Page last updated: 2024-12-06

dihydrochalcone

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

Description

Dihydrochalcones are a class of flavonoid compounds that are structurally similar to chalcones, but with a saturated ketone group. They are found naturally in various plants, including licorice, apple, and berries. Dihydrochalcones have been studied for their potential health benefits, including antioxidant, anti-inflammatory, and anti-cancer properties. They are also used as sweeteners and flavoring agents in food and beverages. The synthesis of dihydrochalcones typically involves the reduction of the double bond in the chalcone molecule. This can be achieved using various reducing agents, such as sodium borohydride or lithium aluminum hydride. Dihydrochalcones are of interest to researchers due to their diverse biological activities and potential applications in various fields, including medicine, agriculture, and food science.'

dihydrochalcone : A member of the class of dihydrochalcones that is acetophenone in which one of the hydrogens of the methyl group is replaced by a benzyl group. [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]

Cross-References

ID SourceID
PubMed CID64802
CHEMBL ID490512
CHEBI ID71231
SCHEMBL ID30572
MeSH IDM0065347

Synonyms (64)

Synonym
h5w525sx7q ,
nsc 12245
beta-phenylpropiophenone
omega-benzyl acetophenone
1-propanone, 1,3-diphenyl-
unii-h5w525sx7q
ai3-22096
BB 0221108
EU-0066881
hydrocinnamophenone
.beta.-phenylpropiophenone
nsc12245
3-phenylpropiophenone
dihydrochalcone
phenyl phenethyl ketone
1,3-diphenyl-1-propanone
2-phenethyl phenyl ketone
.omega.-benzyl acetophenone
1,3-diphenyl-3-propanone
nsc-12245
benzylacetophenone
hydrochalcone
propiophenone, 3-phenyl-
1,3-diphenyl-1-oxopropane
1-propanone,3-diphenyl-
1083-30-3
phenethyl phenyl ketone
benzyl acetophenone
1,3-diphenylpropan-1-one
CHEMDIV2_000107
LMPK12120464
HMS1369E19
CHEMBL490512 ,
chebi:71231 ,
A801855
AKOS001586597
1,3-diphenyl-propan-1-one
1-benzoyl-2-phenylethane
FT-0622933
1,3 diphenylpropan-1-one
SCHEMBL30572
DTXSID7061481
3-phenyl propiophenone
1-propanone,1,3-diphenyl-
mfcd00039563
?-phenylpropiophenone
SR-01000390066-1
sr-01000390066
GS-3688
bdbm50479153
1, 3-diphenyl-3-propanone
w-benzylacetophenone
3-phenyl-propiophenone
laquo omegaraquo -benzyl acetophenone
SY045967
benzylacetophenon
Q2357209
AMY24269
AC9766
beta-phenyl propiophenone
CS-0063340
EN300-102554
D5479
Z385416922

Research Excerpts

Overview

Dihydrochalcones are a class of secondary metabolites, possessing several biological properties such as antitumor, antioxidant, antibacterial, antidiabetic, estrogenic, anti-inflammatory, antithrombotic, antiviral, neuroprotective. They are currently considered promising candidates in the drug discovery process.

ExcerptReferenceRelevance
"Dihydrochalcones are a class of secondary metabolites, possessing several biological properties such as antitumor, antioxidant, antibacterial, antidiabetic, estrogenic, anti-inflammatory, antithrombotic, antiviral, neuroprotective, and immunomodulatory properties; therefore, they are currently considered promising candidates in the drug discovery process. "( Dihydrochalcones as Antitumor Agents.
De Luca, F; Di Chio, C; Ettari, R; Zappalà, M, 2022
)
3.61
"Dihydrochalcones are a class of secondary metabolites, for which demand in biological and pharmacological applications is still growing. "( Dihydrochalcones: Methods of Acquisition and Pharmacological Properties-A First Systematic Review.
Bajek-Bil, A; Broda, D; Stompor, M, 2019
)
3.4
"Dihydrochalcones are a subclass of flavonoids. "( Rapid Structure-Based Annotation and Profiling of Dihydrochalcones in Star Fruit (
Chambers, A; Crane, J; Li, J; Wang, Y; Wang, Z, 2021
)
2.32
"Dihydrochalcones are a family of bicyclic flavonoids, defined by the presence of two benzene rings joined by a saturated three carbon bridge. "( Dihydrochalcones: evaluation as novel radical scavenging antioxidants.
Kohno, H; Miyake, N; Nakamura, Y; Osawa, T; Watanabe, S, 2003
)
3.2

Bioavailability

The bioactive hydrophilic dihydrochalcone, aspalathin, has poor stability and bioavailability hampering its use in functional food ingredients. Low content of diHydrochalcones in plants along with their low solubility andBioavailability restrict the development of these compounds as clinical therapeutics.

ExcerptReferenceRelevance
" To investigate the metabolism and bioavailability of these compounds, nine healthy and five ileostomy human subjects consumed 500 mL of Thatchers Redstreak apple cider containing 46 micromol of phloretin-O-glycosides."( Absorption, metabolism, and excretion of cider dihydrochalcones in healthy humans and subjects with an ileostomy.
Borges, G; Crozier, A; Marks, SC; Mullen, W, 2009
)
0.61
"The bioactive hydrophilic dihydrochalcone, aspalathin, has poor stability and bioavailability hampering its use in functional food ingredients with standardised aspalathin content."( Electrospraying as a suitable method for nanoencapsulation of the hydrophilic bioactive dihydrochalcone, aspalathin.
Aucamp, M; De Beer, D; Human, C; Joubert, E; Van Der Rijst, M, 2019
)
1.04
" However, low content of dihydrochalcones in plants along with their low solubility and bioavailability restrict the development of these compounds as clinical therapeutics."( Dihydrochalcones: Methods of Acquisition and Pharmacological Properties-A First Systematic Review.
Bajek-Bil, A; Broda, D; Stompor, M, 2019
)
2.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role 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]

Drug Classes (1)

ClassDescription
dihydrochalconesAny ketone that is 1,3-diphenylpropanone and its derivatives obtained by substitution.
[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]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1896716Cytotoxicity against human HT-29 cells assessed as reduction in cell viability incubated for 48 hrs by AlamarBlue-based assay2022Bioorganic & medicinal chemistry, Oct-30, Volume: 75Bis-aryl-α,β-unsaturated ketone (ABK) chaperonin inhibitors exhibit selective cytotoxicity to colorectal cancer cells that correlates with levels of aberrant HSP60 in the cytosol.
AID1896718Cytotoxicity against human FHs74Int cells assessed as reduction in cell viability incubated for 48 hrs by AlamarBlue-based assay2022Bioorganic & medicinal chemistry, Oct-30, Volume: 75Bis-aryl-α,β-unsaturated ketone (ABK) chaperonin inhibitors exhibit selective cytotoxicity to colorectal cancer cells that correlates with levels of aberrant HSP60 in the cytosol.
AID1896712Inhibition of refolded rhodanese reporter enzyme (unknown origin)2022Bioorganic & medicinal chemistry, Oct-30, Volume: 75Bis-aryl-α,β-unsaturated ketone (ABK) chaperonin inhibitors exhibit selective cytotoxicity to colorectal cancer cells that correlates with levels of aberrant HSP60 in the cytosol.
AID1896711Inhibition of human mitochondrial HSP60 expressed in Escherichia coli Rosetta 2 (DE3) cells/human mitochondrial HSP10 expressed in Escherichia coli Rosetta 2 (DE3) pLysS cells assessed as inhibition of GroEL/ES-mediated dMDH refolding by reporter analysis2022Bioorganic & medicinal chemistry, Oct-30, Volume: 75Bis-aryl-α,β-unsaturated ketone (ABK) chaperonin inhibitors exhibit selective cytotoxicity to colorectal cancer cells that correlates with levels of aberrant HSP60 in the cytosol.
AID362091Antagonist activity at HA-tagged mouse AT1a angiotensin 2 receptor expressed in HEK293T cells assessed as decrease in angiotensin 2-induced intracellular calcium uptake2008Bioorganic & medicinal chemistry, Aug-15, Volume: 16, Issue:16
Inhibitory effects of benzyl benzoate and its derivatives on angiotensin II-induced hypertension.
AID1896715Cytotoxicity against human DLD-1 cells assessed as reduction in cell viability incubated for 48 hrs by AlamarBlue-based assay2022Bioorganic & medicinal chemistry, Oct-30, Volume: 75Bis-aryl-α,β-unsaturated ketone (ABK) chaperonin inhibitors exhibit selective cytotoxicity to colorectal cancer cells that correlates with levels of aberrant HSP60 in the cytosol.
AID1896719Cytotoxicity against human FHC cells assessed as reduction in cell viability incubated for 48 hrs by AlamarBlue-based assay2022Bioorganic & medicinal chemistry, Oct-30, Volume: 75Bis-aryl-α,β-unsaturated ketone (ABK) chaperonin inhibitors exhibit selective cytotoxicity to colorectal cancer cells that correlates with levels of aberrant HSP60 in the cytosol.
AID1896710Inhibition of Escherichia coli GroEL expressed in NEB-5-alpha Escherichia coli cells/Escherichia coli GroES expressed in Escherichia coli BL21(DE3) cells assessed as inhibition of GroEL/ES-mediated dRho refolding by reporter analysis2022Bioorganic & medicinal chemistry, Oct-30, Volume: 75Bis-aryl-α,β-unsaturated ketone (ABK) chaperonin inhibitors exhibit selective cytotoxicity to colorectal cancer cells that correlates with levels of aberrant HSP60 in the cytosol.
AID1896709Inhibition of Escherichia coli GroEL expressed in NEB-5-alpha Escherichia coli cells/Escherichia coli GroES expressed in Escherichia coli BL21(DE3) cells assessed as inhibition of GroEL/ES-mediated dMDH refolding by reporter analysis2022Bioorganic & medicinal chemistry, Oct-30, Volume: 75Bis-aryl-α,β-unsaturated ketone (ABK) chaperonin inhibitors exhibit selective cytotoxicity to colorectal cancer cells that correlates with levels of aberrant HSP60 in the cytosol.
AID1896713Inhibition of refolded MDH reporter enzyme (unknown origin)2022Bioorganic & medicinal chemistry, Oct-30, Volume: 75Bis-aryl-α,β-unsaturated ketone (ABK) chaperonin inhibitors exhibit selective cytotoxicity to colorectal cancer cells that correlates with levels of aberrant HSP60 in the cytosol.
AID1896717Cytotoxicity against p53-/- human HCT-116 cells assessed as reduction in cell viability incubated for 48 hrs by AlamarBlue-based assay2022Bioorganic & medicinal chemistry, Oct-30, Volume: 75Bis-aryl-α,β-unsaturated ketone (ABK) chaperonin inhibitors exhibit selective cytotoxicity to colorectal cancer cells that correlates with levels of aberrant HSP60 in the cytosol.
AID1896714Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability incubated for 48 hrs by AlamarBlue-based assay2022Bioorganic & medicinal chemistry, Oct-30, Volume: 75Bis-aryl-α,β-unsaturated ketone (ABK) chaperonin inhibitors exhibit selective cytotoxicity to colorectal cancer cells that correlates with levels of aberrant HSP60 in the cytosol.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (151)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (5.96)18.7374
1990's7 (4.64)18.2507
2000's34 (22.52)29.6817
2010's66 (43.71)24.3611
2020's35 (23.18)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 43.07

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index43.07 (24.57)
Research Supply Index5.04 (2.92)
Research Growth Index5.14 (4.65)
Search Engine Demand Index62.47 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (43.07)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews10 (6.49%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other144 (93.51%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]