55379-97-0

Usage

Uses

Used in Skincare Industry:
4-OCTYLOXYCINNAMIC ACID is used as a UV filter for its ability to absorb UVB rays and provide protection against sun damage. It is often combined with other UV filters to offer broad-spectrum protection against both UVA and UVB rays, ensuring comprehensive skin defense.
Used in Sunscreen Products:
In the sunscreen industry, 4-OCTYLOXYCINNAMIC ACID is used as an ingredient to enhance the product's effectiveness in shielding the skin from the sun's harmful rays. Its inclusion in sunscreen formulations helps to create a barrier that minimizes the risk of skin damage, sunburn, and long-term effects such as premature aging and skin cancer.

InChI:InChI=1/C17H24O3/c1-2-3-4-5-6-7-14-20-16-11-8-15(9-12-16)10-13-17(18)19/h8-13H,2-7,14H2,1H3,(H,18,19)

Upstream product

• 141-82-2 malonic acid 
• 24083-13-4 4-octyloxybenzaldehyde 
• 111-83-1 1-bromo-octane 
• 7400-08-0 para-coumaric acid 
• 3943-97-3 methyl p-hydroxycinnamate 
• 81609-53-2 methyl 4-octyloxy-cinnamate 
• 7400-08-0 p-Coumaric Acid 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 1357473-56-3 C₃₀H₃₈O₅ 
• 76622-46-3 (E)-3-(4-Octyloxy-phenyl)-acrylic acid 4-formyl-phenyl ester 
• 1394233-81-8 C₂₇H₃₂O₅ 

Relevant academic research and scientific papers

Synthesis and Mesogenic Properties of Liquid Crystals Based on Cholesterol and Cinnamic Acid Derivatives

A group of new mesomorphic compounds with cholesterol-based, which have derivative of the cinnamic acid, with different lengths of terminal alkoxy chains, are synthesized and characterized. The mesomorphic properties were investigated by DSC and POM. All target compounds showed a cholesteric phase. For 12-TC and 14-TC besides a cholesteric phase, also revealed a SmA* phase. The experimental results demonstrated that with the increase in the terminal chain lengths, the thermal stability of the smectic mesophases of these liquid crystals was increased, and these compounds shows brilliant color changes in the temperature ranges of cholesteric phase.

The effect of position of octadecyloxy tail on the formation of liquid crystal with chalconyl-ester and chalconyl-vinyl ester series: Comparison with corresponding linkage group

Two series of chalconyl-based liquid crystals which differ from each other in the position of the first linking group have been synthesized and characterized by elemental analyses and spectroscopic techniques such as Fourier transform infrared and proton magnetic resonance magnetic resonance [1H NMR] spectroscopy. The mesomorphic properties of these compounds were observed by optical polarized light microscopy (POM) and differential scanning calorimetry (DSC). We have synthesized two homologous series viz. 3-(3-(4-(Octadecyloxy) phenyl) acrylonyl) phenyl 3-(4-n-alkoxyphenyl) acrylate (series-1) and 3-(3-(4-(Octadecyloxy) phenyl) acryloyl) phenyl 4-n-alkoxy benzoate (series-2). Series-1 has chalconyl-ester central linkage group while in series-2 chalconyl-vinyl ester group is present and tail octadecyloxy side chain is common in both homologous series. All the homologous in present series display LC property in enantiotropical manner except first three homologous in both series.

Mesogenic naphthyl derivatives

Two new mesogenic homologous series of liquid crystalline naphthalene derivatives with different central linkages: 2- Naphthyl-4-n-alkoxybenzoates (I) and trans-2-Naphthyl -4-n –alkoxycinnamates(II), have been synthesized and characterized by a combination of elemental analysis and standard spectroscopic methods. Twelve compounds have been synthesized in both the series I and II. In series I, methoxy to n-pentyloxy derivatives are non mesogenic, n-hexyloxy to n-hexadecyloxy derivatives exhibit monotropic nematic mesophase. Smectic A mesophase commences from n-decyloxy derivatives as a monotropy and persist up to the last member synthesized. All the 12 compounds of series II exhibit mesomorphism. Methoxy to n-propyloxy derivatives exhibit monotropic nematic mesophse, and n-butyloxy to n-tetradecyloxy derivatives exhibit enantiotropic nematic mesophase. n-Hexayloxy to n-hexadecyloxy derivatives also exhibit enantiotropic smectic A mesophase. The mesomorphic properties of present series were compared with each other and with a structurally related mesogenic homologous series to evaluate the effects of central linkage on mesomorphism.

Mesomorphism dependence on heterocyclic tail

A novel homologous series of liquid crystal materials containing a heterocyclic ring was synthesized with a view to understanding and establishing the relation between liquid crystal (LC) properties and a molecular structure; and with a view to curing skin-related diseases following biological activity studies. The series consist of 13 (C1 to C18) members. All the members are liquid crystals. The C4 to C18 members are smectogenic of which C4 and C5 are monotropic and remaining members (C6 to C18) are enantiotropic in nature; whereas all C1 to C18 members are enantiotropically nematogenic. Hence the C1, C2, C3 members are only nematogenic and the rest of the homologues are smectogenic in addition to nematogenic. Transition temperatures were determined by an polarizing optical microscope equipped with heating stage. Analytical and spectral data confirmed the molecular structures of homologues. It is a middle ordered melting type series. LC properties of a series are compared with the structurally known series.

Mesomorphism and flexibility of alkyl chains in chalcone esters

A novel homologous series of chalconyl ester liquid crystals (LCs): RO?C6H4–CH:CH–COO?C6H4–CO?CH:CH?C6H4–OC10H21 (n) (para) has been synthesized and studied with a view to understanding and establishing the relationship between molecular structure and LC properties with reference to flexibility of the terminal chain. The novel series consists of eleven homologs (C1–C16). The C1 and C2 homologs are nonliquid crystals and the rest of the homologs (C3–C16) are enantiotropic nematic without exhibition of smectic mesophase. Transition and melting temperatures were determined by an optical polarizing microscope equipped with a heating stage. Textures of nematic phases are threaded or Schlieren. Cr-N/I transition curve adopts a zigzag path in a normal manner with overall descending behaviors. The N-I transition curve exhibits a sharp and shorter odd-even effect from C3 to C6 and it diminishes from and beyond C6 for higher homologs of longer n-alkyl chain (R) in more or less or negligible deviating manner from normal descending tendency. Thermal stability for the nematic is 116.4°C and mesophase length ranges from 19°C to 67°C at the C3 and C12 homolog respectively. The LC properties of present novel series are compared with structurally similar analogous series to derive group efficiency order.

The effect of geometrical shape and molecular rigidity on mesomorphism

A novel nonlinear homologous series RO?C6H4?CH?CH?COO?C6H4 (meta) ?CO?CH?CH?C6H4?OC12H25(n) (para) consisting of three phenyl rings, two central bridges ?CH?CH?COO? and ?CO?CH?CH? as well as ?OR and ?OC12H25(n) as flexible and constant terminal end groups respectively. The object in view is aimed to understand and establish the effect of molecular structure on LC properties of nonlinear inverted “V” shaped molecules. Novel homologous series consists of thirteen homologues. Transition temperatures and textures were determined by polarizing optical microscopy (POM) equipped with a heating stage. Textures of nematic phases are threaded or schlieren and that of a smectic phases are of the type-A or C. Transition curves of a phase diagram behaved in a normal manner. Sm-N and N-I transition curves exhibited odd-even effect. Analytical, Thermal and Spectral data confirms the molecular structure of homologues.

Study of mesomorphism and its relation to molecular structure with special reference to central bridges viz. -COO- and -CH=CH-COO- of the homologous series

Two ester homologous series of mesogens, viz., Methyl-p-(p′-n-alkoxy benzoyloxy) cinnamates (X) and Methyl-p-(p′-n-alkoxy cinnamoyloxy) cinnamates (Y) being structurally similar are discussed. Both (X) and (Y) differ in respect of central bridges linking two phenyl rings. Only enantiotropic nematogenic character is observed without exhibition of any smectic character by all members of series (X) and (Y). Thermal stability of series (X) is relatively low as compared to (Y), but nematogenic mesophase lengths are of reverse order. Solid-nematic/solid-isotropic and nematic-isotropic transition curves in the phase diagrams behave in normal manner.

Dependence of molecular structure on mesomorphic behavior with special reference to central bridge

A novel homologous series of liquid crystalline 4-(4′-n-alkoxy cinnamoyloxy)-4″-methoxy benzyl cinnamates was synthesized and studied with a view to understand and establish the effects of molecular structure on liquid crystal behavior. The series consists of eleven members of the series. None of the homologue derivatives are either nonliquid crystal or smectogenic, i.e. all the eleven members of the novel homologous series are enantiotropcially nematogenic only. Transition and melting temperatures as well as textures of the nematic mesophase were determined on an optical polarizing microscope equipped with a heating stage. The transition curves of the phase diagram show phase behavior in a normal expected manner. An odd-even effect is observed for the nematic-isotropic transition curve. The textures of the nematic mesophase are threaded or Schlieren as determined a by miscibility method. Analytical and spectral data confirm the molecular structures of the homologues. The average thermal stability for nematic is 213.8°C. The isotropic temperatures vary between 190°C and 240°C. The nematogenic mesophase length varies from 17°C to 102°C. Thus, the novel homologous series is entirely nematogenic without the exhibition of smectogenic character. The liquid crystal (LC) properties of the present novel series are compared with structurally similar other known homologous series.

Mesomorphism Dependence on Terminally Substituted End Group

A novel homologous series of liquid crystalline substances has been synthesized and studied with a view to understanding and establishing the relation between liquid crystal properties and molecular structure. The novel ester series consists of eleven enantiotropically smectogenic homologous without exhibition of nematogenic property. Transition temperatures were determined with an optical polarizing microscope equipped with a heating stage. Textures of smectic mesophase are focal conic fan shaped of smectic A or C type. Analytical and spectral data confirms the molecular structures of homologous. Transition curve, Cr-Sm behaved in normal manner. Transition curve Sm-I behaved in a normal manner up to the octyloxy (C8) homolog derivative and then behaved in the unusual manner for the C10, C12, C14, and C16 derivatives. An odd-even effect is observed for the Sm-I transition curve. The series entirely smectogenic with a middle-ordered melting type and a moderate mesophase length. The average thermal stability for smectic is 128.09°C and mesophase length ranges from 8.6°C to 73.2°C. The mesomorphic (LC) behavior of the novel series is compared with structurally similar known homologous series.

Mesomorphism of Novel Symmetric Dimers with Changing Alkoxy Terminal End Group

A novel homologous series of symmetric dimers has been synthesized. It consists of thirteen (C1 to C8, C10, C12, C14, C16 and C18) dimer ester derivatives from trans cinnamic acid with pyrocatechol. Mesomorphic property commences from C7 homologue as smectic. C1 to C6 members of the series are nonmesomorphic. C7 is monotropic smectic and the rest of the homologues from C8 to C18 are enantiotropic smectic. The nematic mesophase is totally absent. Textures and transition temperatures of the homologues are determined by an optical polarizing microscope equipped with a heating stage. IR, 1H NMR spectra, mass spectra, and differential scanning calorimetry of some members is included. The spectroscopic analyses support the molecular structures. Mesomorphic properties of the novel symmetric dimer series are compared with structurally similar series. The novel series is partly nonmesomorphic and predominantly smectogenic with textures of the A or C type, without the exhibition of the nematic phase.