Synonym
Benzobicyclon; SB 500; SB-500; SB500;
IUPAC/Chemical Name
3-(2-chloro-4-(methylsulfonyl)benzoyl)-4-(phenylthio)bicyclo[3.2.1]oct-3-en-2-one
InChi Key
VIXCLRUCUMWJFF-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H19ClO4S2/c1-29(26,27)16-9-10-17(18(23)12-16)21(25)19-20(24)13-7-8-14(11-13)22(19)28-15-5-3-2-4-6-15/h2-6,9-10,12-14H,7-8,11H2,1H3
SMILES Code
O=C1C(C2)CCC2C(SC3=CC=CC=C3)=C1C(C4=CC=C(S(=O)(C)=O)C=C4Cl)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
446.96
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Im SJ, Abd El-Aty AM, Lee YJ, Rahman MM, Kim SW, Choi JH, Shim JH. Analysis of benzobicyclon and its metabolite in brown rice and rice straw after field application using liquid chromatography-tandem mass spectrometry. Food Chem. 2015 Feb 1;168:404-9. doi: 10.1016/j.foodchem.2014.07.096. Epub 2014 Jul 24. PubMed PMID: 25172727.
2: Sun Q, Wang Y, Tian C, Gui W, Guo Y, Zhu G. Residue Analysis of Benzobicyclon in Soil and Sediment Samples by Ultra High-Performance Liquid Chromatography-Tandem Mass Spectrometry. J AOAC Int. 2016 Nov 1;99(6):1628-1635. doi: 10.5740/jaoacint.16-0159. Epub 2016 Sep 20. PubMed PMID: 27653995.
3: Williams KL, Tjeerdema RS. Hydrolytic Activation Kinetics of the Herbicide Benzobicyclon in Simulated Aquatic Systems. J Agric Food Chem. 2016 Jun 22;64(24):4838-44. doi: 10.1021/acs.jafc.6b00603. Epub 2016 Jun 13. PubMed PMID: 27248841.
4: Kang G, Kim J, Lim H, Kim TH. Crystal structure of benzobi-cyclon. Acta Crystallogr E Crystallogr Commun. 2015 Dec 9;71(Pt 12):o1035. doi: 10.1107/S2056989015023221. eCollection 2015 Dec 1. PubMed PMID: 26870484; PubMed Central PMCID: PMC4719965.
5: Williams KL, Kaur R, McFall AS, Kalbfleisch J, Gladfelder JJ, Ball DB, Anastasio C, Tjeerdema RS. Aqueous Photolysis of Benzobicyclon Hydrolysate. J Agric Food Chem. 2018 Jun 6;66(22):5462-5472. doi: 10.1021/acs.jafc.8b01012. Epub 2018 May 22. PubMed PMID: 29754487.
6: Williams KL, Gladfelder JJ, Quigley LL, Ball DB, Tjeerdema RS. Dissipation of the Herbicide Benzobicyclon Hydrolysate in a Model California Rice Field Soil. J Agric Food Chem. 2017 Oct 25;65(42):9200-9207. doi: 10.1021/acs.jafc.7b03679. Epub 2017 Oct 11. PubMed PMID: 28960969.
