Trimethylamine N-Oxide
Structural Formula Vector Image
Title: Trimethylamine N-Oxide
CAS Registry Number: 1184-78-7
CAS Name: N,N-Dimethylmethanamine N-oxide
Additional Names: TMAO
Molecular Formula: C3H9NO
Molecular Weight: 75.11
Percent Composition: C 47.97%, H 12.08%, N 18.65%, O 21.30%
Literature References: Naturally occurring osmolyte found in marine organisms; counteracts protein-destabilizing factors such as urea, temperature, salt, and hydrostatic pressure. The enzymatic reduction to trimethylamine, q.v., is used as an indication of spoilage in stored fish. Prepn of the dihydrate: W. R. Dunstan, E. Goulding, J. Chem. Soc. 75, 792 (1899); of the anhydrous compd: J. A. Soderquist, C. L. Anderson, Tetrahedron Lett. 27, 3961 (1986). Determn in natural waters and biological media: A. D. Hatton, S. W. Gibb, Anal. Chem. 71, 4886 (1999). Review of use as reagent in organometallic chemisty: T.-Y. Luh, Coord. Chem. Rev. 60, 255-276 (1984); in organic synthesis: H.-J. Knölker, J. Prakt. Chem. 338, 190-192 (1996). Review of distribution in marine animals of various habitats: R. H. Kelly, P. H. Yancey, Biol. Bull. 196, 18-25 (1999); of biosynthesis, distribution and biological role: B. A. Seibel, P. J. Walsh, J. Exp. Biol. 205, 297-306 (2002); P. H. Yancey et al., Comp. Biochem. Physiol. A 133, 667-676 (2002).
Properties: Free-flowing large colorless crystals, mp 225-227°. Very hygroscopic.
Melting point: mp 225-227°
Derivative Type: Dihydrate
CAS Registry Number: 62637-93-8
Molecular Formula: C3H9NO.2H2O
Molecular Weight: 111.14
Percent Composition: C 32.42%, H 11.79%, N 12.60%, O 43.19%
Properties: Radiating needles, mp 96°. Sol in water, methanol. Insol in ether.
Melting point: mp 96°
CAUTION: May be irritating to eyes, skin, respiratory system.
Use: Oxidizing reagent in organic synthesis.

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