Methoxymethylfurfural

Methoxymethylfurfural
Names
Preferred IUPAC name
5-[(Methoxy)methyl]furan-2-carbaldehyde
Other names
5-Methoxymethyl furfural; Methoxymethylfurfurol; 5-(Methoxymethyl)furan-2-carbaldehyde; 5-Methoxymethylfurfural; 5-(Methoxymethyl)-2-furaldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.149.478 Edit this at Wikidata
UNII
  • InChI=1S/C7H8O3/c1-9-5-7-3-2-6(4-8)10-7/h2-4H,5H2,1H3
  • O=Cc1oc(cc1)COC
  • COCC1=CC=C(O1)C=O
Properties
C7H8O3
Molar mass 140.138 g·mol−1
Appearance Colorless liquid
Density 1140 kg/m3
Melting point −8 °C (18 °F; 265 K)
Boiling point 109 to 111 °C (228 to 232 °F; 382 to 384 K) at 11-12 tor
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Skin irritation/Skin sensitizer
Related compounds
Related furan-2-carbaldehydes
Furfural
Hydroxymethylfurfural
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methoxymethylfurfural (MMF or 5-methoxymethylfuran-2-carbaldehyde) is an organic compound derived from dehydration of sugars and subsequent etherification with methanol.[1] This colorless liquid is soluble in a wide range of solvents including lower alcohols. The molecule is a derivative of furan, containing both aldehyde and ether (methoxymethyl) functional groups. MMF has been detected in the leaves and roots of Chilean Jaborosa magellanica (Solanaceae).[2] It has a typical odor suggestive of maraschino cherries.[3] MMF can be made from a wide range of carbohydrate containing feedstocks including sugar, starch and cellulose using a chemical catalytic process and is a potential "carbon-neutral" feedstock for fuels and chemicals.

  1. ^ van Putten, R-J., van der Waal J.C. de Jong, E., Rasrendra C.B., Heeres, E.J. and de Vries HG. (2011) Furan-based platform chemicals of the future. Dehydration of hexoses as biosustainable product route. Chemical Reviews submitted.
  2. ^ Podesta, Federico; Fajardo, Victor; Freyer, Alan J.; Shamma, Maurice (1988). "5-Methoxymethyl-2-furaldehyde: A Natural Furanoid fromJaborosa Magellanica (Solanaceae) 5-Methoxymethyl-furfural: Ein natürliches Furanoid ausJaborosa magellanica (Colanaceae)". Archiv der Pharmazie. 321 (12): 949. doi:10.1002/ardp.19883211225. S2CID 86420362.
  3. ^ Hind, J.D. and Crayton, F.H. (1963) Tobacco flavorants. US 3,095,882