A glucosinolate with diverse biological activities
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Sinigrin (hydrate)

Item No. 26028

Technical Information
Formal Name
1-[N-(sulfooxy)-3-butenimidate]1-thio-β-D-glucopyranose, monopotassium salt, hydrate
Molecular Formula
C10H16NO9S2 • K [XH2O]
Formula Weight
Purity
≥95%
A solid
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
227 nm
SMILES
OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](SC(CC=C)=NOS([O-])(=O)=O)O1.[K+].O
InChi Code
InChI=1S/C10H17NO9S2.K.H2O/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10;;/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18);;1H2/q;+1;/p-1/t5-,7-,8+,9-,10+;;/m1../s1
InChi Key
IUBVMJHASFBYGW-JMJVLJGISA-M
Origin
Plant/Brassica juncea
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Sinigrin is a glucosinolate that has been found in Brassica and has diverse biological activities.1,2,3 It inhibits NOD-like receptor protein 3 (NLRP3) inflammasome activation in ATP-stimulated, LPS-primed RAW 264.7 cells in a concentration-dependent manner.1 Sinigrin (1-100 µg/ml) reduces LPS-induced production of nitric oxide (NO) and prostaglandin E2 (PGE2; Item No. 14010), as well as NF-κB activation, in RAW 264.7 cells. It induces cell cycle arrest at the G0/G1 phase in HepG2 hepatocellular carcinoma cells when used at concentrations of 0.1 and 0.5 mM.2 Sinigrin (10 and 20 mg/kg) reduces increases in renal glomerular basement membrane thickness, as well as increases in systolic and diastolic blood pressure, in a rat model of hypertension induced by angiotensin II.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lee, H.-W., Lee, C.G., Rhee, D.-K., et alSinigrin inhibits production of inflammatory mediators by suppressing NF-κB/MAPK pathways or NLRP3 inflammasome activation in macrophages. Int. Immunopharmacol. 45, 163-173 (2017).

    2. Jie, M., Cheung, W.M., Yu, V., et alAnti-proliferative activities of sinigrin on carcinogen-induced hepatotoxicity in rats. PLoS One 9(10), e110145 (2014).

    3. Cong, C., Yuan, X., Hu, Y., et alSinigrin attenuates angiotensin II‑induced kidney injury by inactivating nuclear factor‑κB and extracellular signal‑regulated kinase signaling in vivo and in vitro. Int. J. Mol. Med. 48(2), 161 (2021).