15087-24-8

Usage

Uses

Used in Cosmetics Industry:
BENZYLIDENE CAMPHOR is used as a UVB filter in sunscreens for its ability to absorb and filter out harmful UVB rays from the sun. This helps prevent sunburn and reduces the risk of skin damage, premature aging, and skin cancer.
Used in European Union:
In the European Union, BENZYLIDENE CAMPHOR is approved for use in sunscreens with an allowed concentration of up to 2 percent. This regulation ensures the safety and effectiveness of the compound in providing adequate sun protection for consumers.

InChI:InChI=1/C17H20O/c1-16(2)14-9-10-17(16,3)15(18)13(14)11-12-7-5-4-6-8-12/h4-8,11,14H,9-10H2,1-3H3/b13-11+

Upstream product

• 473929-46-3 (1R,4R)-3-[(E)-(dimethylamino)methylidene]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 18530-01-3 Acetic acid (1S,4R)-3-bromo-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-en-2-yl ester 
• 100-52-7 benzaldehyde 
• 74636-48-9 C₁₀H₁₄LiO^(1-)*Li⁽¹⁺⁾ 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 100-58-3 phenylmagnesium bromide 
• 75-36-5 acetyl chloride 
• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 100-51-6 benzyl alcohol 
• 15087-24-8 (1R,4S,3E)-3-benzylidene-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 98-88-4 benzoyl chloride 
• 864851-06-9 1,2,2-trimethyl-3-styryl-cyclopentanecarboxylic acid 
• 28435-93-0 (1R)-3-((E)-chloromethylene)-1,7,7-trimethyl-norbornan-2-one 

Downstream Products

• 864851-06-9 1,2,2-trimethyl-3-styryl-cyclopentanecarboxylic acid 
• 118205-69-9 (1R,3R,4R)-3-benzyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 38253-64-4 (1R,3S,4R)-3-benzyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 91419-02-2 3-trans-benzylideneisobornyl acetate endo-oxide 
• 91419-02-2 3-trans-benzylideneisobornyl acetate exo-oxide 
• 91419-01-1 3-trans-benzylideneisoborneol endo-oxide 
• 91419-01-1 3-trans-benzylideneisoborneol exo-oxide 
• 77078-79-6 3-exo-benzyl-1,7,7-trimethylbicyclo<2.2.1>heptane-3-endo-2-exo-diol 
• 77078-79-6 3-endo-benzyl-1,7,7-trimethylbicyclo<2.2.1>heptane-2-exo-3-exo-diol 
• 28070-25-9 3-trans-benzylideneisobornyl acetate 
• 28070-24-8 3-trans-benzylideneisoborneol 
• 87420-27-7 [(1R)-exo]-3-exo-(diphenylmethyl)borneol 
• 21653-28-1 3-benzhydryl-1,7,7-trimethyl-norbornan-2-one 

Related news

Study of the photochemical behaviour of sunscreens — BENZYLIDENE CAMPHOR (cas 15087-24-8) and derivatives II: Photosensitized isomerization by aromatic ketones and deactivation of the 8-methoxypsoralen triplet state07/27/2019

The benzophenone- and acetophenone-photosensitized E—Z isomerization of benzylidene camphor (BC) and p-trimethylammoniobenzylidene camphor methylsulphate was studied quantitatively. Initial sensitized quantum yields and concentrations of both isomers in the photostationary state were measured i...detailed

Photochemical E ⇄ Z isomerization of some BENZYLIDENE CAMPHOR (cas 15087-24-8) and benzylidene tetrahydrofuranone derivatives07/25/2019

The E ⇄ Z photoisomerization of benzylidene camphor and benzylidene tetrahydrofuranone was examined in various solvents. The isomerization quantum yields determined from different methods were found to be independent of the concentration and of the irradiation wavelength. No solvent and oxygen e...detailed

Relevant academic research and scientific papers

A simple iron-catalyst for alkenylation of ketones using primary alcohols

Herein, we developed a simple iron-catalyzed system for the α-alkenylation of ketones using primary alcohols. Such acceptor-less dehydrogenative coupling (ADC) of alcohols resulted in the synthesis of a series of important α,β-unsaturated functionalized ketones, having aryl, heteroaryl, alkyl, nitro, nitrile and trifluoro-methyl, as well as halogen moieties, with excellent yields and selectivity. Initial mechanistic studies, including deuterium labeling experiments, determination of rate and order of the reaction, and quantitative determination of H2 gas, were performed. The overall transformations produce water and dihydrogen as byproducts.

Synthesis and structural characterization of novel camphor-derived amines

Two novel 4-substituted camphidine derivatives 10a,b have been prepared from (+)-camphor (1) in five steps, the Beckmann rearrangement being the bottleneck of the synthesis. Isoborneol derivative 5b, formed as a side product during the hydrogenation of arylidene ketone 3b, under Beckmann rearrangement conditions yielded interesting novel rearrangement products 11 and 12. (1S)-(+)-Camphorquinone (13) was transformed into diamines 15 and 16 in two steps, the former being cyclized into an imidazoline salt 17, an N-heterocyclic carbene precursor. The structures of all novel compounds have been meticulously characterized using NMR techniques and/or single crystal X-ray analysis. Copyright

Synthesis and structural elucidation of novel camphor-derived thioureas

Nine novel (+)-camphor-derived thioureas have been prepared. 3-((Dimethylamino)methylene)camphor (2) served as the common precursor for the preparation of both, 2-thiourea 15-20 and 3-thiourea functionalized camphor derivatives 6, 7/7′, respectively. Starting from 2, the latter were prepared in two or three steps whereas the former in five steps, respectively. Configuration of all novel compounds has been meticulously determined using NMR techniques and/or single crystal X-ray crystallography. Copyright

Simple and effective protocol for Claisen-Schmidt condensation of hindered cyclic ketones with aromatic aldehydes

A simple and effective methodology for Claisen-Schmidt condensation of (-)-menthone and other hindered cyclic ketones with aromatic aldehydes under highly basic conditions using a polar aprotic solvent and a strong base (alkali metal hydroxide or an alkoxide) is described and discussed. Georg Thieme Verlag Stuttgart.

Stereoselective additions to the exocyclic C{double bond, long}C bond of some α-alkylidene-(+)-camphor derivatives

Stereoselective additions to the exocyclic C{double bond, long}C double bond of some (1R,3E,4S)-3-alkylidene-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones and (1R,4E,5S)-4-alkylidene-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones were studied. All additions took place predominantly from the less hindered endo-face of the methylidene compounds to give the corresponding exo-adducts as the major isomers. Thus, catalytic hydrogenations afforded the α-alkylated (1R,3R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones and (1R,4R,5R)-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones in 28-100% de. Similarly, 1,3-dipolar cycloadditions of 2,4,6-trisubstituted benzonitrile oxides gave the corresponding spiro cycloadducts in 66-100% de. The structures were determined by 2D NMR techniques, NOESY spectroscopy and X-ray diffraction.

A class II aldolase mimic

A class II aldolase-mimicking synthetic polymer was prepared by the molecular imprinting of a complex of cobalt (II) ion and either (1S,3S,4S)-3-benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (4a) or (1R,3R,4R)-3-benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (4b) in a 4-vinylpyridine-styrene-divinylbenzene copolymer. Evidence for the formation of interactions between the functional monomer and the template was obtained from NMR and VIS titration studies. The polymers imprinted with the template demonstrated enantioselective recognition of the corresponding template structure, and induced a 55-fold enhancement of the rate of reaction of camphor (1) with benzaldehyde (2), relative to the solution reactions, and were also compared to reactions with a series of reference polymers. Substrate chirality was observed to influence reaction rate, and the reaction could be competitively inhibited by dibenzoylmethane (6). Collectively, the results presented provide the first example of the use of enantioselective molecularly imprinted polymers for the catalysis of carbon-carbon bond formation.

Synthesis and properties of benzylidene derivatives of terpenoid ketones

Optically active benzylidene derivatives of camphor and menthone were obtained in preparative yields by condensation of the ketones with aromatic aldehydes in DMSO in the presence of t-BuOLi. The synthesized α,β-unsaturated ketones show high specific rotation and thus are suitable to bedoping component to liquid-crystalline compositions.

Cosmetic screening composition containing a UV screen in combination with a polymer obtained by block polymerization in emulsion and its use for the protection of the human epidermis against ultraviolet radiations

Cosmetic screening composition containing a UV screen in combination with a polymer obtained by block polymerization in emulsion and its use for the protection of the human epidermis against ultraviolet radiations.