131487-42-8

Basic information

• Product Name: (+)-(2Z,4E)-(1'R,4'S)-4'-hydroxy-γ-ionylideneacetic acid
• Synonyms: (+)-(2Z,4E)-(1'R,4'S)-4'-hydroxy-γ-ionylideneacetic acid
• CAS NO: 131487-42-8
• Molecular Weight: 250.338
• Mol File: 131487-42-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (+)-(2Z,4E)-(1'R,4'S)-4'-hydroxy-γ-ionylideneacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(2Z,4E)-(1'R,4'S)-4'-hydroxy-γ-ionylideneacetic acid(131487-42-8)
• EPA Substance Registry System: (+)-(2Z,4E)-(1'R,4'S)-4'-hydroxy-γ-ionylideneacetic acid(131487-42-8)

Safety Data

• Hazardous Substances Data: 131487-42-8(Hazardous Substances Data)

Upstream product

• 131426-00-1 (1'R,4'S)-5,6-Dihydro-4-methyl-6-(4'-hydroxy-2',2'-dimethyl-6'-methylenecyclohexyl)-2H-pyran-2-one 
• 128036-09-9 (-)-(1R,4S)-2,2-Dimethyl-6-methylene-4-tetrahydropyranyloxy-1-cyclohexanecarbaldehyde 
• 128036-00-0 (-)-(S)-1-Chloromethyl-3,3-dimethyl-5-tetrahydropyranyloxy-1-cyclohexene 
• 131425-99-5 6-((1R,4S)-4-Hydroxy-2,2-dimethyl-6-methylene-cyclohexyl)-4-methyl-5,6-dihydro-pyran-2-one 
• 19041-17-9 methyl 4-bromo-3-methylbut-2-enoate 

Downstream Products

• 87480-90-8 (+)-(R)-Methyl 4'-oxo-α-ionylideneacetate 
• 107531-23-7 (+)-(1'R,4'S)-Methyl 4'-hydroxy-γ-ionylideneacetate 

Relevant articles and documents

Syntheses of Chiral 4'-Hydroxy and 1',4'-Dihydroxy-γ-ionylideneacetic Acids, Fungal Biosynthetic Intermediates of Abscisic Acid

Both chiral 4'-hydroxy and 1',4'-dihydroxy-γ-ionylideneacetic acids (3, 4 and 5), biosynthetic intermediates of abscisic acid produced by Cercospora cruenta, were synthesized from a chiral starting material, (R)- or (S)-4-hydroxy-2,2-dimethyl-1-cyclohexanone (7). -Sigmatropic rearrangement of (S)-1-chloromethyl-3,3-dimethyl-5-tetrahydropyranyl(THP)oxy-1-cyclohexene (8), followed by the Reformatsky reaction with 4-bromo-3-methyl-2-butenoate (10) gave (1'R,4'S)-4.The diastereomeric isomer, (1'R,4'R)-3, was synthesized in the same manner.The reaction of (S)-2,2-dimethyl-5-methylene-4-THPoxy-1-cyclohexanone (14) with a Grignard reagent prepared from (Z)-3-methyl-2-penten-4-ynyl THP ether (15) and subsequent conversion of the side chain gave (1'S,4'S)-5.These synthetic compounds confirmed the stereochemistry of natural 3, 4 and 5.