Epigoitrin ( (R)-Goitrin; BA-51-090278) is a naturally occurring alkaloid isolated from Isatis indigotica with antiviral, anticancer, and antithyroid activities. Epigoitrin reduces susceptibility to influenza virus via mitochondrial antiviral signaling.
Physicochemical Properties
| Molecular Formula | C5H7NOS |
| Molecular Weight | 129.17 |
| Exact Mass | 129.024 |
| Elemental Analysis | C, 46.49; H, 5.46; N, 10.84; O, 12.39; S, 24.82 |
| CAS # | 1072-93-1 |
| Related CAS # | Goitrin;500-12-9 |
| PubChem CID | 3032313 |
| Appearance | White to yellow solid powder |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 150.6±43.0 °C at 760 mmHg |
| Melting Point | 50ºC |
| Flash Point | 44.9±28.2 °C |
| Vapour Pressure | 3.8±0.3 mmHg at 25°C |
| Index of Refraction | 1.570 |
| LogP | 0.38 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 1 |
| Heavy Atom Count | 8 |
| Complexity | 124 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | S=C1N([H])C([H])([H])[C@@]([H])(C([H])=C([H])[H])O1 |
| InChi Key | UZQVYLOFLQICCT-SCSAIBSYSA-N |
| InChi Code | InChI=1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)/t4-/m1/s1 |
| Chemical Name | 2-Oxazolidinethione, 5-vinyl-, (R)- |
| Synonyms | Epigoitrin; (R)-Goitrin; (R) Goitrin; BA-51-090278; BA 51-090278; BA 51 090278; BA 51090278; BA51090278 |
| 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
| References |
[1]. Epigoitrin, an Alkaloid From Isatis indigotica, Reduces H1N1 Infection in Stress-Induced Susceptible Model in vivo and in vitro. Front Pharmacol. 2019 Feb 7;10:78. [2]. Antiviral activities against influenza virus (FM1) of bioactive fractions and representative compounds extracted from Banlangen (Radix Isatidis). J Tradit Chin Med. 2016 Jun;36(3):369-76. |
| Additional Infomation |
(R)-goitrin is a 5-ethenyl-1,3-oxazolidine-2-thione that has R-configuration. It is a constituent of a traditional Chinese herbal medicine, Radix isatidis. It has a role as an antiviral agent and a plant metabolite. It is an enantiomer of a (S)-goitrin. Epigoitrin has been reported in Brassica oleracea, Diplotaxis harra, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~387.06 mM) Ethanol : ~3.33 mg/mL (~25.78 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (19.35 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 (19.35 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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 (19.35 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.. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (19.35 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.7417 mL | 38.7087 mL | 77.4174 mL | |
| 5 mM | 1.5483 mL | 7.7417 mL | 15.4835 mL | |
| 10 mM | 0.7742 mL | 3.8709 mL | 7.7417 mL |