5-Methylfurfuryl alcohol explained

5-Methylfurfuryl alcohol is an organic compound with the formula . It is one of many volatile compounds present in Nicotiana tabacum,[1] and is formed from the reduction of 5-methylfurfural,[2] a compound formed from the reduction of 5-bromo- or 5-chloromethylfurfural.[3] It is a colorless liquid listed as a food additive with FEMA number 4544 and JECFA number 2099.[4]

Occurrence

5-Methylfurfuryl alcohol naturally occurs as one of many volatile compounds present in Nicotiana tabacum, or cultivated tobacco. The compound appears at much lower concentration in tobacco leaves than the more common aldehyde furfural.

As the reduction product of 5-methylfurfural, 5-methylfurfuryl alcohol occurs in barrel-aged wines along with 5-methylfurfuryl ethyl ether.

Synthesis

5-Methylfurfuryl alcohol can be produced through a reduction of 5-methylfurfural with lithium aluminium hydride, though historically the reduction has been performed starting with methyl 5-methyl–2-furoate rather than 5-methylfurfural.

Notes and References

  1. Peng . Fumin . Sheng . Liangquan . Liu . Baizhan . Tong . Hongwu . Liu . Shaomin . June 2004 . Comparison of different extraction methods: steam distillation, simultaneous distillation and extraction and headspace co-distillation, used for the analysis of the volatile components in aged flue-cured tobacco leaves . Journal of Chromatography A . en . 1040 . 1 . 1–17 . 10.1016/j.chroma.2004.03.057. 15248421 .
  2. 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.
  3. 1934 . 5-Methylfurfural . Organic Syntheses . 14 . 62 . 10.15227/orgsyn.014.0062.
  4. Web site: 2012 . Online Edition: "Specifications for Flavourings" . June 25, 2024 . Food and Agriculture Organization of the United Nations.

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