5-Methylfurfural Explained

5-Methylfurfural is an organic compound with the formula . An aldehyde that is derived through various extractions and reductions from cellulose products,^[1] it has applications as a synthetic intermediate^[2] relevant to the fields of medicine, agriculture and cosmetics.^[3] It is a food additive, and has FEMA number 270s and JECFA number 745.^[4] Reduction of 5-methylfurfural gives the product 5-methylfurfuryl alcohol.^[5]

Synthesis

The synthesis of 5-methylfurfural has been documented from as early as 1891. It was originally synthesized from rhamnose, but can be produced from the dehydration of sucrose and other cellulose products.^[6] Several synthetic pathways have been proposed from 5-hydroxymethylfurfural. The compound has been produced in the 21st century using the historical precursor of rhamnose with the aim to use it as a precursor to biogasoline.^[7]

Notes and References

1. Moe . Størker T. . Marcotullio . Gianluca . Opedal . Mihaela Tanase . Brusletto . Rune . December 2022 . Formation of 5-methylfurfural and 2-acetylfuran from lignocellulosic biomass and by Cr3+-catalyzed dehydration of 6-deoxyhexoses . Carbohydrate Research . en . 522 . 108672 . 10.1016/j.carres.2022.108672. 36183617 . 11250/3055856 . free .
2. Li . Shaopeng . Dong . Minghua . Yang . Junjuan . Cheng . Xiaomeng . Shen . Xiaojun . Liu . Shulin . Wang . Zhi-Qiang . Gong . Xue-Qing . Liu . Huizhen . Han . Buxing . January 26, 2021 . Selective hydrogenation of 5-(hydroxymethyl)furfural to 5-methylfurfural over single atomic metals anchored on Nb2O5 . Nature Communications . en . 12 . 1 . 584 . 10.1038/s41467-020-20878-7 . 2041-1723 . 7838200 . 33500400.
3. Peng . Yang . Li . Xianghua . Gao . Tian . Li . Teng . Yang . Weiran . 2019 . Preparation of 5-methylfurfural from starch in one step by iodide mediated metal-free hydrogenolysis . Green Chemistry . en . 21 . 15 . 4169–4177 . 10.1039/C9GC01645G . 1463-9262.
4. Web site: 2002 . Online Edition: "Specifications for Flavourings" . June 25, 2024 . Food and Agriculture Organization of the United Nations.
5. Spillman . Philip J. . Pollnitz . Alan P. . Liacopoulos . Dimitra . Pardon . Kevin H. . Sefton . Mark A. . 1998-02-01 . Formation and Degradation of Furfuryl Alcohol, 5-Methylfurfuryl Alcohol, Vanillyl Alcohol, and Their Ethyl Ethers in Barrel-Aged Wines . Journal of Agricultural and Food Chemistry . en . 46 . 2 . 657–663 . 10.1021/jf970559r . 10554294 . 0021-8561.
6. 1934 . 5-METHYLFURFURAL . Organic Syntheses . 14 . 62 . 10.15227/orgsyn.014.0062.
7. Feng . Yunchao . Li . Zheng . Long . Sishi . Sun . Yong . Tang . Xing . Zeng . Xianhai . Lin . Lu . 2020 . Direct conversion of biomass derived l -rhamnose to 5-methylfurfural in water in high yield . Green Chemistry . en . 22 . 18 . 5984–5988 . 10.1039/D0GC02105A . 1463-9262.