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furfuryl crotonate

Furfuryl crotonate is a flavor compound with a mushroom-like odor, chemically known as 2-butenoic acid, 2-furanylmethyl ester, (2E)-, used mainly in natural extractive applications.

General Material Description

Furfuryl crotonate is an organic ester classified under flavor compounds, specifically exhibiting a mushroom-like odor. Its chemical designation is 2-butenoic acid, 2-furanylmethyl ester, (2E)-, and it carries several synonyms including 2-furylmethyl (E)-but-2-enoate and 2-furyl methyl (E)-2-butenoate. This compound is represented by the molecular formula C9H10O3 and has a molecular weight of approximately 166.18 g/mol. It appears as a clear liquid with sensory characteristics noted for their resemblance to mushrooms, making it relevant in flavor applications. Furfuryl crotonate is catalogued in authoritative databases such as PubChem. It is typically obtained through chemical synthesis processes involving furanyl and crotonate moieties, positioning it within natural substances and extractives used for flavor and fragrance formulations.

Occurrence, Applicability & Potential Uses

Furfuryl crotonate occurs predominantly as a synthetic flavor ester used within the domain of natural substances and extractives. Its characteristic mushroom-like odor renders it suitable for applications aiming to replicate or enhance such sensory profiles in flavor and fragrance complexes. Due to its sensory specificity, it is applicable in natural product flavor design and can be employed in food, beverage, or aroma formulations where mushroom notes are desired. Usage recommendations are guided by standards including FEMA (US) evaluations, although current guidance advises against its inclusion in fragrances or flavors due to undefined toxicity profiles, reflecting precaution in regulatory practices. Continued research and standardization may expand its applicability in specialized niches of flavor chemistry.

Physico-Chemical Properties Summary

Furfuryl crotonate exhibits physicochemical characteristics influential in its formulation and application. It possesses a boiling point range between 96 and 98 degrees Celsius at reduced pressure (11 mm Hg), indicating moderate volatility under controlled conditions. The compound is moderately soluble in water, with an estimated solubility of approximately 818 mg/L at 25 degrees Celsius. These properties suggest that furfuryl crotonate can be incorporated into aqueous or semi-aqueous matrices under certain conditions but requires consideration of its vapor pressure and solubility for formulation stability. Its estimated partition coefficient (xlogP3aa) of 1.50 suggests balanced lipophilicity, supporting its blendability in both hydrophilic and lipophilic systems. These factors collectively inform handling, storage, and integration into product development cycles.

FAQ

What is furfuryl crotonate and what are its main properties?
Furfuryl crotonate is an organic ester known chemically as 2-butenoic acid, 2-furanylmethyl ester, (2E)-. It has a mushroom-like flavor profile and appears as a clear liquid with the molecular formula C9H10O3. Its boiling point ranges from 96 to 98 degrees Celsius at reduced pressure, and it exhibits moderate water solubility. The compound is primarily used for its distinctive sensory properties in flavor chemistry.
Where is furfuryl crotonate typically used and how is it sourced?
Furfuryl crotonate is mainly applied as a flavor compound within natural substances and extractives to impart mushroom-like notes. It is generally synthesized chemically rather than extracted directly from natural sources, allowing controlled production for industrial use. Its incorporation usually occurs in flavor formulations rather than fragrances, due to regulatory guidelines. The compound's origin and manufacturing comply with relevant chemical synthesis standards to ensure quality for flavor applications.
What regulations or recommendations exist for the use of furfuryl crotonate?
Current regulatory data and safety evaluations, including those referenced by FEMA (US), advise caution regarding the use of furfuryl crotonate. Recommendations indicate it is not intended for fragrance or flavor use at this time, primarily because toxicological information is not fully determined. No specific hazard classifications under OSHA HCS have been identified, but usage guidelines reflect prudent restraint pending further research. Users should consult relevant safety datasheets and regulatory databases before incorporation into products.

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

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Literature & References

furan-2-ylmethyl (E)-but-2-enoate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):21954672
Pubchem (sid):37461117
Publications by US Patents
3,952,024 - Furfurylthioacetone
Certain 2,5-dimethyl-3-thiopyrazines
Flavoring agent

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
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report

General Material Information

Trivial Name furfuryl crotonate
Short Description 2-butenoic acid, 2-furanylmethyl ester, (2E)-
Formula C9 H10 O3
CAS Number 13678-63-2
FDA UNII Search
Nikkaji Number J354.944E
xLogP3-AA 1.50 (est)
NMR Predictor External link
Synonyms
  • 2-butenoic acid, 2-furanylmethyl ester, (2E)-
  • furan-2-ylmethyl (E)-but-2-enoate
  • 2-furyl methyl (E)-2-butenoate
  • 2-furylmethyl (2E)-2-butenoate

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 166.17630004883
Boiling Point 96 to 98°C @ 11 mm Hg
Solubility
water, 818.1 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Flavor Type: Mushroom
mushroom, fungal
General comment Mushroom-like

Safety Information

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:
natural substances and extractives
Recommendation for furfuryl crotonate usage levels up to:
not for fragrance use.
Recommendation for furfuryl crotonate flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :21954672
National Institute of Allergy and Infectious Diseases:Data
furan-2-ylmethyl (E)-but-2-enoate