2-Furoic acid

Source: Wikipedia, the free encyclopedia.
2-Furoic Acid
Names
Preferred IUPAC name
Furan-2-carboxylic acid[1]
Other names
  • 2-Furoic acid
  • Pyromucic acid
  • 2-Furancarboxylic acid
  • α-Furancarboxylic acid
  • α-Furoic acid
  • 2-Carboxyfuran
Identifiers
3D model (
JSmol
)
110149
ChEBI
ChemSpider
ECHA InfoCard
 100.001.639 Edit this at Wikidata
3056
KEGG
UNII
  • InChI=1S/C5H4O3/c6-5(7)4-2-1-3-8-4/h1-3H,(H,6,7) checkY
    Key: SMNDYUVBFMFKNZ-UHFFFAOYSA-N checkY
  • InChI=1/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;/rC4H9Li/c1-2-3-4-5/h2-4H2,1H3
    Key: MZRVEZGGRBJDDB-NESCHKHYAE
  • OC(=O)C1=CC=CO1
Properties
C5H4O3
Molar mass 112.084 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
Occupational safety and health (OHS/OSH):
Main hazards
 Irritating to eyes, respiratory system and skin.
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Related compounds
Related compounds
 2-Thiophenecarboxylic acid,
3-Furoic acid, Furfuryl alcohol,
2,5-Furandicarboxylic acid,
Furfurylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

2-Furoic acid is an organic compound, consisting of a furan ring and a carboxylic acid side-group. Along with other furans, its name is derived from the Latin word furfur, meaning bran, from which these compounds were first produced.[2] The salts and esters of furoic acids are known as furoates. 2-Furoic acid is most widely encountered in food products as a preservative and a flavouring agent, where it imparts a sweet, earthy flavour.[3]

History

The compound was first described by Carl Wilhelm Scheele in 1780, who obtained it by the dry distillation of mucic acid. For this reason it was initially known as pyromucic acid. This was the first known synthesis of a furan compound, the second being furfural in 1821.[4][5] Despite this, it was furfural which came to set naming conventions for later furans.

Preparation and synthesis

Biotransformation of furfuryl alcohol (R = CH2OH) or furfural (R = CHO) to 2-furoic acid by Nocardia corallina

2-Furoic acid can be synthesized by the oxidation of either furfuryl alcohol or furfural. This can be achieved either chemically or biocatalytically.

The current industrial route involves the

Cannizaro reaction of furfural in an aqueous NaOH solution. This is a disproportionation reaction and produces a 1:1 ratio of 2-furoic acid and furfuryl alcohol (a 50% yield of each).[6] It remains economical because both products have commercial value. The bio-catalytic route involves the microorganism Nocardia corallina. This produces 2-furoic acid in higher yields: 98% from 2-furfuryl alcohol and 88% from 2-furfural,[7]
but has yet to be commercialised.

Applications and occurrences

Diloxanide, an amebicide derived from 2-feroic acid,[8] is on the World Health Organization's List of Essential Medicines.[9]

In terms of commercial uses, 2-furoic acid is often used in the production of furoate esters, some of which are drugs and pesticides.[10]

In foods

It is a flavoring ingredient and achieved a

herbaceous, and earthy.[3]

2-Furoic acid helps sterilize and

pasteurize many foods. It forms in situ from 2-furfural.[11] 2-Furoic acid is also formed during coffee roasting, with up to 205 mg/kg.[12]

Optic properties

2-Furoic acid crystals are highly transparent in the 200–2000 nm wavelength region, are stable up to 130 °C, and generally have low absorption in the

ferroelectrics in temperature ranges > 318 K.[14]

Microbial metabolism

2-Furoic acid can be the sole source of carbon and energy for the organism Pseudomonas putida. The organism aerobically degrades the compound. [15] [16]

Hazards

The LD50 is 100 mg/kg (oral, rats).[17]

References

  1. ISBN 978-0-85404-182-4
    .
  2. ISBN 0-444-52239-5
    .
  3. ^
    ISBN 0-8493-9414-7
    .
  4. doi:10.1002/jlac.18320030206
    . From p. 141: "Ich verbinde mit diese Bitte noch die Bemerkung, … Bittermandelöl riechende Materie enthält, … " (I join to this request also the observation that the formic acid which is formed by the simultaneous reaction of sulfuric acid and manganese peroxide with sugar and which contains a volatile material that appears oily in an isolated condition and that smells like a mixture of cassia and bitter almond oil … )
  5. JSTOR 111080
    .
  6. S2CID 101343477
    .
  7. ^ Pérez, Herminia (2009). "Microbial biocatalytic preparation of 2-furoic acid by oxidation of 2-furfuryl alcohol and 2-furanaldehyde with Nocardia corallina". African Journal of Biotechnology. 8 (10).
  8. S2CID 19657328
    .
  9. hdl:10665/325771
    . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  10. S2CID 42398133
    .
  11. doi:10.1016/j.foodchem.2010.12.017
    .
  12. S2CID 222280614
    .
  13. doi:10.1016/j.physb.2011.04.038
    .
  14. doi:10.1016/j.ijleo.2012.08.075
    .
  15. doi:10.1002/cber.18700030129
    .
  16. PMID 16347977
    .
  17. ISBN 978-3527306732
    .

Further reading
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