5-Methyl furfural

Chemical Properties

5-Methylfurfural has a sweet, spicy, warm odor with a sweet caramel-like flavor. May be prepared from sucrose with HCL, followed by treating with stannous chloride; from various methylpentoses by distillation with acid.

Physical properties

colorless to light yellow liquid. soluble in benzene, toluene, carbon tetrachloride and other solvents, insoluble in water.

Occurrence

Reported found in sour cherry, apple, orange juice, cranberry, blueberry, guava, grapes, raisin, peach, blackberry, strawberry jam, asparagus, carrot, onion, potato, bell pepper, tomato, cinnamon, bark, clove bud, bread, parmesan cheese, yogurt, butter, egg, fatty fish, beef, pork liver, beer, cognac, coffee, tea, barley, filberts, popcorn, peanuts, oats, soybean, roasted coconut, cloudberry, passion fruit, pecan, mushroom, starfruit, trassi, sesame seed, mango, tamarind, rice bran, quince, sweet potato, sukiyaki, calamus, licorice, malt, wort, elderberry, mangosteen, kiwifruit, buchu oil, Bourbon vanilla, wild rice, chicory root, shrimp, oyster, clam, okra, pistachio nut and maté

Uses

5-methylfurfural is an intermediate for the synthesis of s-bioallethrin and prallethrin.It used for blending coffee, chocolate, nuts, caramel, spices and on food fragrance. Used in the synthesis of pharmaceutical intermediates.

Uses

5-Methyl-2-furaldehyde is used as a perfuming agent. It is used a smoke with essence.

Preparation

From sucrose with HCl, followed by treating with stannous chloride; 5-Methyl furfural is produced by distillation of various methylpentoses with acid together.

Definition

ChEBI: 5-methyl-2-furaldehyde is a member of furans and an aldehyde. It has a role as a Maillard reaction product, a human metabolite, an EC 2.2.1.6 (acetolactate synthase) inhibitor and a flavouring agent.

Aroma threshold values

Detection: 6 ppm

Taste threshold values

Taste characteristics at 50 ppm: sweet, brown, caramellic, grain, maple-like.

Synthesis Reference(s)

Tetrahedron, 41, p. 3803, 1985 DOI: 10.1016/S0040-4020(01)91401-2
Tetrahedron Letters, 24, p. 5441, 1983 DOI: 10.1016/S0040-4039(00)94107-8

General Description

5-Methylfurfural is formed during the photoexposition of ranitidine hydrochloride. It is employed as potential age marker for Madeira wine. It is a volatile compound present in Lavandula stoechas, Lavandula angustifolia and Lavandula angustifolia x latifolia unifloral honeys.

Metabolic pathway

The biotransformation of 5-methyl-2-furaldehyde is the conversion to 5-methylfuroylgycine and 5-methyl-2- furylmethylketone by rats.