Physicochemical Properties
| Molecular Formula | C15H22O2 |
| Molecular Weight | 234.33 |
| Exact Mass | 234.161 |
| CAS # | 6754-20-7 |
| Related CAS # | 6754-20-7 |
| PubChem CID | 72503 |
| Appearance | White to off-white solid powder |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 330.7±35.0 °C at 760 mmHg |
| Flash Point | 124.0±22.9 °C |
| Vapour Pressure | 0.0±0.7 mmHg at 25°C |
| Index of Refraction | 1.570 |
| LogP | 3.84 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 17 |
| Complexity | 367 |
| Defined Atom Stereocenter Count | 3 |
| SMILES | C[C@]12CCCC([C@@H]1CC=C([C@@H]2C=O)C=O)(C)C |
| InChi Key | AZJUJOFIHHNCSV-KCQAQPDRSA-N |
| InChi Code | InChI=1S/C15H22O2/c1-14(2)7-4-8-15(3)12(10-17)11(9-16)5-6-13(14)15/h5,9-10,12-13H,4,6-8H2,1-3H3/t12-,13-,15+/m0/s1 |
| Chemical Name | (1R,4aS,8aS)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde |
| 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: 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) |
Biological Activity
| ln Vitro | In standardized susceptibility testing (NCCLS), Polygodial demonstrates fungicidal effectiveness against Saccharomyces cerevisiae, Candida albicans, and other fungal infections. When Saccharomyces cerevisiae cells are treated with polygodial (12.5 μg/mL for 3 hours), they significantly shrink in comparison to controls when the minimum fungicidal concentration (MFC) is set for 106 CFU/mL in RPMI 1640 medium[3]. |
| ln Vivo | Polygodial is a sesquiterpene that was extracted from Drymis winteri's (Winteraceae) bark. Mice given Polygodial (0.5 to 10 mg/kg; 0.5 h; intraperitoneal method) significantly, dose-dependently, and nearly completely inhibits the constrictions in their abdomens caused by Acetic acid, Kaolin, and Zymosan. The estimated maximal inhibitions against acetic acid, kaolin, and zymosan are 90.0±3.0, 98.0±1.0, and 97.0±2.0 %, respectively, with mean ID50 values of 0.8, 2.1, and 2.6 mg/kg. At the ID50 level, polygodial has a potency that is roughly 14–27 times greater than hydroalcoholic extract (HE)[2]. |
| Cell Assay |
Cell Viability Assay[3] Cell Types: S. cerevisiae cells Tested Concentrations: 12.5 μg/mL Incubation Duration: 3 hrs (hours) Experimental Results: Treated cells demonstrated significant shrinkage compared to controls, and the organization of subcellular organelles appeared either disrupted or compacted. |
| Animal Protocol |
Animal/Disease Models: Non-fasted male Swiss mice ( 20-30 g) or male Wistar rats (150-180 g)[2] Doses: 0.1 to 10 mg/kg Route of Administration: Injected ip 0.5 h before the injection of irritant substances Experimental Results: Produced significant inhibition of Acetic acid, Kaolin and Zymosan -induced writhing in mice. |
| References |
[1]. Polygodial, an antifungal potentiator. J Nat Prod. Jan-Feb 1988;51(1):22-9. [2]. Anti-hyperalgesic properties of the extract and of the main sesquiterpene polygodial isolated from the barks of Drymis winteri (Winteraceae). Life Sci. 1998;63(5):369-81. [3]. Effect of polygodial on the mitochondrial ATPase of Saccharomyces cerevisiae. Antimicrob Agents Chemother. 2000 Jul;44(7):1943-53. |
| Additional Infomation |
Polygodial is an aldehyde. Polygodial has been reported in Apopellia endiviifolia, Dendrodoris tuberculosa, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ≥ 100 mg/mL (426.75 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.67 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 (10.67 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (10.67 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 25.0 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 | 4.2675 mL | 21.3374 mL | 42.6749 mL | |
| 5 mM | 0.8535 mL | 4.2675 mL | 8.5350 mL | |
| 10 mM | 0.4267 mL | 2.1337 mL | 4.2675 mL |