90319-80-5

Basic information

• Product Name: (2S)-2-<4-(cis-(1R,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid
• Synonyms: (2S)-2-<4-(cis-(1R,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid
• CAS NO: 90319-80-5
• Molecular Weight: 248.322
• Mol File: 90319-80-5.mol

Chemical Properties

• CAS DataBase Reference: (2S)-2-<4-(cis-(1R,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-<4-(cis-(1R,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid(90319-80-5)
• EPA Substance Registry System: (2S)-2-<4-(cis-(1R,2R)-2-hydroxycyclopentylmethyl)phenyl>propionic acid(90319-80-5)

Safety Data

• Hazardous Substances Data: 90319-80-5(Hazardous Substances Data)

Upstream product

• 89631-53-8 methyl 2-<4-(cis-2-acetoxycyclopentylmethyl)phenyl>propionate 
• 72748-99-3 (R)-1-Amino-2-(methoxymethyl)pyrrolidine 
• 589-29-7 p-xylylene glycol 
• 1333080-48-0 4-((4-methoxybenzyloxy)methyl)benzaldehyde 
• 1333080-45-7 (R)-2-[4-((S)-2-hydroxy-1-methylethyl)benzyl]cyclopentanone 
• 1333080-43-5 C₃₁H₃₈O₂Si 
• 1333080-42-4 [(S)-2-(4-bromomethylphenyl)propoxy]-tert-butyldiphenylsilane 
• 1333080-41-3 {4-[(S)-2-(tert-butyldiphenylsilanyloxy)-1-methylethyl]phenyl}methanol 
• 1333080-40-2 tert-butyl{(S)-2-[4-(4-methoxybenzyloxymethyl)phenyl]propoxy}diphenylsilane 
• 1333080-39-9 (S)-2-(4-(4-methoxybenzyloxy)phenyl)propan-1-ol 
• 1333080-31-1 (4-((4-methoxybenzyloxy)methyl)phenyl)methanol 
• 1333080-37-7 C₂₀H₂₄O₄ 
• 1333080-35-5 2-(4-((4-methoxybenzyloxy)methyl)phenyl)propan-1-ol 
• 1333080-33-3 1-(4-methoxybenzyloxymethyl)-4-isopropenylbenzene 

Downstream Products

• 89631-57-2 methyl (+/-)-2-<4-(cis-2-hydroxycyclopentylmethyl)phenyl>propionate 
• 89631-57-2 methyl (+/-)-2-<4-(trans-2-hydroxycyclopentylmethyl)phenyl>propionate 
• 88378-29-4 {2-[4-((1R,2S)-2-Acetoxy-cyclopentylmethyl)-phenyl]-propionylamino}-acetic acid ethyl ester 
• 88378-26-1 2-{2-[4-((1S,2R)-2-Hydroxy-cyclopentylmethyl)-phenyl]-propionylamino}-ethanesulfonic acid 
• 88378-27-2 {2-[4-((1S,2R)-2-Hydroxy-cyclopentylmethyl)-phenyl]-propionylamino}-acetic acid 
• 88378-28-3 2-[4-((1R,2S)-2-Acetoxy-cyclopentylmethyl)-phenyl]-propionic acid 

Relevant articles and documents

Evaluation of loxoprofen and its alcohol metabolites for potency and selectivity of inhibition of cyclooxygenase-2

Loxoprofen, its trans-alcohol and cis-alcohol metabolites were evaluated for selectivity of inhibition of COX-2 over COX-1. The (2S,1′R,2′S)- trans-alcohol derivative was found to be the most active metabolite and to be a potent and nonselective inhibitor of COX-2 and COX-1 in both enzyme and human whole blood assays.

Asymmetric synthesis of the active form of loxoprofen and its analogue

The asymmetric synthesis of the active form of the antiinflammatory drug loxoprofen has been reported in this article. Enzymatic kinetic resolution/racemization of a substituted homo-benzylic primary alcohol with lipase-PS, asymmetric alkylation of cyclic ketones using either Enders' or Meyers' strategy followed by a stereoselective biocatalytic reduction of carbonyl group are the key reactions employed successfully to achieve the target molecule and one of its analogue.

Properties and synthesis of 2-{2-fluoro (or bromo)-4-[(2-oxocyclopentyl) methyl]phenyl}propanoic acid: Nonsteroidal anti-inflammatory drugs with low membrane permeabilizing and gastric lesion-producing activities

We previously proposed that membrane permeabilization activity of NSAIDs is involved in NSAID-induced gastric lesions. We here synthesized derivatives of loxoprofen that have lower membrane permeabilization activity than other NSAIDs. Compared to loxoprofen, the derivatives 10a and 10b have lower membrane permeabilization activity and their oral administration produced fewer gastric lesions but showed an equivalent anti-inflammatory effect. These results suggest that 10a and 10b are likely to be therapeutically beneficial as safer NSAIDs.

Reduction of drug ketones by dihydrodiol dehydrogenases, carbonyl reductase and aldehyde reductase of human liver

In this study, we compared the enzymatic reduction of 10 drugs with a ketone group by homogeneous carbonyl reductase, aldehyde reductase and three dihydrodiol dehydrogenases of human liver cytosol. At least one and in some cases all of the three dihydrodi

Synthesis of the eight possible optically active isomers of 2-[4-(2-hydroxycyclopentylmethyl)phenyl]propionic acid

A recently synthesized compound, (±)-2-[4-(2-oxocyclopentylmethyl)phenyl]propionic acid, had good anti-inflammatory and analgesic activities. One of the metabolites of this compound showed more potent prostaglandin synthetase inhibitory activity than the