| Size | Price | Stock | Qty |
|---|---|---|---|
| 500mg |
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| Other Sizes |
| Targets |
Human Endogenous Metabolite
Guaiazulene exhibits a wide range of bioactivities across various biological assays. It is an inhibitor of lamin A splicing, ROR gamma transcriptional activity, JMJD2A Tudor domain, histone lysine methyltransferase G9a, and the malarial parasite plastid. It also targets the human endogenous metabolite system and has antioxidant effects. The compound may also interact with inflammatory and oxidative stress pathways, contributing to its anti-inflammatory and antioxidant properties. |
|---|---|
| ln Vitro |
In vitro, guaiazulene has cytotoxic activity against neurons and N2a neuroblastoma (N2a-NB) cells. Studies have shown that guaiazulene induces cytotoxicity in rat neuronal cells and N2a neuroblastoma cells at high concentrations, with the cytotoxic activity related to the pro-oxidation state of the compound. It also exhibits antioxidant effects by scavenging free radicals. Additionally, guaiazulene inhibits lamin A splicing and ROR gamma transcriptional activity, which may contribute to its anti-inflammatory properties.
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| ln Vivo |
In vivo, guaiazulene has been studied for its anti-inflammatory and antioxidant effects in animal models. It reduces inflammation and oxidative stress when administered topically or systemically. The compound is also used as a cosmetic ingredient for its soothing and anti-irritant properties. However, detailed in vivo pharmacological data for this compound as a drug are limited, as it is primarily studied as a natural product and cosmetic ingredient rather than an approved therapeutic agent.
|
| Enzyme Assay |
For non-cellular assays (enzyme inhibition), guaiazulene is tested for its ability to inhibit specific enzymes. For example, for RORgamma transcriptional activity, a luciferase reporter assay is used: HEK293 cells are co-transfected with a GAL4-RORgamma ligand-binding domain (LBD) fusion protein and a GAL4-responsive luciferase reporter. Guaiazulene (0.1-50 uM) is added to the cells for 24 hours, and luciferase activity is measured. For lamin A splicing, mini-gene splicing assays are performed in HeLa cells treated with guaiazulene (1-20 uM) for 24-48 hours, and splicing products are analyzed by RT-PCR.
|
| Cell Assay |
For cell-based assays, rat neuronal cells (primary cortical neurons from embryonic rats) or N2a neuroblastoma cells are cultured in DMEM with 10% FBS. Cells are seeded in 96-well plates (1×10⁴ cells/well) and allowed to adhere. Guaiazulene is dissolved in DMSO (final DMSO concentration ≤0.1%) and added at concentrations of 0-200 uM for 24-72 hours. Cell viability is assessed using MTT assay (0.5 mg/mL, 4h) or Alamar Blue. ROS production is measured using DCFH-DA (10 uM, 30 min). Apoptosis is evaluated by Hoechst 33342 staining or Annexin V/PI flow cytometry.
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| Animal Protocol |
For in vivo animal experiments, guaiazulene is typically administered topically or orally in rodent models of inflammation. For anti-inflammatory studies, female ICR mice (6-8 weeks old) are treated with guaiazulene (10-100 mg/kg, oral or intraperitoneal) 1 hour prior to induction of inflammation. Acute inflammation is induced by subcutaneous injection of 1% carrageenan into the hind paw. Paw volume is measured using a plethysmometer at 1, 2, 3, 4, and 6 hours after induction. Alternatively, for topical application, guaiazulene (0.1-1%) is applied to the ear 30 minutes before application of 12-O-tetradecanoylphorbol-13-acetate (TPA, 2 ug/ear). Ear thickness is measured with a micrometer at 6-24 hours.
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| ADME/Pharmacokinetics |
Guaiazulene is a lipophilic compound with a molecular weight of 198.3 g/mol and a logP of approximately 6.2 (highly lipophilic). It is insoluble in water but soluble in organic solvents (ethanol, DMSO, oils). The compound is characterized by its distinctive blue color due to the azulene chromophore.
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| Toxicity/Toxicokinetics |
Guaiazulene is generally considered safe for topical use at low concentrations as a cosmetic ingredient. For research use, standard precautions should be taken. No significant acute toxicity has been reported in animal studies at moderate doses. However, high concentrations may cause cytotoxicity as observed in vitro. Standard laboratory safety precautions for handling organic compounds should be followed.
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| References |
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| Additional Infomation |
Guaiazulene is a sesquiterpene. It is derived from the hydride of guaiacolane. Guaiazulene has been reported to exist in Artemisia, Magnolia officinalis, and other organisms with relevant data.
Guaiazulene is not an approved drug but is widely used as a cosmetic ingredient (colorant, anti-irritant) in skincare and personal care products. It has been studied for its potential as an anti-inflammatory agent and as an antioxidant. No clinical trials for therapeutic use have been registered for guaiazulene. It is also used as a reference compound in natural product research and analytical chemistry. Its mechanism involves antioxidant and anti-inflammatory activities, but it is not developed as a pharmaceutical drug. |
| Molecular Formula |
C15H18
|
|---|---|
| Molecular Weight |
198.30
|
| Exact Mass |
198.14
|
| CAS # |
489-84-9
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| PubChem CID |
3515
|
| Appearance |
Solid-Liquid Mixture
|
| Density |
0.976
|
| Boiling Point |
305.4±22.0 °C at 760 mmHg
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| Melting Point |
31.5 °C
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| Flash Point |
142.3±13.1 °C
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| Vapour Pressure |
0.0±0.3 mmHg at 25°C
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| Index of Refraction |
1.573
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| LogP |
5.71
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
0
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
15
|
| Complexity |
206
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C([H])(C([H])([H])[H])(C([H])([H])[H])C1C([H])=C([H])C(C([H])([H])[H])=C2C([H])=C([H])C(C([H])([H])[H])=C2C=1[H]
|
| InChi Key |
FWKQNCXZGNBPFD-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3
|
| Chemical Name |
1,4-dimethyl-7-propan-2-ylazulene
|
| 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 |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO: 50 mg/mL (252.14 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 6.25 mg/mL (31.52 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 62.5 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: ≥ 6.25 mg/mL (31.52 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 62.5 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.0429 mL | 25.2143 mL | 50.4286 mL | |
| 5 mM | 1.0086 mL | 5.0429 mL | 10.0857 mL | |
| 10 mM | 0.5043 mL | 2.5214 mL | 5.0429 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.
Link: https://clinicaltrials.gov/ct2/show/NCT04553003
Conditions:Drug-induced Liver InjuryProducts are for research use only; We do not sell to patients
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