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W313203

Sigma-Aldrich

2-Isobutyl-3-methoxypyrazine

≥99%, FG

Synonym(s):

2-methoxy-3-(2-methylpropyl)pyrazine, 2-methoxy-3-isobutylpyrazine

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About This Item

Empirical Formula (Hill Notation):
C9H14N2O
CAS Number:
Molecular Weight:
166.22
FEMA Number:
3132
EC Number:
Council of Europe no.:
11338
MDL number:
UNSPSC Code:
12164502
PubChem Substance ID:
Flavis number:
14.043
NACRES:
NA.21

biological source

synthetic

Quality Level

grade

FG
Fragrance grade
Halal
Kosher

Agency

follows IFRA guidelines
meets purity specifications of JECFA

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 178/2002

Assay

≥99%

refractive index

n20/D 1.49 (lit.)

density

0.99 g/mL at 25 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

Organoleptic

green; vegetable; pepper

SMILES string

COc1nccnc1CC(C)C

InChI

1S/C9H14N2O/c1-7(2)6-8-9(12-3)11-5-4-10-8/h4-5,7H,6H2,1-3H3

InChI key

UXFSPRAGHGMRSQ-UHFFFAOYSA-N

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General description

2-Isobutyl-3-methoxypyrazine is the main characteristic flavor/aroma constituent of bell peppers. It is also found in fresh jalapeno peppers and baked potato.

Application


  • RIFM Fragrance Ingredient Safety Assessment, 2-Isobutyl-3-methoxypyrazine, CAS Registry Number 24683-00-9.: This safety assessment reviews the toxicological data of 2-Isobutyl-3-methoxypyrazine, ensuring its safe use in fragrances (Api et al., 2024).

  • Source-Sink Manipulations Have Major Implications for Grapevine Berry and Wine Flavonoids and Aromas That Go Beyond the Changes in Berry Sugar Accumulation.: This article discusses the impact of 2-Isobutyl-3-methoxypyrazine on wine aroma, focusing on agricultural practices and their influence on grape quality (Martínez-Lüscher and Kurtural, 2023).

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

176.0 °F - closed cup

Flash Point(C)

80 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Volatile flavour components of baked potato flesh. A comparison of eleven potato cultivars.
Duckham SC, et al.
Molecular Nutrition And Food Research, 45(5), 317-323 (2001)
Volatile components and pungency in fresh and processed Jalapeno peppers.
Huffman VL, et al.
Journal of Food Science, 43(6), 1809-1811 (1978)
Julie Roy et al.
Biophysical journal, 99(1), 218-226 (2010-07-27)
The mouse major urinary protein (MUP) has proved to be an intriguing test bed for detailed studies on protein-ligand recognition. NMR, calorimetric, and modeling investigations have revealed that the thermodynamics of ligand binding involve a complex interplay between competing enthalpic
Maria Staiano et al.
Biopolymers, 89(4), 284-291 (2007-12-22)
The effects of hydrostatic pressure on the structure and stability of porcine odorant-binding protein (pOBP) in the presence and absence of the odorant molecule 2-isobutyl-3-methoxypyrazine (IBMP) were studied by steady-state and time-resolved fluorescence spectroscopy as well as by molecular dynamics
Richard J Bingham et al.
Journal of the American Chemical Society, 126(6), 1675-1681 (2004-02-12)
In the present study we examine the thermodynamics of binding of two related pyrazine-derived ligands to the major urinary protein, MUP-I, using a combination of isothermal titration calorimetry (ITC), X-ray crystallography, and NMR backbone (15)N and methyl side-chain (2)H relaxation

Protocols

Separation of 2-Isopropyl-3-methoxypyrazine 20 ppt; 2-Isobutyl-3-methoxypyrazine; 2-Methylisoborneol; (±)-Geosmin 10 ppt

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