2-Acetylfuran

This was one of two molecules for this week.
November 23, 2020
You might get a whiff of us this week.
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Happy Thanksgiving! If you are like many of us, sweet potatoes (aka yams) are one of the highlights of your Turkey Day meal. The aroma of a casserole baking in the oven adds to that comfort-food feeling.

A chemist would naturally ask, “Why do roasting or baking sweet potatoes smell so good?” Ola Lasekan* and Li Shing Teoh at University Putra Malaysia (Serdang), identified 29 aroma compounds in roasting white yam (Dioscorea rotundata)1. Among them, the two that had the highest odor activity factors were 2-acetylfuran (2AF, aka 2-furyl methyl ketone) and 2-acetylpyrrole (2AP, aka 2-pyrrolyl methyl ketone).

According to the authors, 2AF “elicited an almond-like note” whereas 2AP had “a popcorn-like note”. The aromas emitted by the other components, mostly furans, pyrroles, and pyrazines, were given labels such as “toasty”, “caramel”, “chamomile flower–like”, and “smoky”.

The focus of this study was to identify the aroma compounds that contribute to the potatoes’ antioxidant properties. Using an established test based on substances’ ability to inhibit the oxidation of hexanal, the authors found that the pyrrole-containing aroma components were substantially superior antioxidants to the furans and especially the pyrazines.

A glance at the hazard information tables shown here might give you pause. 2AF in particular looks as if it might kill you as you’re enjoying the holiday. But rest assured that these, like many other odorous substances, are detectable in air at very low concentrations.

So, this Thanksgiving Day, while you’re watching the virtual Macy’s parade and NFL football games, take satisfaction that some of the food aromas you’re inhaling add to your antioxidant supply.

1. Full disclosure: Dioscorea spp. are “true yams”, as opposed to the orange-colored sweet potatoes (Convolvulaceae spp.) that some Americans call yams. The baking and roasting aromas of both yam genera contain 2AF and 2AP.

2-Acetylfuran hazard information

Hazard class* Hazard statement
Flammable liquids, category 4

H227—Combustible liquid

Acute toxicity, oral, category 2 H300—Fatal if swallowed Chemical Safety Warning
Acute toxicity, dermal , category 3 H311—Toxic in contact with skin Chemical Safety Warning
Serious eye damage/eye irritation, category 1 H318—Causes serious eye damage Chemical Safety Warning
Acute toxicity, inhalation, category 2  H330—Fatal if inhaled Chemical Safety Warning

*Globally Harmonized System of Classification and Labeling of Chemicals.  
Explanation of pictograms.

2-Acetylpyrrole hazard information

Hazard class* Hazard statement
Acute toxicity, oral, category 4 H302—Harmful if swallowed Chemical Safety Warning
Skin corrosion/irritation, category 2 H315—Causes skin irritation Chemical Safety Warning
Specific target organ toxicity, single exposure, respiratory tract irritation, category 3 H335—May cause respiratory irritation Chemical Safety Warning

*Globally Harmonized System of Classification and Labeling of Chemicals.  
Explanation of pictograms.

2-Acetylfuran fast facts

CAS Reg. No. 1192-62-7
SciFinder
nomenclature
Ethanone, 1-(2-furanyl)-
Empirical formula C6H6O2
Molar mass 110.11 g/mol
Appearance Yellow to brown liquid or solid
Melting range 26–33 ºC
Boiling point 175 ºC
Water solubility  Very slight

2-Acetylpyrrole fast facts

CAS Reg. No. 1072-83-9
SciFinder
nomenclature
Ethanone, 1-(1H-pyrrol-2-yl)-
Empirical formula C6H7NO
Molar mass 109.13 g/mol
Appearance White to beige crystals or powder
Melting point 90.0–90.5 ºC
Water solubility  274 g/L
Chemical Abstract Service - a division of ACS

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