in most media |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Description |
at 0.10 % in dipropylene glycol. Green pea, green bell-pepper-like green, pepper GREEN PAPRIKA, EARTHY, GALBANUM bell-pepper, peas, galbanum, natural, nutty, roasted Bright, fresh, natural, sweet aroma of juicy fruits bell peppers with light notes of galbanum
|
| Taste Description |
green bell pepper green pea galbanum Green pea, green bell-pepper-like strong green note green bell pepper green pea galbanum
|
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | gavage-mouse LD50 2000 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| 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 |
| baked goods | - |
| beverages(nonalcoholic) | - |
| beverages(alcoholic) | - |
| breakfast cereal | - |
| cheese | - |
| chewing gum | - |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | - |
| fruit ices | - |
| gelatins / puddings | - |
| 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 | - |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
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Potential Uses
Natural Occurrence
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
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
PubMed:
Key aroma compounds in roasted in-shell peanuts.
PubMed:
Comparison of the key aroma compounds in organically grown, raw West-African peanuts (Arachis hypogaea) and in ground, pan-roasted meal produced thereof.
PubMed:
Growth behavior of off-flavor-forming microorganisms in apple juice.
PubMed:
Odor thresholds of microbially induced off-flavor compounds in apple juice.
PubMed:
Effect of cultivar and storage time on the volatile flavor components of baked potato.
PubMed:
Characteristic aroma components of British Farmhouse Cheddar cheese.
PubMed:
Solid-phase microextraction method development for headspace analysis of volatile flavor compounds.
PubMed:
Electrochemical detection of the 2-isobutyl-3-methoxypyrazine model odorant based on odorant-binding proteins: The proof of concept.
PubMed:
Dynamics of odorant binding to thin aqueous films of rat-OBP3.
PubMed:
Identification of a specific olfactory receptor for 2-isobutyl-3-methoxypyrazine.
PubMed:
Selectable one-dimensional or two-dimensional gas chromatography-olfactometry/mass spectrometry with preparative fraction collection for analysis of ultra-trace amounts of odor compounds.
PubMed:
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.
PubMed:
Following in their footprints: cuticular hydrocarbons as overwintering aggregation site markers in Hippodamia convergens.
PubMed:
Simultaneous determination of ten taste and odor compounds in drinking water by solid-phase microextraction combined with gas chromatography-mass spectrometry.
PubMed:
A methyltransferase essential for the methoxypyrazine-derived flavour of wine.
PubMed:
The role of semiochemicals in short-range location of aggregation sites in Adalia bipunctata (Coleoptera, Coccinellidae).
PubMed:
Defensive allomones function as aggregation pheromones in diapausing Ladybird Beetles, Hippodamia convergens.
PubMed:
Genetic analysis of the biosynthesis of 2-methoxy-3-isobutylpyrazine, a major grape-derived aroma compound impacting wine quality.
PubMed:
Detection and quantification of natural contaminants of wine by gas chromatography-differential ion mobility spectrometry (GC-DMS).
PubMed:
Key aroma compounds in roasted in-shell peanuts.
PubMed:
Behavior of 3-isobutyl-2-hydroxypyrazine (IBHP), a key intermediate in 3-isobutyl-2-methoxypyrazine (IBMP) metabolism, in ripening wine grapes.
PubMed:
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.).
PubMed:
Fruit ripening in Vitis vinifera: light intensity before and not during ripening determines the concentration of 2-methoxy-3-isobutylpyrazine in Cabernet Sauvignon berries.
PubMed:
Occurrence of dissolved and particle-bound taste and odor compounds in Swiss lake waters.
PubMed:
Accurate analysis of trace earthy-musty odorants in water by headspace solid phase microextraction gas chromatography-mass spectrometry.
PubMed:
The effect of pyrazine odor on body weight and the weight of various organs in chicks (Gallus gallus domesticus).
PubMed:
Simultaneous determination of eight common odors in natural water body using automatic purge and trap coupled to gas chromatography with mass spectrometry.
PubMed:
Purification and characterization of two odorant-binding proteins from nasal tissue of rabbit and pig.
PubMed:
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.
PubMed:
2-Methoxy-3-isobutylpyrazine in grape berries and its dependence on genotype.
PubMed:
Effect of enzyme activity and frozen storage on jalapeño pepper volatiles by selected ion flow tube-mass spectrometry.
PubMed:
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.
PubMed:
Long-timescale molecular-dynamics simulations of the major urinary protein provide atomistic interpretations of the unusual thermodynamics of ligand binding.
PubMed:
Identification of alkyl-methoxypyrazines as the malodorous compounds in water supplies from Northwest Spain.
PubMed:
Automated trace determination of earthy-musty odorous compounds in water samples by on-line purge-and-trap-gas chromatography-mass spectrometry.
PubMed:
Why has porcine VEG protein unusually high stability and suppressed binding ability?
PubMed:
Three odorant-binding proteins from rabbit nasal mucosa.
PubMed:
Multiple types and forms of odorant-binding proteins in the Old-World porcupine Hystrix cristata.
PubMed:
Ligand-binding properties and structural characterization of a novel rat odorant-binding protein variant.
PubMed:
Odorant-binding proteins of the mouse.
PubMed:
Purification and characterisation of an odorant-binding protein from cow nasal tissue.
PubMed:
Survey of 3-alkyl-2-methoxypyrazine content of South African Sauvignon blanc wines using a novel LC-APCI-MS/MS method.
PubMed:
Rapid measurement of 3-alkyl-2-methoxypyrazine content of winegrapes to predict levels in resultant wines.
PubMed:
Volatile composition of Catharanthus roseus (L.) G. Don using solid-phase microextraction and gas chromatography/mass spectrometry.
PubMed:
Structural basis of the broad specificity of a general odorant-binding protein from honeybee.
PubMed:
Odor thresholds of microbially induced off-flavor compounds in apple juice.
PubMed:
The molecular basis for wine grape quality--a volatile subject.
PubMed:
Van der Waals interactions dominate ligand-protein association in a protein binding site occluded from solvent water.
PubMed:
Removal of earthy-musty odorants in drinking water by powdered activated carbon.
PubMed:
Effect of cultivar and storage time on the volatile flavor components of baked potato.
PubMed:
The determination of six taste and odour compounds in water using Ambersorb 572 and high resolution mass spectrometry.
PubMed:
Odorant and pheromone binding by aphrodisin, a hamster aphrodisiac protein.
PubMed:
Complexes of porcine odorant binding protein with odorant molecules belonging to different chemical classes.
PubMed:
Quantitative determination of 2-methoxy-3-isobutylpyrazine in red wines and grapes of Bordeaux using a stable isotope dilution assay.
PubMed:
Membrane receptor for odour-binding proteins.
PubMed:
Odorant-sensitive adenylate cyclase: rapid, potent activation and desensitization in primary olfactory neuronal cultures.
PubMed:
Activation by odorants of a multistate cation channel from olfactory cilia.
PubMed:
The odorant-sensitive adenylate cyclase of olfactory receptor cells. Differential stimulation by distinct classes of odorants.
PubMed:
Isolation and characterization of an olfactory receptor protein for odorant pyrazines.
PubMed:
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.
PubMed:
Determination of characteristic odorants from Harmonia axyridis beetles using in vivo solid-phase microextraction and multidimensional gas chromatography-mass spectrometry-olfactometry.
PubMed:
Evidence of chemical exchange in recombinant Major Urinary Protein and quenching thereof upon pheromone binding.
PubMed:
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.
PubMed:
Thermodynamics of binding of 2-methoxy-3-isopropylpyrazine and 2-methoxy-3-isobutylpyrazine to the major urinary protein.
PubMed:
Absolute configuration of 2-sec-butyl-4,5-dihydrothiazole in male mouse urine.
PubMed:
Characteristic aroma components of British Farmhouse Cheddar cheese.
PubMed:
Solid-phase microextraction method development for headspace analysis of volatile flavor compounds.
PubMed:
Similar increases in extracellular lactic acid in the limbic system during epileptic and/or olfactory stimulation.
PubMed:
Conformational stability and binding properties of porcine odorant binding protein.
PubMed:
Subtypes of odorant-binding proteins--heterologous expression and ligand binding.
PubMed:
Lipocalins of boar salivary glands binding odours and pheromones.
PubMed:
Isolation of two odorant-binding proteins from mouse nasal tissue.
PubMed:
Ligand binding characteristics of homologous rat and mouse urinary proteins and pyrazine-binding protein of calf.
PubMed:
Ultrastructural characteristics of sustentacular cells in control and odorant-treated olfactory mucosae of the salamander.
PubMed:
Odorant stimulation of secretory and neural processes in the salamander olfactory mucosa.
PubMed:
Immunocytochemical localization of pyrazine-binding protein in bovine nasal mucosa.
PubMed:
Occurrence of a pyrazine binding protein in the nasal mucosa of some vertebrates.