2-Furoic acid
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| Names | |
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Preferred IUPAC name
Furan-2-carboxylic acid
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| Other names
2-Furoic acid; pyromucic acid; 2-furancarboxylic acid; α-furancarboxylic acid; α-furoic acid; 2-carboxyfuran
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| Identifiers | |
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3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.001.639 |
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PubChem CID
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| Properties | |
| C5H4O3 | |
| Molar mass | 112.08 g·mol−1 |
| Appearance | White/ Off-White (Beige) Crystalline Powder |
| Density | 0.55 g/cm3 |
| Melting point | 128 to 132 °C (262 to 270 °F; 401 to 405 K) |
| Boiling point | 230 to 232 °C (446 to 450 °F; 503 to 505 K) |
| Easily soluble in cold and hot water, 27.1 g/L | |
| Acidity (pKa) | 3.12 at 25 °C |
| Hazards | |
| Main hazards | Irritating to eyes, respiratory system and skin. |
| NFPA 704 | |
| Related compounds | |
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Related compounds
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2-Thiophenecarboxylic acid, 3-Furoic acid, Furfuryl alcohol, 2,5-Furandicarboxylic acid, Furfurylamine |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
2-Furoic acid is a heterocyclic carboxylic acid, consisting of a five-membered aromatic ring and a carboxylic acid group. Its name is derived from the Latin word furfur, meaning bran. The salts and esters of furoic acids are known as furoates.
2-Furoic acid is an organic compound most widely found in food products as a preservative and a flavoring agent. Other uses for 2-furoic acid include nylon preparation and optic technologies.
2-Furoic acid was first described by Carl Wilhelm Scheele in 1780 as the first derivative of the compound furan. Since then, the compound's reactivity with different substances and organisms was tested. It was discovered that 2-furoic acid can be the sole source of carbon and energy for the organism Pseudomonas putida. The organism aerobically degrades the compound.
2-Furoic acid can be synthesized by the oxidation of either furfuryl alcohol or furfural. This can be achieved either chemically or biocatalytically. Currently the industrial route involves the Cannizaro reaction of furfural in an aqueous NaOH solution; this route produces both 2-furoic acid and furfuryl alcohol. The bio-catalytic route involves the microorganism Nocardia corallina. Experiments involving this microbial conversion resulted in high yields: 98% from 2-furfuryl alcohol and 88% from 2-furanaldehyde. Oxidation with N. corallina is unique because most other microorganisms produce two products from the oxidation, the acid and the alcohol. Furthermore, aromatic ring destruction does not occur.
In industrial use, 2-furoic acid is a preservative, acting as a bactericide and fungicide. It is also considered an acceptable flavoring ingredient and achieved a generally recognized as safe (GRAS) status in 1995 by the Flavor and Extract Manufacturers Association (FEMA). 2-Furoic acid is characterized as a colorless liquid and has a distinct odor described in the Encyclopedia of Food and Color Additives as sweet, oily, herbaceous, and earthy. 2-Furoic acid is often used as a starting material for the production of furoate esters. It and its derivatives also aid in the production of nylons, and are often used in biomedical research.
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