ChemicalBook CAS DataBase List 1072-93-1

1072-93-1

Name	GOITRINE
CAS	1072-93-1
Molecular Formula	C5H7NOS
MDL Number	MFCD01709801
Molecular Weight	129.18
MOL File	1072-93-1.mol

Chemical Properties

Melting point	47.5°C
Boiling point	150.6±43.0 °C(Predicted)
density	1.170 (estimate)
refractive index	1.5480 (estimate)
storage temp.	Amber Vial, -20°C Freezer
solubility	DMSO (Slightly), Methanol (Slightly)
form	solid
pka	13.34±0.40(Predicted)
color	White to Off-White
InChI	InChI=1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)/t4-/m1/s1
InChIKey	UZQVYLOFLQICCT-SCSAIBSYSA-N
SMILES	O1[C@H](C=C)CNC1=S

Safety Data

Safety Statements	24/25 less more
HS Code	29349990
Toxicity	mouse,LD50,unreported,1260mg/kg (1260mg/kg),Journal of Agricultural and Food Chemistry. Vol. 17, Pg. 483, 1969. less more

Hazard Information

Chemical Properties

Derived from the root of Isatis indigotica Fort.

Uses

Goitrine is a cyclic thiocarbamate that is seen reducing production of thyroid hormones.

Definition

ChEBI:(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.

Biological Activity

Epigoitrin is a sulfur containing alkaloid isolated from Isatis indigotica (Ban Lan Gen) th at exhibits antiviralanticancerand antithyroid activities. Epigoitrin significantly decreases the susceptibility of restraint mice to H1N1 influenza virus. Epigoitrin and goitrin appear to show virucidal effect on influenza virus A (H1N1) in vitro and in ovo.

in vivo

Epigoitrin (88-176 mg/kg/d; oral administration; once daily; for 7 consecutive days) reduces the susceptibility of mice to influenza virus in a restraint - stress - induced H1N1 virus - infected mouse model, manifested as reduced mortality, attenuated inflammation, and decreased viral replication in the lungs^[1].
Epigoitrin (50-100 mg/kg; added to the feed; for 12 weeks) reduces fat deposition, improves glucose tolerance and insulin sensitivity, and increases energy expenditure in a high-fat diet-induced obese mouse model^[3].

Animal Model:	Five-week-old male C57BL/6J mice were fed a high-fat diet to establish an obesity model^[3].
Dosage:	50 mg/kg, 100 mg/kg
Administration:	Added to the feed, continuously administered for 12 weeks
Result:	Reduced fat deposition in HFD mice. Reduced adipocyte hypertrophy. Alleviated hepatic steatosis, as shown by reduced liver lipid droplets and lower liver and serum TG and TC levels. Had no effect on food intake.

Animal Model:	Specific-pathogen-free male Kunming mice (4 weeks of age; 12-15 g) loaded with restraint stress^[1]
Dosage:	88 mg/kg, 176 mg/kg
Administration:	Oral administration, once daily, for 7 days
Result:	Increased the survival rate, prolonged the mean day to death, and reduced the morbidity sign. Significantly decreased the virus titer in the lungs, reduced the infiltration of inflammatory cells in the lungs, and lowered the levels of TNF-α and IL-1β in bronchoalveolar lavage fluid. Increased the protein expressions of MAVS, IFN-β, and IFITM3 in the lung tissue, and decreased the protein level of MFN2 and virus nucleoprotein (NP) in stressed mice.

target

Influenza virus

storage

4°C, protect from light

Spectrum Detail

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