118916-57-7

Basic information

• Product Name: Balaphonin
• Synonyms: Balaphonin;Balanophonin;(E)-3-[(2R,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal
• CAS NO: 118916-57-7
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.37
• Mol File: 118916-57-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Balaphonin(CAS DataBase Reference)
• NIST Chemistry Reference: Balaphonin(118916-57-7)
• EPA Substance Registry System: Balaphonin(118916-57-7)

Safety Data

• Hazardous Substances Data: 118916-57-7(Hazardous Substances Data)

Usage

General Description

Balaphonin is a chemical compound that is derived from the Balaphon plant, a member of the family Rubiaceae. It is a naturally occurring compound that has been found to have various pharmacological properties, including anti-inflammatory, analgesic, and antioxidant effects. Balaphonin has been studied for its potential as a treatment for conditions such as arthritis, chronic pain, and oxidative stress-related conditions. Its anti-inflammatory properties make it a promising candidate for the development of new medications for these conditions. Additionally, balaphonin has been found to have neuroprotective effects, making it of interest for the treatment of neurodegenerative diseases. Further research is needed to fully understand the potential therapeutic applications of this compound.

Upstream product

• 4263-87-0 (±)-trans-(E)-4-(3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-7-methoxy-2,3-dihydrobenzofuran-2-yl)-2-methoxyphenol 
• 118799-81-8 methyl (E)-3-<(2R*,3R*)-2,3-dihydro-7-methoxy-3-methoxycarbonyl-2-(3-methoxy-4-methoxymethoxyphenyl)-1-benzofuran-5-yl>propenoate 
• 118799-80-7 (E)-methyl 3-<(2RS,3SR)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonyl-1-benzofuran-5-yl>-1-propenoate 
• 2309-07-1 Methyl ferulate 
• 365211-52-5 2-(2-benzyloxy-5-bromo-3-methoxy-phenyl)-1-(4-benzyloxy-3-methoxy-phenyl)-propane-1,3-diol 
• 458-35-5 coniferal alcohol 
• 33050-60-1 2,3-dihydroxy-4-methoxy-9H-xanthen-9-one 
• 118799-85-2 (E)-3-[(2R*,3S*)-2,3-dihydro-3-hydroxymethyl-7-methoxy-2-(3-methoxy-4-methoxymethoxyphenyl)-1-benzofuran-5-yl]-2-propenal 
• 118799-83-0 (E)-3-<(2R*,3S*)-2,3-dihydro-3-hydroxymethyl-7-methoxy-2-(3-methoxy-4-methoxymethoxyphenyl)-1-benzofuran-5-yl>-2-propen-1-ol 

Relevant articles and documents

Pinus taeda phenylpropenal double-bond reductase: Purification, cDNA cloning, heterologous expression in Escherichia coli, and subcellular localization in P. taeda

A phenylpropenal double-bond reductase (PPDBR) was obtained from cell suspension cultures of loblolly pine (Pinus taeda L.). Following trypsin digestion and amino acid sequencing, the cDNA encoding this protein was subsequently cloned, with the functional recombinant protein expressed in Escherichia coli and characterized. PPDBR readily converted both dehydrodiconiferyl and coniferyl aldehydes into dihydrodehydrodiconiferyl and dihydroconiferyl aldehydes, when NADPH was added as cofactor. However, it was unable to reduce directly either the double bond of dehydrodiconiferyl or coniferyl alcohols in the presence of NADPH. During this reductive step, the corresponding 4-proR hydrogen was abstracted from [4R-3H]-NADPH during hydride transfer. This is thus the first report of a double-bond reductase involved in phenylpropanoid metabolism, and which is presumed to be involved in plant defense. In situ mRNA hybridization indicated that the PPDBR transcripts in P. taeda stem sections were localized to the vascular cambium, as well as to radial and axial parenchyma cell types. Additionally, using P. taeda cell suspension culture crude protein extracts, dehydrodiconiferyl and coniferyl alcohols could be dehydrogenated to afford dehydrodiconiferyl and coniferyl aldehydes. Furthermore, these same extracts were able to convert dihydrodehydrodiconiferyl and dihydroconiferyl aldehydes into the corresponding alcohols. Taken together, these results indicate that in the crude extracts dehydrodiconiferyl and coniferyl alcohols can be converted to dihydrodehydrodiconiferyl and dihydroconiferyl alcohols through a three-step process, i.e. by initial phenylpropenol oxidation, then sequential PPDBR and phenylpropanal reductions, respectively.

Synthesis and structural elucidation of xanthonolignoids: Trans-(±)- kielcorin B and trans-(±)-isokielcorin B

This paper reports the synthesis and characterization of two isomeric xanthonolignoids - trans-(±)-kielcorin B and trans-(±)isokielcorin B. The synthetic approach is based on the oxidative coupling of 2,3-dihydroxy-4- methoxyxanthone with coniferyl alcohol in the presence of silver carbonate. The structural elucidation of these compounds was achieved by extensive NMR studies: 1H and 13C NMR spectra, homonuclear correlation spectroscopy (COSY, COSYLR), heteronuclear correlation spectroscopy (HETCOR), nuclear Overhauser effect (NOE) and one-dimensional selective INEPT. The NMR spectroscopic techniques used in this study led to an unambiguous characterisation of trans-(±)-kielcorin B and trans-(±)-isokielcorin B, which includes the assignment of all proton and carbon resonances and the establishment of the substituents orientation and protons configurational relationship on their 1,4-dioxane ring.