MedKoo Cat#: 526295 | Name: Saccharin 1-methylimidazole
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Saccharin 1-methylimidazole, also known as SMI, is a chemical activator commonly used in solid-phase synthesis of DNA and RNA oligonucleotides. Saccharin 1-methylimidazole has been used to synthesize single-stranded DNA oligonucleotides that are resistant to nuclease digestion.

Chemical Structure

Saccharin 1-methylimidazole
Saccharin 1-methylimidazole
CAS#482333-74-4 (1-methylimidazole)

Theoretical Analysis

MedKoo Cat#: 526295

Name: Saccharin 1-methylimidazole

CAS#: 482333-74-4 (1-methylimidazole)

Chemical Formula: C11H11N3O3S

Exact Mass: 265.0521

Molecular Weight: 265.29

Elemental Analysis: C, 49.80; H, 4.18; N, 15.84; O, 18.09; S, 12.09

Price and Availability

Size Price Availability Quantity
50mg USD 150.00 Ready to ship
100mg USD 250.00 Ready to ship
200mg USD 425.00 Ready to ship
500mg USD 900.00 Ready to ship
1g USD 1,450.00 Ready to ship
2g USD 2,450.00 Ready to ship
5g USD 4,950.00 Ready to ship
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Synonym
Saccharin 1-methylimidazole; SMI;
IUPAC/Chemical Name
1,1-Dioxide-1,2-benzisothiazol-3(2H)-one 1-methyl-1H-imidazole salt
InChi Key
DMSNKRPEUQVMNF-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H5NO3S.C4H6N2/c9-7-5-3-1-2-4-6(5)12(10,11)8-7;1-6-3-2-5-4-6/h1-4H,(H,8,9);2-4H,1H3
SMILES Code
O=S(C1=C(C=CC=C1)C2=O)(N2)=O.CN3C=NC=C3
Appearance
Solid powder
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, DMF, and ethanol
Shelf Life
>2 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
2934.99.9001
More Info
Biological target:
Saccharin 1-methylimidazole catalyzes the phosphoramidite coupling reaction of the 5' hydroxy of immobilized nucleosides and the amine group of nucleoside phosphoramidite.
In vitro activity:
Extracellular calcium deprivation arrested the proliferative development of T51B rat liver cells in late G1 or S phases. These arrested cells initiated DNA synthesis within an hr after addition of calcium or a tumor promoter, one being saccharin. Reference: Cancer Res. 1980 Dec;40(12):4541-5. https://pubmed.ncbi.nlm.nih.gov/7438088/
In vivo activity:
To be determined
Solvent mg/mL mM
Solubility
DMSO 52.7 198.54
Water 53.0 199.78
Ethanol 10.0 37.69
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 265.29 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Boynton AL, Whitfield JF. Stimulation of DNA synthesis in calcium-deprived T51B liver cells by the tumor promoters phenobarbital, saccharin, and 12-O-tetradecanoylphorbol-13-acetate. Cancer Res. 1980 Dec;40(12):4541-5. PMID: 7438088.
In vitro protocol:
1. Boynton AL, Whitfield JF. Stimulation of DNA synthesis in calcium-deprived T51B liver cells by the tumor promoters phenobarbital, saccharin, and 12-O-tetradecanoylphorbol-13-acetate. Cancer Res. 1980 Dec;40(12):4541-5. PMID: 7438088.
In vivo protocol:
To be determined
Tsukamoto, M., & Hayakawa, Y. (2018). Various Coupling Agents in the Phosphoramidite Method for Oligonucleotide Synthesis. Synthesis of Therapeutic Oligonucleotides, 17-39.