5919-91-5

Usage

antimicrobial properties

MI is effective in killing or inhibiting the growth of bacteria, fungi, and other microorganisms, which is why it is used as a preservative.

Associated with allergic reactions

MI has been linked to a high risk of allergic reactions, particularly in individuals with sensitive skin.

Regulation and restriction

Due to the potential health risks associated with MI, its use in certain products and regions has been restricted or banned.

Effectiveness vs

While MI has proven effective as a preservative, its potential for causing skin irritation and allergies has led to increased scrutiny and regulation of its use in consumer products.

Upstream product

• 32328-83-9 4-(3-methyl-2-butenoxy)phenol 
• 104108-29-4 prenyl tributylstannane 
• 106-51-4 p-benzoquinone 
• 114067-34-4 (3-methyl-2-butenyl)trifluorosilane 
• 5594-02-5 2-(3-methyl-2-buten-1-yl)-2,5-cyclohexadiene-1,4-dione 
• 115-18-4 2-methyl-3-buten-2-ol 
• 123-31-9 hydroquinone 
• 78-79-5 isoprene 
• 34125-69-4 1-methoxy-4-(3-methylbut-2-enyloxy)-benzene 
• 123-08-0 4-hydroxy-benzaldehyde 
• 870-63-3 prenyl bromide 
• 556-82-1 3-methyl-2-buten-1-ol 
• 1138-41-6 4-hydroxy-3-prenylbenzoic acid 
• 150-76-5 4-methoxy-phenol 

Downstream Products

• 19012-99-8 6-hydroxy-2,2-dimethyl-2H-chromene 
• 5594-02-5 2-(3-methyl-2-buten-1-yl)-2,5-cyclohexadiene-1,4-dione 
• 378198-04-0 1,4-dibenzyloxy-2-(3-methyl-2-butenyl)benzene 
• 378198-07-3 [(E)-(1R,2R)-4-Benzenesulfonyl-8-(2,5-bis-benzyloxy-phenyl)-2,6-dimethyl-1-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-oct-6-enyloxy]-tert-butyl-dimethyl-silane 
• 378198-08-4 (2R,3R,7E)-2-(tert-butyldimethylsiliyloxy)-9-(2,5-dibenzyloxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonene 
• 378198-09-5 (2R,3R,7E)-9-(2,5-dibenzyloxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonen-2-ol 
• 378198-10-8 (2R,3R,7E)-9-(2,5-dihydroxyphenyl)-3,7-dimethyl-1-[(1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-naphthalenyl]-7-nonen-2-ol 
• 1026602-48-1 2-[(E)-(7R,8R)-8-Hydroxy-3,7-dimethyl-9-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-non-2-enyl]-[1,4]benzoquinone 
• 378198-05-1 (E)-4-(2,5-dibenzyloxy)-2-methyl-2-buten-1-ol 
• 378198-06-2 2-[(E)-4-bromo-3-methyl-2-butenyl]-1,4-dibenzyloxybenzene 

Relevant academic research and scientific papers

Magnesium dicarboxylates promote the prenylation of phenolics that is extended to the total synthesis of icaritin

The prenylation of phenolic substrates promoted by magnesium dicarboxylates was developed. An investigation of the scope demonstrated that substrates with electron-donating group(s) gave better yields than those with electron-withdrawing group(s). Althoug

Construction of a meroterpenoid-like compound collection by precursor-assisted biosynthesis

Natural products (NPs) and their derivatives play a pivotal role in drug discovery due to their complexity and diversity. The strategies to rapidly generate NP-like compounds offer unique opportunities to access bioactive compounds. Here we present a new approach, precursor-assisted biosynthesis (PAB), for the creation of NP-like compounds by combination of artificial supplementation of common precursors and divergent post-modifications of precursor-deficient fungi. This method was applied to construct a meroterpenoid-like compound collection containing 43 compounds with diverse molecular scaffolds. Extensive bioactive screening of the collection revealed novel STING (stimulator of interferon genes) inhibitors, cytotoxic and antifungal compounds. This result indicates that PAB is an effective methodology for producing compound collections for the purpose of drug discovery.

Synthesis and antitumor activity evaluation of compounds based on toluquinol

Encouraged by the promising antitumoral, antiangiogenic, and antilymphangiogenic properties of toluquinol, a set of analogues of this natural product of marine origin was synthesized to explore and evaluate the effects of structural modifications on their cytotoxic activity. We decided to investigate the effects of the substitution of the methyl group by other groups, the introduction of a second substituent, the relative position of the substituents, and the oxidation state. A set of analogues of 2-substituted, 2,3-disubstituted, and 2,6-disubstituted derived from hydroquinone were synthesized. The results revealed that the cytotoxic activity of this family of compounds could rely on the hydroquinone/benzoquinone part of the molecule, whereas the substituents might modulate the interaction of the molecule with their targets, changing either its activity or its selectivity. The methyl group is relevant for the cytotoxicity of toluquinol, since its replacement by other groups resulted in a significant loss of activity, and in general the introduction of a second substituent, preferentially in the para position with respect to the methyl group, was well tolerated. These findings provide guidance for the design of new toluquinol analogues with potentially better pharmacological properties.

Alkylation of Phenol And Hydroquinone by Prenol in the Presence of Organoaluminum Catalysts

Prenylphenols and 2,2-dimethylbenzopyrans were synthesized via alkylation of phenol and hydroquinone with prenol in the presence of organoaluminum catalysts, i.e., aluminum phenoxide and isopropoxide. Reaction products were isolated and characterized. Sev

A Monooxygenase from Boreostereum vibrans Catalyzes Oxidative Decarboxylation in a Divergent Vibralactone Biosynthesis Pathway

The oxidative decarboxylation of prenyl 4-hydroxybenzoate to prenylhydroquinone has been frequently proposed for the biosynthesis of prenylated (hydro)quinone derivates (sometimes meroterpenoids), yet no corresponding genes or enzymes have so far been reported. A FAD-binding monooxygenase (VibMO1) was identified that converts prenyl 4-hydroxybenzoate into prenylhydroquinone and is likely involved in the biosynthesis of vibralactones and other meroterpenoids in the basidiomycete Boreostereum vibrans. Feeding of 3-allyl-4-hydroxybenzylalcohol, an analogue of the vibralactone pathway intermediate 3-prenyl-4-hydroxybenzylalcohol, generated 20 analogues with different scaffolds. This demonstrated divergent pathways to skeletally distinct compounds initiating from a single precursor, thus providing the first insight into a novel biosynthetic pathway for 3-substituted γ-butyrolactones from a shikimate origin.

Avarol derivatives as competitive AChE inhibitors, non hepatotoxic and neuroprotective agents for Alzheimer's disease

Avarol is a marine sesquiterpenoid hydroquinone, previously isolated from the marine sponge Dysidea avara Schmidt (Dictyoceratida), with antiinflammatory, antitumor, antioxidant, antiplatelet, anti-HIV, and antipsoriatic effects. Recent findings indicate

Alternative Lewis acids to effect Claisen rearrangement

Yb(OTf)3 and DIBAL-H are developed as alternative Lewis acids for effecting Claisen rearrangement of allyl, crotyl and prenyl aryl ethers.

Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid-phase synthesis of benzopyrans

Herein we report a novel strategy for the design and construction of natural and natural product-like libraries based on the principle of privileged structures, a term originally introduced to describe structural motifs capable of interacting with a variety of unrelated molecular targets. The identification of such privileged structures in natural products is discussed, and subsequently the 2,2-dimethylbenzopyran moiety is selected as an inaugural template for the construction of natural product-like libraries via this strategy. Initially, a novel solid-phase synthesis of the benzopyran motif is developed employing a unique cycloloading strategy that relies on the use of a new, polystyrene-based selenenyl bromide resin. Once the loading, elaboration, and cleavage of these benzopyrans was established, this new solid-phase method was then thoroughly validated through the construction of six focused combinatorial libraries designed around natural and designed molecules of recent biological interest.

Reaction between phenols and isoprene under zeolite catalysis. Highly selective synthesis of chromans and o-isopentenylphenols

Chromans 3 and o-isopentenylphenols 4 are synthesized in satisfactory to good yields and selectivities by the reaction of phenols and isoprene in the presence of the commercially available acid faujasite zeolite HSZ-360.

Total synthesis of polyprenylhydroquinols and benzoquinones

The total synthesis of polyprenylhydroquinols and benzoquinones is described.First, two appropriate aromatic allyl carbonates (moieties with one and two prenyls) and two activated bifunctional terpenyl derivatives (moieties with two and three prenyls) were synthesized.These molecules were then reacted together using a highly regio- and stereoselective coupling with Pd(PPh3)4 as a catalyst.The synthesis was achieved by functional group elimination and formation of quinonic and hydroquinonic moieties. - Keywords: polyprenylbenzoquinol; polyprenylhydroquinone; allylcarbonate; ?-allyl palladium complex