20585-38-0

Basic information

• Product Name: Benzeneacetic acid, a-cyclohexyl-a-hydroxy-, methyl ester, (R)-
• CAS NO: 20585-38-0
• Molecular Formula: C15H20O3
• Molecular Weight: 248.322
• Mol File: 20585-38-0.mol

Chemical Properties

• CAS DataBase Reference: Benzeneacetic acid, a-cyclohexyl-a-hydroxy-, methyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a-cyclohexyl-a-hydroxy-, methyl ester, (R)-(20585-38-0)
• EPA Substance Registry System: Benzeneacetic acid, a-cyclohexyl-a-hydroxy-, methyl ester, (R)-(20585-38-0)

Safety Data

• Hazardous Substances Data: 20585-38-0(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 20585-37-9 (R)-(-)-2-Cyclohexyl-2-hydroxy-2-phenyl-acetaldehyd 
• 186581-53-3 diazomethane 
• 20585-39-1 (2R)-2-Cyclohexyl-2-hydroxy-2-phenylacetic acid 
• 611-71-2 (R)-Mandelic Acid 
• 116907-30-3 (2R,5R)-2-(tert-butyl)-5-phenyl-1,3-dioxolan-4-one 
• 20585-36-8 (1R)-1-C-Cyclohexyl-1-C-phenyl-D-arabinit 
• 584-08-7 potassium carbonate 
• 74-88-4 methyl iodide 

Downstream Products

• 20585-39-1 (2R)-2-Cyclohexyl-2-hydroxy-2-phenylacetic acid 
• 71579-76-5 (R)-N-methylpiperidin-4-yl 2-cyclohexyl-2-hydroxyphenylacetate 
• 1310687-23-0 C₂₇H₃₉NO₅ 

Relevant articles and documents

Stereoselective synthesis and biodistribution of potent [11C]-labeled antagonists for positron emission tomography imaging of muscarinic receptors in the airways

Quantitation of muscarinic receptors in the lungs in vivo with positron emission tomography (PET) is of clinical interest. For that purpose we decided to develop [11C]-labeled ligands with a high affinity (K(D) 11C]CH3I with their tertiary amine precursors. The enantiomerically pure tertiary amine precursors were prepared by stereoselective synthesis starting from (R)-(-)-mandelic acid. In vitro binding assay of 1b and 2 demonstrated that both ligands bind with very high affinity to the muscarinic receptor subtypes M1, M2, and M3. They are more potent than the muscarinic antagonist (R)-N-methylquinuclidinyl benzilate ((R)-MQNB). Distribution studies with 1a, 1b, and 2 in control and atropine- treated male Wistar rats demonstrated significant specific binding (90-99% of total issue uptake) in tissues containing cholinoceptors (heart, intestine, lung, pancreas, spleen, stomach, submandibular gland). Because the tissue/plasma concentration ratios of lb are most favorable, this ligand was used for further evaluation. Analysis of plasma samples showed a very rapid clearance (t(1/2) = 0.3 min) of the radioligand 1b and a relatively slow appearance of a hydrophilic metabolite. At 15 min postinjection of 1b, analysis of heart, lungs, and liver showed that respectively 99%, 88%, and 8% of the tissue radioactivity corresponded with the parent compound. Ligand 1b appears to be an excellent candidate for PET studies of mAChR receptors in heart and lungs.

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