| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
(-)-Dihydroguaiaretic acid targets the lipoxygenase family of enzymes. It inhibits the oxidation of unsaturated fatty acids, a key step in the inflammatory cascade. Additionally, it has strong free radical scavenging abilities, providing an antioxidant effect. This dual mechanism contributes to its anti-inflammatory and anticancer activities reported in the literature. Its anticancer activity has been characterized against various cancer cell lines.
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| ln Vitro |
In vitro, (-)-Dihydroguaiaretic acid functions as a lipoxygenase inhibitor and a free radical scavenger, inhibiting the oxidation of unsaturated fatty acids. It has demonstrated significant anti-cancer activity, with an IC50 value of 7.49 microM against A549 human lung adenocarcinoma cells. This cytotoxic effect forms the basis for its use in cancer research. By blocking lipid peroxidation and subsequent cell death pathways, it helps elucidate the role of oxidative stress in disease.
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| ln Vivo |
In vivo activity data for (-)-Dihydroguaiaretic acid is not extensively detailed in the provided sources. As a natural product with anti-inflammatory and antioxidant properties, it is hypothesized to be effective in animal models of inflammation. Its effects could be studied by administering the compound to animals and measuring reductions in pro-inflammatory cytokines or markers of oxidative stress. Published studies are needed to confirm its specific in vivo efficacy.
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| Enzyme Assay |
The enzyme inhibitory activity of (-)-Dihydroguaiaretic acid can be assessed using a standard cell-free lipoxygenase assay. Soybean 15-lipoxygenase is incubated with a reaction buffer and increasing concentrations of DHGA (e.g., 1-100 uM). The reaction is initiated by adding the substrate linoleic acid. The formation of the conjugated diene hydroperoxide product is measured spectrophotometrically by the increase in absorbance at 234 nm over a 2-5 minute period. The IC50 is calculated from the inhibition curves.
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| Cell Assay |
For cytotoxicity assays, A549 human lung adenocarcinoma cells are seeded in 96-well plates. The cells are treated with (-)-Dihydroguaiaretic acid at various concentrations (e.g., 0-50 uM) for 48 hours. Cell viability is then measured using a standard MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. The IC50 is determined by plotting cell viability against the log of the compound concentration. Cytotoxicity can also be assessed in non-cancerous cell lines to evaluate selectivity.
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| Animal Protocol |
For in vivo studies, (-)-Dihydroguaiaretic acid can be evaluated in a xenograft mouse model of human cancer. Mice are subcutaneously implanted with A549 cells. When tumors reach a certain volume, mice are randomized and treated intraperitoneally or orally with various doses of DHGA (e.g., 20-100 mg/kg) daily or every other day. Tumor volume is measured with calipers twice weekly, and body weight is monitored as a general indicator of toxicity. At the study endpoint, tumors are excised, weighed, and analyzed for markers of apoptosis and proliferation.
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| ADME/Pharmacokinetics |
Detailed pharmacokinetic data for (-)-Dihydroguaiaretic acid is limited. The compound has a molecular weight of 330.42 g/mol and a predicted LogP of 4.33, indicating high lipophilicity, which may affect its oral bioavailability and distribution. For in vivo use, it is typically formulated in DMSO and diluted in PEG300, saline, or corn oil. Researchers should conduct pilot PK studies to determine half-life, Cmax, and bioavailability in their specific animal model.
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| Toxicity/Toxicokinetics |
Published toxicology data for (-)-Dihydroguaiaretic acid is not detailed in the provided sources. In vitro, it shows cytotoxic effects on cancer cells at micromolar concentrations (IC50 of 7.49 uM). For any animal study, preliminary dose-finding experiments would be essential to establish a non-toxic dose range before starting an efficacy study. Standard laboratory safety precautions for handling natural products should be followed.
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| References |
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| Additional Infomation |
According to reports, the Chinese scarab beetle, wild clover, and other organisms with available data contain (-)-dihydroguaiac acid.
(-)-Dihydroguaiaretic acid is a research-grade natural product, not an approved drug. It is used as a reference standard for the quality control of botanical extracts (e.g., from Larrea tridentata). It also serves as a tool in mechanistic studies of lipoxygenase activity and in anti-cancer drug discovery as a lead compound. The compound should be stored at -20degC as a powder, protected from light and moisture. For research use only. |
| Molecular Formula |
C20H26O4
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|---|---|
| Molecular Weight |
330.42
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| Exact Mass |
330.183
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| CAS # |
124649-78-1
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| PubChem CID |
11602375
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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-ZIAGYGMSSA-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-/m1/s1
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| Chemical Name |
4-[(2R,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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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 : PEG300 ：Tween 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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| 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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