153219-51-3

Basic information

• Product Name: (6E,8E,10E,12E)-14-hydroxy-4,5-didehydro-5,14-dihydroretinol
• Synonyms: 3,5,7-Nonatriene-1,2-diol, 3,7-dimethyl-9-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-, (3E,5E,7E,9E)-; 3,5,7-Nonatriene-1,2-diol, 3,7-dimethyl-9-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-, (all-E)-
• CAS NO: 153219-51-3
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.451
• Mol File: 153219-51-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 470.8°C at 760 mmHg
• Flash Point: 210.8°C
• Density: 1.015g/cm³
• Vapor Pressure: 7.65E-11mmHg at 25°C
• Refractive Index: 1.563
• CAS DataBase Reference: (6E,8E,10E,12E)-14-hydroxy-4,5-didehydro-5,14-dihydroretinol(CAS DataBase Reference)
• NIST Chemistry Reference: (6E,8E,10E,12E)-14-hydroxy-4,5-didehydro-5,14-dihydroretinol(153219-51-3)
• EPA Substance Registry System: (6E,8E,10E,12E)-14-hydroxy-4,5-didehydro-5,14-dihydroretinol(153219-51-3)

Safety Data

• Hazardous Substances Data: 153219-51-3(Hazardous Substances Data)

Upstream product

• 162189-70-0 (R)-2,2,4,4-Tetraisopropyl-6-((E)-1-methyl-but-1-en-3-ynyl)-[1,3,5,2,4]trioxadisilepane 
• 162189-65-3 [(E)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-pent-3-en-1-ynyl]-trimethyl-silane 
• 162189-72-2 (E)-(S)-1-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-hex-3-en-5-yn-2-ol 
• 162189-69-7 (R)-(-)-3-hexen-5-yne-1,2-diol 
• 162189-67-5 (S)-(+)-3-hexen-5-yne-1,2-diol 
• 162189-68-6 Benzoic acid (E)-(R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-pent-2-en-4-ynyl ester 
• 79-77-6 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one 
• 166584-44-7 Acetic acid (3E,5E,7E)-(1S,2S)-1-acetoxymethyl-2-hydroxy-2,6-dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3,5,7-trienyl ester 
• 166584-42-5 Acetic acid (4E,6E,8E)-(2S,3S)-2,3-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trienyl ester 
• 127-47-9 Retinol acetate 
• 166528-78-5 Acetic acid (2E,4E,6E)-(R)-1-acetoxymethyl-2,6-dimethyl-8-[2,6,6-trimethyl-cyclohex-2-en-(E)-ylidene]-octa-2,4,6-trienyl ester 

Relevant articles and documents

Studies on the apoptotic activity of natural and synthetic retinoids: Discovery of a new class of synthetic terphenyls that potently support cell growth and inhibit apoptosis in neuronal and HL-60 cells

New terphenyl derivatives have been synthesized and tested for their effect on cell survival in serum-free cultures. These compounds protected HL60 cells from death and supported their growth with an activity higher than that of the natural 14-hydroxy-retro-retinol. Terphenyls 26 and 28 also possess antiapoptotic activity on neuronal cells, proving them as possible candidates for the treatment of neurodegenerative and ischemic diseases.

Practical total syntheses of (R)-(+)- and (S)-(-)-14-hydroxy-4,14-retro- retinol

Practical and facile total syntheses of the remarkably unstable (R)-(+)- 14-hydroxy-4, 14-retro-retinol [(R)-14HRR] 1 and of its enantiomer 2 have been achieved via an acid-catalyzed dehydration reaction of the respective tetraeneol intermediates 10 and i