82889-99-4

Basic information

• Product Name: Pentanoic acid,5-[hexahydro-5-hydroxy-4-(3- hydroxy-4-methyl-1-octen-6-ynyl)-2(1H)- pentalenylidene]-
• Synonyms: Iloprost;5-CIS ILOPROST
• CAS NO: 82889-99-4
• Molecular Formula: C22H32O4
• Molecular Weight: 360.494
• Mol File: 82889-99-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Pentanoic acid,5-[hexahydro-5-hydroxy-4-(3- hydroxy-4-methyl-1-octen-6-ynyl)-2(1H)- pentalenylidene]- (CAS DataBase Reference)
• NIST Chemistry Reference: Pentanoic acid,5-[hexahydro-5-hydroxy-4-(3- hydroxy-4-methyl-1-octen-6-ynyl)-2(1H)- pentalenylidene]- (82889-99-4)
• EPA Substance Registry System: Pentanoic acid,5-[hexahydro-5-hydroxy-4-(3- hydroxy-4-methyl-1-octen-6-ynyl)-2(1H)- pentalenylidene]- (82889-99-4)

Safety Data

• Hazardous Substances Data: 82889-99-4(Hazardous Substances Data)

Upstream product

• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 79812-95-6 (3aS,4R,5R,6aR)-5-hydroxy-4-((3S,E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl)hexahydropentalen-2(1H)-one 
• 146380-17-8 (3aS,4R,5R,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-((E)-(S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-hexahydro-pentalen-2-one 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 70073-58-4 dimethyl (2-oxo-3-methylhept-5-ynyl)-phosphonate 
• 116484-93-6 (+/-)-2-methylhex-4-ynoic acid ethyl ester 
• 182809-41-2 diethyl 2-(but-2-yn-1-yl)-2-methylmalonate 
• 1202227-32-4 (3aS,4R,5R,6aR)-5-((tert-butyldimethylsilyl)oxy)-4-((3S,E)-3-((tert-butyldimethylsilyl)oxy)-4-methyloct-1-en-6-yn-1-yl)hexahydropentalen-2(1H)-one 
• 1202227-23-3 (3S,E)-1-((3aS,4R,5R,6aR)-5-((tert-butyldimethylsilyl)oxy)-5',5'-dimethylhexahydro-1H-spiro[pentalene-2,2'-[1,3]dioxan]-4-yl)-4-methyloct-1-en-6-yn-3-ol 
• 871095-04-4 (3aS,4S,5R,6aR)-5-((tert-butyldimethylsilyl)oxy)-4-(hydroxymethyl)hexahydropentalen-2(1H)-one 
• 104172-98-7 (3aS,4S,5R,6aR)-5-((tert-butyldimethylsilyl)oxy)-4-(((tert-butyldimethylsilyl)oxy)methyl)hexahydropentalen-2(1H)-one 
• 117624-93-8 (1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one 
• 74818-68-1 (3aS,5R,6aR)-4-[(E)-(S)-4-Methyl-3-(tetrahydro-pyran-2-yloxy)-oct-1-en-6-ynyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-pentalen-2-one 
• 74818-49-8 (3aS,5R,6aR)-5-Hydroxy-4-((E)-(S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-hexahydro-pentalen-2-one 

Relevant articles and documents

An alternative synthesis for iloprost via a key bicyclic aldehyde intermediate

An alternative synthesis for iloprost has been accomplished in 14 steps via a convergent synthesis starting from commercially available (?)-Corey lactone diol. The syntheses employ a new and key chiral bicyclic aldehyde (4) intermediate, which is primed for attachment of the required α-side chain and ω-side chain.

ANTIHYPERTENSIVE THERAPY

A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.

Keto reduction of carbacyclin intermediates

The invention relates to a new process for the reduction of 15-keto carbacyclin intermediates in the presence of cerium(III) Salts.