Methoxymethylfurfural (MMF or 5-methoxymethylfuran-2-carbaldehyde) is an organic compound derived from dehydration of sugars and subsequent etherification with methanol.

[4] Bicker reported first order kinetics for the dehydration of fructose, etherification of HMF into MMF and by-products formation in methanol.

Reactions in various alcohols by Brown et al. led to the formation of the appropriate HMF ether and levulinic acid ester.

[12] The addition of MMF and other alkoxymethyl furfurals to a tobacco product has been patented because it acts as a fragrance to provide a sweet flavor in the smoke.

[2] On the contrary EMF, the ethanol ether of HMF can be found in many alcoholic beverages such as beer and wine, especially those who still contain high sugar levels at the end of the fermentation.

[11] However, the first phase of REACH testing has shown that the oral LD50 value of MMF in Wistar rats was established to exceed 2000 mg/kg body weight.

MMF can routinely been analyzed on a GC using for example a Varian VF-WAXms column with a temperature profile up to 250˚C and FID detector.

The IR sample below was recorded on a Nicolet 6700 FT-IR at room temperature using the liquid film (diamond ATR-cell) procedure.

The first publication on MMF dates from 1927, by Haworth et al., in which it was observed as a product of tetramethylfructose dehydration in an attempt to deduce the structure of sucrose.