91307-39-0

Usage

Uses

Used in Personal Care Industry:
Ethyl 4-hydroxy-2-naphthoate is used as a UV filter for its capacity to absorb and scatter UV radiation, thereby providing protection against sunburn and skin damage. This application is particularly important in sunscreens and other skincare products that aim to shield the skin from the harmful effects of the sun.
However, there are concerns regarding the potential for skin irritation, allergic reactions, and environmental toxicity associated with the use of ethyl 4-hydroxy-2-naphthoate. These concerns have led to regulations and restrictions on its use in cosmetics in some countries. As a result, ongoing research is essential to fully understand the safety and environmental impacts of ethyl 4-hydroxy-2-naphthoate, ensuring that its benefits can be harnessed while mitigating any potential risks.

InChI:InChI=1/C13H12O3/c1-2-16-13(15)10-7-9-5-3-4-6-11(9)12(14)8-10/h3-8,14H,2H2,1H3

Upstream product

• 136131-48-1 2-(ethoxycarbonyl)-1,4-dihydro-1,4-epoxynaphthalene 
• 33295-46-4 ethyl 4-acetoxynaphthalene-2-carboxylate 
• 64-17-5 ethanol 
• 1573-91-7 3-hydroxynaphthoic acid 
• 118-92-3 anthranilic acid 

Downstream Products

• 216310-04-2 4-Benzyloxy-1-bromo-naphthalene-2-carboxylic acid ethyl ester 
• 216310-07-5 4-Benzyloxy-1-bromo-naphthalene-2-carbaldehyde 
• 216310-06-4 (4-Benzyloxy-1-bromo-naphthalen-2-yl)-methanol 
• 216310-08-6 1-(4-Benzyloxy-1-bromo-naphthalen-2-yl)-but-3-en-1-ol 
• 216310-10-0 5-Benzyloxy-3-methoxy-1-methylene-2,3-dihydro-1H-cyclopenta[a]naphthalene 
• 216310-09-7 4-Benzyloxy-1-bromo-2-(1-methoxy-but-3-enyl)-naphthalene 
• 216310-12-2 (5-Benzyloxy-3-methoxy-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-yl)-methanol 
• 216310-14-4 Methanesulfonic acid 5-benzyloxy-3-methoxy-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ylmethyl ester 
• 851077-04-8 4-(benzyloxy)-2-naphthaldehyde 
• 188863-65-2 (4-(benzyloxy)naphthalen-2-yl)methanol 

Relevant academic research and scientific papers

Photoreaction of halomethyl substituted benzocyclic ketones with amines: Radical cyclization and ring expansion reactions promoted through photoinduced electron transfer processes

Photoreaction of ethyl 2-bromomethyl-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate 1a or other related compounds 1b-d with Me3SiCH2NEt2 in aqueous MeCN afforded ethyl 5-oxo-6,7,8,9-tetrahydrobenzocycloheptene-7-carboxylate 2a or corresponding ring expansion products 2a-d respectively.

MCL-1 INHIBITORS AND METHODS OF USE THEREOF

Disclosed are Mcl-1 inhibitors, pharmaceutical compositions comprising the same and methods of using the same.

Photoinduced electron-transfer reaction of α-bromomethyl-substituted benzocyclic β-keto esters with amines: Selective reaction pathways depending on the nature of the amine radical cations

Photoinduced electron-transfer reaction of α-bromomethyl-substituted benzocyclic β-keto esters with tertiary amines was investigated. Debrominated β-keto esters and ring-expanded γ-keto esters were obtained as major products. On the basis of mechanistic experiments it was concluded that these products are formed via a reaction sequence of selective carbon-bromine bond cleavage and subsequent competitive hydrogen abstraction and Dowd-Beckwith ring-expansion of the resulting primary alkyl radicals. The characteristic product distribution observed for the type of amine used is rationalized on the basis of selective reaction pathways of generated radical intermediates that depend on the nature of the amine radical cations.

A total synthesis of yellowish aphid pigment furanaphin through fries rearrangement assisted by boron trifluoride-acetic acid complex

The yellowish aphid pigment furanaphin, isolated from Aphis spiraecola and possessing cytotoxicity against HL-60 (human promyelocytic leukemia-60) cells, was synthesized by utilizing the Fries rearrangement assisted with a BFmiddot;2AcOH complex as a key step. It was confirmed that the complex effectively mediated the reaction even though the compounds had an electron-withdrawing substituent.

MORPHOLINE DERIVATIVE

The present invention provides a morpholine derivative of the formula [I]; wherein R1 is a substituted alkyl group, an optionally substituted aryl group, an optionally substituted heterocyclo group, a cycloalkyl group or an alkyl group; R2 is a substituted alkyl group, an optionally substituted aryl group, an optionally substituted heterocyclo group, an optionally substituted alkylcarbonyl group, an optionally substituted arylcarbonyl group, an optionally substituted heterocyclo-substituted carbonyl group or a cycloalkylcarbonyl group; T is a methylene group or a carbonyl group; R3, R4, R5 and R6 are the same or different and a hydrogen atom, an optionally substituted carbamoyl group or an optionally substituted alkyl group; or pharmaceutically acceptable salts thereof. These compounds are useful as a renin inhibitor.

Synthesis and photochromic properties of methoxy substituted 2,2-diaryl-2H-naphtho[1,2-b]pyrans

A series of methoxy-substituted 2,2-di(4-methoxyphenyl)-2H-naphtho[1,2-b]pyrans has been synthesised from 3-alkoxycarbonyl-1-naphthols and 1,1-di(4-methoxyphenyl)prop-2-yn-1-ol. The influence of the methoxy group on the wavelength of maximum absorption an

Studies on the Synthesis of highly substituted naphthol: Preparation of 6-Hydroxy-5,7-Dimethoxy-2-Naphthoic Acid, Isolated From Ulmus Thomasii

An improvement of a known procedure, affording substituted 4-hydroxy-2-naphthoic acid derivatives from aromatic aldehydes is described and its general applicability is shown through the preparation of a natural naphthalene derivative isolated from Ulmus thomasii.

Synthesis and evaluation of a carbocyclic analogue of the CC-1065 and duocarmycin alkylation subunits: Role of the vinylogous amide and implications on DNA alkylation catalysis

The synthesis and chemical properties of 1,2,9,9a-tetrahydro-1H- cyclopropa[c]benz[e]inden-4-one (CBIn, 10), a carbocyclic C-ring analogue of the alkylation subunits of CC-1065 and the duocarmycins, are detailed. The core structure of CBIn was prepared with an intramolecular Heck reaction for assembly of the key tricyclic skeleton and a final Winstein Ar-3' spirocyclization to install the reactive cyclopropane. A study of the CBIn solvolysis reactivity, regioselectivity, and mechanism revealed that removal of the nitrogen and resulting vinylogous amide stabilization increased the reactivity 3200 x (pH 3) and reversed the inherent regioselectivity, but did not alter the S(N)2 reaction mechanism. Thus, the vinylogous amide found in the naturally occurring alkylation subunits is responsible for their unusual stability and significantly impacts the regioselectivity without altering the inherent S(N)2 mechanism of nucleophilic addition. More importantly, this solvolysis reactivity proved independent of pH throughout the range of 4-12 including the physiologically relevant range of 5.0-8.0 where CBI is completely stable. Rate constants of 0.093 ± 0.001 M-1 s-1 and 4.2 ± 0.4 x 10-5 s-1 for the respective acid-catalyzed and uncatalyzed reactions were established, and the uncatalyzed reaction dominates at pH ≥ 4. These observations have important implications on the source of catalysis for the CC-1065/duocarmycin DNA alkylation reaction supporting the recent proposal that it is not derived from acid catalysis and C4 carbonyl protonation but rather a DNA binding-induced conformational change that disrupts the cross-conjugated vinylogous amide stabilization.

First example of samarium diiodide-promoted sequential cyclization and ring-expansion reactions of α-bromomethyl cyclic β-keto esters to homologated γ-keto esters

SmI2 reductions of some aromatic as well as aliphatic α-bromomethyl cyclic β-keto esters produced one-carbon homologated γ-keto esters in modest to good yields.