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Vanillyl alcohol

Cat No.:V30407 Purity: ≥98%
Vanillyl alcohol (p-(Hydroxymethyl)guaiacol), developed from vanillin, is a phenolic alcohol used as a flavoring in foods and beverages.
Vanillyl alcohol
Vanillyl alcohol Chemical Structure CAS No.: 498-00-0
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
Vanillyl alcohol (p-(Hydroxymethyl)guaiacol), developed from vanillin, is a phenolic alcohol used as a flavoring in foods and beverages.
Vanillyl alcohol (CAS#: 498-00-0), also known as 4-hydroxy-3-methoxybenzyl alcohol, is a natural phenolic compound with anti-inflammatory, anti-angiogenic, anticonvulsive, antioxidant, neuroprotective, and anti-nociceptive activities. It is a component of Gastrodia elata, a traditional Chinese herb widely used to treat convulsive disorders or dizziness. At a concentration of 200 ppm, vanillyl alcohol demonstrated 90% antioxidant activity by the DPPH method, whereas vanillin exhibited much lower antioxidant activity under identical conditions. Its molecular formula is C8H10O3 with a molecular weight of 154.16 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
Vanillyl alcohol targets multiple pathways involved in inflammation, angiogenesis, oxidative stress, and neuronal excitability. It possesses anti-angiogenic, anticonvulsive, anti-inflammatory, antioxidant, neuroprotective, and anti-nociceptive activities. The compound's antioxidant activity involves scavenging DPPH and alkyl radicals. Its anti-inflammatory activity involves modulation of inflammatory mediators. Its anticonvulsive effects involve modulation of neuronal excitability. Vanillyl alcohol is a phenolic compound derived from vanillin.
ln Vitro
In vitro, Vanillyl alcohol demonstrates 90% antioxidant activity by the DPPH method at 200 ppm. It possesses anti-angiogenic, anticonvulsive, anti-inflammatory, antioxidant, neuroprotective, and anti-nociceptive activities. The compound shows considerable radical scavenging activity against DPPH and alkyl radicals. Vanillyl alcohol is used in the anti-asthmatic activity of phenolic compounds from the roots of Gastrodia elata. Its neuroprotective effects have been demonstrated in neuronal cell models.
ln Vivo
In vivo, Vanillyl alcohol is a component of Gastrodia elata, a traditional Chinese herb widely used to treat convulsive disorders or dizziness. It has both anticonvulsive and suppressive effects on seizures. The compound possesses anti-inflammatory, anti-angiogenic, anticonvulsive, antioxidant, neuroprotective, and anti-nociceptive activities. Vanillyl alcohol is used in food and beverages as a flavoring agent. Further in vivo studies have evaluated its neuroprotective and anti-inflammatory effects.
Enzyme Assay
Vanillyl alcohol antioxidant assays involve measuring DPPH, ABTS, or other free radical scavenging activity. At 200 ppm, the compound demonstrates 90% antioxidant activity by the DPPH method. Anti-inflammatory activity is assessed by measuring inhibition of pro-inflammatory cytokine production or COX/LOX activity. Anti-angiogenic activity is assessed using endothelial cell tube formation assays. Anticonvulsive activity is evaluated using neuronal excitability assays. Neuroprotective activity is assessed in neuronal cell models of oxidative stress or excitotoxicity. Assays are performed in appropriate buffer systems with positive controls such as known antioxidants (e.g., vitamin C).
Cell Assay
Vanillyl alcohol cell-based assays are conducted in neuronal cells, endothelial cells, immune cells, and other relevant cell types. Cells are cultured in appropriate media at 37°C with 5% CO2 and treated with Vanillyl alcohol at varying concentrations. Cell viability is assessed by MTT or CCK-8 assays. Antioxidant activity is assessed by measuring intracellular ROS levels. Anti-inflammatory activity is assessed by measuring cytokine levels by ELISA. Anti-angiogenic activity is assessed by measuring endothelial cell tube formation. Neuroprotective effects are assessed in neuronal cells exposed to oxidative stress or excitotoxicity. Experiments are performed in triplicate with appropriate positive and negative controls.
Animal Protocol
Vanillyl alcohol in vivo studies are conducted in animal models of inflammation, seizures, neurodegeneration, and oxidative stress. Animals are treated with Vanillyl alcohol via oral administration or injection. For anticonvulsive studies, seizure induction models such as pentylenetetrazole-induced seizures are used. For anti-inflammatory studies, animal models of inflammation are used. For neuroprotection studies, models of neurodegeneration are employed. For antioxidant studies, models of oxidative stress are used. Dosing regimens are optimized based on pharmacokinetic data. Animals are monitored for clinical signs. Tissues and blood samples are collected for histopathological and biomarker analysis. Studies are conducted in accordance with institutional animal care guidelines.
ADME/Pharmacokinetics
Vanillyl alcohol (MW 154.16 g/mol, C8H10O3) is a small phenolic compound. It is soluble in DMSO and other organic solvents. The compound is stable under recommended storage conditions. Vanillyl alcohol is a natural compound found in Gastrodia elata and other plant sources. It is used as a flavoring agent in food and beverages. Pharmacokinetic parameters such as half-life, bioavailability, and tissue distribution would be determined in species-specific studies. The compound is typically used in natural product and pharmacological research.
Toxicity/Toxicokinetics
Vanillyl alcohol is generally well-tolerated in preclinical studies. The compound is a natural phenolic compound found in traditional Chinese herbs with a long history of use. Its antioxidant, anti-inflammatory, neuroprotective, and anticonvulsive activities have been demonstrated with acceptable safety profiles. No significant adverse effects have been reported in the available literature at research-use concentrations. The compound is intended for research use only. Standard safety precautions should be followed when handling. Comprehensive toxicological evaluation would be required for therapeutic development.
References

[1]. Establishing an Artificial Pathway for De Novo Biosynthesis of Vanillyl Alcohol in Escherichia coli. ACS Synth Biol. 2017 Sep 15;6(9):1784-1792.

Additional Infomation
Vanillyl is a monomethoxybenzene compound, a 2-methoxyphenol with a hydroxymethyl group substituted at the 4-position. It is a plant metabolite belonging to the guaiacol and benzyl alcohol classes. Vanillyl has been used in clinical trials for smoking cessation treatment. It has been reported to be found in poplar trees, chili peppers, and other organisms with relevant data.
Vanillyl alcohol (4-hydroxy-3-methoxybenzyl alcohol) is a natural phenolic compound with anti-inflammatory, anti-angiogenic, anticonvulsive, antioxidant, neuroprotective, and anti-nociceptive activities. It is a component of Gastrodia elata, a traditional Chinese herb used for convulsive disorders. Vanillyl alcohol demonstrates 90% antioxidant activity at 200 ppm by DPPH method. It is used as a flavoring agent in food and beverages. All applications are limited to non-human research use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H10O3
Molecular Weight
154.1632
Exact Mass
154.062
CAS #
498-00-0
PubChem CID
62348
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
313.1±27.0 °C at 760 mmHg
Melting Point
110-117 °C(lit.)
Flash Point
143.2±23.7 °C
Vapour Pressure
0.0±0.7 mmHg at 25°C
Index of Refraction
1.570
LogP
0
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Heavy Atom Count
11
Complexity
116
Defined Atom Stereocenter Count
0
InChi Key
ZENOXNGFMSCLLL-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H10O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,9-10H,5H2,1H3
Chemical Name
4-(hydroxymethyl)-2-methoxyphenol
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)
DMSO : ~100 mg/mL (~648.68 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (13.49 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 20.8 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: ≥ 2.08 mg/mL (13.49 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 20.8 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: ≥ 2.08 mg/mL (13.49 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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.4868 mL 32.4338 mL 64.8677 mL
5 mM 1.2974 mL 6.4868 mL 12.9735 mL
10 mM 0.6487 mL 3.2434 mL 6.4868 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
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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