 Chemical Structure.png)
Sesamolin (AI320978) is a naturally occurring substance with antioxidant activity that was isolated from Justicia orbiculata. Human lymphocytic leukemia cells' ability to proliferate in culture is inhibited by sesaminol, which also inhibits lipid peroxidation and exhibits neuroprotective properties. By preventing the phosphorylation of JNK, p38 MAPKs, and caspase-3 but not ERK-MAPK expression, sesaminol effectively inhibits MAPK cascades.
Physicochemical Properties
| Molecular Formula | C20H18O7 |
| Molecular Weight | 370.3527 |
| Exact Mass | 370.105 |
| Elemental Analysis | C, 64.86; H, 4.90; O, 30.24 |
| CAS # | 526-07-8 |
| Related CAS # | 526-07-8 |
| PubChem CID | 101746 |
| Appearance | White to off-white solid powder |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 520.8±50.0 °C at 760 mmHg |
| Melting Point | 93 - 94ºC (Decomposes) |
| Flash Point | 219.2±30.0 °C |
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
| Index of Refraction | 1.622 |
| LogP | 2.88 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 27 |
| Complexity | 544 |
| Defined Atom Stereocenter Count | 4 |
| SMILES | O1C([H])([H])[C@]2([H])[C@@]([H])(OC3C([H])=C([H])C4=C(C=3[H])OC([H])([H])O4)OC([H])([H])[C@]2([H])[C@@]1([H])C1C([H])=C([H])C2=C(C=1[H])OC([H])([H])O2 |
| InChi Key | ZZMNWJVJUKMZJY-AFHBHXEDSA-N |
| InChi Code | InChI=1S/C20H18O7/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)27-12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1 |
| Chemical Name | 5-[[(3S,3aR,6R,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]oxy]-1,3-benzodioxole |
| Synonyms | Sesamolin; AI3 20978; AI320978; AI3-20978 |
| HS Tariff Code | 2934.99.03.00 |
| 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
| References |
[1]. Sesamin, sesamolin and the origin of sesame. Biochemical Systematics and Ecology. Volume 13, Issue 2, 23 May 1985, Pages 133-139. [2]. Sesamolin Inhibits Lipid Peroxidation in Rat Liver and Kidney. The Journal of Nutrition, Volume 128, Issue 6, June 1998, Pages 1018–1022. [3]. Protective effects of sesamin and sesamolin on hypoxic neuronal and PC12 cells. [4]. Comparative analysis of sesame lignans (sesamin and sesamolin) in affecting hepatic fatty acid metabolism in rats. Br J Nutr. 2007 Jan;97(1):85-95. |
| Additional Infomation |
Sesamolin is a member of benzodioxoles. Sesamolin has been reported in Iberodes linifolia, Coleus scutellarioides, and other organisms with data available. See also: Sesame Oil (part of). |
Solubility Data
| Solubility (In Vitro) | DMSO: ~100 mg/mL (~270.0 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (6.75 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. 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 (6.75 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 (6.75 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 | 2.7001 mL | 13.5007 mL | 27.0015 mL | |
| 5 mM | 0.5400 mL | 2.7001 mL | 5.4003 mL | |
| 10 mM | 0.2700 mL | 1.3501 mL | 2.7001 mL |