Title:  Meglutol 
CAS Registry Number:  503-49-1 
CAS Name:  3-Hydroxy-3-methylpentanedioic acid 
Additional Names:  3-hydroxy-3-methylglutaric acid;  dicrotalic acid;  medroglutaric acid;  HMG;  HMGA 
Manufacturers' Codes:  CB-337 
Trademarks:  Lipoglutaren (Ausonia);  Mevalon (Guidotti) 
Molecular Formula:  C6H10O5 
Molecular Weight:  162.14 
Percent Composition:  C 44.45%, H 6.22%, O 49.34% 
Literature References:  Hypolipidemic agent that decreases the rate of cholesterol synthesis.  Prepn via Reformatsky reaction between ethyl acetoacetate and ethyl bromoacetate:  R. Adams, B. L. Van Duuren, J. Am. Chem. Soc. 75, 2377 (1953).  Synthesis via oxidation of diallylmethylcarbinol with ozone and hydrogen peroxide:  H. J. Klosterman, F. Smith, ibid. 76, 1229 (1954); J. L. Rabinowitz, Biochem. Prep. 6, 25 (1958).  Caution:  attempts to increase batch size of the ozonolysis resulted in an explosion, cf. Chem. Eng. News 51(6), 29 (1973).  Improved synthesis:  A. Yavrouian et al., Synthesis 1981, 791.  Hypocholesteremic properties:  Z. H. Beg, M. Siddiqi, Experientia 23, 380 (1967); M. Siddiqi, Z. H. Beg, US 3629449 (1971); Z. H. Beg, P. J. Lupien, Biochim. Biophys. Acta 260, 439 (1972); A. N. K. Yusufi, M. Siddiqi, Atherosclerosis 20, 517 (1974); C. D. Padova et al., Life Sci. 30, 1907 (1982).  Biosynthetic studies:  L. W. White, H. Rudney, Biochemistry 9, 2713 (1970); L. Hagenfeldt, K. Hellstrom, Life Sci. 9, Pt. 2, 991 (1970).  Organ distribution:  L. L. Savoie, P. J. Lupien, Can. J. Physiol. Pharmacol. 53, 638 (1975).  Effectiveness in familial hypercholesteremia:  P. J. Lupien et al., J. Clin. Pharmacol. 19, 120 (1979).  GC study in patients with organic acidurias:  K. Tanaka, D. J. Hine, J. Chromatogr. 239, 301 (1982).  Toxicological study:  L. L. Savoie, P. J. Lupien, Arzneim.-Forsch. 25, 1284 (1975). 
Properties:  Cryst from ether/petr ether, mp 108-109°.  Sol in water.  Stable when stored dry.  LD50 in mice (g/kg):  7.33 orally; 3.23 i.p. (Savoie, Lupien). 
Melting point:  mp 108-109° 
Toxicity data:  LD50 in mice (g/kg):  7.33 orally; 3.23 i.p. (Savoie, Lupien) 
Therap-Cat:  Antilipemic. 
Keywords:  Antilipemic.   |