Furaneol

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Furaneol
Category Others
Catalog number BBF-04726
CAS 3658-77-3
Molecular Weight 128.1
Molecular Formula C6H8O3
Purity > 95 % by HPLC

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Description

Furan phenol is a derivative of furan, which is used in perfume and perfume industries.

Specification

Synonyms 2,5-Dimethyl-4-hydroxy-3(2H)-furanone
Storage Store at -20 °C
IUPAC Name 4-hydroxy-2,5-dimethylfuran-3-one
Canonical SMILES CC1C(=O)C(=C(O1)C)O
InChI InChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3
InChI Key INAXVXBDKKUCGI-UHFFFAOYSA-N

Properties

Appearance White to light yellow crystalline powder
Boiling Point 188 °C
Melting Point 73-77 °C (lit.)
Flash Point 90.5°C
Density 1.05 g/cm3
Solubility Soluble in Water
LogP 0.76370

Reference Reading

1. Key Food Furanones Furaneol and Sotolone Specifically Activate Distinct Odorant Receptors
Franziska Haag, Sandra Hoffmann, Dietmar Krautwurst J Agric Food Chem. 2021 Sep 22;69(37):10999-11005. doi: 10.1021/acs.jafc.1c03314. Epub 2021 Sep 8.
Furanones formed during the Maillard reaction often are natural aroma-determining compounds found in numerous foods. Prominent economically relevant representatives are the structural homologues Furaneol and sotolone, which are important natural flavoring compounds because of their distinct caramel- and seasoning-like odor qualities. These, however, cannot be predicted by the odorants' molecular shape, rather their receptors' activation parameters help to decipher the encoding of odor quality. Here, the distinct odor qualities of Furaneol and sotolone suggested an activation of at least two out of our ca. 400 different odorant receptor types, which are the molecular biosensors of our chemical sense of olfaction. While an odorant receptor has been identified for sotolone, a receptor specific for Furaneol has been elusive. Using a bidirectional screening approach employing 616 receptor variants and 187 key food odorants in a HEK-293 cell-based luminescence assay, we newly identified OR5M3 as a receptor specifically activated by Furaneol and homofuraneol.
2. Flexible Screen Printed Aptasensor for Rapid Detection of Furaneol: A Comparison of CNTs and AgNPs Effect on Aptasensor Performance
Ali Douaki, Biresaw Demelash Abera, Giuseppe Cantarella, Bajramshahe Shkodra, Asma Mushtaq, Pietro Ibba, Akm Sarwar Inam, Luisa Petti, Paolo Lugli Nanomaterials (Basel). 2020 Jun 15;10(6):1167. doi: 10.3390/nano10061167.
Furaneol is a widely used flavoring agent, which can be naturally found in different products, such as strawberries or thermally processed foods. This is why it is extremely important to detect furaneol in the food industry using ultra-sensitive, stable, and selective sensors. In this context, electrochemical biosensors are particularly attractive as they provide a cheap and reliable alternative measurement device. Carbon nanotubes (CNTs) and silver nanoparticles (AgNPs) have been extensively investigated as suitable materials to effectively increase the sensitivity of the biosensors. However, a comparison of the performance of biosensors employing CNTs and AgNPs is still missing. Herein, the effect of CNTs and AgNPs on the biosensor performance has been thoughtfully analyzed. Therefore, disposable flexible and screen printed electrochemical aptasensor modified with CNTs (CNT-ME), or AgNPs (AgNP-ME) have been developed. Under optimized conditions, CNT-MEs showed better performance compared to AgNP-ME, yielding a linear range of detection over a dynamic concentration range of 1 fM-35 μM and 2 pM-200 nM, respectively, as well as high selectivity towards furaneol. Finally, our aptasensor was tested in a real sample (strawberry) and validated with high-performance liquid chromatography (HPLC), showing that it could find an application in the food industry.
3. Levels of Furaneol in Msalais Wines: A Comprehensive Overview of Multiple Stages and Pathways of Its Formation during Msalais Winemaking
Li-Xia Zhu, Meng-Meng Zhang, Zheng Liu, Yin Shi, Chang-Qing Duan Molecules. 2019 Aug 27;24(17):3104. doi: 10.3390/molecules24173104.
4-Hydroxy-2,5-dimethyl-3(2H)-furanone (furaneol) is present in food. It has a caramel-like flavor, which affects the quality of food, and is formed via multiple pathways. Msalais is a traditional wine fermented from boiled local grape juice in Xinjiang (China). It has a strong caramel odor, which suggests high furaneol content. Furaneol formation during Msalais-making had not been investigated to date. Here, high-performance liquid chromatography and different fermentation models of Msalais-making were used to investigate the furaneol content and formation during Msalais-making. The furaneol content of Msalais is high, between 27.59 ± 0.493 mg/L and 117.6 ± 0.235 mg/L. It is formed throughout the entire Msalais-making process. The formation pathways include the Maillard reaction and chemical hydrolysis of bound furaneol during grape juice concentration; enzymatic release and/or chemical acidic hydrolysis of furaneol glucosides, and biosynthesis from Maillard products and d-fructose-1,6-diphosphate during fermentation; chemical transformation of Maillard products at room temperature (16-25 °C) and hydrolysis of furaneol glucosides during storage. Importantly, furaneol is formed by an efficient biotransformation of Maillard products. These findings suggest that furaneol content can be used as an important indicator of wine quality, and could be controlled by controlling the grape quality, grape juice concentration, fermentation, and wine storage.

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