5919-91-5

Basic information

• Product Name: 2-(3-methylbut-2-en-1-yl)benzene-1,4-diol
• Synonyms: 1,4-Benzenediol, 2-(3-methyl-2-butenyl)-; 2-(3-Methyl-2-butenyl)-1,4-benzenediol
• CAS NO: 5919-91-5
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.2277
• Mol File: 5919-91-5.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 331.9°C at 760 mmHg
• Flash Point: 161°C
• Density: 1.099g/cm³
• Vapor Pressure: 7.83E-05mmHg at 25°C
• Refractive Index: 1.572
• CAS DataBase Reference: 2-(3-methylbut-2-en-1-yl)benzene-1,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-methylbut-2-en-1-yl)benzene-1,4-diol(5919-91-5)
• EPA Substance Registry System: 2-(3-methylbut-2-en-1-yl)benzene-1,4-diol(5919-91-5)

Safety Data

• Hazardous Substances Data: 5919-91-5(Hazardous Substances Data)

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

• 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 
• 556-82-1 3-methyl-2-buten-1-ol 
• 870-63-3 prenyl bromide 
• 1138-41-6 4-hydroxy-3-prenylbenzoic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 150-76-5 4-methoxy-phenol 
• 25974-58-7 4-methoxy-2-(3-methylbut-2-enyl)phenol 
• 34125-69-4 1-methoxy-4-(3-methylbut-2-enyloxy)-benzene 

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 
• 378198-06-2 2-[(E)-4-bromo-3-methyl-2-butenyl]-1,4-dibenzyloxybenzene 
• 378198-05-1 (E)-4-(2,5-dibenzyloxy)-2-methyl-2-buten-1-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 
• 378198-10-8 (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 
• 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 
• 378198-08-4 (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 
• 378198-07-3 [(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 

Relevant articles and documents

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

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.

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.