124151-33-3

Basic information

• Product Name: coniferin
• Synonyms: coniferin;(E)-3-[3-Methoxy-4-(β-D-glucopyranosyloxy)phenyl]-2-propene-1-ol;(E)-Coniferin;[4-[(E)-3-Hydroxy-1-propenyl]-2-methoxyphenyl]β-D-glucopyranoside;2-Methoxy-4-[(E)-3-hydroxy-1-propenyl]phenyl β-D-glucopyranoside;4-[(E)-3-Hydroxy-1-propenyl]-2-methoxyphenyl β-D-glucopyranoside;Coniferyl alcohol 4-O-glucoside;trans-Coniferin
• CAS NO: 124151-33-3
• Molecular Formula: C₁₆H₂₂O₈
• Molecular Weight: 342.34108
• Mol File: 124151-33-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 625.4±55.0 °C(Predicted)
• Appearance: /
• Density: 1.432±0.06 g/cm3(Predicted)
• PKA: 12.81±0.70(Predicted)
• CAS DataBase Reference: coniferin(CAS DataBase Reference)
• NIST Chemistry Reference: coniferin(124151-33-3)
• EPA Substance Registry System: coniferin(124151-33-3)

Safety Data

• Hazardous Substances Data: 124151-33-3(Hazardous Substances Data)

Usage

Uses

A metabolite, and key biosynthetic intermediate for cell wall lignifcation within phenylpropanoid biosynthesis of coniferous trees. A substrate for Coniferin β-D-Glucosidase.

Upstream product

• 133-89-1 UDP-glucose 
• 458-35-5 coniferol 
• 121-33-5 vanillin 
• 51482-43-0 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)vanillin 
• 83-87-4 D-glucose pentaacetate 
• 458-35-5 coniferal alcohol 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 131723-87-0 4-(3-acetoxy-1-propenyl)-2-methoxyphenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 67-56-1 methanol 
• 62604-84-6 [4-(3-hydroxy-trans-propenyl)-2-methoxy-phenyl]-(tetra-O-acetyl-β-D-glucopyranoside) 
• 23598-08-5 methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 62604-85-7 3-methoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde 

Downstream Products

• 50-99-7 D-glucose 
• 458-35-5 coniferal alcohol 
• 132748-08-4 coniferyl aldehyde 4-O-β-D-glucopyranoside 

Relevant articles and documents

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Anti-inflammatory terpenes from Schefflera rubriflora C. J. Tseng & G. Hoo with their TNF-α and IL-6 inhibitory activities

The 95% ethanol extract and its EtOAc and n-BuOH fractions obtained from the leaves and twigs of Schefflera rubriflora C. J. Tseng & G. Hoo showed significant inhibitory activities (33.6%, 35.7% and 40.6%, respectively) against croton oil-induced ear inflammation in mice. Bioactivity-guided isolation and separation gave eight previously undescribed terpenes or terpene glycosides. Structural elucidation was based on UV, IR, and NMR spectroscopy, MS, experimental and calculated ECD data, and Mosher's method. To identify anti-inflammatory components from the extract, all the compounds were evaluated for tumor necrosis factor-α (TNF-α) and interleukine-6 (IL-6) inhibitory activities. Four undescribed compounds inhibited mRNA expression of TNF-α and IL-6 with IC50 values of 15.3–52.4 μM.

Coniferyl alcohol metabolism in conifers - I. Glucosidic turnover of cinnamyl aldehydes by UDPG: Coniferyl alcohol glucosyltransferase from pine cambium

UDPG: coniferyl alcohol glucosyltransferase (CAGT; EC 2.4.1.111) isolated from cambial tissues of Pinus strobus was able to convert cinnamyl aldehydes as well as dihydroconiferyl alcohol into their corresponding 4-O-β-D-glucosides in vitro, Cinnamyl aldeh

SYNTHESIS AND AGROBACTERIUM vir-INDUCING ACTIVITIES OF CONIFERYL ALCOHOL &β-GLYCOSIDES

Coniferyl alcohol β-glycosides were synthesized by coupling coniferyl alcohol sodium salt in aqueous acetone with peracetylated glycosyl halides of D-glucopyranose, D-galactopyranose and L-fucopyranose.After O-deacetylation by sodium methoxide, the glycosides were tested for their potential vir gene-inducing activities in Agrobacterium tumefaciens A348/psM358 and A348/psM243cd harbouring, respectively, vir E::lacZ and virB::lacZ fusion plasmids.In the large range of concentrations tested, these synthetic derivatives had vir-inducing activity on strain A348/psM358: D-Gal > D-Glc.The dose-response curves of these glycosylated compounds were completely different from those of free coniferyl alcohol; the β-galactopyranoside at 500 μM exhibited interestingly a greater activity than the free aglycone after 12 hr incubation period.The coniferyl alcohol β-glucopyranoside was a better inducer than the related β-galactopyranoside on strain A348/psM243cd.The β-L-fucopyranoside was inactive with both A. tumefaciens strains.The activities of these glycosylated inducers were correlated with the presence of intracellular glycosylhydrolases from the various A. tumefaciens strains studied.It is noteworthy that the vir-gene induction activity of the coniferyl alcohol β-galactopyranoside on strain A348/psM358 was due to a high basal level of expression of the virE::lacZ fusion gene.