27113-22-0

Basic information

• Product Name: 1-(4-hydroxy-3-methoxyphenyl)decan-5-one
• Synonyms: 1-(4-hydroxy-3-methoxyphenyl)decan-5-one;3-Decanone, 1-(4-hydroxy-3-methoxyphenyl)-;6-paradol;PARADOL;1-(3-Methoxy-4-hydroxyphenyl)-3-decanone;1-(4-Hydroxy-3-methoxyphenyl)decan-3-one;1-(4-Hydroxy-3-methoxyphenyl)-3-decanone;5-Paradol
• CAS NO: 27113-22-0
• Molecular Formula: C₁₇H₂₆O₃
• Molecular Weight: 278.38654
• EINECS: 248-228-1
• Mol File: 27113-22-0.mol

Chemical Properties

• Boiling Point: 406.4 °C at 760 mmHg
• Flash Point: 140 °C
• Appearance: /
• Density: 1.016 g/cm³
• Vapor Pressure: 3.46E-07mmHg at 25°C
• Refractive Index: 1.5232 (589.3 nm 20℃)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.02±0.20(Predicted)
• CAS DataBase Reference: 1-(4-hydroxy-3-methoxyphenyl)decan-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-hydroxy-3-methoxyphenyl)decan-5-one(27113-22-0)
• EPA Substance Registry System: 1-(4-hydroxy-3-methoxyphenyl)decan-5-one(27113-22-0)

Safety Data

• Hazardous Substances Data: 27113-22-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-hydroxy-3-methoxyphenyl)decan-5-one is used as a pharmaceutical compound for its potential therapeutic effects. The compound's unique structure allows it to interact with various biological targets, making it a candidate for the development of new drugs.
Used in Cosmetic Industry:
1-(4-hydroxy-3-methoxyphenyl)decan-5-one is used as an active ingredient in the cosmetic industry for its antioxidant and anti-aging properties. The compound's ability to scavenge free radicals and protect the skin from oxidative stress makes it a valuable addition to skincare products.
Used in Flavor and Fragrance Industry:
1-(4-hydroxy-3-methoxyphenyl)decan-5-one is used as a flavor and fragrance ingredient for its unique scent and taste. The compound's aromatic properties make it suitable for use in the creation of perfumes, colognes, and other fragrances, as well as in the flavoring of food and beverages.
Used in Antioxidant Applications:
1-(4-hydroxy-3-methoxyphenyl)decan-5-one is used as an antioxidant agent, particularly for its ability to prevent oxidative damage in various biological systems. The compound's antioxidant properties make it a potential candidate for use in the prevention and treatment of diseases associated with oxidative stress, such as cancer, cardiovascular diseases, and neurodegenerative disorders.
Used in Cancer Prevention:
1-(4-hydroxy-3-methoxyphenyl)decan-5-one is used as a cancer preventive agent due to its antioxidant activity and potential to modulate oncological signaling pathways. The compound's ability to inhibit tumor growth and progression, as well as its synergistic effects when combined with conventional chemotherapeutic drugs, makes it a promising candidate for cancer prevention and treatment.

InChI:InChI=1/C17H26O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h10,12-13,19H,3-9,11H2,1-2H3

Upstream product

• 39886-76-5 [6]-gingerol 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 121-33-5 vanillin 
• 629-04-9 1-Bromoheptane 
• 60998-35-8 4-chloromethyl-2-methoxyphenyl acetate 
• 498-00-0 4-hydroxymethyl-2-methoxyphenol 
• 821-55-6 2-Nonanone 
• 555-66-8 [6]-shogaol 
• 878006-06-5 (E)-1-(4'-hydroxy-3'-methoxyphenyl)dec-1-en-3-one 
• 53172-10-4 1-(4-hydroxy-3-methoxy-phenyl)-dec-1-en-3-one 

Downstream Products

• 878006-06-5 (E)-1-(4'-hydroxy-3'-methoxyphenyl)dec-1-en-3-one 

Relevant articles and documents

Stereoselective Biocatalyzed Reductions of Ginger Active Components Recovered from Industrial Wastes

Ginger is among the most widespread and widely consumed traditional medicinal plants around the world. Its beneficial effects, which comprise e. g. anticancer and anti-inflammatory activities as well as gastrointestinal regulatory effects, are generally attributed to a family of non-volatile compounds characterized by an arylalkyl long-chained alcohol, diol, or ketone moiety. In this work, ginger active components have been successfully recovered from industrial waste biomass of fermented ginger. Moreover, their recovery has been combined with the first systematic study of the stereoselective reduction of gingerol-like compounds by isolated alcohol dehydrogenases (ADHs), obtaining the enantioenriched sec-alcohol derivatives via a sustainable biocatalytic path in up to >99 % conversions and >99 % enantiomeric/diastereomeric excesses.

Concise and Efficient Synthesis of [6]-Paradol

An efficient synthesis of [6]-paradol (1) has been performed in four steps with a 72.0% overall yield. The present method highlights commercially available materials, convenient isolation with multiple crystallization without involving column chromatography, and a high-purity product (more than 99.2%), and it is amenable to large-scale synthesis.

Synthesis method of paradol

The invention discloses a synthesis method of paradol. The synthesis method comprises the following synthesis steps: 1, carrying out alkylation reaction on 4-chloromethyl-2-methoxyphenyl acetate serving as a raw material and diethyl malonate under the action of alkali, and carrying out acylation reaction on the reaction product and capryloyl chloride under the action of alkali to generate 2-(4-acetoxy-3-methoxyphenyl)-2-octanoyl diethyl malonate; and 2, carrying out hydrolysis reaction on 2-(4-acetoxy-3-methoxyphenyl)-2-octanoyl diethyl malonate in acid and water to obtain the target product paradol. The synthesis method is simple and convenient to operate, does not need special reaction conditions, and is more suitable for industrial production.

Paradol synthesis method

The invention discloses a complete synthesis method of a natural product paradol, the route being represented as the specification. The method employs feasible raw materials and simple operation, is high in yield and low in cost, is high in final product purity, is controllable in quality, and is suitable for industrial production.

GINGEROL DERIVATIVE HAVING INHIBITORY ACTIVITY AGAINST BIOFILM FORMATION AND PHARMACEUTICAL COMPOSITION COMPRISING SAME AS EFFECTIVE INGREDIENT FOR PREVENTING OR TREATING BIOFILM-CAUSED INFECTION SYMPTOM

The present invention relates to a gingerol derivative having inhibitory activity against biofilm formation and a pharmaceutical composition for preventing or treating infections caused by biofilms including the gingerol derivative as an active ingredient. The gingerol derivative of the present invention exhibits significantly improved binding affinity for LasR and inhibitory activity against biofilm formation. Therefore, the gingerol derivative of the present invention can act on various membrane surfaces where biofilms tend to form and can effectively inhibit the formation of the corresponding biofilms. In addition, the use of the pharmaceutical composition according to the present invention can fundamentally prevent or treat a variety of infections caused by biofilms due to the presence of the gingerol derivative in the pharmaceutical composition.

KETONES AND METHOD FOR MANUFACTURING ANALOG THEREOF

PROBLEM TO BE SOLVED: To provide a technique for efficiently producing ketones by using cellulose after extracting chitin and chitosan extracted from the crustacean or sucrose from the beet in order to effectively using wastes, such as a crustacean or a beat to prepare a solid catalyst. SOLUTION: A method for manufacturing 1-phenyl-3-ketones and an analog (a compound 3) comprises using at least one kind selected from a group consisting of cellulose, chitin and chitosan as a carrier and reacting benzyl alcohols (a compound 1) with ketones (a compound 2) in the presence of a solid catalyst obtained by supporting a group 8-10 transition metal and a base. The following chemical formula 1 is shown. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Simple Synthesis of Phytochemicals by Heterogeneous Pd- and Ir-Catalyzed Hydrogen-Borrowing C–C Bond Formation

Chitin-supported palladium and iridium catalysts (i.e., Pd/chitin, Ir/chitin) successfully promote the hydrogen borrowing C–C bond formation reaction to afford phytochemicals and aroma compounds in excellent yields.

Structure-Activity Relationships of 6- and 8-Gingerol Analogs as Anti-Biofilm Agents

Pseudomonas aeruginosa is a causative agent of chronic infections in immunocompromised patients. Disruption of quorum sensing circuits is an attractive strategy for treating diseases associated with P. aeruginosa infection. In this study, we designed and synthesized a series of gingerol analogs targeting LasR, a master regulator of quorum sensing networks in P. aeruginosa. Structure-activity relationship studies showed that a hydrogen-bonding interaction in the head section, stereochemistry and rotational rigidity in the middle section, and optimal alkyl chain length in the tail section are important factors for the enhancement of LasR-binding affinity and for the inhibition of biofilm formation. The most potent compound 41, an analog of (R)-8-gingerol with restricted rotation, showed stronger LasR-binding affinity and inhibition of biofilm formation than the known LasR antagonist (S)-6-gingerol. This new LasR antagonist can be used as an early lead compound for the development of anti-biofilm agents to treat P. aeruginosa infections.

Paradol preparation method

The invention provides a paradol preparation method which comprises the steps: firstly mixing the raw materials of vanillin, 2-nonanone and N,N-dimethyl formamide, then adding glacial acetic acid water solution, stirring, cooling to room temperature, filtering, washing and drying to obtain ketene intermediate; then adding metal sodium, anhydrous sodium acetate and tetrahydrofuran into a reaction bottle, adding the ketene intermediate dissolved into ethyl alcohol into the reaction bottle under protection of nitrogen, decoloring through activated carbon after reaction finishes, filtering and recovering solvent to obtain faint yellow grease, namely paradol. The preparation method disclosed by the invention can avoid generating a lot of hydroxyl byproducts in a hydrogenation reduction process, improves yield, simplifies after-treatment operation, avoids additional catalyst, and greatly shortens operation period; equipment utilization rate is high, total cost is lower and economical benefit is higher.

Ginger metabolites and uses thereof

The present application generally relates to the use of metabolites of ginger and analogs thereof for the treatment and prevention of diseases, including but not limited to, cancer.