5-Hydroxymethyl-2-furancarboxylic acid
(Synonyms: 5-羟甲基-2-呋喃甲酸) 目录号 : GC30189
A major metabolite of 5-hydroxymethyl-2-furfural
Cas No.:6338-41-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
5-Hydroxymethyl-2-furancarboxylic acid is the main metabolite of 5-hydroxymethyl-2-furfural, a product of acid-catalyzed degradation of sugars during the heating and storage of foods that influences taste and physiological functions in the body.1 5-Hydroxymethyl-2-furancarboxylic acid can be used as a building block in the enzymatic synthesis of macrocyclic oligoesters.2
1.J?bstl, D., Hus?y, T., Alexander, J., et al.Analysis of 5-hydroxymethyl-2-furoic acid (HMFA) the main metabolite of alimentary 5-hydroxymethyl-2-furfural (HMF) with HPLC and GC in urineFood Chem.123(3)814-818(2010) 2.Hirai, H., Naito, K., Hamasaki, T., et al.Syntheses of macrocyclic oligoesters from 5-hydroxymethyl-2-furancarboxylic acidMacromol. Chem. Phys.185(11)2347-2359(1984)
| Cas No. | 6338-41-6 | SDF | |
| 别名 | 5-羟甲基-2-呋喃甲酸 | ||
| Canonical SMILES | C1=C(OC(=C1)CO)C(=O)O | ||
| 分子式 | C6H6O4 | 分子量 | 142.11 |
| 溶解度 | DMSO : ≥ 150 mg/mL (1055.52 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 7.0368 mL | 35.184 mL | 70.368 mL |
| 5 mM | 1.4074 mL | 7.0368 mL | 14.0736 mL |
| 10 mM | 0.7037 mL | 3.5184 mL | 7.0368 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Characterization of a thermotolerant aryl-alcohol oxidase from Moesziomyces antarcticus oxidizing 5-Hydroxymethyl-2-furancarboxylic acid
Appl Microbiol Biotechnol 2021 Nov;105(21-22):8313-8327.34643786 PMC8557139
The development of enzymatic processes for the environmentally friendly production of 2,5-furandicarboxylic acid (FDCA), a renewable precursor for bioplastics, from 5-hydroxymethylfurfural (HMF) has gained increasing attention over the last years. Aryl-alcohol oxidases (AAOs) catalyze the oxidation of HMF to 5-formyl-2-furancarboxylic acid (FFCA) through 2,5-diformylfuran (DFF) and have thus been applied in enzymatic reaction cascades for the production of FDCA. AAOs are flavoproteins that oxidize a broad range of benzylic and aliphatic allylic primary alcohols to the corresponding aldehydes, and in some cases further to acids, while reducing molecular oxygen to hydrogen peroxide. These promising biocatalysts can also be used for the synthesis of flavors, fragrances, and chemical building blocks, but their industrial applicability suffers from low production yield in natural and heterologous hosts. Here we report on heterologous expression of a new aryl-alcohol oxidase, MaAAO, from Moesziomyces antarcticus at high yields in the methylotrophic yeast Pichia pastoris (recently reclassified as Komagataella phaffii). Fed-batch fermentation of recombinant P. pastoris yielded around 750 mg of active enzyme per liter of culture. Purified MaAAO was highly stable at pH 2-9 and exhibited high thermal stability with almost 95% residual activity after 48 h at 57.5 °C. MaAAO accepts a broad range of benzylic primary alcohols, aliphatic allylic alcohols, and furan derivatives like HMF as substrates and some oxidation products thereof like piperonal or perillaldehyde serve as building blocks for pharmaceuticals or show health-promoting effects. Besides this, MaAAO oxidized 5-Hydroxymethyl-2-furancarboxylic acid (HMFCA) to FFCA, which has not been shown for any other AAO so far. Combining MaAAO with an unspecific peroxygenase oxidizing HMFCA to FFCA in one pot resulted in complete conversion of HMF to FDCA within 144 h. MaAAO is thus a promising biocatalyst for the production of precursors for bioplastics and bioactive compounds. KEY POINTS: ‿MaAAO from M. antarcticus was expressed in P. pastoris at 750 mg/l. ‿MaAAO oxidized 5-Hydroxymethyl-2-furancarboxylic acid (HMFCA). ‿Complete conversion of HMF to 2,5-furandicarboxylic acid by combining MaAAO and UPO.
Efficient synthesis of 5-Hydroxymethyl-2-furancarboxylic acid by Escherichia coli overexpressing aldehyde dehydrogenases
J Biotechnol 2020 Jan 10;307:125-130.31726082 10.1016/j.jbiotec.2019.11.007
Catalytic transformation of biomass-derived furans into value-added chemicals and biofuels has received considerable interest recently. In this work, aldehyde dehydrogenases (ALDHs) were identified from Comamonas testosteroni SC1588 for the oxidation of bio-based furans into furan carboxylic acids. Of the whole-cell biocatalysts constructed, Escherichia coli expressing a vanillin dehydrogenase (E. coli_CtVDH1) proved to be the best for the oxidation of 5-hydroxymethylfurfural (HMF). 5-Hydroxymethyl-2-furancarboxylic acid (HMFCA) was obtained in the yield of approximately 92 % within 12 h using this recombinant strain when the HMF concentration was up to 200 mM. In a fed-batch process, 292 mM of HMFCA was produced within 20.5 h, thereby providing a productivity as high as 2.0 g/L h. Other furan carboxylic acids were synthesized in the yields of 83-95%. Besides, the partially purified HMF was smoothly converted into HMFCA by this recombinant strain, with a 90% yield.
Improved biosynthesis of 5-Hydroxymethyl-2-furancarboxylic acid and furoic acid from biomass-derived furans with high substrate tolerance of recombinant Escherichia coli HMFOMUT whole-cells
Bioresour Technol 2020 May;303:122930.32037191 10.1016/j.biortech.2020.122930
The main aim of this work was to firstly develop a selective oxidation approach for biologically converting 5-hydroxymethylfurfural and furfural into the corresponding furan-based carboxylic acids with recombinant Escherichia coli HMFOMUT. Whole-cells of this recombinant strain harbored good biocatalytic activity in a narrow pH range (pH 6.5-7.0), which had high tolerance toward furfural (up to 50 mM) and 5-hydroxymethylfurfural (up to 150 mM), well-known potential inhibitors against microorganisms. 5-Hydroxymethyl-2-furancarboxylic acid and furoic acid could be obtained at 96.9% and 100% yield from 5-hydroxymethylfurfural (150 mM) and furfural (50 mM) at 30 °C and pH 7.0. The improved substrate tolerance of Escherichia coli HMFOMUT is gaining a great interest to synthesize value-added furan-based carboxylic acids, which has potential industrial applications.
Valorization of Gelidium amansii for dual production of D-galactonic acid and 5-Hydroxymethyl-2-furancarboxylic acid by chemo-biological approach
Microb Cell Fact 2020 May 14;19(1):104.32410635 PMC7227364
Background: Marine macroalgae Gelidium amansii is a promising feedstock for production of sustainable biochemicals to replace petroleum and edible biomass. Different from terrestrial lignocellulosic biomass, G. amansii is comprised of high carbohydrate content and has no lignin. In previous studies, G. amansii biomass has been exploited to obtain fermentable sugars along with suppressing 5-hydroxymethylfurfural (HMF) formation for bioethanol production. In this study, a different strategy was addressed and verified for dual production of D-galactose and HMF, which were subsequently oxidized to D-galactonic acid and 5-Hydroxymethyl-2-furancarboxylic acid (HMFCA) respectively via Pseudomonas putida. Results: G. amansii biomass was hydrolyzed by dilute acid to form D-galactose and HMF. The best result was attained after pretreatment with 2% (w/w) HCl at 120 °C for 40 min. Five different Pseudomonas sp. strains including P. putida ATCC 47054, P. fragi ATCC 4973, P. stutzeri CICC 10402, P. rhodesiae CICC 21960, and P. aeruginosa CGMCC 1.10712, were screened for highly selective oxidation of D-galactose and HMF. Among them, P. putida ATCC 47054 was the outstanding suitable biocatalyst converting D-galactose and HMF to the corresponding acids without reduced or over-oxidized products. It was plausible that the pyrroloquinoline quinone-dependent glucose dehydrogenase and undiscovered molybdate-dependent enzyme(s) in P. putida ATCC 47054 individually played pivotal role for D-galactose and HMF oxidation. Taking advantage of its excellent efficiency and high selectivity, a maximum of 55.30 g/L D-galactonic acid and 11.09 g/L HMFCA were obtained with yields of 91.1% and 98.7% using G. amansii hydrolysates as substrate. Conclusions: Valorization of G. amansii biomass for dual production of D-galactonic acid and HMFCA can enrich the product varieties and improve the economic benefits. This study also demonstrates the perspective of making full use of marine feedstocks to produce other value-added products.
Aerobic oxidation of 5-hydroxymethylfurfural to 5-Hydroxymethyl-2-furancarboxylic acid and its derivatives by heterogeneous NHC-catalysis
Org Biomol Chem 2018 Nov 28;16(46):8955-8964.30403257 10.1039/c8ob02425a
The application of the oxidative system composed of a heterogeneous triazolium pre-catalyst, iron(ii) phthalocyanine and air is described for the selective conversion of 5-hydroxymethylfurfural (HMF) into the added-value 5-Hydroxymethyl-2-furancarboxylic acid (HMFCA). The disclosed one-pot two-step procedure involved sequential oxidative esterifications of HMF to afford a polyester oligomer having hydroxyl and carboxyl terminal groups (Mw = 389-1258), which in turn was hydrolyzed by a supported base (Ambersep 900 OH) to yield HMFCA in 87% overall yield. The same strategy was adopted for the effective synthesis of ester and amide derivatives of HMFCA by nucleophilic depolymerization of the oligomeric intermediate with methanol and butylamine, respectively. The utilization of the disclosed oxidative system for the direct conversion of HMF and furfural into their corresponding ester, amide, and thioester derivatives is also reported.