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Dihydroferulic acid

Cat No.:V33792 Purity: ≥98%
Dihydroferulic acid (Hydroferulic acid) is one of the major metabolites of curcumin and has antioxidant/free radical scavenging activity with IC50 of 19.5 μM.
Dihydroferulic acid
Dihydroferulic acid Chemical Structure CAS No.: 1135-23-5
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Dihydroferulic acid (Hydroferulic acid) is one of the major metabolites of curcumin and has antioxidant/free radical scavenging activity with IC50 of 19.5 μM. Dihydroferulic acid is a metabolite of human intestinal flora and the precursor of vanillic acid.
Dihydroferulic acid (CAS: 1135-23-5), also known as hydroferulic acid or 3-(4-hydroxy-3-methoxyphenyl)propionic acid, is one of the main metabolites of curcumin and a metabolite of human gut microflora. It is a hydrogenated phenylpropanoic acid derivative that possesses antioxidant and free radical-scavenging properties. The compound serves as a precursor of vanillic acid and is found naturally in various plants.
Biological Activity I Assay Protocols (From Reference)
Targets
Dihydroferulic acid primarily targets reactive oxygen species (ROS) and free radicals in biological systems. It acts as an antioxidant by scavenging free radicals and singlet oxygen. The compound may also interact with cellular antioxidant defense pathways. As a metabolite of curcumin and gut microflora, it contributes to the overall antioxidant effects observed following consumption of curcumin-containing foods. It has an antioxidant IC₅₀ value of 19.5 μM.
ln Vitro
Consumption of 293H cells that were overexpressed in OAT1, OAT2, OAT3, and OAT4 in response to supplemental cinnamic acid. There was a notable consumption of dihydroferulic acid in 293H control cells. Dihydroferulic acid consumption in OAT1-expressing cells. Moreover, food is improved by almost two times[3].
In vitro, dihydroferulic acid demonstrates potent antioxidant and radical-scavenging properties with an IC₅₀ value of 19.5 μM. It is one of the main metabolites of curcumin and shows significant free radical scavenging activity. The compound protects cells from oxidative damage by neutralizing reactive oxygen species. It also serves as a precursor of vanillic acid in metabolic pathways. Its antioxidant activity has been demonstrated in various cell-free and cell-based assays.
ln Vivo
In 20 Zucker diabetic proportions, to assess the impact of an 11-week intervention on the polyphenol serum profile of a whole wheat diet rich in resistant starch (HI-RS-WG, 25% RS) in comparison to a WG control diet (LOW-RS-WG, 6.9% RS) (PPs). In blood samples that belonged to the two carbonic acid groups' specific gravities, five PPs were found and quantified. Total PP serum concentration ratio of HI-RS-WG specific gravity LOW-RS: Two primary components were found using an exploratory data reduction technique based on principal component analysis. These components are linked to fermentation and food absorption, respectively, as well as disruption of degradation. According to the findings, the HI-RS-WG scaffolds' greater fermentation of the harmful bacterial flora than the LOW-RS-WG scaffolds could account for the quantity of hippuric acid and dihydroferulic acid within them [4].
In vivo, dihydroferulic acid is produced as a metabolite of curcumin by human gut microflora. It contributes to the systemic antioxidant effects observed following curcumin consumption. The compound is further metabolized to vanillic acid and other metabolites. Its presence in the circulation reflects the metabolic activity of gut bacteria on dietary polyphenols. The compound may contribute to the health benefits associated with curcumin intake.
Enzyme Assay
For non-cell enzyme/receptor binding assays, dihydroferulic acid antioxidant activity is assessed using cell-free radical-scavenging assays. The compound is incubated with DPPH (2,2-diphenyl-1-picrylhydrazyl) or ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)) radicals, and the decrease in absorbance is measured spectrophotometrically. The IC₅₀ value for radical scavenging is determined from dose-response curves. Oxygen radical absorbance capacity (ORAC) assays can also be employed to quantify antioxidant capacity.
Cell Assay
For in vitro cell-based assays, dihydroferulic acid is tested in cell culture models of oxidative stress. Cells are treated with the compound prior to or simultaneously with oxidative stress inducers such as hydrogen peroxide or UV radiation. Cellular antioxidant capacity is measured by assessing cell viability, ROS levels (using fluorescent probes), and markers of oxidative damage such as lipid peroxidation and protein oxidation. The compound's protective effects are compared to known antioxidants.
Animal Protocol
For in vivo animal experiments, dihydroferulic acid can be administered orally or intravenously to animals to study its metabolism and antioxidant effects. Blood and tissue samples are collected at various time points to measure the compound and its metabolites. The effects on oxidative stress markers in various tissues are assessed. The compound can also be administered as a metabolite of curcumin to study its contribution to curcumin's overall biological effects.
ADME/Pharmacokinetics
Metabolism / Metabolites
The known metabolites of dihydroferulic acid include 3-[3-methoxy-4-(sulfonoxy)phenyl]propionic acid.
Dihydroferulic acid has a molecular weight of 196.20 g/mol and molecular formula C₁₀H₁₂O₄. It appears as a white to light yellow powder or crystal with purity of ≥98% (GC). The compound is soluble in organic solvents and has a melting point consistent with its phenolic acid structure. It should be stored at room temperature in a cool, dry place. The compound is stable under recommended storage conditions.
Toxicity/Toxicokinetics
Dihydroferulic acid is considered a safe natural compound. As a metabolite of curcumin and a component of the human diet, it is generally recognized as safe (GRAS). No significant toxicity has been reported at physiological concentrations. The compound is naturally present in foods and is produced by gut microflora. High doses may cause mild gastrointestinal effects, but no serious toxicity has been documented. It is for research use only in laboratory settings.
References

[1]. Different curcuminoids inhibit T-lymphocyte proliferation independently of their radical scavenging activities. Pharm Res. 2008 Aug;25(8):1822-7.

[2]. Fungicidal activities of dihydroferulic acid alkyl ester analogues. J Nat Prod. 2007 May;70(5):779-82.

[3]. Interaction of hydroxycinnamic acids and their conjugates with organic anion transporters and ATP-binding cassette transporters. Mol Nutr Food Res. 2011 Jul;55(7):979-88.

[4]. Gut fermentation induced by a resistant starch rich whole grain diet explains serum concentration of dihydroferulic acid and hippuric acid in a model of ZDF rats. Journal of Functional Foods. 53 (2019): 286-291.

Additional Infomation
Dihydroferulic acid is a monocarboxylic acid with the structure propionic acid, where a hydrogen atom at the 3-position is replaced by a 4-hydroxy-3-methoxyphenyl group. It can be used as a human xenobiotic metabolite, a plant metabolite, a mouse metabolite, and an antioxidant. It is a monocarboxylic acid, a phenylpropanoid compound belonging to the guaiacol class. Its function is related to propionic acid. It is the conjugate acid of dihydroferulic acid. 3-(4-hydroxy-3-methoxyphenyl)propionic acid has been reported to exist in Stellaria dichotoma, Melicope semecarpifolia, and other organisms with relevant data.
Dihydroferulic acid is a naturally occurring phenylpropanoic acid derivative found in various plants. It is one of the main metabolites of curcumin, the active component of turmeric, and is produced by human gut microflora. The compound serves as a precursor for vanillic acid and contributes to the antioxidant properties associated with curcumin consumption. It has been studied for its potential health benefits, including antioxidant, anti-inflammatory, and neuroprotective effects. No clinical trials have been conducted for this compound as a therapeutic agent.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H12O4
Molecular Weight
196.19988
Exact Mass
196.073
CAS #
1135-23-5
PubChem CID
14340
Appearance
White to off-white solid powder
Density
1.3±0.1 g/cm3
Boiling Point
376.5±27.0 °C at 760 mmHg
Melting Point
87-93 °C
Flash Point
151.1±17.2 °C
Vapour Pressure
0.0±0.9 mmHg at 25°C
Index of Refraction
1.562
LogP
0.81
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Heavy Atom Count
14
Complexity
193
Defined Atom Stereocenter Count
0
InChi Key
BOLQJTPHPSDZHR-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)
Chemical Name
3-(4-hydroxy-3-methoxyphenyl)propanoic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~100 mg/mL (~509.68 mM)
DMSO : ~100 mg/mL (~509.68 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.74 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (12.74 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (12.74 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 10 mg/mL (50.97 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.0968 mL 25.4842 mL 50.9684 mL
5 mM 1.0194 mL 5.0968 mL 10.1937 mL
10 mM 0.5097 mL 2.5484 mL 5.0968 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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