OMEPRAZOLE Chemical Properties

Melting point:

>47°C (dec.)

Boiling point:

600.0±60.0 °C(Predicted)

Density 

1.37±0.1 g/cm3 (20 ºC 760 Torr)

storage temp. 

Sealed in dry,Room Temperature

solubility 

H₂O: 0.5 mg/mL

form 

solid

pka

8.78±0.10(Predicted)

color 

white

Stability:

Hygroscopic

InChI

InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/t24-/m1/s1

InChIKey

SUBDBMMJDZJVOS-XMMPIXPASA-N

SMILES

C1([S@@](CC2=NC=C(C)C(OC)=C2C)=O)NC2=CC(OC)=CC=C2N=1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

DD9087000

MSDS

• Language:English Provider:SigmaAldrich

OMEPRAZOLE Usage And Synthesis

Uses

R-Form of Omeprazole. Gastric proton-pump inhibitor

Uses

(R)-Omeprazole is the R-enantiomer of Omeprazole (O635000), which binds covalently to proton pump. It inhibits gastric secretion. Used as an anttiulcerative.

Definition

ChEBI: A 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole that has R configuration at the sulfur atom.

Synthesis

GENERAL STEPS: Sulfide (5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]benzimidazole, 100 mmol) and titanium-tannic acid catalyst (1.1 mmol) were dissolved in ethyl acetate (EtOAc, 6.0 mL). The reaction mixture was kept at a constant temperature to the indicated temperature (usually 0°C, or in the range of -20 to +20°C for variable temperature experiments). Subsequently, a 30% aqueous hydrogen peroxide solution (0.105 mmol H2O2) was added all at once. The reaction mixture was continuously stirred at 500 rpm at a constant temperature (usually 24 h). For low-temperature experiments, the reaction time was about 30 h at -10 °C, which could be extended to 10 days at -20 °C. To analyze the progress of the reaction, 20 μL of the reaction mixture was taken into a vial and immediately evaporated carefully to dryness (~15-20 s) with a stream of compressed air. The residual solid was dissolved in isopropanol solution (0.20 mL) containing 1% triethylamine (Et3N), and the residual sulfide, (R)- and (S)-sulfoxide, and sulfone contents were analyzed by chiral HPLC.

References

[1] Catalysis Today, 2017, vol. 279, p. 84 - 89
[2] Heterocyclic Communications, 2016, vol. 22, # 1, p. 17 - 19
[3] Patent: US2008/319195, 2008, A1. Location in patent: Page/Page column 5
[4] Patent: US9228216, 2016, B2. Location in patent: Page/Page column 50-52
[5] Journal of Organic Chemistry, 2018, vol. 83, # 14, p. 7453 - 7458

OMEPRAZOLE(119141-89-8)Related Product Information

• 5-METHOXYBENZIMIDAZOLE