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
| Molecular Formula | C6H6O3 |
| Molecular Weight | 126.11 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Studies on chemical constituents from the root of Polygonatum kingianum]. | 2003 Jun |
|
| [Study on the fingerprints of Achyranthes bidentata Bl. by HPLC/UV/MS]. | 2003 Nov |
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| Amelioration of diabetic nephropathy by dried Rehmanniae Radix (Di Huang) extract. | 2004 |
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| Phenolic and furan type compounds isolated from Gastrodia elata and their anti-platelet effects. | 2004 Apr |
|
| Antibacterial activity of bee honey and its therapeutic usefulness against Escherichia coli O157:H7 and Salmonella typhimurium infection. | 2004 Dec |
|
| Isolation of sterols from the marine fungus Corollospora lacera. | 2004 Dec |
|
| Decomposition kinetics of maltose in subcritical water. | 2004 Jan |
|
| Effect of inhibitors released during steam-explosion treatment of poplar wood on subsequent enzymatic hydrolysis and SSF. | 2004 Jan-Feb |
|
| Optimal experimental condition for hemicellulosic hydrolyzate treatment with activated charcoal for xylitol production. | 2004 Jan-Feb |
|
| From time temperature integrator kinetics to time temperature integrator tolerance levels: heat-treated milk. | 2004 Jan-Feb |
|
| A sphingolipid and tyrosinase inhibitors from the fruiting body of Phellinus linteus. | 2004 Jul |
|
| Hydrothermal upgrading of biomass to biofuel; studies on some monosaccharide model compounds. | 2004 Jul 12 |
|
| PD fluids contain high concentrations of cytotoxic GDPs directly after sterilization. | 2004 Jul-Aug |
|
| Temperature: the single most important factor for degradation of glucose fluids during storage. | 2004 Jul-Aug |
|
| Hydrolysis of lactose in whey permeate for subsequent fermentation to ethanol. | 2004 Jun |
|
| 1H NMR studies on Italian balsamic and traditional balsamic vinegars. | 2004 Jun 2 |
|
| Browning and decomposed products of model orange juice. | 2004 Mar |
|
| 3-Hydroxy-4,5-dimethyl-2(5H)-furanone levels in fortified Madeira wines: relationship to sugar content. | 2004 Nov 3 |
|
| In vitro anti-tyrosinase activity of 5-(hydroxymethyl)-2-furfural isolated from Dictyophora indusiata. | 2004 Oct |
|
| A benzenoid from the stem of Acanthopanax senticosus. | 2004 Sep |
|
| Adaptive response of yeasts to furfural and 5-hydroxymethylfurfural and new chemical evidence for HMF conversion to 2,5-bis-hydroxymethylfuran. | 2004 Sep |
|
| Selection of anion exchangers for detoxification of dilute-acid hydrolysates from spruce. | 2004 Spring |
|
| Optimization of Brewery's spent grain dilute-acid hydrolysis for the production of pentose-rich culture media. | 2004 Spring |
|
| Quality evaluation of honey harvested from selected areas in Tanzania with special emphasis on hydroxymethyl furfural (HMF) levels. | 2004 Summer |
|
| Amla (Emblica officinalis Gaertn.) extracts reduce oxidative stress in streptozotocin-induced diabetic rats. | 2005 Fall |
|
| Effects of glucose, fructose and 5-hydroxymethyl-2-furaldehyde on the presystemic metabolism and absorption of glycyrrhizin in rabbits. | 2005 Feb |
|
| 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 |
|
| Single laboratory validation of a method for the determination of hydroxymethylfurfural in honey by using solid-phase extraction cleanup and liquid chromatography. | 2005 Jan-Feb |
|
| Controlling hydrothermal reaction pathways to improve acetic acid production from carbohydrate biomass. | 2005 Mar 15 |
|
| Honey in combination with vacuum impregnation to prevent enzymatic browning of fresh-cut apples. | 2005 May |
|
| Classifying honeys from the Soria Province of Spain via multivariate analysis. | 2005 May |
|
| Formation and reactivity of free radicals in 5-hydroxymethyl-2-furaldehyde--the effect on isoprenaline photostability. | 2005 May 13 |
|
| Analysis of potential and free furfural compounds in milk-based formulae by high-performance liquid chromatography. Evolution during storage. | 2005 May 27 |
|
| Browning of model orange juice solution: factors affecting the formation of decomposition products. | 2005 Nov |
|
| Troglitazone inhibits long-term glycation and oxidation of low-density lipoprotein. | 2005 Nov |
|
| Role of cultivation media in the development of yeast strains for large scale industrial use. | 2005 Nov 10 |
|
| Application of hydrophilic interaction liquid chromatography/comparative taste dilution analysis for identification of a bitter inhibitor by a combinatorial approach based on Maillard reaction chemistry. | 2005 Nov 16 |
|
| Investigation on the origin of 5-HMF in Shengmaiyin decoction by RP-HPLC method. | 2005 Oct |
|
| [Studies on the changes of 5-hydroxymethyl furfuraldehyde content in Radix Rehmanniae steamed for different time]. | 2005 Sep |
|
| Cytotoxic activities of ethyl acetate extract and a metabolite from a Monocillium species. | 2005 Sep |
|
| Fed-batch cultivation of Mucor indicus in dilute-acid lignocellulosic hydrolyzate for ethanol production. | 2005 Sep |
|
| Effect of storage period under variable conditions on the chemical and physical composition and colour of Spanish refrigerated orange juices. | 2005 Sep |
|
| Glucose reactions with acid and base catalysts in hot compressed water at 473 K. | 2005 Sep 5 |
|
| Acidic sugar degradation pathways: an ab initio molecular dynamics study. | 2005 Spring |
|
| Ammonium hydroxide detoxification of spruce acid hydrolysates. | 2005 Spring |
|
| Enhanced biotransformation of furfural and hydroxymethylfurfural by newly developed ethanologenic yeast strains. | 2005 Spring |
|
| Bioabatement to remove inhibitors from biomass-derived sugar hydrolysates. | 2005 Spring |
|
| 5-(Hydroxymethyl)-2-furfural: a selective inhibitor of DNA polymerase lambda and terminal deoxynucleotidyltransferase. | 2006 Feb 1 |
|
| Tolerance to furfural-induced stress is associated with pentose phosphate pathway genes ZWF1, GND1, RPE1, and TKL1 in Saccharomyces cerevisiae. | 2006 Jul |
|
| 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
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:05:17 GMT 2023
by
admin
on
Fri Dec 15 19:05:17 GMT 2023
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| Record UNII |
70ETD81LF0
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| Record Status |
Validated (UNII)
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| Record Version |
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FDA ORPHAN DRUG |
222406
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412516
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C008046
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100000178271
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DB12298
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HYDROXYMETHYLFURFURAL
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m6141
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SUB193908
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| Related Record | Type | Details | ||
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METABOLITE -> PARENT |
IN-VIVO
URINE
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| Related Record | Type | Details | ||
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PARENT -> IMPURITY |
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