5-(ヒドロキシメチル)フルフラール

外観

黄色～くすんだ黄色～濃い紫色透明液体

解説

5-(ヒドロキシメチル)フルフラール，融点35 ℃，沸点141～142 ℃(0.3 kPa)．λmax 283 nm．水，エタノール，エーテルなどに可溶．塩酸と煮沸するとレプリン酸とギ酸になる．

森北出版「化学辞典（第2版）

用途

HMFはバイオ燃料としての可能性を持っている。HMF を還元して2,5-ジヒドロキシメチルフランへと変換し、水素化分解により合成される2,5-ジメチルフラン (DMF) はエネルギー密度がガソリンと同程度である。

製造

5-(ヒドロキシメチル)フルフラール，ワイン，ハチミツ，果汁などに含まれ，それらの褐変化の一因となっている．ヘキソースを希シュウ酸溶液と加熱すると，その構造や反応条件により種々の収率で生成する．

説明

5-Hydroxymethylfurfural (5-HMF) derived from sugars is the link between biomass and furan-based chemicals. With its various functional groups and associated reaction sites, this small molecule opens the door to a wide range of chemical modifications, which makes 5-HMF a versatile renewable building block.
5-HMF is widely spread in food products and is formed in sugar containing food when exposed to heat. It is widely used as an indicator of quality in food products. It is also employed to indicate the adulteration of food products with acid converted invert syrups.

化学的特性

Beige Coloured Crystalline Solid.
Among the organic compounds that can be obtained from biomass, 5-Hydroxymethylfurfural (5-HMF) is one of the most interesting ones. 5-HMF is an organic compound derived from dehydration of certain sugars (hexoses). This yellow, low-melting solid is highly water-soluble. The molecule consists of a furan ring, containing both aldehyde and alcohol functional groups. HMF as natural substance has been identified in a wide variety of heat-processed foods including milk, fruit juices, spirits, honey, etc. HMF, which is derived from cellulose, is a potential "carbon-neutral" feedstock for a number of chemical substances.

使用

An antioxidant for grape and apple juice.

定義

ChEBI: 5-hydroxymethylfurfural is a member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo. It has a role as an indicator and a Maillard reaction product. It is a member of furans, an arenecarbaldehyde and a primary alcohol.

製造方法

5-Hydroxymethylfurfural (HMF) was synthesized from glucose in a slug flow capillary microreactor, using a combination of AlCl3 and HCl as the homogeneous catalyst in the aqueous phase and methyl isobutyl ketone as the organic phase for in-situ HMF extraction.
Continuous synthesis of 5-hydroxymethylfurfural from glucose using a combination of AlCl3 and HCl as catalyst in a biphasic slug flow capillary microreactor

主な応用

5-Hydroxymethylfurfural has been used as a standard in the high performance liquid chromatographic (HPLC) analysis for the determination of 5-(hydroxymethyl)furfural content in co-hydrolysates and fermentation broth of lignocellulosic biomass for the lipid accumulation in M. isabellina type of microorganisms. 5-(Hydroxymethyl)furfural may be used as an analytical reference standard for the quantification of the analyte in vinegar and fruit juice samples using chromatography techniques.
5-Hydroxymethylfurfural has been used as standard in the high performance liquid chromatographic (HPLC) analysis for the determination of 5-(hydroxymethyl)furfural content in co-hydrolysates and fermentation broth of lignocellulosic biomass for the lipid accumulation in M. isabellina type of microorganisms.

一般的な説明

5-(Hydroxymethyl)furfural is an organic compound, widely spread in food products and is formed in sugar containing food when exposed to heat. It is widely used as an indicator of quality in food products. It is also employed to indicate the adulteration of food products with acid converted invert syrups.

生物活性

5-Hydroxymethylfurfural is a furanic compound derived from the degradation of sugars. It can be derived from reducing sugars via acid-catalyzed degradation or the Maillard reaction during the heating and storage of foods. 5-Hydroxymethylfurfural is an intermediate in the synthesis of a variety of compounds including 2,5-diformylfuran (DFF), 2,5-furandicarboxylic acid (FDA), 2,5-bis(hydroxymethyl)furan (5-(hydroxymethyl)furfuryl alcohol; Item No. 20658), and dimethylfuran (DMF), among others. 5-Hydroxymethylfurfural has been found in the marine algae L. undulata and scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH), hydroxyl, alkyl, and superoxide radicals in cell-free assays (IC50s = 27.1, 22.8, 45, and 33.5 μM, respectively).

安全性プロファイル

Questionable carcinogen with experimental tumorigenic data.Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES

代謝経路

When 5-hydroxymethyl-2-furaldehyde (HMF) is administered orally or intravenously to rats, HMF or its metabolites are rapidly eliminated in the urine with the recovery of 95 ? 100% after 24 h. HMF is completely converted to two metabolites which are identified as 5- hydroxymethyl-2-furoic acid and N-(5-hydroxymethyl-2- furoyl)glycine.

純化方法

Crystallise it from diethyl ether/pet ether. [Beilstein 18 III/IV 100, 18/1 V 130.]