104801-96-9

Basic information

• Product Name: 3-Hexyltetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one
• Synonyms: 3-Hexyltetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one;(3S,4S,6R)-3-hexyltetrahydro-4-hydroxy-6-undecyl-2H-Pyran-2-one;(3S,4S,6R)-3-Hexyl-4-hydroxy-6-undecyltetrahydro-2H-pyran-2-one
• CAS NO: 104801-96-9
• Molecular Formula: C₂₂H₄₂O₃
• Molecular Weight: 354.571
• Mol File: 104801-96-9.mol

Chemical Properties

• Melting Point: 108-109 ºC
• Boiling Point: 483.15 °C at 760 mmHg
• Flash Point: 183.676 °C
• Appearance: /
• Density: 0.931
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.465
• Storage Temp.: 2-8°C
• PKA: 13.57±0.60(Predicted)
• CAS DataBase Reference: 3-Hexyltetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hexyltetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one(104801-96-9)
• EPA Substance Registry System: 3-Hexyltetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one(104801-96-9)

Safety Data

• Hazardous Substances Data: 104801-96-9(Hazardous Substances Data)

Usage

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.

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

Upstream product

• 68711-40-0 (3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone 
• 112836-64-3 (6R)-3-hexyl-5,6-dihydro-6-undecyl-2H-pyran-2,4(3H)-dione 
• 136807-65-3 2-hexyl-3,5-dioxo-hexadecanoic acid methyl ester 
• 717129-75-4 (3S,5R)-2-Hexyl-3,5-dihydroxy-hexadecanoic acid methyl ester 
• 111-25-1 1-bromo-hexane 
• 112-29-8 1-bromo dodecane 
• 29736-80-9 3,5-dioxohexanoic acid methyl ester 
• 717129-83-4 methyl 3,5-dioxohexadecanoate 
• 124-07-2 Octanoic acid 
• 112763-97-0 (R)-3-phenylmethyloxy-tetradecanal 
• 112836-65-4 (3S,4S)-3-hexyl-4-<(R)-2-<(tetrahydro-2H-pyran-2-yl)-oxy>tridecyl>-2-oxetanone 
• 104871-98-9 (2S,3S,5R)-2-hexyl-3-hydroxy-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoic acid 
• 112764-01-9 (3S,4S,6R)-4-(benzyloxy)-3-hexyl-3,4,5,6-tetrahydro-6-undecyl-2H-pyran-2-one 
• 112763-98-1 (5R)-5-(benzyloxy)-3-hydroxy-2-hexylhexadecanoic acid 

Downstream Products

• 112764-01-9 (3S,4S,6R)-4-(benzyloxy)-3-hexyl-3,4,5,6-tetrahydro-6-undecyl-2H-pyran-2-one 
• 104871-99-0 (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one 
• 104872-04-0 Orlistat 
• 68711-40-0 (3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone 
• 112764-03-1 benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-hydroxyhexadecanoate 
• 112764-04-2 benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-<(tetrahydro-2H-pyran-2-yl)oxy>hexadecanoate 
• 112764-05-3 (S)-N-(benzyloxycarbonyl)asparagine (S)-1-<<(2S,3S)-3-hexyl-4-oxo-2-oxetanyl>methyl>dodecyl ester 
• 114299-20-6 (2S,3S,5R)-5-(benzyloxy)-3-hydroxy-2-hexylhexadecanoic acid 

Relevant 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

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.

Orlistat impurity as well as F preparation method and application thereof (by machine translation)

The preparation method disclosed by the invention is F low in cost, simple .and convenient to operate, and capable of qualitatively, and quantitatively, analyzing the orlistat impurity and, providing a reference substance for qualitative and quantitative analysis of orlistat, impurities, so that the foundation is rammed for quality research of orlistat crude. drugs and related preparations. (by machine translation)

Highly enantioselective hydrogenation of 3,5-diketo esters: A formal synthesis of tetrahydrolipstatin

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.

Synthesis of Tetrahydrolipstatin and Tetrahydroesterastin, Compounds with a β-Lactone Moiety. Stereoselective Hydrogenation of a β-Keto δ-Lactone and Convertion of the δ-Lactone into a β-Lactone

Stereoselective syntheses of tetrahydrolipstatin (1) and tetrahydroesterastin (2) are described.The key intermediate β-ketoδ-lactone 7 is hydrogenated stereoselectively to yield hydroxy δ-lactone 9, which is transformed into hydroxy β-lactone 10.Esterification of 10 with (S)-N-formylleucine under Mitsunobu's conditions yields tetrahydrolipstatin (1).Esterification of 10 with (S)-N-acetylasparagine under the same conditions yields 17 (mixture of two diastereomers), which gives by saponification hydroxy β-lactone 18.Reaction of the latter with the mixed anhydride of (S)-N-Z-asparagine, hydrogenation, and acetylation give tetrahydroesterastin (2).