Goitrin ((S)-Goitrin) is a product of the glucosinolate-myrosinase reaction and is a potent inhibitor of thyroid peroxidase. Goitrin inhibits the use of iodine by the thyroid gland. Goitrin also has anti-influenza virus (H1N1) activity.

Physicochemical Properties

Molecular Formula	C5H7NOS
Molecular Weight	129.18
Exact Mass	129.025
CAS #	500-12-9
Related CAS #	Epigoitrin;1072-93-1
PubChem CID	7568320
Appearance	Large prisms from ether
Melting Point	50 °C
LogP	0.774
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	C=CC1CNC(=S)O1
InChi Key	UZQVYLOFLQICCT-BYPYZUCNSA-N
InChi Code	InChI=1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)/t4-/m0/s1
Chemical Name	(5S)-5-ethenyl-1,3-oxazolidine-2-thione
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
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 Madin-Darby canine kidney (MDCK) cells, goitrin (0.1–1 μM; 72 h) demonstrates dose-dependent anti–influenza virus (H1N1) action, with an IC50 of 0.19 μM[3].
ADME/Pharmacokinetics	Absorption, Distribution and Excretion A total of six cows, divided into 3 groups, were fed various amounts of rape cake containing 6 g of goitrin/kg over a period of 7 days. The cows were milked twice a day ... . When rape cake was fed at 0.39, 1.9 and 3.9% resp. of the total feed this resulted in medium goitrin values of 37, 163 and 707 ug/l milk. These values correspond to a transfer of about 0.1% of the original progoitrin content in the feed. 12 h after the last rape feeding the amount of goitrin in the milk was below the detection limit of 7 ppb.
Toxicity/Toxicokinetics	Interactions Goitrin is a potent goitrogen that has been shown to induce glutathione S-transferase (GST) activity and to increase aflatoxin detoxification. goitrin --a naturally occurring compound in cruciferous vegetables and rape--could be easily nitrosated by treatment with nitrite under stomach conditions, yielding with loss of sulfur the N-nitroso- oxazolidone 4. This product has a mutagenicity pattern and potency similar to that of N-nitroso-N-methyl-N'- nitroguanidine (MNNG) in the Ames Salmonella/mammalian microsome test.
References	[1]. Concentrations of thiocyanate and goitrin in human plasma, their precursor concentrations in brassica vegetables, and associated potential risk for hypothyroidism. Nutr Rev. 2016 Apr;74(4):248-58. [2]. Genetics and bitter taste responses to goitrin, a plant toxin found in vegetables. Chem Senses. 2010 Oct;35(8):685-92. [3]. Antiviral activity of Isatidis Radix derived glucosinolate isomers and their breakdown products against influenza A in vitro/ovo and mechanism of action. J Ethnopharmacol. 2020 Apr 6;251:112550.
Additional Infomation	(S)-goitrin is a 5-ethenyl-1,3-oxazolidine-2-thione that has S-configuration. It is a constituent of a traditional Chinese herbal medicine, Radix isatidis. It has a role as an antiviral agent, a plant metabolite and an antithyroid drug. It is an enantiomer of a (R)-goitrin. Goitrin has been reported in Brassica oleracea, Crambe kotschyana, and other organisms with data available. Mechanism of Action A wide variety of chemicals, drugs, and other xenobiotics affect the second step in thyroid hormone biosynthesis. The stepwise binding of iodide to the tyrosyl residues in thyroglobulin requires oxidation of inorganic iodide (I2) to molecular (reactive) iodine (I2) by the thyroid peroxidase present in the luminal aspect (microvillar membranes) of follicular cells and adjacent colloid. Classes of chemicals that inhibit the organification of thyroglobulin include ... the thionamides (such as ... goitrin)... .

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	7.7411 mL	38.7057 mL	77.4114 mL
	5 mM	1.5482 mL	7.7411 mL	15.4823 mL
	10 mM	0.7741 mL	3.8706 mL	7.7411 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.