(R)-2-sec-butyl-3-methoxypyrazine

(R)-2-sec-butyl-3-methoxypyrazine is a heterocyclic organic compound classified as a methoxypyrazine. This molecule has the molecular formula C₉H₁₄N₂O and a molecular weight of approximately 166.22 g/mol. It is also known under several synonyms including (R)-asparagus pyrazine and 2-[(2R)-butan-2-yl]-3-methoxypyrazine. The compound is characterized by a distinctive green, earthy odor reminiscent of asparagus, which emerges strongly even at low concentrations, such as 0.10% in dipropylene glycol. Its structure consists of a pyrazine ring substituted with a methoxy group and a sec-butyl side chain. This flavor and fragrance-related compound is primarily accessed from chemical synthesis for analytical or research purposes rather than natural extraction or commercial flavoring. More information about its chemistry and structure can be found in controlled vocabularies like PubChem.

(R)-2-sec-butyl-3-methoxypyrazine naturally occurs in trace amounts in various vegetables and fruits, contributing to green, earthy aroma notes. Despite this, the compound is not typically utilized commercially in fragrances or food flavors due to its intense sensory profile and limited formulation benefits. Regulatory frameworks such as FEMA (US) classify this compound for informational use only and do not recommend it for flavor or fragrance applications. Its primary role is in research contexts examining pyrazine odorants and their sensory thresholds. The distinct green odor offers potential insights into aroma chemistry but practical use in product formulations remains restricted and generally discouraged.

(R)-2-sec-butyl-3-methoxypyrazine exhibits moderate hydrophobicity with an estimated XLogP3 of 1.60, suggesting balanced lipophilic and hydrophilic characteristics. It possesses a low water solubility near 229.6 mg/L at 25 °C, indicating partial miscibility in aqueous environments. The flash point is approximately 0 °C (32 °F), which denotes a relatively low ignition temperature and necessitates prudent handling during processing. The compound's stability and odor persistence are influenced by its heterocyclic pyrazine core and alkyl substituents. These properties affect its suitability during analytical evaluation or formulation trials, primarily due to volatility and sensory strength. Overall, its physicochemical profile requires controlled conditions to prevent alteration of sensory attributes.

Leffingwell:	Chirality or Article
	2-[(2R)-butan-2-yl]-3-methoxypyrazine
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	6951558
Pubchem (sid):	43559475

(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
HMDB (The Human Metabolome Database):	Search
ChemSpider:	View

Safety information

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:
information only not used for fragrances or flavors
Recommendation for (R)-2-sec-butyl-3-methoxypyrazine usage levels up to:
	not for fragrance use.
Recommendation for (R)-2-sec-butyl-3-methoxypyrazine flavor usage levels up to:
	not for flavor use.

Safety references

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Laboratory Chemical Safety Summary :6951558

2-[(2R)-butan-2-yl]-3-methoxypyrazine