1303501-13-4

Basic information

• Product Name: 1,9-bis(4-hydroxyphenyl)-3,7-dihydroxynonan-5-one
• Synonyms: 1,9-bis(4-hydroxyphenyl)-3,7-dihydroxynonan-5-one
• CAS NO: 1303501-13-4
• Molecular Weight: 358.434
• Mol File: 1303501-13-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,9-bis(4-hydroxyphenyl)-3,7-dihydroxynonan-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,9-bis(4-hydroxyphenyl)-3,7-dihydroxynonan-5-one(1303501-13-4)
• EPA Substance Registry System: 1,9-bis(4-hydroxyphenyl)-3,7-dihydroxynonan-5-one(1303501-13-4)

Safety Data

• Hazardous Substances Data: 1303501-13-4(Hazardous Substances Data)

Upstream product

• 1425335-01-8 ericanone 3-O-β-D-xylopyranoside 
• 1421598-64-2 C₂₆H₃₈O₄Si 
• 1421598-63-1 C₂₆H₃₈O₃Si 
• 622397-33-5 (S)-1-(4-((tert-butyldimethylsilyl)oxy)phenyl)hex-5-en-3-ol 
• 147974-20-7 3-[4-(tert-butyl-dimethyl-silanyloxy)phenyl]propionaldehyde 
• 183140-16-1 C₁₇H₂₆O₃Si 
• 1421598-67-5 (+)-(3S,7S)-1,9-bis(4-(tert-butyldimethylsilyloxy)phenyl)-3,7-dihydroxynonan-5-one 
• 123-08-0 4-hydroxy-benzaldehyde 
• 522602-18-2 ethyl 3-(4-((tert-butyl(dimethyl)silyl)oxy)phenyl)propanoate 
• 120743-99-9 p-[(tert-butyldimethylsilyl)oxy]benzaldehyde 

Relevant articles and documents

Concise Asymmetric Construction of C2-symmetric 1,9-Diarylnonanoids Using a Hypervalent Silicon Complex: Total Synthesis of (-)-Ericanone

By using a phosphine oxide-catalyzed enantioselective double aldol reaction, we achieved the concise construction of C2-symmetric 1,9-diarylnonanoids, enabling the synthesis of (-)-ericanone from p-hydroxybenzaldehyde in 6 steps with 65 % overall yield. The enantioselective double aldol reaction is useful for establishing C2-symmetric 1,9-diaryl-3,7-dihydroxy-5-nonanones with a single operation. Furthermore, the use of o-nosyl-protected p-hydroxybenzaldehyde and a 4,4′-disubstituted BINAP dioxide catalyst dramatically improved the reactivity and selectivity in the double aldol reaction, enabling the total synthesis of (-)-ericanone with high yield and with excellent enantiopurity.

Three further 1,9-diarylnonanoid 3-O-glycosides from Erica cinerea

In addition to the six diarylnonanoids and diarylnonanoid 3-O-glucosides previously reported from Erica cinerea, the multistep chromatographic processing of the acetone extract of the fresh aerial parts resulted in the isolation of three more representatives as glycosides derived from either (-)-ericanone or (-)-α-ericadione. From the spectroscopic data, the new structures were elucidated as (-)-(3S,7S)-ericanone 3-O-β-d-xylopyranoside, (-)-(3S,7S)-3″-hydroxyericanone 3-O-β-d-glucopyranoside, and (-)-(3S)-3″-hydroxy-α-ericadione 3-O-β-d-glucopyranoside respectively. In the 1H and 13C NMR spectra run in CD 3OD, the latter metabolite was as (-)-α-ericadione 3-O-β-d-glucopyranoside, also found as a permanent mixture of the major s-trans (70%) and the minor s-cis (30%) conformers. Such result - in connection with the protic solvent - seems to have never been reported earlier for α-alkadiones. Moreover, mild acid hydrolysis of such a glucoside led directly to the 3,4-dehydrated aglycone moiety accompanied by its 6,7-dehydrated tautomer, according to two successive dehydrations of the anticipated aglycone. Furthermore, although missing in this species, the postulated β-ericadione continues to be regarded as an essential intermediate at the crossroads of the biogenesis of most of the E. cinerea 1,9-diarylnonanoids.