Physicochemical Properties
| Molecular Formula | C17H24O11 |
| Molecular Weight | 404.3659 |
| Exact Mass | 404.131 |
| CAS # | 50816-24-5 |
| PubChem CID | 92043450 |
| Appearance | White to off-white solid powder |
| Density | 1.6±0.1 g/cm3 |
| Boiling Point | 653.5±55.0 °C at 760 mmHg |
| Flash Point | 234.8±25.0 °C |
| Vapour Pressure | 0.0±4.5 mmHg at 25°C |
| Index of Refraction | 1.613 |
| LogP | -2.38 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 28 |
| Complexity | 664 |
| Defined Atom Stereocenter Count | 9 |
| SMILES | C[C@H]1CC(=O)[C@]2([C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O |
| InChi Key | PRZVXHGUJJPSME-CZMSZWGTSA-N |
| InChi Code | InChI=1S/C17H24O11/c1-6-3-9(19)17(24)7(14(23)25-2)5-26-15(10(6)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h5-6,8,10-13,15-16,18,20-22,24H,3-4H2,1-2H3/t6-,8+,10-,11+,12-,13+,15-,16-,17+/m0/s1 |
| Chemical Name | methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,6,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate |
| Synonyms | Hastatoside |
| 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 Vivo | Hastatoside (0.32-0.64 mmol/kg; oral; 9-hour duration; male rats of the Sprague-Dawley strain) treatment increased the total duration of non-rapid eye movement sleep over 9 hours, with a lag time of approximately 3-5 hours post-dose , 20:00 (lights out time). Hastatoside also increases delta activity during non-rapid eye movement sleep [1]. |
| Animal Protocol |
Animal/Disease Models: Male SD (SD (Sprague-Dawley)) strain rat (8 weeks old; 260-280 g) [1] Doses: 0.32 mmol/kg, 0.48 mmol/kg, 0.64 mmol/kg Route of Administration: oral; . 9-hour Experimental Results: Total time in non-rapid eye movement sleep increased over 9 hrs (hrs (hours)), with a lag time of approximately 3-5 hrs (hrs (hours)) after dosing at 20:00 (lights-out time). Delta activity during non-rapid eye movement sleep was also increased. |
| References |
[1]. Hastatoside and verbenalin are sleep-promoting. |
| Additional Infomation |
Hastatoside is an iridoid monoterpenoid with formula C17H24O11 that is isolated from several plants including Verbena officinalis and exhibits a sleep-promoting effect. It has a role as a plant metabolite and a hepatoprotective agent. It is a beta-D-glucoside, an iridoid monoterpenoid, a cyclopentapyran, a monosaccharide derivative, a monoterpene glycoside, an alpha,beta-unsaturated carboxylic ester and a methyl ester. Hastatoside has been reported in Penstemon secundiflorus, Penstemon nitidus, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~247.30 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.18 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 (6.18 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 (6.18 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 | 2.4730 mL | 12.3649 mL | 24.7298 mL | |
| 5 mM | 0.4946 mL | 2.4730 mL | 4.9460 mL | |
| 10 mM | 0.2473 mL | 1.2365 mL | 2.4730 mL |