5-(Hydroxymethyl)-2-furancarboxylic acid

5-Hydroxymethyl-2-furancarboxylic acid is the main metabolite of 5-hydroxymethyl-2-furfural (HMF) in the body and eliminated renally.

Solid

5-hydroxymethyl-2-furoic acid is a member of the class of furoic acids that is 2-furoic acid substituted at position 5 by a hydroxymethyl group. It has a role as a human urinary metabolite, a nematicide, a bacterial xenobiotic metabolite and a fungal metabolite. It is a furoic acid and an aromatic primary alcohol.

ALD-003 (5mg), NOX-009 or NOX-001 (5mg) and NAD or NADP (2Omol% based upon the amount of ALD-003) was added to 0.5mL 0.25M KPi (pH 8.5). The pH was adjusted to pH 8.5 with 1M NaOH. 10mM DFF or HMF was added and the reaction was left in ashaking incubator at 35C. After a specified time the reaction was quenched with 1 M HCI, centrifuged and analysed by RP-HPLC. The results are found in Tables 5, 6, and 7A. Reaction Conditions: 0.SmL KPi 0.25M pH 8.5, 5mg CFE, 2Omol% cofactor, 5mg NOX, 10mM Substrate, 35C, reaction time 30 minutes.0.2g of 5-hydroxymethylfurfural, 0.05g Ag-PVP/ZrO2 catalyst (Ag:PVP=1:0.5 (molar ratio), 2.5% load), 0.126g NaOH, 50mL water was added to a 150mL three-necked flask, And oxygen is introduced, the oxygen flow rate is 60 mL/min, and the reaction is carried out at a temperature of 20 C.Real-time sampling, The product was determined by high performance liquid chromatography for the content of 5-hydroxymethylfurfural and 5-hydroxymethylnonanoic acid.When the reaction is 12h, The conversion rate of 5-hydroxymethylfurfural is 99%.Yield of 5-hydroxymethyl-furoic acid 99%The selectivity is 100%.Take 0.317 g of HMF, 2 g of NaOH (20%) and 3 ml of water into the autoclave. The reaction vessel was charged with 10 ml of polytetrafluoroethylene lined autoclave with 0.30 g Pt / NaY (Pt lwt% As the catalyst, the program temperature to 80 C, filled with 0.5MPa oxygen, the reaction 12 hours, the reaction process continue to add oxygen to ensure that the reaction at constant temperature and constant pressure. The reaction product was centrifuged and the supernatant was removed and analyzed using HPLC. The results showed that the conversion rate of HMF was 100% and the yield of HMFA was 92%. The reaction results are shown in Table 1.Catalytic Reaction Of HMF To FDCA For this reaction, Na2C03 was used as the base. 1 g of extracted HMF was first dissolved in 5 g of water. The Na2C03 was separately prepared by dissolving Na2C03 in water. The oxidation catalyst was then added follow by the HMF solution at ambient room temperature. With oxygen gas bubbling, the solution was first heated to 50C for 2 hours, and HMF was fully converted to HFCA. After that, the reaction was heat to 95C and kept for 7 hour. The pH of the aqueous solution was then adjusted to 1 and FDCA was precipitated from the solution. The precipitate was filtered and washed with ethanol.10 g of HMF, 150 g of water, and 1 g of catalyst (4% Au/TiO2) were added into a round bottom bottle (250 mL) and then heated to 70 C. Air under atmosphere pressure was introduced into the liquid in the flask. The pH value of the above reaction was controlled to 10 by adding a sodium hydroxide aqueous solution into the flask. The reaction was continued for 7 hours to obtain a crude aqueous solution. The crude aqueous solution was extracted by 200 mL of ethyl acetate two times, and the aqueous phase of the extractions was collected by a separatory funnel. The collected aqueous phase was titrated by concentrated hydrochloric acid (HCl) until its pH value reached 3. The acidified aqueous phase was extracted by 200 mL of ethyl acetate two times, and the organic phase of the extractions was collected. The collected organic phase was vacuumed concentrated to obtain 2.74 g of solid, which was 5-hydroxymethyl-2-furoic acid (HMFCA). The above reaction is shown in Formula 8. The product of Formula 8 had NMR spectra as below: 1H NMR (400 MHz, d-DMSO): 13.08 (br, 1H), 7.14 (d, 1H, J=3.4 Hz), 6.45 (d, 1H, J=3.4 Hz), 5.59 (s, 1H), 4.44 (s, 2H); 13C NMR (100 M Hz, d-DMSO): 160.1, 159.8, 144.4, 119.0, 109.4, 56.2.10 g of HMF, 150 g of water, And 1 g of 4% Au / TiO2 catalyst250 mL of a round bottom flask, Heated to 70 C, And air was introduced under normal pressure.The pH of the reaction was then controlled to 10 with the addition of aqueous sodium hydroxide, After 7 hours of continuous reaction, an aqueous solution of the crude product was obtained.The crude aqueous solution was added to 200 mL of ethyl acetate for extraction twice, The water layer was taken in a separatory funnel.The aqueous layer was titrated with concentrated hydrochloric acid (HCl) until the pH was 3.After extraction twice with 200 mL of ethyl acetate, the organic layer was taken.The organic layer was concentrated under reduced pressure to give 2.74 g of a solid, 5-hydroxymethyl-2-furoic acid (HMFCA).The above reaction is shown in Formula 8 below.The Au / MgO (Au0.5 wt%) catalyst, 1 mmol of 5-hydroxymethylfurfural, NaOH, 10 ml of water was charged to a stainless steel autoclave with a Teflon-lined internal metal, 5-hydroxymethylfurfural: NaOH = 0.015: 1: 4 (mol: mol: mol).Using automatic temperature control program temperature to the reaction temperature of 30 C, adding 0.3MPa oxygen, reaction 5 hours, the reaction process to maintain the same pressure.The reaction product was analyzed by HPLC.General procedure: Typically, 4 mL of phosphate buffer (0.2 M, pH 7) containing 50mMFF and 50 mg (cell wet weight) per mL microbial cells was incubated at30 C and 160 r/min. Aliquots were withdrawn from the reaction mixturesat specified time intervals and diluted with the correspondingmobile phase prior to HPLC analysis. The conversion was defined as theratio of the consumed substrate amount to the initial substrate amount(in mol). The yield was defined as the ratio of the formed productamount to the theoretical value based on the initial substrate amount(in mol). The selectivity was defined as the ratio of the formed productamount to the total amount of all products (in mol). All the experimentswere conducted at least in duplicate, and the values were expressed asthe means ± standard deviations.

Molecular Weight:142.11
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:142.02660867
Monoisotopic Mass:142.02660867
Topological Polar Surface Area:70.7
Heavy Atom Count:10
Complexity:134
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes