22009-38-7

Basic information

• Product Name: 7-Hydroxy-1-tetralone
• Synonyms: 7-Hydroxy-3,4-dihydronaphthalen-1(2H);1(2H)-Naphthalenone,3,4-dihydro-7-hydroxy-;7-HYDROXY-1-TETRALONE;7-Hydroxy-3,4-dihydro-2H-naphthalen-1-one;7-hydroxyl-1-tetralone;4-dihydro-7-hydroxy-;7-hydroxy-3,4-dihydronaphthalen-1(2H)-one;7-Hydroxy-1-tetralone 7-Hydroxy-3,4-dihydronaphthalen-1(2H)
• CAS NO: 22009-38-7
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• EINECS: 219-048-0
• Mol File: 22009-38-7.mol

Chemical Properties

• Melting Point: 164.0 to 168.0 °C
• Boiling Point: 215°C/12mmHg(lit.)
• Flash Point: 146.8 °C
• Appearance: /
• Density: 1.236 g/cm³
• Vapor Pressure: 3.25E-05mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.44±0.20(Predicted)
• CAS DataBase Reference: 7-Hydroxy-1-tetralone(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Hydroxy-1-tetralone(22009-38-7)
• EPA Substance Registry System: 7-Hydroxy-1-tetralone(22009-38-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 22009-38-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-Hydroxy-1-tetralone is used as a pharmacological tool for studying the human histamine H3 receptor. It plays a crucial role in modulating various physiological processes, including wakefulness, appetite, and cognitive function. The compound has shown potential in the development of drugs targeting the histamine H3 receptor for the treatment of various disorders, such as attention deficit hyperactivity disorder (ADHD), Alzheimer's disease, and obesity.
Used in Enzyme Inhibition:
7-Hydroxy-1-tetralone and its derivatives have been studied as inhibitors of monoamine oxidase (MAO), an enzyme involved in the breakdown of neurotransmitters such as serotonin, dopamine, and norepinephrine. Inhibition of MAO can help maintain the levels of these neurotransmitters in the brain, which may be beneficial in the treatment of various psychiatric and neurological disorders, including depression, anxiety, and Parkinson's disease.
Used in Fluorescent Chalcone Synthesis:
7-Hydroxy-1-tetralone and related fluorescent chalcones have been used in the development of novel fluorescent probes for biological imaging and sensing applications. These chalcones exhibit strong fluorescence properties, making them suitable for detecting and monitoring various biological processes and interactions at the molecular level.

InChI:InChI=1/C10H10O2/c11-8-5-4-7-2-1-3-10(12)9(7)6-8/h4-6,11H,1-3H2

Upstream product

• 6836-19-7 7-Methoxy-1-tetralone 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 51417-24-4 4a-acetoxy-5,6,7,8-tetrahydro-4aH-naphthalen-2-one 
• 575-38-2 1,7-Dihydroxynaphthalene 
• 1125-78-6 5,6,7,8-Tetrahydro-2-naphthol 
• 58008-75-6 7-Oxa-bicyclo[4.1.0]heptan-2-one oxime 
• 67730-57-8 3-nitro-2-cyclohexen-1-ol 
• 77970-17-3 3-nitrocyclohex-2-ene-1-one 

Downstream Products

• 22129-60-8 1,2,3,4-tetrahydronaphthalene-1,7-diol 
• 85178-55-8 BE 2392 
• 144464-65-3 7-Trifluoromethanesulphonyloxy-1,2,3,4-tetrahydronaphthalen-1-one 
• 936352-24-8 7-(2-morpholino-4-yl-ethoxy)-1-tetralone 
• 32263-64-2 7-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one 
• 6836-19-7 7-Methoxy-1-tetralone 
• 204588-81-8 7-tert-butyldimethylsilyloxy-1,2,3,4-tetrahydronaphthalen-1-one 
• 229006-58-0 7-(4-methylphenyl)-3,4-dihydronaphthalen-1(2H)-one 
• 724767-18-4 3-(4-methylphenyl)-5,7,8,9-tetrahydro-6H-benzo[a][7]annulen-6-one 
• 724767-19-5 2-(4-methylphenyl)-6,7-dihydro-5H-benzo[a][7]annulen-8-yl trifluoromethanesulfonate 
• 204588-82-9 7-tert-butyldimethylsilyloxy-1,2,3,4-tetrahydro-1-naphthol 

Relevant articles and documents

Synthesis and evaluation of tetrahydroisoquinoline derivatives against Trypanosoma brucei rhodesiense

Human African Trypanosomiasis (HAT) is a neglected tropical disease caused by the parasitic protozoan Trypanosoma brucei (T. b.), and affects communities in sub-Saharan Africa. Previously, analogues of a tetrahydroisoquinoline scaffold were reported as having in vitro activity (IC50 = 0.25–70.5 μM) against T. b. rhodesiense. In this study the synthesis and antitrypanosomal activity of 80 compounds based around a core tetrahydroisoquinoline scaffold are reported. A detailed structure activity relationship was revealed, and five derivatives (two of which have been previously reported) with inhibition of T. b. rhodesiense growth in the sub-micromolar range were identified. Four of these (3c, 12b, 17b and 26a) were also found to have good selectivity over mammalian cells (SI > 50). Calculated logD values and preliminary ADME studies predict that these compounds are likely to have good absorption and metabolic stability, with the ability to passively permeate the blood brain barrier. This makes them excellent leads for a blood-brain barrier permeable antitrypanosomal scaffold.

The evaluation of 1-tetralone and 4-chromanone derivatives as inhibitors of monoamine oxidase

Abstract: Monoamine oxidase (MAO) is of much clinical relevance, and inhibitors of this enzyme are used in the treatment for neuropsychiatric and neurodegenerative disorders such as depression and Parkinson’s disease. The present study synthesises and evaluates the MAO inhibition properties of a series of 33 1-tetralone and 4-chromanone derivatives in an attempt to discover high-potency compounds and to expand on the structure–activity relationships of MAO inhibition by these classes. Among these series, eight submicromolar MAO-A inhibitors and 28 submicromolar MAO-B inhibitors are reported, with all compounds acting as specific inhibitors of the MAO-B isoform. The most potent inhibitor was a 1-tetralone derivative (1h) with IC50 values of 0.036 and 0.0011?μM for MAO-A and MAO-B, respectively. Interestingly, with the reduction of 1-tetralones to the corresponding alcohols, a decrease in MAO inhibition potency is observed. Among these 1-tetralol derivatives, 1p (IC50 = 0.785?μM) and 1o (IC50 = 0.0075?μM) were identified as particularly potent inhibitors of MAO-A and MAO-B, respectively. Potent compounds such as those reported here may act as leads for the future development of MAO-B specific inhibitors. Graphic abstract: The present study describes the MAO inhibitory activities of a series of 1-tetralone and 4-chromanone derivatives. Numerous high-potency MAO-B specific inhibitors were identified.[Figure not available: see fulltext.].

POLYMERIZABLE ABSORBERS OF UV AND HIGH ENERGY VISIBLE LIGHT

Described are polymerizable high energy light absorbing compounds of formula I: wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, and X are as described herein. The compounds absorb various wavelengths of ultraviolet and/or high energy visible light and are suitable for incorporation in various products, such as biomedical devices and ophthalmic devices.

COMPOUNDS WITH A BENZO[A]CARBAZOLE STRUCTURE AND USE THEREOF

The invention relates to compounds of general formula (I), and their use for the treatment and diagnosis of degenerative disorders characterised by high cell proliferation and/or tissue degeneration.

Process for preparing 7-hydroxy-3,4-dihydro-2H-1-naphthalenone

The invention discloses a process for preparing 7-hydroxy-3,4-dihydro-2H-1-naphthalenone. The process comprises preparation processes of salting reactions and hydrolysis reactions. The method for preparing 7-hydroxy-3,4-dihydro-2H-1-naphthalenone, which is disclosed by the invention, has the advantages that the fineness of aluminum trichloride is lowly required, only one solvent is used, the solvent is simple to recycle and treat, the production cost is low, the yield is high, the product purity is high, the process is applicable to industrial production.

Rapid probing of the reactivity of P450 monooxygenases from the CYP116B subfamily using a substrate-based method

Developing a detailed understanding of the reactivity of self-sufficient Type IV P450 monooxygenases, four types of O-methylated substrates were designed as probes, including monoterpenes, cycloalkanes, aromatic compounds and steroids, and the efficiency of their oxyfunction was determined using a colorimetric assay which was based on the reaction between the enzymatic demethylation product, formaldehyde, and Purpald dye. The activity-based fingerprints of new P450RpMO, P450ArMO and P450CtMO (CYP116B members) indicated that CYP116B P450s preferentially oxidize substrates with aromatic components. Moreover, the hydroxylated products were detected based on the preference results. This rapid and efficient strategy, when coupled with GCMS, enables the exploration of the reactivity of other CYP116B members.

The Synthesis and Evaluation of C7-Substituted α-Tetralone Derivatives as Inhibitors of Monoamine Oxidase

Based on a previous report that α-tetralone (3,4-dihydro-2H-naphthalen-1-one) is a promising scaffold for the design of highly potent inhibitors of the enzyme, monoamine oxidase, the present study investigates the monoamine oxidase inhibitory properties of a synthetic series of fifteen C7-substituted α-tetralone derivatives. Arylalkyloxy substitution on C7 of the α-tetralone moiety yielded compounds with high inhibition potencies toward the human monoamine oxidase-B isoform with all compounds possessing IC50 values in the submicromolar range (0.00089-0.047 μm). The C7-substituted α-tetralones also were highly potent monoamine oxidase-A inhibitors with thirteen (of fifteen) compounds possessing IC50 values in the submicromolar range (0.010-0.741 μm). The α-tetralones were, however, in each instance selective for monoamine oxidase-B over the monoamine oxidase-A isoform. Dialyses of enzyme-inhibitor mixtures show that, while a representative inhibitor acts as a reversible monoamine oxidase-A inhibitor, inhibition of monoamine oxidase-B is not readily reversed by dialysis. Using a molecular modeling approach, possible binding orientations and interactions of selected α-tetralones with the active sites of the monoamine oxidases are also proposed. This study suggests that C7-substituted α-tetralones are promising monoamine oxidase inhibitors and may represent lead compounds for the development of therapies for Parkinson's disease and depression. C7-Substituted α-tetralones act as high potency reversible inhibitors of human MAO-A and MAO-B. This class of compounds represent promising leads for the development of therapies for Parkinson's disease and depression.

Synthesis of the dopamine D2/D3 receptor agonist (+)-PHNO via supercritical fluid chromatography: Preliminary PET imaging study with [3-11C]-(+)PHNO

Carbon-11 labeled (+)-4-[1-11C]propyl-3,4,4a,5,6,10b-hexahydro- 2H-naphtho[1,2-b][1,4]oxazin-9-ol ([1-11C]-(+)-PHNO) is a dopamine D3-preferring agonist radiopharmaceutical used for medical imaging by positron emission tomography (PET). We report the synthesis of (+)-PHNO using supercritical fluid chromatography for enantiomeric resolution of its norpropyl derivative, HNO, followed by propylation. (+)-HNO was used to prepare the radiolabeling precursor, (+)-trans-4-acetyl-9-triisopropylsilyloxy-2,3,4a,5,6, 10b-hexahydro-4H-naphth[1,2b][1,4]oxazine, in 12 steps. Modifications to the labeling procedure were made to ensure consistent preparation of [3- 11C]-(+)-PHNO via [11C]CH3I. A preliminary PET imaging study was carried out with this tracer in an attempt to image dopamine receptors in brown adipose tissue (brown fat) in vivo.

4H-THIENO[3,2-C]CHROMENE-BASED INHIBITORS OF NOTUM PECTINACETYLESTERASE AND METHODS OF THEIR USE

Compounds that may be used to inhibit Notum Pectinacetylesterase are described, as well as compositions comprising them, and methods of their use to treat diseases and disorders affecting bone.

Ferrocene tagged functional polymer: A robust solid-phase reagent for O-demethylation

Ferrocene tagged functional polymer was synthesized by exploiting the propensity of the Merrifield resin to undergo quaternization with N-ferrocenylmethyl benzimidazole followed by subsequent anion metathesis reaction. The synthesized polymer when employed as a solid-phase reagent for O-demethylation of aryl methyl ethers, showed TON in the range of 7373-8930 and TOF in the range of 279-494 h-1.