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kahweofuran

Kahweofuran is a sulfurous compound present in roasted coffee known for its roasted smoky odor and structural formula C7H8OS.
Chemical Structure

General Material Description

Kahweofuran is an organosulfur compound with the molecular formula C7H8OS. It belongs to the class of thieno[2,3-c]furans and is specifically identified as 2,3-dihydro-6-methylthieno[2,3-c]furan among its systematic synonyms. This compound features a bicyclic structure incorporating sulfur and oxygen heterocycles. It is typically encountered as a colorless to pale liquid with a characteristically sulfurous aroma. Kahweofuran occurs naturally and is primarily sourced from roasted coffee, contributing to its distinctive smoky and sulfurous notes. Additional chemical and safety details are cataloged in public databases such as PubChem, where its Chemical ID is 526931. This compound is relevant to studies of natural extractives due to its sensory properties and origin.

Occurrence, Applicability & Potential Uses

Kahweofuran naturally occurs in roasted coffee and is considered a component contributing to the volatile profile of coffee aroma. Its sulfurous and smoky odor characteristics suggest a role in flavor chemistry, particularly in the sensory complexity of roasted foods. While recognized as a natural substance, it is primarily investigated for analytical purposes rather than direct flavor or fragrance formulation. According to the Flavor and Extract Manufacturers Association (FEMA) (US), there are no recommended usage levels for kahweofuran in flavor or fragrance products. This aligns with its present classification as a natural extract rather than a compound for additive applications. Research interest often focuses on its identification and quantification in complex food matrices.

Physico-Chemical Properties Summary

Kahweofuran exhibits a boiling point range of 193 to 194°C at standard atmospheric pressure (760 mm Hg), which influences its volatility in aroma release. Its estimated log P (octanol-water partition coefficient) value is approximately 0.4, indicating moderate hydrophilicity. The compound has a measurable water solubility of about 281 mg/L at 25°C, supporting some aqueous dispersion potential. Vapor pressure at 25°C is relatively low (0.663 mmHg), suggesting limited volatility compared to highly volatile aroma compounds. Kahweofuran’s flash point is approximately 70°C (159°F), which is an important safety parameter for handling and storage. These physicochemical attributes affect its sensory impact and behavior during food processing or extraction.

FAQ

What is kahweofuran and where is it found?
Kahweofuran is a sulfur-containing organic compound classified chemically as 2,3-dihydro-6-methylthieno[2,3-c]furan. It is primarily found in roasted coffee, where it contributes to the characteristic roasted, smoky, and sulfurous aroma profile. The compound has a bicyclic molecular structure comprising sulfur and oxygen atoms, and its presence is significant in studies related to coffee flavor chemistry.
How is kahweofuran's chemical profile relevant to its use in products?
Kahweofuran’s physicochemical properties, such as a boiling point near 193°C and moderate water solubility, influence its volatility and extraction behavior. These properties dictate how it contributes to aroma perception in roasted coffee. Because of its sulfurous odor and low vapor pressure, it plays a subtle but important role in complex flavor profiles. Despite its natural occurrence, kahweofuran is not recommended for direct use in flavor or fragrance formulations due to regulatory considerations and limited safety data.
What regulatory or safety information is associated with kahweofuran?
According to safety classifications aligned with 29 CFR 1910 (OSHA HCS) standards in the United States, kahweofuran has no listed GHS hazard classifications, indicating no formally identified hazards under these regulations. Usage guidelines indicate it is categorized under natural substances and extractives, but it is not approved for flavor or fragrance use at specified levels. Comprehensive toxicological data on oral, dermal, and inhalation toxicity have not been fully determined. Hence, it is primarily of interest for analytical research rather than commercial application in consumer products.

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

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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):HMDB32922
FooDB:FDB010905
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia: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

Preferred name kahweofuran
Trivial Name Kahweofuran
Short Description thieno[2,3-c]furan, 2,3-dihydro-6-methyl-
Formula C7 H8 O S
CAS Number 26693-24-3
FDA UNII Search
Nikkaji Number J19.927C
xLogP3-AA 1.90 (est)
NMR Predictor External link
Synonyms
  • bicyclo[3.3.0]-3-oxa-8-thia-1,4-octadiene, 2-methyl
  • 2,3-dihydro-6-methyl-thieno[2,3c]furan
  • 6-methyl-2,3-dihydrothieno(2,3-c)furan
  • 6-methyl-2,3-dihydrothieno[2,3-c]furan
  • thieno[2,3-c]furan, 2,3-dihydro-6-methyl-
  • 6-methyl-2,3-dihydrothieno[2,3-c]furan
  • 2,3-Dihydro-6-methylthieno[2,3-c]furan

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 140.20495605469
Boiling Point 193 to 194°C @ 760 mm Hg
Vapor Pressure 0.663 mmHg @ 25 °C
Flash Point TCC Value 70.5 °C TCC
logP (o/w) 0.402 est
Solubility
water, 280.9 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Sulfurous
roasted, smoky, sulfurous
General comment At 0.01 % in propylene glycol. roasted smoky sulfurous

Occurrences

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 kahweofuran usage levels up to:
not for fragrance use.
Recommendation for kahweofuran 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 :526931
National Institute of Allergy and Infectious Diseases:Data
6-methyl-2,3-dihydrothieno[2,3-c]furan
Chemidplus:0026693243