Saccharin

Saccharin

Names
IUPAC name 1H-1λ6,2-Benzothiazole-1,1,3(2H)-trione
Other names ortho-benzoic sulfimide ortho sulphobenzimide
Identifiers
Jmol-3D images	Image
SMILES O=C2c1ccccc1S(=O)(=O)N2
Properties
Chemical formula	C7H5NO3S
Molar mass	183.18 g/mol
Appearance	White crystalline solid
Odor	Odorless
Density	0.828 g/cm3
Melting point	228.8–229.7 °C (443.8–445.5 °F; 501.9–502.8 K)
Solubility in water	0.2 g/100 ml (20 °C) 0.4 g/100 ml (35 °C) 0.7 g/100 ml (50 °C) 1.3 g/100 ml (75 °C)
Solubility	Soluble acetone, DMSO, ethanol, methanol Sparingly soluble in benzene, toluene
Vapor pressure	~0 mmHg
Acidity (pKa)	1.6
Hazards
Safety data sheet	ChemicalBook
Related compounds
Related compounds	N-nitrosaccharin, N-fluorosaccharin, N-chlorosaccharin, N-bromosaccharin, N-iodosaccharin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Saccharin is an organic chemical compound, commonly used as a sweetener, as well as in organic synthesis.

Saccharin is a sulfonamide that is about 500 times sweeter than sucrose, but has a bitter or metallic aftertaste, especially at high concentrations.

Properties

Chemical

To be added

Physical

Saccharin is a white odorless crystal. It is slightly soluble in water but soluble in polar organic solvents.

Availability

In some countries, there are sweeteners containing a 10:1 sodium cyclamate–saccharin blend that can be bought from most food stores. Extraction of saccharin from this product is possible, although large amounts of sweetener is needed to obtain useful amounts.

Can be bought from chemical suppliers.

Preparation

To be added

Projects

• Make N-halosaccharins. Some of these, like N-chlorosaccharin and N-bromosaccharin are simple and use reagents and equipment that are easily accessible. Higher-mass halosaccharins are more complicated, as sourcing them requires doing some preparative physics.
• Make N-nitrosaccharin
• Make N-pseudohalosaccharins (cyanato-, thiocyanato-, etc.)

Handling

Safety

Saccharin has low toxicity, and it's approved to use as artificial sweetener. As not everyone agrees with its taste, it is often mixed with other sweeteners, like cyclamate, to change its taste perception.

The International Agency for Research on Cancer (IARC) originally classified saccharin in Group 2B ("possibly carcinogenic to humans") based on the rat studies, but downgraded it to Group 3 ("not classifiable as to the carcinogenicity to humans") upon review of the subsequent research.

People with sulfonamide allergies may experience allergic reactions to saccharin, although it has been suggested that this may be due to a general predisposition to allergic reactions rather than a specific cross-reaction between antimicrobial sulfonamides and non-antimicrobial ones (like saccharin).

Storage

In closed airtight containers, mostly to keep it from contaminating things nearby.

Disposal

No special disposal is required. May be poured down the drain or dumped in trash.

References

Relevant Sciencemadness threads

• Issues Synthesizing Saccharin from Anthranilic Acid