4049-39-2

Basic information

• Product Name: 3-HYDROXY-4-BENZYLOXY BENZALDEHYDE
• Synonyms: 4-BENZYLOXY-3-HYDROXYBENZALDEHYDE;3-HYDROXY-4-BENZYLOXY BENZALDEHYDE;4-HYDROXY-4-BENZYLOXYBENZALDEHYDE;4-BENZLOXY-3-HYDROXYBENZALDEHYLE;4-BENZLOXY-3-HYDROXYBENZALDEHYDE;3-Hydroxy-4-(phenylmethoxy)benzaldehyde;Protocatechuic Aldehyde-4-benzyl Ether
• CAS NO: 4049-39-2
• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 228.24
• Product Categories: Aromatics
• Mol File: 4049-39-2.mol

Chemical Properties

• Melting Point: 120 °C(Solv: ethanol (64-17-5))
• Boiling Point: 403.3°Cat760mmHg
• Flash Point: 155.4°C
• Appearance: /
• Density: 1.238g/cm³
• Vapor Pressure: 4.41E-07mmHg at 25°C
• Refractive Index: 1.636
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.79±0.35(Predicted)
• CAS DataBase Reference: 3-HYDROXY-4-BENZYLOXY BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-4-BENZYLOXY BENZALDEHYDE(4049-39-2)
• EPA Substance Registry System: 3-HYDROXY-4-BENZYLOXY BENZALDEHYDE(4049-39-2)

Safety Data

• Hazardous Substances Data: 4049-39-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxy-4-benzyloxy benzaldehyde is used as a key intermediate in the synthesis of quinazoline derivatives for the pharmaceutical industry. These derivatives are known for their diverse biological activities, including anti-cancer, anti-bacterial, and anti-viral properties. 3-HYDROXY-4-BENZYLOXY BENZALDEHYDE's unique structure allows for the development of new drugs with improved efficacy and reduced side effects.
Used in Chemical Industry:
In the chemical industry, 3-hydroxy-4-benzyloxy benzaldehyde is utilized as a building block for the creation of various complex organic molecules. Its versatile structure enables the synthesis of a wide array of compounds with different functional groups, making it a valuable asset in the development of new materials and chemicals for various applications.
Used in Research and Development:
3-Hydroxy-4-benzyloxy benzaldehyde is also employed in research and development settings, where it is used to study the properties and reactivity of aromatic aldehydes. This knowledge can be applied to the design and synthesis of new compounds with specific characteristics, such as improved stability, solubility, or reactivity.

InChI:InChI=1/C14H12O3/c15-9-12-6-7-14(13(16)8-12)17-10-11-4-2-1-3-5-11/h1-9,16H,10H2

Upstream product

• 120-57-0 piperonal 
• 20194-18-7 sodium phenyl-methanolate 
• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 100-39-0 benzyl bromide 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 

Downstream Products

• 128944-40-1 2-(Benzyloxy)-5-(2-nitroethenyl)phenol 
• 135203-56-4 ethyl 4-(2-benzyloxy-5-formylphenoxy)benzoate 
• 2572-08-9 2-Benzyloxy-4',5-diformyl-2'-nitro-diphenyl-aether 
• 64974-45-4 4-(benzyloxy)-3-(methoxymethoxy)benzaldehyde 
• 172919-15-2 ethyl 3-(3'-hydroxy-4'-benzyloxyphenyl)-2E-propenoate 
• 149428-76-2 4-(benzylbenzyloxy)-3-phenoxybenzaldehyde 
• 383423-91-4 4-benzyloxy-3-pent-4-enyloxy-benzaldehyde 
• 383423-90-3 4-benzyloxy-3-but-3-enyloxy-benzaldehyde 
• 383423-97-0 4-benzyloxy-3-decyloxy-benzaldehyde 
• 214847-86-6 3-allyloxy-4-benzyloxy-benzaldehyde 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 486395-55-5 4,4'-bis(benzyloxy)-3,3'-oxybis(ethyleneoxy)dibenzaldehyde 
• 650606-30-7 4-benzyloxy-3-hexyloxybenzaldehyde 
• 149428-94-4 4-Benzyloxy-3-(2-phenylethoxy)phenylacetic acid 

Relevant articles and documents

Fluoroethoxylanin as well as preparation method and application thereof

The invention relates to fluoroethoxylanin as well as a preparation method and application thereof. The preparation method comprises the following steps: firstly, 3,4 -hydroxybenzaldehyde and benzyl chloride serve as raw materials, and 3 -hydroxy -4 -benzyloxybenzaldehyde is prepared. The product is reacted with bromomethyl methyl ether, and the product is sequentially subjected Wittig reaction, reduction reaction and alkylation reaction, and the obtained product is reacted with p-toluenesulfonic acid chloride to obtain fifth intermediate. Finally fifth intermediate and complexing agent K are added. 2.2.2 . Reaction of potassium fluoride and acidification of the product gave the above fluoroethoxylanolin. Compared with the prior art, the fluoroethoxylanin prepared by the invention can reflect the distribution of the tracer in the local tissue of the organism, thereby visualizing the tumors, and providing the metabolic information targeting metabolic pathway types and.

NOVEL BENZYLIDENEACETONE DERIVATIVE AND USE THEREOF

The present invention relates to novel benzylideneacetone derivatives or uses thereof, more specifically, the present invention relates to a pharmaceutical composition for preventing or treating, or food composition for ameliorating a cancer or a bone disease comprising a compound defined by Formula 1 or pharmaceutically acceptable salt thereof as an active ingredient. Since compounds according to the present invention exhibit strong inhibitory activity on proliferation and differentiation of osteoclast, and activity on proliferation and differentiation of osteoblast, it can be usefully used to develop safe and effective anti-cancer agents, and therapeutic agents for preventing and treating or foods for ameliorating bone diseases including osteoporosis, and the like.

Synthesis of a Photo-Caged DOPA Derivative by Selective Alkylation of 3,4-Dihydroxybenzaldehyde

Natural and synthetic polymers containing the catechol moiety of noncoded amino acid 3,4-dihydroxyphenylalanine (DOPA) are capable of metal-coordination and adhesion under wet conditions. Masking the catechol subunit with a photo-cleavable group would provide an opportunity to design tunable adhesion properties that are especially important for biomaterial and biomedicine applications. Herein, we report the regioselective synthesis of a photo-caged DOPA bearing an ortho-nitrobenzyl (oNB) group that is capable of undergoing cleavage upon irradiation with UV light. We developed a selective synthetic route towards a 3-O-oNB alkylated DOPA regioisomer that can be readily incorporated into proteins by using a previously developed bio-expression platform. The synthesis is based on a regioselectivity switch in 3,4-dihydrozybenzaldehyde alkylation upon application of different equivalents of deprotonating base. The enantiomerically pure 3-O-oNB-DOPA was prepared on a gram scale and proved to be generally compatible with the solid-phase peptide synthesis conditions. We also demonstrate the general applicability of the developed synthetic strategy by providing the synthesis of 3-O-methyl-DOPA.

Neladenoson Bialanate Hydrochloride: A Prodrug of a Partial Adenosine A1 Receptor Agonist for the Chronic Treatment of Heart Diseases

Adenosine is known to be released under a variety of physiological and pathophysiological conditions to facilitate the protection and regeneration of injured ischemic tissues. The activation of myocardial adenosine A1 receptors (A1Rs) has been shown to inhibit myocardial pathologies associated with ischemia and reperfusion injury, suggesting several options for new cardiovascular therapies. When full A1R agonists are used, the desired protective and regenerative cardiovascular effects are usually overshadowed by unintended pharmacological effects such as induction of bradycardia, atrioventricular (AV) blocks, and sedation. These unwanted effects can be overcome by using partial A1R agonists. Starting from previously reported capadenoson we evaluated options to tailor A1R agonists to a specific partiality range, thereby optimizing the therapeutic window. This led to the identification of the potent and selective agonist neladenoson, which shows the desired partial response on the A1R, resulting in cardioprotection without sedative effects or cardiac AV blocks. To circumvent solubility and formulation issues for neladenoson, a prodrug approach was pursued. The dipeptide ester neladenoson bialanate hydrochloride showed significantly improved solubility and exposure after oral administration. Neladenoson bialanate hydrochloride is currently being evaluated in clinical trials for the treatment of heart failure.

Generation of Benzyne Species from Diphenylphosphoryl Derivatives: Simultaneous Exchange of Three Functional Groups

Interaction of (2-diphenylphosphoryl-3-iodo-4-methoxy-phenyl) methanol with NaH in DMF at ambient temperature results in the generation of benzyne intermediates that can be trapped by furan or DMF. Trapping with DMF forms 3-(dimethylaminomethyl)-2-hydroxy-6-methoxybenzaldehyde demonstrating the simultaneous exchange of three functionalities in a single step. The presence of the alkoxy substituent adjacent to iodine is critical for high regioselectivity addition of DMF. The corresponding bromide or triflate can be used in place of the iodide with equal efficiency. This methodology was used to synthesize the reported structure of gigasol and leading to a structural reassignment of this biscoumarin natural product.

Total Synthesis of the Antiviral Natural Product Houttuynoid B

The first total synthesis of houttuynoid B, a powerful antiviral flavonoid glycoside from the Chinese plant Houttuynia cordata, is described. In a key step, a Baker-Venkataraman rearrangement employing an already glycosylated substrate was used to efficiently set up the fully functionalized carbon skeleton. The required benzofuran building block was prepared through a domino Sonogashira coupling/5-endo-dig cyclization and converted into a stable 1-hydroxybenzotriazole-derived active ester prior to linking with a galactosylated hydroxyacetophenone unit. The elaborated synthesis requires only nine steps (11 % overall yield) along the longest linear sequence and paves the way for the preparation of structurally related compounds for further biological evaluation.

NOVEL FLAVONOID COMPOUNDS AND USES THEREOF

The present disclosure provides a compound of the following formula, racemates, enantiomers, prodrugs and salts thereof: Formula (I). Also provided is the use of these compounds for the treatment of ischemia and reperfusion injuries. Further applications include the treatment of diseases caused by cell apoptosis and / or cell necrosis.

First total synthesis of salvianolic acid C, tournefolic acid A, and Tournefolal

First total synthesis of the natural product salvianolic acid C, tournefolal and tournefolic acid A has been described. The key benzofuran skeletons are prepared via selective iodination and Sonogashira reaction. ARKAT-USA, Inc.

New 5-benzylidenethiazolidin-4-one inhibitors of bacterial MurD ligase: Design, synthesis, crystal structures, and biological evaluation

Mur ligases (MurC-MurF), a group of bacterial enzymes that catalyze four consecutive steps in the formation of cytoplasmic peptidoglycan precursor, are becoming increasingly adopted as targets in antibacterial drug design. Based on the crystal structure of MurD cocrystallized with thiazolidine-2,4-dione inhibitor I, we have designed, synthesized, and evaluated a series of improved glutamic acid containing 5-benzylidenerhodanine and 5-benzylidenethiazolidine-2, 4-dione inhibitors of MurD with IC50 values up to 28 μM. Inhibitor 37, with an IC50 of 34 μM, displays a weak antibacterial activity against S. aureus ATCC 29213 and E. faecalis ATCC 29212 with minimal inhibitory concentrations of 128 μg/mL. High-resolution crystal structures of MurD in complex with two new inhibitors (compounds 23 and 51) reveal details of their binding modes within the active site and provide valuable information for further structure-based optimization.

Regioselective alkylation of catechols via Mitsunobu reactions

A mild and efficient Mitsunobu protocol for the regioselective alkylation of catechols such as 3,4-dihydroxybenzaldehyde and methyl 3,4-dihydroxybenzoate is described. The para-alkylation products could be easily prepared via the Mitsunobu reaction with high selectivity in moderate to good yields. Georg Thieme Verlag Stuttgart - New York.