Hydroxymethylfurfural

Last updated
Hydroxymethylfurfural
Hydroxymethylfurfural-2D-skeletal.png
Hydroxymethylfurfural 3D ball.png
Hydroxymethylfurfural 3D spacefill.png
Names
Preferred IUPAC name
5-(Hydroxymethyl)furan-2-carbaldehyde [1]
Other names
5-(Hydroxymethyl)-2-furaldehyde [1]
5-(Hydroxymethyl)furfural [1]
Identifiers
3D model (JSmol)
110889
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.595 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-654-9
278693
KEGG
PubChem CID
UNII
  • InChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2 Yes check.svgY
    Key: NOEGNKMFWQHSLB-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2
    Key: NOEGNKMFWQHSLB-UHFFFAOYAB
  • c1cc(oc1CO)C=O
Properties
C6H6O3
Molar mass 126.111 g·mol−1
AppearanceLow melting white solid
Odor Buttery, caramel
Density 1.29 g/cm3
Melting point 30 to 34 °C (86 to 93 °F; 303 to 307 K)
Boiling point 114 to 116 °C (237 to 241 °F; 387 to 389 K) (1 mbar)
UV-vis (λmax)284 nm [2]
Related compounds
Related furan-2-carbaldehydes
 Furfural

Methoxymethylfurfural

Hazards
GHS labelling:
GHS-pictogram-exclam.svg [3]
Warning [3]
H315, H319, H335 [3]
P261, P305+P351+P338, P310 [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Hydroxymethylfurfural (HMF), also known as 5-(hydroxymethyl)furfural, is an organic compound formed by the dehydration of reducing sugars. [4] [5] It is a white low-melting solid (although commercial samples are often yellow) which is highly soluble in both water and organic solvents. The molecule consists of a furan ring, containing both aldehyde and alcohol functional groups.

Contents

HMF can form in sugar-containing food, particularly as a result of heating or cooking. Its formation has been the topic of significant study as HMF was regarded as being potentially carcinogenic to humans. However, so far in vivo genotoxicity was negative. No relevance for humans concerning carcinogenic and genotoxic effects can be derived. [6] HMF is classified as a food improvement agent [7] and is primarily being used in the food industry in form of a food additive as a biomarker as well as a flavoring agent for food products. [8] [9] It is also produced industrially on a modest scale [10] as a carbon-neutral feedstock for the production of fuels [11] and other chemicals. [12]

Production and reactions

HMF was first reported in 1875 as an intermediate in the formation of levulinic acid from sugar and sulfuric acid. [13] This remains the classical route, with 6-carbon sugars (hexoses) such as fructose undergoing acid catalyzed poly-dehydration. [14] [15] When hydrochloric acid is used 5-chloromethylfurfural is produced instead of HMF. Similar chemistry is seen with 5-carbon sugars (pentoses), which react with aqueous acid to form furfural.

fructopyranose 1, fructofuranose 2, two intermediate stages of dehydration (not isolated) 3,4 and finally HMF 5 NewhydroxymethylfurfuralSynthesis.png
fructopyranose 1, fructofuranose 2, two intermediate stages of dehydration (not isolated) 3,4 and finally HMF 5

The classical approach tends to suffer from poor yields as HMF continues to react in aqueous acid, forming levulinic acid. [4] As sugar is not generally soluble in solvents other than water, the development of high-yielding reactions has been slow and difficult; hence while furfural has been produced on a large scale since the 1920s, [16] HMF was not produced on a commercial scale until over 90 years later. The first production plant coming online in 2013. [10] Numerous synthetic technologies have been developed, including the use of ionic liquids, [17] [18] continuous liquid-liquid extraction, reactive distillation and solid acid catalysts to either remove the HMF before it reacts further or to otherwise promote its formation and inhibit its decomposition. [19]

Derivatives

HMF itself has few applications. It can however be converted into other more useful compounds. [12] Of these the most important is 2,5-furandicarboxylic acid, which has been proposed as a replacement for terephthalic acid in the production of polyesters. [20] [21] HMF can be converted to 2,5-dimethylfuran (DMF), a liquid that is a potential biofuel with a greater energy content than bioethanol. Hydrogenation of HMF gives 2,5-bis(hydroxymethyl)furan. Acid-catalysed hydrolysis converts HMF into gamma-hydroxyvaleric acid and gamma-valerolactone, with loss of formic acid. [5] [4]

Occurrence in food

HMF is practically absent in fresh food, but it is naturally generated in sugar-containing food during heat-treatments like drying or cooking. Along with many other flavor- and color-related substances, HMF is formed in the Maillard reaction as well as during caramelization. In these foods it is also slowly generated during storage. Acid conditions favour generation of HMF. [22] HMF is a well known component of baked goods. Upon toasting bread, the amount increases from 14.8 (5 min.) to 2024.8 mg/kg (60 min). [5] It is also formed during coffee roasting, with up to 769 mg/kg. [23]

It is a good wine storage time−temperature marker, [24] especially in sweet wines such as Madeira [25] and those sweetened with grape concentrate arrope. [26]

Phallus indusiatus. Cooktown, Queensland, Australia. The fruiting body contains hydroxymethylfurfural. Dictyophora indusiata Feb 2010.JPG
Phallus indusiatus . Cooktown, Queensland, Australia. The fruiting body contains hydroxymethylfurfural.

HMF can be found in low amounts in honey, fruit-juices and UHT-milk. Here, as well as in vinegars, jams, alcoholic products or biscuits, HMF can be used as an indicator for excess heat-treatment. For instance, fresh honey contains less than 15 mg/kg—depending on pH-value and temperature and age, [27] and the codex alimentarius standard requires that honey have less than 40 mg/kg HMF to guarantee that the honey has not undergone heating during processing, except for tropical honeys which must be below 80 mg/kg. [28]

Higher quantities of HMF are found naturally in coffee and dried fruit. Several types of roasted coffee contained between 300 – 2900 mg/kg HMF. [29] Dried plums were found to contain up to 2200 mg/kg HMF. In dark beer 13.3 mg/kg were found, [30] bakery-products contained between 4.1 – 151 mg/kg HMF. [31]

It can be found in glucose syrup.

HMF can form in high-fructose corn syrup (HFCS), levels around 20 mg/kg HMF were found, increasing during storage or heating. [27] This is a problem for American beekeepers because they use HFCS as a source of sugar when there are not enough nectar sources to feed honeybees, and HMF is toxic to them. Adding bases such as soda ash or potash to neutralize the HFCS slows the formation of HMF. [27]

Depending on production-technology and storage, levels in food vary considerably. To evaluate the contribution of a food to HMF intake, its consumption-pattern has to be considered. Coffee is the food that has a very high relevance in terms of levels of HMF and quantities consumed.

HMF is a natural component in heated food but usually present in low concentrations. The daily intake of HMF may underlie high variations due to individual consumption-patterns. It has been estimated that the intakes range between 4 mg - 30 mg per person per day, while an intake of up to 350 mg can result from, e.g., beverages made from dried plums. [6] [32]

Biomedical

A major metabolite in humans is 5-hydroxymethyl-2-furoic acid (HMFA), also known as Sumiki's acid, which is excreted in urine.

HMF bind intracellular sickle hemoglobin (HbS). Preliminary in vivo studies using transgenic sickle mice showed that orally administered 5HMF inhibits the formation of sickled cells in the blood. [33] Under the development code Aes-103, HMF has been considered for the treatment of sickle cell disease. [34]

Quantification

Today, HPLC with UV-detection is the reference-method (e.g. DIN 10751–3). Classic methods for the quantification of HMF in food use photometry. The method according to White is a differential UV-photometry with and without sodium bisulfite-reduction of HMF. [35] Winkler photometric method is a colour-reaction using p-toluidine and barbituric acid (DIN 10751–1). Photometric test may be unspecific as they may detect also related substances, leading to higher results than HPLC-measurements. Test-kits for rapid analyses are also available (e.g. Reflectoquant HMF, Merck KGaA). [36] [37]

Other

HMF is an intermediate in the titration of hexoses in the Molisch's test. In the related Bial's test for pentoses, the hydroxymethylfurfural from hexoses may give a muddy-brown or gray solution, but this is easily distinguishable from the green color of pentoses.

Acetoxymethyl furfural (AMF) is also bio-derived green platform chemicals as an alternative to HMF. [38]

Related Research Articles

<span class="mw-page-title-main">Honey</span> Sweet and viscous substance made by bees mostly using nectar from flowers

Honey is a sweet and viscous substance made by several species of bees, the best-known of which are honey bees. Honey is made and stored to nourish bee colonies. Bees produce honey by gathering and then refining the sugary secretions of plants or the secretions of other insects, like the honeydew of aphids. This refinement takes place both within individual bees, through regurgitation and enzymatic activity, and during storage in the hive, through water evaporation that concentrates the honey's sugars until it is thick and viscous.

<span class="mw-page-title-main">Fructose</span> Simple ketonic monosaccharide found in many plants

Fructose, or fruit sugar, is a ketonic simple sugar found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galactose, that are absorbed by the gut directly into the blood of the portal vein during digestion. The liver then converts both fructose and galactose into glucose, so that dissolved glucose, known as blood sugar, is the only monosaccharide present in circulating blood.

<span class="mw-page-title-main">Sucrose</span> Disaccharide made of glucose and fructose

Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula C
12H
22O
11.

Furfural is an organic compound with the formula C4H3OCHO. It is a colorless liquid, although commercial samples are often brown. It has an aldehyde group attached to the 2-position of furan. It is a product of the dehydration of sugars, as occurs in a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust. The name furfural comes from the Latin word furfur, meaning bran, referring to its usual source. Furfural is only derived from dried biomass. In addition to ethanol, acetic acid, and sugar, furfural is one of the oldest organic chemicals available readily purified from natural precursors.

Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans.

<span class="mw-page-title-main">Molisch's test</span> Chemical test for the presence of carbohydrates

Molisch's test is a sensitive chemical test, named after Austrian botanist Hans Molisch, for the presence of carbohydrates, based on the dehydration of the carbohydrate by sulfuric acid or hydrochloric acid to produce an aldehyde, which condenses with two molecules of a phenol, resulting in a violet ring.

Humins are carbon-based macromolecular substances, that can be found in soil chemistry or as a by-product from saccharide-based biorefinery processes.

<span class="mw-page-title-main">High-fructose corn syrup</span> Processed corn syrup

High-fructose corn syrup (HFCS), also known as glucose–fructose, isoglucose and glucose–fructose syrup, is a sweetener made from corn starch. As in the production of conventional corn syrup, the starch is broken down into glucose by enzymes. To make HFCS, the corn syrup is further processed by D-xylose isomerase to convert some of its glucose into fructose. HFCS was first marketed in the early 1970s by the Clinton Corn Processing Company, together with the Japanese Agency of Industrial Science and Technology, where the enzyme was discovered in 1965.

<span class="mw-page-title-main">Caffeic acid</span> Chemical compound

Caffeic acid is an organic compound with the formula (HO)2C6H3CH=CHCO2H. It is a polyphenol. It is a yellow solid. Structurally, it is classified as a hydroxycinnamic acid. The molecule consists of both phenolic and acrylic functional groups. It is found in all plants as an intermediate in the biosynthesis of lignin, one of the principal components of biomass and its residues. It is unrelated to caffeine.

<span class="mw-page-title-main">Furfuryl alcohol</span> Chemical compound

Furfuryl alcohol is an organic compound containing a furan substituted with a hydroxymethyl group. It is a colorless liquid, but aged samples appear amber. It possesses a faint odor of burning and a bitter taste. It is miscible with but unstable in water. It is soluble in common organic solvents.

<span class="mw-page-title-main">Agave syrup</span> Sweetener

Agave syrup, also known as maguey syrup or agave nectar, is a sweetener commercially produced from several species of agave, including Agave tequilana and Agave salmiana. Blue-agave syrup contains 56% fructose as a sugar providing sweetening properties.

<span class="mw-page-title-main">2,5-Dimethylfuran</span> Chemical compound

2,5-Dimethylfuran is a heterocyclic compound with the formula (CH3)2C4H2O. Although often abbreviated DMF, it should not be confused with dimethylformamide. A derivative of furan, this simple compound is a potential biofuel, being derivable from cellulose.

<span class="mw-page-title-main">2,5-Furandicarboxylic acid</span> Chemical compound

2,5-Furandicarboxylic acid (FDCA) is an organic chemical compound consisting of two carboxylic acid groups attached to a central furan ring. It was first reported as dehydromucic acid by Rudolph Fittig and Heinzelmann in 1876, who produced it via the action of concentrated hydrobromic acid upon mucic acid. It can be produced from certain carbohydrates and as such is a renewable resource, it was identified by the US Department of Energy as one of 12 priority chemicals for establishing the “green” chemistry industry of the future. Furan-2,5-dicarboxylic acid (FDCA) has been suggested as an important renewable building block because it can substitute for terephthalic acid (PTA) in the production of polyesters and other current polymers containing an aromatic moiety.

István T. Horváth was a Hungarian American chemist, working on greener and more sustainable chemistry since its inception. In particular, he focuses on homogeneous transition metal catalysis and in situ spectroscopy. He was highly involved and very influential in the now enormous field of fluorous solvents and technologies.

<span class="mw-page-title-main">2,5-Bis(hydroxymethyl)furan</span> Chemical compound

2,5-Bis(hydroxymethyl)furan (BHMF) is a heterocyclic organic compound, and is a derivative of a broader class of compounds known as furans. It is produced from cellulose and has received attention as a biofeedstock. It is a white solid, although commercial samples can appear yellowish or tan.

<span class="mw-page-title-main">Methoxymethylfurfural</span> Chemical compound

Methoxymethylfurfural is an organic compound derived from dehydration of sugars and subsequent etherification with methanol. 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). It has a typical odor suggestive of maraschino cherries. 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.

<span class="mw-page-title-main">2-Furoic acid</span> Chemical compound

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. 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.

Dionisios G. Vlachos is an American chemical engineer, the Allan & Myra Ferguson Endowed Chair Professor of Chemical Engineering at the University of Delaware and director of the Catalysis Center for Energy Innovation, a U.S. Department of Energy - Energy Frontiers Research Center. Throughout his career at University of Delaware and the University of Minnesota, he has advanced the study of catalysts and reaction engineering including catalytic applications in biomass utilization, alkane conversion and zeolites. He is a fellow of the American Association for the Advancement of Science and recipient of the Wilhelm Award of the American Institute of Chemical Engineers (2011).

1,2,6-Hexanetriol is a trivalent alcohol with two primary and one secondary hydroxy group. It is similar to glycerol in many respects and is used as a substitute for glycerol in many applications due to its more advantageous properties, such as higher thermal stability and lower hygroscopicity.

<span class="mw-page-title-main">2,5-Furandicarboxaldehyde</span> Chemical compound

2,5-Furandicarboxaldehyde (FDC) is an organic compound with the molecular formula C4H2O(CHO)2. It consists of a furan ring with aldehyde groups on the 2 and 5 position. It is therefore classified as a dialdehyde.

References

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  38. ↑ Kang, Eun-Sil; Hong, Yeon-Woo; Chae, Da Won; Kim, Bora; Kim, Baekjin; Kim, Yong Jin; Cho, Jin Ku; Kim, Young Gyu (13 April 2015). "From Lignocellulosic Biomass to Furans via 5-Acetoxymethylfurfural as an Alternative to 5-Hydroxymethylfurfural". ChemSusChem. 8 (7): 1179–1188. doi:10.1002/cssc.201403252. ISSN   1864-564X. PMID   25619448.
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