Physicochemical Properties
| Molecular Formula | C₉H₁₀O₄ |
| Molecular Weight | 182.17 |
| Exact Mass | 182.057 |
| CAS # | 134-96-3 |
| PubChem CID | 8655 |
| Appearance | Light brown to brown solid powder |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 322.1±37.0 °C at 760 mmHg |
| Melting Point | 110-113 °C(lit.) |
| Flash Point | 130.1±20.0 °C |
| Vapour Pressure | 0.0±0.7 mmHg at 25°C |
| Index of Refraction | 1.568 |
| LogP | 0.86 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 13 |
| Complexity | 157 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | KCDXJAYRVLXPFO-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3 |
| Chemical Name | 4-hydroxy-3,5-dimethoxybenzaldehyde |
| Synonyms | VND3207 Syringaldehyde NSC-41153NSC41153NSC 41153 NSC-41153 SM707SM 707 SM-707VND-3207VND 3207 |
| 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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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 | Syringaldehyde has an IC50 of 3.5 μg/mL and inhibits COX-2 activity in a dose-dependent manner[2] |
| ln Vivo | In a rat model of diabetes caused by streptozotocin, syringaldehyde exhibits antihyperglycemic properties. Syringaldehyde has been shown to have anti-inflammatory properties in addition to its antioxidant capacity. This is because it has been shown to inhibit cyclooxygenase-2 (COX-2) in mouse macrophage cell lines [1]. |
| References |
[1]. Protective effect of syringaldehyde on biomolecular oxidation, inflammation and histopathological alterations in isoproterenol induced cardiotoxicity in rats. Biomed Pharmacother. 2018 Dec;108:625-633. [2]. Cyclooxygenase-2 inhibitory and antioxidant compounds from the truffle Elaphomyces granulatus. Phytother Res. 2009 Apr;23(4):575-8. |
| Additional Infomation |
Syringaldehyde is a hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity. It has a role as a hypoglycemic agent and a plant metabolite. It is a hydroxybenzaldehyde and a dimethoxybenzene. Syringaldehyde has been reported in Rhinacanthus nasutus, Magnolia officinalis, and other organisms with data available. Syringaldehyde is a metabolite found in or produced by Saccharomyces cerevisiae. |
Solubility Data
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~548.94 mM) H2O : < 0.1 mg/mL |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.72 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 (13.72 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 (13.72 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 | 5.4894 mL | 27.4469 mL | 54.8938 mL | |
| 5 mM | 1.0979 mL | 5.4894 mL | 10.9788 mL | |
| 10 mM | 0.5489 mL | 2.7447 mL | 5.4894 mL |