61152-62-3

Usage

Uses

Used in Pharmaceutical Industry:
4-(3,4-Dihydroxyphenyl)-2-butane is used as a therapeutic agent for the treatment of Parkinson's disease, a neurological disorder characterized by the degeneration of dopamine-producing cells in the brain. It functions by replenishing dopamine levels in the patients' brains, effectively alleviating their symptoms and improving motor function.
Used in Neurotransmitter Synthesis:
L-Dopa serves as a precursor in the biosynthesis of important neurotransmitters such as dopamine, norepinephrine, and epinephrine. These neurotransmitters are essential for various brain functions, including mood regulation, motor control, and cognitive processes. By providing L-Dopa, the body can maintain optimal levels of these neurotransmitters, supporting overall brain health and function.

Upstream product

• 5471-51-2 4-(4-hydroxyphenyl)-2-oxobutane 
• 121-33-5 vanillin 
• 1080-12-2 Dehydrozingerone 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 123694-03-1 (E)-4-(3′,4′-dihydroxyphenyl)but-3-en-2-one 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 

Downstream Products

• 61152-58-7 4-(3',4'-dihydroxyphenyl)-2-butanol 
• 79622-76-7 3,4-Dimethoxy-(3'-hydroxybutyl)-benzol 
• 63212-99-7 (4E,6E)-1-(3,4-dihydroxyphenyl)-7-phenylhepta-4,6-dien-3-one 

Relevant academic research and scientific papers

Synthesis of Yakuchinone B-Inspired Inhibitors against Islet Amyloid Polypeptide Aggregation

Type 2 diabetes mellitus (T2DM) is associated with pancreatic β-cell dysfunction and insulin resistance. Islet amyloid polypeptide (IAPP) aggregation is found to induce islet β-cell death in T2DM patients. Recently, we demonstrated that yakuchinone B deri

Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal

Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.

Synthesis and studies of the inhibitory effect of hydroxylated phenylpropanoids and biphenols derivatives on tyrosinase and laccase enzymes

The impaired activity of tyrosinase and laccase can provoke serious concerns in the life cycles of mammals, insects and microorganisms. Investigation of inhibitors of these two enzymes may lead to the discovery of whitening agents, medicinal products, anti-browning substances and compounds for controlling harmful insects and bacteria. A small collection of novel reversible tyrosinase and laccase inhibitors with a phenylpropanoid and hydroxylated biphenyl core was prepared using naturally occurring compounds and their activity was measured by spectrophotometric and electrochemical assays. Biosensors based on tyrosinase and laccase enzymes were constructed and used to detect the type of protein-ligand interaction and half maximal inhibitory concentration (IC50). Most of the inhibitors showed an IC50 in a range of 20–423 nM for tyrosinase and 23–2619 nM for laccase. Due to the safety concerns of conventional tyrosinase and laccase inhibitors, the viability of the new compounds was assayed on PC12 cells, four of which showed a viability of roughly 80% at 40 μM. In silico studies on the crystal structure of laccase enzyme identified a hydroxylated biphenyl bearing a prenylated chain as the lead structure, which activated strong and effective interactions at the active site of the enzyme. These data were confirmed by in vivo experiments performed on the insect model Tenebrio molitur.

Tyrosinase-catalyzed oxidation of the leukoderma-inducing agent raspberry ketone produces (E)-4-(3-Oxo-1-butenyl)-1,2-benzoquinone: Implications for melanocyte toxicity

The exposure of human skin to 4-(4-hydroxyphenyl)-2-butanone (raspberry ketone, RK) is known to cause chemical/occupational leukoderma. RK has a structure closely related to 4-(4-hydroxyphenyl)-2-butanol (rhododendrol), a skin whitening agent that was found to cause leukoderma in the skin of consumers in 2013. Rhododendrol is a good substrate for tyrosinase and causes a tyrosinase-dependent cytotoxicity to melanocytes, cells that are responsible for skin pigmentation. Therefore, it is expected that RK exerts its cytotoxicity to melanocytes through the tyrosinase-catalyzed oxidation to cytotoxic oquinones. The results of this study demonstrate that the oxidation of RK by mushroom tyrosinase rapidly produces 4-(3- oxobutyl)-1,2-benzoquinone (RK-quinone), which is converted within 10-20 min to (E)-4-(3-oxo-1-butenyl)-1,2-benzoquinone (DBL-quinone). These quinones were identified as their corresponding catechols after reduction by ascorbic acid. RK-quinone and DBL-quinone quantitatively bind to the small thiol N-acetyl-L-cysteine to form thiol adducts and can also bind to the thiol protein bovine serum albumin through its cysteinyl residue. DBL-quinone is more reactive than RK-quinone, as judged by their half-lives (6.2 min vs 10.5 min, respectively), and decays rapidly to form an oligomeric pigment (RK-oligomer). The RKoligomer can oxidize GSH to GSSG with a concomitant production of hydrogen peroxide, indicating its pro-oxidant activity, similar to that of the RD-oligomer. These results suggest that RK is cytotoxic to melanocytes through the binding of RK-derived quinones to thiol proteins and the pro-oxidant activity of the RK-oligomer.

Synthesis of new biosynthetically important diarylheptanoids and their oxa- and fluoro-analogues by three different strategies

Wittig, aldol and Wittig-Horner reactions have been used to synthesize new diarylheptanoids, which are putative intermediates in phenylphenalenone biosynthesis in plants. The Wittig-Horner approach was most suitable and gave significantly higher yields in comparison with other methods.

Dihydroxyphenyl compounds and glucoside compounds thereof

The present invention is a compound represented by the following formula (1) or (2): where one of R1 and R2 is hydrogen and the other one is hydrogen or glucose residue. The compound is effective for reforming obese constitution, sup

Very long-chain phenylpropyl and phenylbutyl esters from Taxus baccata needle cuticular waxes

The cuticular wax of Taxus baccata L. needles was found to contain four different classes of long-chain esters that were identified by various chemical transformations with product assignment employing GC-MS. Homologous series of (1) 3-(4′-hydroxyphenyl)-propyl esters of C20-C36 fatty acids, (2) 4-(4′-hydroxyphenyl)-2-butyl esters of C18-C28 fatty acids, (3) 3-(3′,4′-dihydroxyphenyl)-propyl esters of C20-C32 fatty acids, and (4) 4-(3′,4′-dihydroxyphenyl)-2-butyl esters of C18-C28 fatty acids were identified. The four compound classes amounted to 0.1-3.6 μg/cm2 of needle surface area, corresponding to 0.2-7.6% of the wax mixture, respectively. While both phenylpropyl ester series had a maximum for the homolog containing tetracosanoic acid, in the phenylbutyl esters homologs containing eicosanoic and docosanoic acids predominated.

PHENYLBUTAN-2-ONE β-D-GLUCOSIDES FROM RASPBERRY FRUIT

From a methanolic extract of raspberry fruit, the 4'-O-β-D-glucopyranoside of 4-(4'-hydroxyphenyl)butan-2-one (raspberry ketone) and the 3'-O-β-D-glucopyranoside of 4-(3',4'-dihydroxyphenyl)butan-2-one were isolated by liquid chromatography on XAD-2, Sephadex LH-20 and RP-18 as well as by HPLC on a diol phase.Identifications were carried out by 1H and 13C NMR spectroscopy, using synthetic reference compounds.Assignment of the carbon resonances was made by DEPT and INADEQUATE experiments.The effects of glucosylation on the 13C NMR spectra of phenylbutanone derivatives are discussed.