Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H6O3 |
Molecular Weight | 126.11 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OCC1=CC=C(O1)C=O
InChI
InChIKey=NOEGNKMFWQHSLB-UHFFFAOYSA-N
InChI=1S/C6H6O3/c7-3-5-1-2-6(4-8)9-5/h1-3,8H,4H2
5-(hydroxymethyl)-2-furaldehyde (5-Hydroxymethyl-2-furancarboxaldehyde, 5‐hydroxymethyl‐2‐furfural) is found in garden onion. It is obtainable from various carbohydrates. 5-Hydroxymethyl-2-furancarboxaldehyde is present in tomatoes, tobacco oil etc. It is a constituent of numerous plant species. 5-Hydroxymethyl-2-furancarboxaldehyde is used as an index of heat treatment and deterioration in food such as tomato paste, honey and fruit juices. Also an indicator of adulteration with acid-converted invert sugars. The heterocyclic aldehyde 5‐hydroxymethyl‐2‐furfural (5HMF, Aes‐103, BAX 555) interacts allosterically with the abnormal form of haemoglobin (Hb), HbS, in red blood cells (RBCs) from patients with sickle cell disease (SCD), thereby increasing oxygen affinity and decreasing HbS polymerization and RBC sickling during hypoxia. 5HMF markedly reduced the deoxygenation-induced dehydration of RBCs whether in response to maintained deoxygenation or to cyclical deoxygenation/re-oxygenation. 5HMF was found to inhibit Psickle, an effect which correlated with its effects on sickling. Deoxygenation-induced activation of the Gardos channel and exposure of phosphatidylserine were also inhibited, probably indirectly via reduced entry of Ca(2+) through the Psickle pathway. Effects of 5HMF on KCC were more modest with a slight inhibition in N-ethylmaleimide (NEM, 1 mm)-treated RBCs and stimulation in RBCs untreated with NEM. These findings support the hypothesis that 5HMF may also be beneficial through effects on RBC ion and water homeostasis. AesRx is developing Aes-103 as an orally bioavailable, chronic therapy for SCD. Aes‐103 is currently in phase II clinical trials in SCD patients in the USA and UK. Aes-103 has received orphan designation from the US Food and Drug Administration and is eligible for orphan status in Europe.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Derivative spectrophotometric determination of 5-(hydroxymethyl)-2-furaldehyde (HMF) and furfural in Locust bean extract. | 2001 Feb |
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Glucose degradation products in peritoneal dialysis fluids may have both local and systemic effects: a study of residual fluid and mesothelial cells. | 2001 Nov-Dec |
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The influence of bark on the fermentation of Douglas-fir whitewood pre-hydrolysates. | 2002 Aug |
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Inhibition effects of furfural on alcohol dehydrogenase, aldehyde dehydrogenase and pyruvate dehydrogenase. | 2002 May 1 |
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Antioxidant effects of isorhamnetin 3,7-di-O-beta-D-glucopyranoside isolated from mustard leaf (Brassica juncea) in rats with streptozotocin-induced diabetes. | 2002 Sep 11 |
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Erythritol attenuates the diabetic oxidative stress through modulating glucose metabolism and lipid peroxidation in streptozotocin-induced diabetic rats. | 2002 Sep 11 |
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Kinetics of hydroxymethylfurfural, lactulose and furosine formation in milk with different fat content. | 2003 Feb |
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Affinity adsorption of glucose degradation products improves the biocompatibility of conventional peritoneal dialysis fluid. | 2003 Jan |
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2-Furoylmethyl amino acids and hydroxymethylfurfural as indicators of honey quality. | 2003 Jul 16 |
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[Studies on chemical constituents from the root of Polygonatum kingianum]. | 2003 Jun |
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[Study on the fingerprints of Achyranthes bidentata Bl. by HPLC/UV/MS]. | 2003 Nov |
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Limits for alkaline detoxification of dilute-acid lignocellulose hydrolysates. | 2003 Spring |
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Amelioration of diabetic nephropathy by dried Rehmanniae Radix (Di Huang) extract. | 2004 |
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Antibacterial activity of bee honey and its therapeutic usefulness against Escherichia coli O157:H7 and Salmonella typhimurium infection. | 2004 Dec |
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Isolation of sterols from the marine fungus Corollospora lacera. | 2004 Dec |
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Browning and decomposed products of model orange juice. | 2004 Mar |
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Isolation of microorganisms for biological detoxification of lignocellulosic hydrolysates. | 2004 Mar |
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3-Hydroxy-4,5-dimethyl-2(5H)-furanone levels in fortified Madeira wines: relationship to sugar content. | 2004 Nov 3 |
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In vitro anti-tyrosinase activity of 5-(hydroxymethyl)-2-furfural isolated from Dictyophora indusiata. | 2004 Oct |
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Selection of anion exchangers for detoxification of dilute-acid hydrolysates from spruce. | 2004 Spring |
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Optimization of Brewery's spent grain dilute-acid hydrolysis for the production of pentose-rich culture media. | 2004 Spring |
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Quality evaluation of honey harvested from selected areas in Tanzania with special emphasis on hydroxymethyl furfural (HMF) levels. | 2004 Summer |
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Effects of glucose, fructose and 5-hydroxymethyl-2-furaldehyde on the presystemic metabolism and absorption of glycyrrhizin in rabbits. | 2005 Feb |
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V79-hCYP2E1-hSULT1A1, a cell line for the sensitive detection of genotoxic effects induced by carbohydrate pyrolysis products and other food-borne chemicals. | 2005 Feb 7 |
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Browning of model orange juice solution: factors affecting the formation of decomposition products. | 2005 Nov |
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Role of cultivation media in the development of yeast strains for large scale industrial use. | 2005 Nov 10 |
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[Studies on the changes of 5-hydroxymethyl furfuraldehyde content in Radix Rehmanniae steamed for different time]. | 2005 Sep |
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Ammonium hydroxide detoxification of spruce acid hydrolysates. | 2005 Spring |
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5-(Hydroxymethyl)-2-furfural: a selective inhibitor of DNA polymerase lambda and terminal deoxynucleotidyltransferase. | 2006 Feb 1 |
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Superheated steam pyrolysis of biomass elemental components and Sugi (Japanese cedar) for fuels and chemicals. | 2006 Jul |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Sickle Cell Disease: Subjects randomized 3:1 to receive 4 times daily dosing of 1,000 mg of Aes-103 or placebo for 28 days https://clinicaltrials.gov/ct2/show/NCT01987908
Double-blind, placebo-controlled, ascending single dose study evaluated the safety, pharmacokinetics and pharmacodynamics of Aes-103 given as an oral solution at 300 mg, 1000 mg, 2000 mg and 4000 mg to healthy normal subjects. In each dosing cohort, 6 subjects received 5-HMF and 2 received placebo. A total of 20 adult subjects of African descent with normal hemoglobin (Hb), received a single dose of study drug or placebo on up to 2 occasions separated by 2–4 weeks.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25015917
The dose-dependence of 5HMF for increased oxygen affinity and reduction of sickling indicate an IC50 of about 1 mM. Significant levels of inhibition of Psickle, the Gardos channel and PS exposure were apparent at 5HMF concentrations of 1 mM, 0.1 mM and 2 mM, respectively. In these deoxygenated RBCs, stimulation of KCC was significant by 5 mM.
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222406
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METABOLITE (PARENT)
SUBSTANCE RECORD