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| 5mg |
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| Targets |
Dihydroguaiaretic acid targets multiple pathways. Its neuroprotective effect is mediated through its antioxidative activity. It inhibits the COX-2-dependent phase of PGD₂ generation, contributing to its anti-inflammatory activity. It also exhibits antibacterial activity against Gram-negative bacteria.
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| ln Vitro |
Human ovarian cancer cells and A2780 human endometrial cancer cell Ishikawa are both inhibited by dihydroguaiaretic acid, with IC50 values of 27.17 μM and 45.46 μM, respectively [1].
In vitro, Dihydroguaiaretic acid significantly protects primary cultured neuronal cells against glutamate-induced oxidative stress via its antioxidative activity. It inhibits the COX-2-dependent phase of prostaglandin D₂ (PGD₂) generation. It also exhibits antibacterial activity. |
| ln Vivo |
In vivo, the neuroprotective and anti-inflammatory properties of Dihydroguaiaretic acid suggest potential therapeutic applications. Its ability to protect against glutamate-induced neurotoxicity is particularly relevant for studying neurodegenerative diseases. However, specific in vivo data are limited.
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| Enzyme Assay |
In vitro non-cell enzyme assays for Dihydroguaiaretic acid typically involve measuring its antioxidant activity using DPPH, ABTS, or FRAP assays. Its inhibition of COX-2 can be measured using an enzyme activity assay with arachidonic acid as a substrate and measuring prostaglandin production.
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| Cell Assay |
In vitro cell-based assays for Dihydroguaiaretic acid use primary neuronal cell cultures exposed to glutamate. Cells are treated with the compound, and cell viability is assessed using MTT or similar assays. Oxidative stress markers (e.g., ROS, MDA) are measured. Its anti-inflammatory activity is assessed in LPS-stimulated macrophages by measuring cytokine production.
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| Animal Protocol |
In vivo animal studies for Dihydroguaiaretic acid would likely employ models of neurodegenerative diseases (e.g., excitotoxicity models) or inflammation. The compound would be administered to the animals, and neuroprotection would be assessed by measuring neuronal survival and behavioral outcomes.
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| ADME/Pharmacokinetics |
Dihydroguaiaretic acid has a molecular weight of 330.42 g/mol and a molecular formula of C₂₀H₂₆O₄. It is a lignan compound with a purity of ≥98%. It is soluble in organic solvents. Detailed pharmacokinetic parameters have not been extensively characterized.
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| Toxicity/Toxicokinetics |
The toxicity profile of Dihydroguaiaretic acid has not been fully characterized. As a natural compound, it is generally considered to have low toxicity. However, its potent biological activities suggest it should be used with caution.
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| References | |
| Additional Infomation |
Mesodihydroguaiac acid is a lignan formed by replacing 2,3-dimethylbutane at the 1 and 4 positions with 2-methoxyphenol, respectively. It has been isolated from the bark of Gentiana robusta. It is a plant metabolite belonging to the guaiacol class of lignans. Mesodihydroguaiac acid has also been reported in Gentiana sinensis, Gentiana wangi, and other organisms with relevant data. See also: whole plant (partial) of Laria tridentata; dihydroguaiac acid (note moved to).
Dihydroguaiaretic acid is a natural lignan with significant antioxidative, anti-inflammatory, neuroprotective, and antibacterial activities. It is also known as meso-dihydroguaiaretic acid. It is a valuable research tool for studying oxidative stress, neurodegeneration, and inflammation. Not approved for clinical use. |
| Molecular Formula |
C20H26O4
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|---|---|
| Molecular Weight |
330.4180
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| Exact Mass |
330.183
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| CAS # |
66322-34-7
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| PubChem CID |
476856
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
488.3±40.0 °C at 760 mmHg
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| Flash Point |
249.1±27.3 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.564
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| LogP |
4.33
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
24
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| Complexity |
328
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| Defined Atom Stereocenter Count |
2
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| SMILES |
C[C@H](CC1=CC(=C(C=C1)O)OC)[C@@H](C)CC2=CC(=C(C=C2)O)OC
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| InChi Key |
ADFOLUXMYYCTRR-OKILXGFUSA-N
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| InChi Code |
InChI=1S/C20H26O4/c1-13(9-15-5-7-17(21)19(11-15)23-3)14(2)10-16-6-8-18(22)20(12-16)24-4/h5-8,11-14,21-22H,9-10H2,1-4H3/t13-,14+
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| Chemical Name |
4-[(2S,3R)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl]-2-methoxyphenol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~151.32 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.57 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 (7.57 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.57 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0265 mL | 15.1323 mL | 30.2645 mL | |
| 5 mM | 0.6053 mL | 3.0265 mL | 6.0529 mL | |
| 10 mM | 0.3026 mL | 1.5132 mL | 3.0265 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.
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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