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

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

Uses

Used in Pharmaceutical Industry:
Balaphonin is used as an anti-inflammatory agent for its potential in treating conditions such as arthritis and chronic pain. Its ability to reduce inflammation and alleviate pain makes it a valuable component in the development of new medications for these conditions.
Used in Neurodegenerative Disease Treatment:
Balaphonin is used as a neuroprotective agent for its potential in treating neurodegenerative diseases. Its neuroprotective effects suggest that it could play a role in the development of treatments for conditions such as Alzheimer's and Parkinson's disease.
Used in Oxidative Stress-Related Conditions:
Balaphonin is used as an antioxidant for its potential in treating oxidative stress-related conditions. Its antioxidant properties may help protect cells from damage caused by reactive oxygen species, reducing the risk of various diseases associated with oxidative stress.

Upstream product

• 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 
• 458-35-5 coniferal alcohol 
• 33050-60-1 2,3-dihydroxy-4-methoxy-9H-xanthen-9-one 
• 4263-87-0 (±)-trans-(E)-4-(3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-7-methoxy-2,3-dihydrobenzofuran-2-yl)-2-methoxyphenol 
• 365211-52-5 2-(2-benzyloxy-5-bromo-3-methoxy-phenyl)-1-(4-benzyloxy-3-methoxy-phenyl)-propane-1,3-diol 
• 2309-07-1 Methyl ferulate 
• 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 
• 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 
• 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 

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.

A new synthesis of two naturally occurring dihydrobenzo[b]furan-type neolignans of potential biological activity

A new synthesis of the racemates of two naturally occurring neolignans 1 and 2 was achieved via the 2,3-dihydrobenzo[b]furan derivative 3, starting from the commercially available materials o-vanillin (6) and acetovanillone (9). Benzofurans, Neolignan, Heck Reaction.

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.

Total Synthesis of Two Naturally Occurring Neolignans of Potential Biological Activity

The first synthesis of the racemates of two naturally occurring neolignans, 1 and 2, was accomplished starting from methyl ferulate.