Page last updated: 2024-12-07

1,5-anhydrofructose

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

## 1,5-Anhydrofructose: A Sweet Molecule with Research Potential

1,5-anhydrofructose is a modified form of the simple sugar fructose, where the hydroxyl group on carbon 1 is linked to the hydroxyl group on carbon 5, forming a cyclic ether. This modification results in a molecule with unique properties compared to fructose.

**Why is it important for research?**

1,5-anhydrofructose holds potential in several research areas due to its:

**1. Biological Activity:**

* **Antioxidant properties:** Studies suggest that 1,5-anhydrofructose exhibits antioxidant activity, potentially protecting cells from oxidative damage.
* **Potential therapeutic benefits:** It has been shown to possess anti-inflammatory and anti-diabetic properties, making it a promising candidate for further investigation as a potential drug or therapeutic agent.
* **Metabolic effects:** 1,5-anhydrofructose has been shown to influence insulin signaling and glucose metabolism, suggesting its potential role in regulating metabolic pathways.

**2. Chemical Properties:**

* **Stability:** The cyclic ether formation increases 1,5-anhydrofructose's stability compared to fructose, making it suitable for use in various applications.
* **Reactivity:** 1,5-anhydrofructose can be used as a starting material for synthesizing various valuable compounds, including pharmaceuticals and biomaterials.

**3. Research Applications:**

* **Drug development:** 1,5-anhydrofructose is being explored as a potential scaffold for drug development, particularly in the areas of diabetes and inflammation.
* **Biomaterials:** The unique chemical structure of 1,5-anhydrofructose makes it a promising candidate for designing and developing new biomaterials for tissue engineering and drug delivery.
* **Food science:** 1,5-anhydrofructose's properties have potential applications in food processing and preservation, as a sweetener, or as a flavor enhancer.

**Current Research:**

Ongoing research focuses on:

* **Understanding the mechanism of action** of 1,5-anhydrofructose in its biological activity.
* **Developing efficient and cost-effective methods** for its synthesis and purification.
* **Exploring new applications** for 1,5-anhydrofructose in various fields, including medicine, food science, and materials science.

**Overall, 1,5-anhydrofructose is a versatile molecule with significant potential for research and applications in diverse fields. Its unique properties and promising biological activities warrant further investigation to fully exploit its potential.**

1,5-anhydrofructose: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID126517
CHEMBL ID1234723
CHEBI ID16715
SCHEMBL ID246685
MeSH IDM0140531

Synonyms (22)

Synonym
1,5-anhydrofructose
CHEMBL1234723 ,
1,5-anhydro-d-threo-hex-2-ulose
CHEBI:16715 ,
75414-43-6
C06485 ,
1,5-anhydro-d-fructose
(4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-one
(4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)dihydro-2h-pyran-3(4h)-one
1,5-anhydro-d-arabino-hex-2-ulose
(4s,5s)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-one
NHF ,
AC1Q6ETX ,
d-fructose, 1:5-anhydro-
SCHEMBL246685
OCLOLUFOLJIQDC-HSUXUTPPSA-N
(4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-one
surecn246685
DTXSID10996864
1,5-anhydrohex-2-ulose
Q27102040
bdbm50276379

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Effective dosage levels would be 500-4000 mg kg(-1), depending on food type."( Ascopyrone P, a novel antibacterial derived from fungi.
Delves-Broughton, J; Elsser, D; Ingram, RE; Refdahl, C; Thomas, LV; Yu, S, 2002
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (6)

ClassDescription
anhydrohexoseAny anhydro sugar formally arising by elimination of water from two hydroxy groups of a single molecule of a hexose or hexose derivative.
organic heterocyclic compoundA cyclic compound having as ring members atoms of carbon and at least of one other element.
cyclic ketone
3-pyronesA pyranone based on the structure of 2H-pyran-3(4H)-one or 2H-pyran-3(6H)-one, and their substituted derivatives.
cyclic etherAny ether in which the oxygen atom forms part of a ring.
triolA chemical compound containing three hydroxy groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
1,5-anhydrofructose degradation111
glycogen degradation III (via anhydrofructose)27

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
NACHT, LRR and PYD domains-containing protein 3 Mus musculus (house mouse)IC50 (µMol)29,000.00000.00041.441910.0000AID1498932
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
cytosolNACHT, LRR and PYD domains-containing protein 3 Mus musculus (house mouse)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID1498932Inhibition of nigericin-induced NLRP3 inflammasome activation in C57BL/6 mouse bone marrow derived macrophages assessed as reduction in LPS-stimulated IL-1beta secretion incubated for 1 hr followed by nigericin addition measured after 1 hr by ELISA2018Bioorganic & medicinal chemistry, 07-30, Volume: 26, Issue:13
Synthesis of 1,5-Anhydro-d-fructose derivatives and evaluation of their inflammasome inhibitors.
AID1498937Inhibition of nigericin-induced NLRP3 inflammasome activation in PMA-differentiated human THP1 cells assessed as reduction in LPS-stimulated IL-1beta secretion at 60 mM incubated for 1 hr prior to stimulation with nigericin for 1 hr by ELISA2018Bioorganic & medicinal chemistry, 07-30, Volume: 26, Issue:13
Synthesis of 1,5-Anhydro-d-fructose derivatives and evaluation of their inflammasome inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (40)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (2.50)18.7374
1990's8 (20.00)18.2507
2000's19 (47.50)29.6817
2010's8 (20.00)24.3611
2020's4 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.77

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.77 (24.57)
Research Supply Index3.74 (2.92)
Research Growth Index5.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.77)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews5 (12.20%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other36 (87.80%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]