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Isovanillic acid

Isovanillic acid (3-Hydroxy-4-methoxybenzoic acid) is a phenolic acid compound extracted from Scrophularia ningpoensis and has anti~inflammatory activity.
Isovanillic acid
Isovanillic acid Chemical Structure CAS No.: 645-08-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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100mg
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Product Description
Isovanillic acid (3-Hydroxy-4-methoxybenzoic acid) is a phenolic acid compound extracted from Scrophularia ningpoensis and has anti~inflammatory activity.
Isovanillic acid (CAS 645-08-9) is a phenolic acid and a metabolite of isovanillin, with a molecular formula of C₈H₈O₄ and a molecular weight of 168.15 g/mol. It is an isomer of vanillic acid, differing in the position of the methoxy group on the aromatic ring. Isovanillic acid is a natural compound found in various plants and is used as a research reagent in studies of phenolic acid metabolism, antioxidant activity, and as a reference standard in analytical chemistry.
Biological Activity I Assay Protocols (From Reference)
Targets
Isovanillic acid targets oxidative stress pathways and exhibits antioxidant activity through its phenolic hydroxyl group, which can scavenge free radicals. As a phenolic acid, it may also modulate inflammatory signaling pathways and interact with enzymes involved in phenolic acid metabolism.
ln Vitro
Isovanillic acid exhibits antioxidant activity through its ability to scavenge free radicals and reduce oxidative stress. It may also have anti-inflammatory properties. The compound is used as a research tool for studying the biological activities of phenolic acids and their potential health benefits.
ln Vivo
Isovanillic acid is a metabolite of isovanillin that is excreted in urine. It is formed through the metabolism of dietary phenolic compounds and may contribute to the antioxidant and anti-inflammatory effects of phenolic acid-rich foods. The compound's levels in biological fluids reflect dietary intake and metabolism of phenolic compounds.
Enzyme Assay
In vitro non-cell assays for Isovanillic acid typically involve antioxidant activity measurements using DPPH, ABTS, or FRAP assays. The compound is incubated with the radical-generating system, and the decrease in absorbance is measured spectrophotometrically to calculate the scavenging activity and IC₅₀ values.
Cell Assay
In vitro cell-based assays for Isovanillic acid use cell lines to study its effects on oxidative stress and inflammation. Cells are treated with the compound and exposed to oxidative insults or inflammatory stimuli. Parameters such as reactive oxygen species levels, antioxidant enzyme activities, and inflammatory cytokine production are measured.
Animal Protocol
In vivo animal studies for Isovanillic acid may involve oral administration of the compound to rodents to study its absorption, metabolism, and biological effects. Parameters assessed include plasma and tissue levels of the compound and its metabolites, oxidative stress markers, and inflammatory markers.
ADME/Pharmacokinetics
Isovanillic acid has a molecular weight of 168.15 g/mol and a molecular formula of C₈H₈O₄. It is soluble in water and organic solvents. The compound is a natural phenolic acid found in various plants. Detailed pharmacokinetic parameters have not been extensively characterized.
Toxicity/Toxicokinetics
Isovanillic acid is generally considered to have low toxicity as a natural phenolic compound. Standard laboratory safety precautions should be followed when handling the compound. The compound is classified as a research reagent and is not intended for human therapeutic use.
References

[1]. Anti-inflammatory activity in rats and mice of phenolic acids isolated from Scrophularia frutescens. J Pharm Pharmacol. 1998 Oct;50(10):1183-6.

Additional Infomation
3-Hydroxy-4-methoxybenzoic acid is a methoxybenzoic acid derivative formed by introducing a hydroxyl substituent at the 3-position of 4-methoxybenzoic acid. It possesses antibacterial activity and is also a plant metabolite. It is both a methoxybenzoic acid and a monohydroxybenzoic acid. It is the conjugate acid of 3-hydroxy-4-methoxybenzoic acid ester. 3-Hydroxy-4-methoxybenzoic acid has been reported to exist in Hypericum erectum, Euphorbia polycaulis, and other organisms with relevant data.
Isovanillic acid is a phenolic acid and a metabolite of isovanillin. It is an isomer of vanillic acid and is used as a research reagent in studies of phenolic acid metabolism and antioxidant activity. Not approved for therapeutic use; intended for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H8O4
Molecular Weight
168.1467
Exact Mass
168.042
CAS #
645-08-9
PubChem CID
12575
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
344.3±27.0 °C at 760 mmHg
Melting Point
250-253 °C(lit.)
Flash Point
145.2±17.2 °C
Vapour Pressure
0.0±0.8 mmHg at 25°C
Index of Refraction
1.586
LogP
1.35
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
2
Heavy Atom Count
12
Complexity
168
Defined Atom Stereocenter Count
0
InChi Key
LBKFGYZQBSGRHY-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H8O4/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4,9H,1H3,(H,10,11)
Chemical Name
3-hydroxy-4-methoxybenzoic 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

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
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)
DMSO : ~100 mg/mL (~594.71 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.9471 mL 29.7354 mL 59.4707 mL
5 mM 1.1894 mL 5.9471 mL 11.8941 mL
10 mM 0.5947 mL 2.9735 mL 5.9471 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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