Page last updated: 2024-12-05

dihydroferulic acid

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

Description

Dihydroferulic acid (DHFA) is a phenolic compound found in various plants, including rice, barley, and wheat. It is a derivative of ferulic acid, with the double bond in the side chain reduced. DHFA has been shown to possess antioxidant and anti-inflammatory activities, potentially contributing to the health benefits associated with whole grains. Research on DHFA focuses on its potential to protect against oxidative stress, inflammation, and chronic diseases such as cancer and cardiovascular disease. Synthesis of DHFA can be achieved through chemical reduction of ferulic acid or by enzymatic reduction using ferulic acid reductase enzymes. DHFA's biological activity is attributed to its ability to scavenge free radicals and modulate signaling pathways involved in inflammation.'

dihydroferulic acid: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

dihydroferulic acid : A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 3 has been replaced by a 4-hydroxy-3-methoxyphenyl group.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 CID14340
CHEMBL ID387842
CHEBI ID86612
SCHEMBL ID347918
MeSH IDM0511061

Synonyms (51)

Synonym
dihydroconiferylic acid
.beta.-(4-hydroxy-3-methoxyphenyl)propionic acid
3-(4-hydroxy-3-methoxyphenyl)propionic acid ,
1135-23-5
hydroferulic
benzenepropanoic acid, 4-hydroxy-3-methoxy
3-(4-hydroxy-3-methoxy-phenyl)propanoic acid
hydroferulic acid
3-(4-hydroxy-3-methoxyphenyl)propionic acid, >=96.0% (t)
H1180
AKOS000166726
CHEMBL387842
dihydroferulic acid
3-(4-hydroxy-3-methoxyphenyl)propanoic acid
BMSE010023
STK662207
einecs 214-489-5
benzenepropanoic acid, 4-hydroxy-3-methoxy-
unii-o01rnc700m
o01rnc700m ,
FT-0613672
3-methoxy-4-hydroxyphenylpropionic acid
3-methoxyphloretic acid
.beta.-3-methoxy-4-hydroxyphenylpropionic acid
(4-hydroxy-3-methoxyphenyl)propionic acid
3-(3-methoxy-4-hydroxyphenyl)propanoic acid
hydrocinnamic acid, 4-hydroxy-3-methoxy-
S5135
F1905-6428
SCHEMBL347918
3-(4-hydroxy-3-methoxy-phenyl)-propionic acid
3-(4-hydroxy-3-methoxy-phenyl)propionic acid
3-(4-hydroxy-3-methoxyphenyl)-propionic acid
3-(4-hydroxymethyl)propionic acid
CHEBI:86612
3-(4-hydroxy-3-methoxyphenyl)propanoic acid #
DTXSID90150427
J-002977
mfcd00016558
CS-0030749
HY-N7080
DS-6102
Q10395564
A50645
AMY3788
CCG-266549
4-hydroxy-3-methoxy-benzenepropanoic acid
dihydro ferulic acid
EN300-111281
SY048397
Z317038020

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Several studies have shown the effect on animal models of artichoke extracts, while information on human bioavailability and metabolism of hydroxycinnamates derivatives is still lacking."( Absorption and metabolism of bioactive molecules after oral consumption of cooked edible heads of Cynara scolymus L. (cultivar Violetto di Provenza) in human subjects: a pilot study.
Azzini, E; Bugianesi, R; Catasta, G; Di Venere, D; Durazzo, A; Foddai, MS; Linsalata, V; Maiani, G; Miccadei, S; Romano, F, 2007
)
0.34
" Peak plasma concentration and urinary excretion values showed trends towards a reduced bioavailability of chlorogenic acids associated with the highest dose ingested, when expressed as percentages of intake."( Impact of dose on the bioavailability of coffee chlorogenic acids in humans.
Crozier, A; Stalmach, A; Williamson, G, 2014
)
0.4
" Although the bioavailability of AVAs has been investigated previously, little is known about their metabolism."( Oat avenanthramide-C (2c) is biotransformed by mice and the human microbiota into bioactive metabolites.
Chen, H; Fu, J; McBride, J; Sang, S; Wang, P; Zhu, Y, 2015
)
0.42
"This work aimed at investigating absorption, metabolism, and bioavailability of phenolic compounds after consumption of wholegrain bread or bread enriched with an aleurone fraction."( Bioavailability and metabolism of phenolic compounds from wholegrain wheat and aleurone-rich wheat bread.
Bresciani, L; Brighenti, F; Dall'Aglio, E; Dall'Asta, M; Del Rio, D; Leonardi, R; Melegari, C; Newell, M; Ray, S; Scazzina, F, 2016
)
0.43
" The bioavailability of ferulic acid was significantly higher from the aleurone-enriched bread when all ferulic acid metabolites were accounted for."( Bioavailability and metabolism of phenolic compounds from wholegrain wheat and aleurone-rich wheat bread.
Bresciani, L; Brighenti, F; Dall'Aglio, E; Dall'Asta, M; Del Rio, D; Leonardi, R; Melegari, C; Newell, M; Ray, S; Scazzina, F, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
human xenobiotic metaboliteAny human metabolite produced by metabolism of a xenobiotic compound in humans.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
antioxidantA substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
[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 (3)

ClassDescription
monocarboxylic acidAn oxoacid containing a single carboxy group.
phenylpropanoidAny organic aromatic compound with a structure based on a phenylpropane skeleton. The class includes naturally occurring phenylpropanoid esters, flavonoids, anthocyanins, coumarins and many small phenolic molecules as well as their semi-synthetic and synthetic analogues. Phenylpropanoids are also precursors of lignin.
guaiacolsAny phenol carrying an additional methoxy substituent at the ortho-position.
[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 (1)

PathwayProteinsCompounds
Flavan-3-ol metabolic pathway070

Bioassays (5)

Assay IDTitleYearJournalArticle
AID287020Growth inhibition of wild type Saccharomyces cerevisiae BY47411 at 5 mM after 48 hrs relative to control2007Journal of natural products, May, Volume: 70, Issue:5
Fungicidal activities of dihydroferulic acid alkyl ester analogues.
AID1591909Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitirc oxide production preincubated for 1 hr followed by LPS-stimulation and measured after 18 hrs by Griess assay2019Bioorganic & medicinal chemistry letters, 08-15, Volume: 29, Issue:16
Bioactive triterpene glycosides from the fruit of Stauntonia hexaphylla and insights into the molecular mechanism of its inflammatory effects.
AID499283Antioxidant activity assessed as inhibition of AAPH-induced lipid peroxidation in liposomes measured as Trolox equivalent antioxidant capacity2010Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16
Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties.
AID287019Antifungal activity against wild type Saccharomyces cerevisiae BY47411 after 24 hrs2007Journal of natural products, May, Volume: 70, Issue:5
Fungicidal activities of dihydroferulic acid alkyl ester analogues.
AID499282Redox potential at pH 7.3 by differential pulse and cyclic voltametry2010Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16
Lipophilic phenolic antioxidants: correlation between antioxidant profile, partition coefficients and redox properties.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (25.00)29.6817
2010's10 (62.50)24.3611
2020's2 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.10

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

MetricThis Compound (vs All)
Research Demand Index31.10 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index32.40 (26.88)
Search Engine Supply Index1.83 (0.95)

This Compound (31.10)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (6.25%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (93.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]