29569-91-3

Basic information

• Product Name: 4,4-dimethyl-1-phenyl-1-penten-3-one
• Synonyms: 4,4-dimethyl-1-phenyl-1-penten-3-one
• CAS NO: 29569-91-3
• Molecular Formula: C₁₃H₁₆O
• Molecular Weight: 188.26554
• Mol File: 29569-91-3.mol
• Article Data: 45

Chemical Properties

• Boiling Point: 296°Cat760mmHg
• Flash Point: 108.4°C
• Appearance: /
• Density: 0.972g/cm³
• CAS DataBase Reference: 4,4-dimethyl-1-phenyl-1-penten-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-dimethyl-1-phenyl-1-penten-3-one(29569-91-3)
• EPA Substance Registry System: 4,4-dimethyl-1-phenyl-1-penten-3-one(29569-91-3)

Safety Data

• Hazardous Substances Data: 29569-91-3(Hazardous Substances Data)

Usage

General Description

4,4-dimethyl-1-phenyl-1-penten-3-one, also known as B-Damascone, is a chemical compound widely used in the fragrance and flavor industry. It is a colorless to pale yellow liquid with a sweet, floral, and slightly fruity odor. B-Damascone is commonly used as a scent in perfumes, lotions, and soaps, as well as a flavoring agent in food and beverages. Its unique and pleasant aroma makes it a popular ingredient in various cosmetic and culinary products. Additionally, B-Damascone has been studied for its potential health benefits, including antioxidant and anti-inflammatory properties.

Upstream product

• 28435-47-4 (Z)-4,4-dimethyl-1-phenylpent-1-en-3-one 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 100-52-7 benzaldehyde 
• 32398-67-7 4,4-dimethyl-1-phenyl-1-pentyn-3-one 
• 5195-24-4 4,4-dimethyl-1-phenylpentan-3-one 
• 100-39-0 benzyl bromide 
• 17474-12-3 4,4-dimethyl-1-phenyl-pent-2-yn-1-ol 
• 288390-74-9 3,3-dimethyl-1-(triphenylphosphanylidene)butan-2-one 
• 81023-75-8 3,3-dimethyl-1-(phenylsulfonyl)butan-2-one 
• 100-53-8 phenylmethanethiol 
• 5469-26-1 1-Bromopinacolon 
• 1486-28-8 diphenyl(methyl)phosphine 
• 1415237-06-7 (3,3-dimethyl-2-oxobutan-1-yl)methyldiphenylphosphonium bromide 
• 866562-21-2 4,4-dimethyl-1-phenylpent-2-ynyl acetate 

Downstream Products

• 5195-24-4 4,4-dimethyl-1-phenylpentan-3-one 
• 31611-82-2 (1RS,2SR)-1,2-dibromo-4,4-dimethyl-1-phenyl-pentan-3-one 
• 101115-14-4 2,2-dimethyl-6-nitro-5-phenylhexane-3-one 
• 97060-88-3 (E,3RS,1'RS)-3-(1'-tert-butyl-1'-hydroxy-3'-phenyl-2'-propenyl)-1-methyl-2-pyrrolidone 
• 122969-27-1 (3RS,1'RS)-3-(4',4'-dimethyl-3'-oxo-1'-phenylpentyl)-1-methyl-2-pyrrolidinone 
• 122969-28-2 (3RS,1'SR)-3-(4',4'-dimethyl-3'-oxo-1-phenylpentyl)-1-methyl-2-pyrrolidinone 
• 97060-89-4 3-(4,4-dimethyl-3-oxo-1-phenylpentyl)-N-methylpyrrolidone 
• 88834-70-2 2,2-Dimethyl-5-phenyl-3-nonanon 
• 95740-78-6 (2S,3R)-2,6,6-Trimethyl-5-oxo-3-phenyl-heptanoic acid tert-butyl ester 
• 177314-49-7 (1R,2S)-trans-1,2-epoxy-4,4-dimethyl-1-phenylpentan-3-one 
• 177314-48-6 (1R,2S)-trans-1,2-epoxy-4,4-dimethyl-1-phenylpentan-3-one 
• 60843-66-5 1,2-epoxy-4,4-dimethyl-1-phenylpentan-3-one 
• 1208946-59-1 (E)-benzaldehyde O-pivaloyl oxime 

Relevant articles and documents

Preparation of hindered aniline cyanh and application in the allyl-ni-catalyzed α,β-dehydrogenation of carbonyls

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Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation

The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.

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Celecoxib, is a selective cyclooxygenase-2 (COX2) inhibitor with a 1,5-diaryl pyrazole scaffold. Celecoxib has a better safety profile compared to other COX2 inhibitors having side effects of systemic hypertension and thromboembolic complications. This may be partly attributed to an off-target activity involving phosphodiesterase 5 (PDE5) inhibition and the potentiation of NO/cGMP signalling allowing coronary vasodilation and aortic relaxation. Inspired by the structure of celecoxib, we synthesized a chemically diverse series of compounds containing a 1,3,5-trisubstituted pyrazoline scaffold to improve PDE5 inhibitory potency, while eliminating COX2 inhibitory activity. SAR studies for PDE5 inhibition revealed an essential role for a carboxylic acid functionality at the 1-phenyl and the importance of the non-planar pyrazoline core over the planar pyrazole with the 5-phenyl moiety tolerating a range of substituents. These modifications led to new PDE5 inhibitors with approximately 20-fold improved potency to inhibit PDE5 and no COX-2 inhibitory activity compared with celecoxib. PDE isozyme profiling of compound 11 revealed a favorable selectivity profile. These results suggest that trisubstituted pyrazolines provide a promising scaffold for further chemical optimization to identify novel PDE5 inhibitors with potential for less side effects compared with available PDE5 inhibitors used for the treatment of penile erectile dysfunction and pulmonary hypertension.