18430-91-6

Usage

Uses

Used in Cosmetic and Personal Care Industry:
1-(2-hydroxyphenyl)pentan-1-one is used as a fragrance ingredient for its sweet, floral scent, enhancing the sensory experience of various cosmetic and personal care products.
Used in Pharmaceutical Industry:
1-(2-hydroxyphenyl)pentan-1-one is used as an anti-inflammatory and anti-cancer agent due to its potential therapeutic effects, which are currently being studied for their efficacy in treating inflammation and cancer.
Used in Chemical Formulations:
1-(2-hydroxyphenyl)pentan-1-one is used as a stabilizer in certain formulations, leveraging its antioxidant properties to prevent degradation and extend the shelf life of products.

InChI:InChI=1/C11H14O2/c1-2-3-7-10(12)9-6-4-5-8-11(9)13/h4-6,8,13H,2-3,7H2,1H3

Upstream product

• 20115-23-5 phenyl valerate 
• 109-72-8 n-butyllithium 
• 69-72-7 salicylic acid 
• 611-20-1 salicylonitrile 
• 1009-14-9 phenyl butyl ketone 
• 1433-61-0 2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 
• 109-65-9 1-bromo-butane 
• 119-36-8 methyl salicylate 
• 90-02-8 salicylaldehyde 
• 106-99-0 buta-1,3-diene 
• 870010-43-8 2-(pent-1-yn-1-yl)phenol 
• 24635-48-1 chloro(butyl)diphenylsilane 
• 19311-91-2 N,N-diethylsalicylamide 
• 995-45-9 tributylchlorosilane 

Downstream Products

• 17403-75-7 2-<1-Butylpenten-(1)-yl>-phenol 
• 17404-22-7 2-<1-Butyl-hepten-(1)-yl>-phenol 
• 71289-75-3 1-[2-(2,4-Dichloro-benzyloxy)-phenyl]-pentan-1-one 
• 1359967-07-9 11-butyl-6,7,8,9,10,11-hexahydro-6,11-epoxydibenzo[b,e]oxepine 
• 1359967-04-6 2-(1-butyl-3-methoxy-1,3,4,5,6,7-hexahydroisobenzofuran-1-yl)phenol 
• 1359967-08-0 C₂₀H₃₀O₄ 
• 1270412-14-0 2-(1-aminopentyl)phenol 
• 21326-84-1 N-butylbenzo[d]oxazol-2-amine 
• 6797-49-5 2-butylbenzo[d]oxazole 
• 17508-89-3 4,6-Dinitro-2-(1-butylheptyl)-phenol 
• 17508-84-8 4,6-Dinitro-2-(1-butylpentyl)-phenol 
• 17404-53-4 2-(1-Butylheptyl)-phenol 
• 17404-48-7 2-(1-Butylpentyl)-phenol 
• 89423-49-4 (R)-o-<1-((S)-1-α-naphthylethylamino)pentyl>phenol 

Relevant academic research and scientific papers

Nucleophilic addition reaction with dearomatization of naphthalene ring

Various aromatic lactones have been synthesized and their regioselectivity (1,2-addition vs. 1,4- or 1,6-addition) investigated in reactions with organolithium species, particularly n-BuLi and sec-BuLi. The regioselectivity varied greatly depending on various factors, such as the bulkiness of both substrates and organolithium species, and types of solvent and cosolvent. In particular, 1,4-addition with dearomatization occurred preferentially using sec-BuLi as the nucleophile in tetrahydrofuran (THF) with hexamethylphosphoramide (HMPA) or N,N′-dimethylpropyleneurea (DMPU) as cosolvent. For sec-BuLi, the reaction was estimated to proceed through a single-electron transfer mechanism.

Ruthenium-Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2

A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible -OH group.

Rhodium-Catalyzed Annulations of 1,3-Dienes and Salicylaldehydes/2-Hydroxybenzyl Alcohols Promoted by 2-Ethylacrolein

A rhodium-catalyzed 2-ethylacrolein-promoted protocol enables the annulation reactions of 1,3-dienes with either salicylaldehydes or 2-hydroxybenzyl alcohols leading to 2-alkylchroman-4-ones with high regioselectivity. This research highlights the use of 2-ethylacrolein which probably serves as a tool of bidentate coordination to rhodium intermediates. Mechanistic studies reveal that the transformation proceeds through the 1,4-hydroacylation pathway to access unsaturated linear ketones with subsequent oxo-Michael addition. (Figure presented.).

PtO2/PTSA system catalyzed regioselective hydration of internal arylalkynes bearing electron withdrawing groups

A highly efficient PtO2/PTSA catalyst system for the hydration of a wide array of alkynes was developed. This method proved to be compatible with a large range of functional groups and the ketone products were obtained in high yields. The scope of this methodology was also extended to the synthesis of 3-Aryl-isochromenones,-indoles and-benzofurans.

THIOSEMICARBAZONES INHIBITORS OF LYSOPHOSPHATIDIC ACID ACYLTRANSFERASE AND USES THEREOF

Lysophosphatidic acid acyltransferase-beta (LPAAT-β) catalyzes the production of phosphatidic acid (PA) from lysophosphatidic acid (LPA). The lipid cofactor PA contributes to the activation of c-Raf, BRAF, mTOR and PKC-ζ. LPAAT-β expression is a prognostic factor in gynecologic malignancies and is being investigated as a therapeutic target in a variety of tumor types. A class of thiosemicarbazones was identified as inhibitors of LPAAT-β from a screen of a library of small molecules. A focused library of thiosemicarbazones derivatives was prepared and led to the development of compounds which potently inhibit LPAAT-β and inhibit the growth of MiaPaCa2 human pancreatic cancer cells.

Lithiation of a silyl ether: Formation of an ortho-fries hydroxyketone

A hydroxy-directed alkylation of an N,N-diethylarylamide using CIPE-assisted α-silyl carbanions (CIPE=complex-induced proximity effect) has been developed using a simple reagent combination of LDA (lithium diisopropylamide) and chlorosilane. A study of the mechanism, and the application of the procedure to an anionic Snieckus-Fries rearrangement for a highly efficient synthesis of the potent phosphatidylinositol 3-kinase (PI3K) inhibitor LY294002, are reported.

3-Ylidenephthalides as a new class of transient receptor potential channel TRPA1 and TRPM8 modulators

Following the recent identification of the naturally occurring 3-ylidene-4,5-dihydrophthalide ligustilide and its oxidation product dehydroligustilide as novel TRPA1 modulators, a series of seventeen 3-ylidenephthalides was synthesized and tested on TRPA1 and TRPM8 channels. Most of these compounds acted as strong modulators of the two channel types with EC50 and/or IC50 values distinctly lower than those of the reference compounds.

Palladium-catalyzed ortho-CH-bond oxygenation of aromatic ketones

A palladium-catalyzed C(sp2)-H bond oxygenation reaction is described. This protocol represents the first example of a C-H bond cleavage/C-O bond formation sequence, by employing a ketone moiety as the directing group. With this new catalytic method, a variety of ortho-acylphenols can be easily accessed from arylketones.

Hg(OTf)2-catalyzed vinylogous semi-pinacol rearrangement leading to 1,4-dihydroquinolines

An efficient method for the construction of dihydroquinoline derivatives possessing a quaternary carbon center is developed by an application of Hg(OTf)2-catalyzed vinylogous semi-pinacol-type rearrangement. The reaction was found to be specifi

Rational design of inhibitors of VirA-VirG two-component signal transduction

VirA-VirG two-component system regulates the vir (virulence) operon in response to specific host factors (xenognosins) in the plant pathogen Agrobacterium tumefaciens. Using whole cell assays, stable inhibitors inspired by the labile natural benzoxazinone inhibitor HDMBOA are developed. It is found that aromatic aldehydes represent a minimal structural unit for activity. In particular, 3-hydroxy-4,6-dimethoxy-3H-isobenzofuran-1-one (HDI) was found to have the highest activity, making it the most potent developed inhibitor of virulence gene expression in Agrobacterium.