104801-96-9 Usage
Description
3-Hexyltetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one, also known as Orlistat impurity F, is a chemical compound derived from the synthesis process of Orlistat, an anti-obesity medication. It is characterized by its unique molecular structure, which includes a tetrahydro-2H-pyran-2-one ring with hexyl and undecyl side chains, as well as a hydroxyl group. 3-Hexyltetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one plays a significant role in the pharmaceutical industry, particularly in the quality control and analysis of Orlistat and its active pharmaceutical ingredients.
Uses
Used in Pharmaceutical Industry:
3-Hexyltetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one is used as an impurity reference standard for the quality control of Orlistat and its active pharmaceutical ingredients. It is essential for ensuring the purity, safety, and efficacy of Orlistat, which is prescribed for weight management and obesity treatment. By monitoring the presence and levels of this impurity, pharmaceutical companies can maintain strict quality standards and protect patients from potential adverse effects.
In the preparation of Orlistat impurity F:
3-Hexyltetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one is used as a reference compound in the development and validation of analytical methods for the detection and quantification of impurities in Orlistat. This helps in the assessment of the manufacturing process, ensuring that the final product meets the required specifications and regulatory guidelines. The use of this compound as a reference standard aids in the accurate identification and quantification of impurities, which is crucial for maintaining the overall quality and safety of Orlistat.
Check Digit Verification of cas no
The CAS Registry Mumber 104801-96-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,4,8,0 and 1 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 104801-96:
(8*1)+(7*0)+(6*4)+(5*8)+(4*0)+(3*1)+(2*9)+(1*6)=99
99 % 10 = 9
So 104801-96-9 is a valid CAS Registry Number.
InChI:InChI=1/C22H42O3/c1-3-5-7-9-10-11-12-13-14-16-19-18-21(23)20(22(24)25-19)17-15-8-6-4-2/h19-21,23H,3-18H2,1-2H3
104801-96-9Relevant articles and documents
Enantioselective synthesis of a key intermediate in a new process for orlistat using asymmetric hydrogenation and a grignard reagent promoted lactone cyclization
Schwindt, Mark A.,Fleming, Michael P.,Han, Yeun-Kwei,Hodges, Lewis M.,Johnston, David A.,Micheli, Roger P.,Roberts, Chris R.,Snyder, Roger,Topping, Robert J.,Puentener, Kurt,Scalone, Michelangelo
, p. 524 - 533 (2007)
A new enantioselective synthesis of Orlistat suitable for large-scale preparation is described. Therein, the first isolated key intermediate (R)-3-hexyl-5,6-dihydro-4-hydroxy-6-undecyl-2H-pyran-2-one (12) is prepared via (a) the asymmetric hydrogenation of methyl 3-oxotetradecanoate to (S)-3-hydroxytetrade-canoate (9); (b) the acylation of 9 with 2-bromooctanoyl halide (bromide/chloride) to (R)-3-[(2-bromo-1-oxooctyl)oxy]-tetradecanoic acid methyl ester (11) and finally (c) the tert-butyl magnesium chloride promoted cyclization of 11 to the single enantiomer 12. The single enantiomer intermediate 12, previously published as a mixture of enantiomers 2, has been carried on through several steps to Orlistat (1) without any process changes.
Highly enantioselective hydrogenation of 3,5-diketo esters: A formal synthesis of tetrahydrolipstatin
Polkowska, Jolanta,?ukaszewicz, Ewa,Kiegiel, Jaros?aw,Jurczak, Janusz
, p. 3873 - 3875 (2007/10/03)
Compound 4, obtained via a sequence of two consecutive alkylations of methyl 3,5-dioxohexanoate (5), was transformed into the enantiomerically pure lactone (3S,4S,6R)-2 being the precursor of tetrahydrolipstatin (1). The reaction sequence involves asymmetric catalytic hydrogenation of 4 as a crucial step.
OXETANONES
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, (2008/06/13)
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