106325-78-4

Basic information

• Product Name: 1,3-Benzenediol, 5-(2-phenylethenyl)-, (Z)-
• Synonyms: cis-pinosylvin;UNII-SUT6G9WH0N
• CAS NO: 106325-78-4
• Molecular Formula: C14H12O2
• Molecular Weight: 212.24400
• Mol File: 106325-78-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,3-Benzenediol, 5-(2-phenylethenyl)-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Benzenediol, 5-(2-phenylethenyl)-, (Z)-(106325-78-4)
• EPA Substance Registry System: 1,3-Benzenediol, 5-(2-phenylethenyl)-, (Z)-(106325-78-4)

Safety Data

• Hazardous Substances Data: 106325-78-4(Hazardous Substances Data)

Upstream product

• 107030-46-6 C₂₆H₄₀O₂Si₂ 
• 103929-86-8 3,5-di-t-butyldimethylsilyloxybenziltriphenylphosphonium chloride 
• 103929-84-6 [3,5-di(tert-butyldimethylsilanyloxy)phenyl]methanol 
• 103929-83-5 methyl 3,5-bis(tert-butyldimethylsilyloxy)benzoate 
• 100-52-7 benzaldehyde 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 21956-55-8 1,3-dimethoxy-5-[(1Z)-2-phenylethenyl]benzene 

Downstream Products

• 22139-77-1 pinosylvin 

Relevant articles and documents

ENDOGENEOUS PINE WOOD NEMATICIDAL SUBSTANCES IN PINES, PINUS MASSONIANA, P. STROBUS AND P. PALUSTRIS

The presence of the repellents and nematicides to the pine wood nematode, Bursaphelenchus xylophilus, was found in the heartwood and bark of Pinus massoniana, P. strobus and P. palustris, which have a resistance to the pine wood nematode.The heartwood of P. massoniana contained a repellent, α-humulene and two nematicidal substances, pinosylvin monomethylether (PMS) and (-)-nortrachelogenin for the nematode.The bark of the pine contained two nematicides, methyl ferulate and (+)-pinoresinol.PMS, which showed the highest nematicidal activity (LD 50 was 4 ppm), was also contained in the heartwood of P. strobus and the heartwood and bark of P. palustris.The resistance of these pines to the pine wood nematode is considered to be attributed to the presence of these endogenously defending substances.Further, the relationship between the structure and the nematicidal activity was elucidated for PSM and methyl ferulate.Moreover, PSM showed little anti-acetylcholinesterase activity.

Synthesis and nematocidal activity of hydroxystilbenes

Various (E)-hydroxystilbenes were synthesized from (E)/(Z) mixtures of methoxystilbenes through a new (Z)-(E) isomerization method followed by demethylation. The nematocidal activity appears when methoxystilbenes are demethylated to hydroxystilbenes. For this activity, a hydroxy group at the C-2 or C-3 position is necessary. Thus, 2-hydroxy-, 3-hydroxy-, 2,6-dihydroxy-, 3,4-dihydroxy-, 3,5-dihydroxy-, 2,2'-dihydroxy-, 3,3'-dihydroxy-, 3,4'dihydroxy-, 2-hydroxy-4-methoxy-, 5-hydroxy-2-methoxy-, 2-hydroxy-6-methoxy-, 6-allyloxy-2-hydroxy-, 3-hydroxy-5-methoxy-, and 5-allyloxy-3-hydroxystilbenes showed rather potent nematocidal activity. The activity of 5-allyloxy-3-hydroxystilbene was the strongest [minimal lethal concentration (MLC) = 30 μM]. The activities of the (E) and (Z) isomers were comparable. The activities were also retained, though they were weaker, in the dihydro derivatives, hydroxybibenzyls.