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Eco-friendly methodologies for the synthesis of some aromatic esters, well-known cosmetic ingredients.

International journal of cosmetic science

Villa C, Baldassari S, Gambaro R, Mariani E, Loupy A.
PMID: 18492177
Int J Cosmet Sci. 2005 Feb;27(1):11-6. doi: 10.1111/j.1467-2494.2004.00246.x.

Solid-liquid solvent-free phase transfer catalysis (PTC) and acidic catalysis in dry media were applied, with noticeable improvement and simplification over classical procedures in a Green Chemistry context, to the synthesis of some aromatic esters useful as cosmetic ingredients: 3-methylbutyl...

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Villa C, Baldassari S, Gambaro R, et al. Eco-friendly methodologies for the synthesis of some aromatic esters, well-known cosmetic ingredients. Int J Cosmet Sci. 2005;27(1):11-6doi: 10.1111/j.1467-2494.2004.00246.x.
Villa, C., Baldassari, S., Gambaro, R., Mariani, E., & Loupy, A. (2005). Eco-friendly methodologies for the synthesis of some aromatic esters, well-known cosmetic ingredients. International journal of cosmetic science, 27(1), 11-6. https://doi.org/10.1111/j.1467-2494.2004.00246.x
Villa, C, et al. "Eco-friendly methodologies for the synthesis of some aromatic esters, well-known cosmetic ingredients." International journal of cosmetic science vol. 27,1 (2005): 11-6. doi: https://doi.org/10.1111/j.1467-2494.2004.00246.x
Villa C, Baldassari S, Gambaro R, Mariani E, Loupy A. Eco-friendly methodologies for the synthesis of some aromatic esters, well-known cosmetic ingredients. Int J Cosmet Sci. 2005 Feb;27(1):11-6. doi: 10.1111/j.1467-2494.2004.00246.x. PMID: 18492177.
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Structure reactivity relationship in the reaction of DNA guanyl radicals with hydroxybenzoates.

Radiation physics and chemistry (Oxford, England : 1993)

Do TT, Tang VJ, Aguilera JA, Milligan JR.
PMID: 21966099
Radiat Phys Chem Oxf Engl 1993. 2010 Nov 01;79(1):1144-1148. doi: 10.1016/j.radphyschem.2010.06.006.

In DNA, guanine bases are the sites from which electrons are most easily removed. As a result of hole migration to this stable location on guanine, guanyl radicals are major intermediates in DNA damage produced by the direct effect...

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Do TT, Tang VJ, Aguilera JA, et al. Structure reactivity relationship in the reaction of DNA guanyl radicals with hydroxybenzoates. Radiat Phys Chem Oxf Engl 1993. 2010;79(1):1144-1148doi: 10.1016/j.radphyschem.2010.06.006.
Do, T. T., Tang, V. J., Aguilera, J. A., & Milligan, J. R. (2010). Structure reactivity relationship in the reaction of DNA guanyl radicals with hydroxybenzoates. Radiation physics and chemistry (Oxford, England : 1993), 79(1), 1144-1148. https://doi.org/10.1016/j.radphyschem.2010.06.006
Do, Trinh T, et al. "Structure reactivity relationship in the reaction of DNA guanyl radicals with hydroxybenzoates." Radiation physics and chemistry (Oxford, England : 1993) vol. 79,1 (2010): 1144-1148. doi: https://doi.org/10.1016/j.radphyschem.2010.06.006
Do TT, Tang VJ, Aguilera JA, Milligan JR. Structure reactivity relationship in the reaction of DNA guanyl radicals with hydroxybenzoates. Radiat Phys Chem Oxf Engl 1993. 2010 Nov 01;79(1):1144-1148. doi: 10.1016/j.radphyschem.2010.06.006. PMID: 21966099; PMCID: PMC3182468.
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Formation, structure and conformational dynamics of highly substituted diphenylcarbonates.

Chemistry (Weinheim an der Bergstrasse, Germany)

Godt A, Unsal O, Enkelmann V.
PMID: 11072817
Chemistry. 2000 Oct 02;6(19):3522-30. doi: 10.1002/1521-3765(20001002)6:19<3522::aid-chem3522>3.0.co;2-r.

The symmetrical carbonates 5-8 were prepared from ethyl 4-hydroxybenzoates with aryl-, 4-(arylethynyl)-phenyl-, arylethynyl- or arylbutadiynyl-substituents in the 3- and 5-positions, by reaction with triphosgene. The choice of base (pyridine, DMAP, NaH) had a strong influence on the conversion: For...

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Godt A, Unsal O, Enkelmann V. Formation, structure and conformational dynamics of highly substituted diphenylcarbonates. Chemistry. 2000;6(19):3522-30doi: 10.1002/1521-3765(20001002)6:19<3522::aid-chem3522>3.0.co;2-r.
Godt, A., Unsal, O., & Enkelmann, V. (2000). Formation, structure and conformational dynamics of highly substituted diphenylcarbonates. Chemistry (Weinheim an der Bergstrasse, Germany), 6(19), 3522-30. https://doi.org/10.1002/1521-3765(20001002)6:19<3522::aid-chem3522>3.0.co;2-r
Godt, et al. "Formation, structure and conformational dynamics of highly substituted diphenylcarbonates." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 6,19 (2000): 3522-30. doi: https://doi.org/10.1002/1521-3765(20001002)6:19<3522::aid-chem3522>3.0.co;2-r
Godt A, Unsal O, Enkelmann V. Formation, structure and conformational dynamics of highly substituted diphenylcarbonates. Chemistry. 2000 Oct 02;6(19):3522-30. doi: 10.1002/1521-3765(20001002)6:19<3522::aid-chem3522>3.0.co;2-r. PMID: 11072817.
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Isoaromatization of 4-Alkylidene-3-oxo-1- cyclohexene-1-carboxylates. Convenient Synthesis of Methyl 4-Alkyl-3-hydroxybenzoates.

The Journal of organic chemistry

Campbell E, Martin JJ, Bordner J, Kleinman EF.
PMID: 11667416
J Org Chem. 1996 Jul 12;61(14):4806-4809. doi: 10.1021/jo9522724.

No abstract available.

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Campbell E, Martin JJ, Bordner J, et al. Isoaromatization of 4-Alkylidene-3-oxo-1- cyclohexene-1-carboxylates. Convenient Synthesis of Methyl 4-Alkyl-3-hydroxybenzoates. J Org Chem. 1996;61(14):4806-4809doi: 10.1021/jo9522724.
Campbell, E., Martin, J. J., Bordner, J., & Kleinman, E. F. (1996). Isoaromatization of 4-Alkylidene-3-oxo-1- cyclohexene-1-carboxylates. Convenient Synthesis of Methyl 4-Alkyl-3-hydroxybenzoates. The Journal of organic chemistry, 61(14), 4806-4809. https://doi.org/10.1021/jo9522724
Campbell, Erin, et al. "Isoaromatization of 4-Alkylidene-3-oxo-1- cyclohexene-1-carboxylates. Convenient Synthesis of Methyl 4-Alkyl-3-hydroxybenzoates." The Journal of organic chemistry vol. 61,14 (1996): 4806-4809. doi: https://doi.org/10.1021/jo9522724
Campbell E, Martin JJ, Bordner J, Kleinman EF. Isoaromatization of 4-Alkylidene-3-oxo-1- cyclohexene-1-carboxylates. Convenient Synthesis of Methyl 4-Alkyl-3-hydroxybenzoates. J Org Chem. 1996 Jul 12;61(14):4806-4809. doi: 10.1021/jo9522724. PMID: 11667416.
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Synthesis of 3,5-disubstituted 4-hydroxybenzoates by aryl-aryl and alkynyl-aryl coupling.

The Journal of organic chemistry

Godt A, Unsal O, Roos M.
PMID: 10808469
J Org Chem. 2000 May 09;65(9):2837-42. doi: 10.1021/jo991907m.

No abstract available.

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Godt A, Unsal O, Roos M. Synthesis of 3,5-disubstituted 4-hydroxybenzoates by aryl-aryl and alkynyl-aryl coupling. J Org Chem. 2000;65(9):2837-42doi: 10.1021/jo991907m.
Godt, A., Unsal, O., & Roos, M. (2000). Synthesis of 3,5-disubstituted 4-hydroxybenzoates by aryl-aryl and alkynyl-aryl coupling. The Journal of organic chemistry, 65(9), 2837-42. https://doi.org/10.1021/jo991907m
Godt, et al. "Synthesis of 3,5-disubstituted 4-hydroxybenzoates by aryl-aryl and alkynyl-aryl coupling." The Journal of organic chemistry vol. 65,9 (2000): 2837-42. doi: https://doi.org/10.1021/jo991907m
Godt A, Unsal O, Roos M. Synthesis of 3,5-disubstituted 4-hydroxybenzoates by aryl-aryl and alkynyl-aryl coupling. J Org Chem. 2000 May 09;65(9):2837-42. doi: 10.1021/jo991907m. PMID: 10808469.
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pHBMT1, a BAHD-family monolignol acyltransferase, mediates lignin acylation in poplar.

Plant physiology

de Vries L, MacKay HA, Smith RA, Mottiar Y, Karlen SD, Unda F, Muirragui E, Bingman C, Vander Meulen K, Beebe ET, Fox BG, Ralph J, Mansfield SD.
PMID: 34977949
Plant Physiol. 2021 Nov 22; doi: 10.1093/plphys/kiab546. Epub 2021 Nov 22.

Poplar (Populus) lignin is naturally acylated with p-hydroxybenzoate ester moieties. However, the enzyme(s) involved in the biosynthesis of the monolignol-p-hydroxybenzoates have remained largely unknown. Here, we performed an in vitro screen of the Populus trichocarpa BAHD acyltransferase superfamily (116...

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de Vries L, MacKay HA, Smith RA, et al. pHBMT1, a BAHD-family monolignol acyltransferase, mediates lignin acylation in poplar. Plant Physiol. 2021;doi: 10.1093/plphys/kiab546.
de Vries, L., MacKay, H. A., Smith, R. A., Mottiar, Y., Karlen, S. D., Unda, F., Muirragui, E., Bingman, C., Vander Meulen, K., Beebe, E. T., Fox, B. G., Ralph, J., & Mansfield, S. D. (2021). pHBMT1, a BAHD-family monolignol acyltransferase, mediates lignin acylation in poplar. Plant physiology, . https://doi.org/10.1093/plphys/kiab546
de Vries, Lisanne, et al. "pHBMT1, a BAHD-family monolignol acyltransferase, mediates lignin acylation in poplar." Plant physiology vol. (2021). doi: https://doi.org/10.1093/plphys/kiab546
de Vries L, MacKay HA, Smith RA, Mottiar Y, Karlen SD, Unda F, Muirragui E, Bingman C, Vander Meulen K, Beebe ET, Fox BG, Ralph J, Mansfield SD. pHBMT1, a BAHD-family monolignol acyltransferase, mediates lignin acylation in poplar. Plant Physiol. 2021 Nov 22; doi: 10.1093/plphys/kiab546. Epub 2021 Nov 22. PMID: 34977949.
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Electrochemical Sensing and Assessment of Parabens in Hydro- Alcoholic Solutions and Water Using a Boron-Doped Diamond Electrode.

Sensors (Basel, Switzerland)

Radovan C, Cinghită D, Manea F, Mincea M, Cofan C, Ostafe V.
PMID: 27879939
Sensors (Basel). 2008 Jul 25;8(7):4330-4349. doi: 10.3390/s8074330.

In this paper, the electrochemical behaviour of several parabens preservatives, i.e. esters of p-hydroxybenzoic acid, methyl-, ethyl- and propyl-4-hydroxybenzoates as methyl-, ethyl- and propyl-parabens (MB, EB, and PB), has been investigated at a commercial boron-doped diamond electrode (BDDE), especially...

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Radovan C, Cinghită D, Manea F, et al. Electrochemical Sensing and Assessment of Parabens in Hydro- Alcoholic Solutions and Water Using a Boron-Doped Diamond Electrode. Sensors (Basel). 2008;8(7):4330-4349doi: 10.3390/s8074330.
Radovan, C., Cinghită, D., Manea, F., Mincea, M., Cofan, C., & Ostafe, V. (2008). Electrochemical Sensing and Assessment of Parabens in Hydro- Alcoholic Solutions and Water Using a Boron-Doped Diamond Electrode. Sensors (Basel, Switzerland), 8(7), 4330-4349. https://doi.org/10.3390/s8074330
Radovan, Ciprian, et al. "Electrochemical Sensing and Assessment of Parabens in Hydro- Alcoholic Solutions and Water Using a Boron-Doped Diamond Electrode." Sensors (Basel, Switzerland) vol. 8,7 (2008): 4330-4349. doi: https://doi.org/10.3390/s8074330
Radovan C, Cinghită D, Manea F, Mincea M, Cofan C, Ostafe V. Electrochemical Sensing and Assessment of Parabens in Hydro- Alcoholic Solutions and Water Using a Boron-Doped Diamond Electrode. Sensors (Basel). 2008 Jul 25;8(7):4330-4349. doi: 10.3390/s8074330. PMID: 27879939; PMCID: PMC3697178.
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Structure and Stability of Long Rod-like Dodecyltrimethylammonium Chloride Micelles in Solutions of Hydroxybenzoates: A Molecular Dynamics Simulation Study.

Langmuir : the ACS journal of surfaces and colloids

Gujt J, Bešter-Rogač M, Spohr E.
PMID: 27442259
Langmuir. 2016 Aug 16;32(32):8275-86. doi: 10.1021/acs.langmuir.6b02076. Epub 2016 Aug 02.

The relative position of the hydroxylic and carboxylic groups in the isomeric hydroxybenzoate (HB) anions is experimentally known to have a large impact on the thermodynamics of micellization of cationic surfactants, such as dodecyltrimethylammonium chloride (DTAC), and on the...

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Gujt J, Bešter-Rogač M, Spohr E. Structure and Stability of Long Rod-like Dodecyltrimethylammonium Chloride Micelles in Solutions of Hydroxybenzoates: A Molecular Dynamics Simulation Study. Langmuir. 2016;32(32):8275-86doi: 10.1021/acs.langmuir.6b02076.
Gujt, J., Bešter-Rogač, M., & Spohr, E. (2016). Structure and Stability of Long Rod-like Dodecyltrimethylammonium Chloride Micelles in Solutions of Hydroxybenzoates: A Molecular Dynamics Simulation Study. Langmuir : the ACS journal of surfaces and colloids, 32(32), 8275-86. https://doi.org/10.1021/acs.langmuir.6b02076
Gujt, Jure, et al. "Structure and Stability of Long Rod-like Dodecyltrimethylammonium Chloride Micelles in Solutions of Hydroxybenzoates: A Molecular Dynamics Simulation Study." Langmuir : the ACS journal of surfaces and colloids vol. 32,32 (2016): 8275-86. doi: https://doi.org/10.1021/acs.langmuir.6b02076
Gujt J, Bešter-Rogač M, Spohr E. Structure and Stability of Long Rod-like Dodecyltrimethylammonium Chloride Micelles in Solutions of Hydroxybenzoates: A Molecular Dynamics Simulation Study. Langmuir. 2016 Aug 16;32(32):8275-86. doi: 10.1021/acs.langmuir.6b02076. Epub 2016 Aug 02. PMID: 27442259.
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Mineralization of phenol and its derivatives by Pseudomonas sp. strain CP4.

World journal of microbiology & biotechnology

Babu KS, Ajithkumar PV, Kunhi AA.
PMID: 24415017
World J Microbiol Biotechnol. 1995 Nov;11(6):661-4. doi: 10.1007/BF00361012.

A Pseudomonas sp. strain, CP4, was isolated that used phenol up to 1.5 g/l as sole source of carbon and energy. Optimal growth on 1.5 g phenol/l was at pH 6.5 to 7.0 and 30°C. Unadapted cells needed 72...

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Babu KS, Ajithkumar PV, Kunhi AA. Mineralization of phenol and its derivatives by Pseudomonas sp. strain CP4. World J Microbiol Biotechnol. 1995;11(6):661-4doi: 10.1007/BF00361012.
Babu, K. S., Ajithkumar, P. V., & Kunhi, A. A. (1995). Mineralization of phenol and its derivatives by Pseudomonas sp. strain CP4. World journal of microbiology & biotechnology, 11(6), 661-4. https://doi.org/10.1007/BF00361012
Babu, K S, et al. "Mineralization of phenol and its derivatives by Pseudomonas sp. strain CP4." World journal of microbiology & biotechnology vol. 11,6 (1995): 661-4. doi: https://doi.org/10.1007/BF00361012
Babu KS, Ajithkumar PV, Kunhi AA. Mineralization of phenol and its derivatives by Pseudomonas sp. strain CP4. World J Microbiol Biotechnol. 1995 Nov;11(6):661-4. doi: 10.1007/BF00361012. PMID: 24415017.
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Solution and Solid State Structural Chemistry of Th(IV) and U(IV) 4-Hydroxybenzoates.

Inorganic chemistry

Vanagas NA, Wacker JN, Rom CL, Glass EN, Colliard I, Qiao Y, Bertke JA, Van Keuren E, Schelter EJ, Nyman M, Knope KE.
PMID: 29877086
Inorg Chem. 2018 Jun 18;57(12):7259-7269. doi: 10.1021/acs.inorgchem.8b00919. Epub 2018 Jun 07.

Organic ligands with carboxylate functionalities have been shown to affect the solubility, speciation, and overall chemical behavior of tetravalent metal ions. While many reports have focused on actinide complexation by relatively simple monocarboxylates such as amino acids, in this...

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Vanagas NA, Wacker JN, Rom CL, et al. Solution and Solid State Structural Chemistry of Th(IV) and U(IV) 4-Hydroxybenzoates. Inorg Chem. 2018;57(12):7259-7269doi: 10.1021/acs.inorgchem.8b00919.
Vanagas, N. A., Wacker, J. N., Rom, C. L., Glass, E. N., Colliard, I., Qiao, Y., Bertke, J. A., Van Keuren, E., Schelter, E. J., Nyman, M., & Knope, K. E. (2018). Solution and Solid State Structural Chemistry of Th(IV) and U(IV) 4-Hydroxybenzoates. Inorganic chemistry, 57(12), 7259-7269. https://doi.org/10.1021/acs.inorgchem.8b00919
Vanagas, Nicole A, et al. "Solution and Solid State Structural Chemistry of Th(IV) and U(IV) 4-Hydroxybenzoates." Inorganic chemistry vol. 57,12 (2018): 7259-7269. doi: https://doi.org/10.1021/acs.inorgchem.8b00919
Vanagas NA, Wacker JN, Rom CL, Glass EN, Colliard I, Qiao Y, Bertke JA, Van Keuren E, Schelter EJ, Nyman M, Knope KE. Solution and Solid State Structural Chemistry of Th(IV) and U(IV) 4-Hydroxybenzoates. Inorg Chem. 2018 Jun 18;57(12):7259-7269. doi: 10.1021/acs.inorgchem.8b00919. Epub 2018 Jun 07. PMID: 29877086.
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Surface-enhanced Raman scattering of hydroxybenzoic acids adsorbed on silver nanoparticles.

Journal of colloid and interface science

Castro JL, Arenas JF, López-Ramírez MR, Peláez D, Otero JC.
PMID: 19167008
J Colloid Interface Sci. 2009 Apr 01;332(1):130-5. doi: 10.1016/j.jcis.2008.12.029. Epub 2009 Jan 22.

Surface-enhanced Raman scattering (SERS) of hydroxybenzoic acids has been studied on silver sols in H(2)O and D(2)O solutions. The adsorption behavior of 4-hydroxybenzoic acid (4HBA) is different from that of salicylic (2HBA) and 3-hydroxybenzoic (3HBA) acids. It was concluded...

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Castro JL, Arenas JF, López-Ramírez MR, et al. Surface-enhanced Raman scattering of hydroxybenzoic acids adsorbed on silver nanoparticles. J Colloid Interface Sci. 2009;332(1):130-5doi: 10.1016/j.jcis.2008.12.029.
Castro, J. L., Arenas, J. F., López-Ramírez, M. R., Peláez, D., & Otero, J. C. (2009). Surface-enhanced Raman scattering of hydroxybenzoic acids adsorbed on silver nanoparticles. Journal of colloid and interface science, 332(1), 130-5. https://doi.org/10.1016/j.jcis.2008.12.029
Castro, J L, et al. "Surface-enhanced Raman scattering of hydroxybenzoic acids adsorbed on silver nanoparticles." Journal of colloid and interface science vol. 332,1 (2009): 130-5. doi: https://doi.org/10.1016/j.jcis.2008.12.029
Castro JL, Arenas JF, López-Ramírez MR, Peláez D, Otero JC. Surface-enhanced Raman scattering of hydroxybenzoic acids adsorbed on silver nanoparticles. J Colloid Interface Sci. 2009 Apr 01;332(1):130-5. doi: 10.1016/j.jcis.2008.12.029. Epub 2009 Jan 22. PMID: 19167008.
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Salicylate isomer-specific effect on the micellization of dodecyltrimethylammonium chloride: large effects from small changes.

Langmuir : the ACS journal of surfaces and colloids

Šarac B, Mériguet G, Ancian B, Bešter-Rogač M.
PMID: 23477611
Langmuir. 2013 Apr 09;29(14):4460-9. doi: 10.1021/la400161n. Epub 2013 Mar 25.

Specific effects of the sodium salts of m- and p-hydroxybenzoates (m-HB and p-HB) on the aggregation process of dodecyltrimethylammonium chloride have been investigated by isothermal titration calorimetry, electrical conductivity, and (1)H NMR and compared with already reported data for...

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Šarac B, Mériguet G, Ancian B, et al. Salicylate isomer-specific effect on the micellization of dodecyltrimethylammonium chloride: large effects from small changes. Langmuir. 2013;29(14):4460-9doi: 10.1021/la400161n.
Šarac, B., Mériguet, G., Ancian, B., & Bešter-Rogač, M. (2013). Salicylate isomer-specific effect on the micellization of dodecyltrimethylammonium chloride: large effects from small changes. Langmuir : the ACS journal of surfaces and colloids, 29(14), 4460-9. https://doi.org/10.1021/la400161n
Šarac, Bojan, et al. "Salicylate isomer-specific effect on the micellization of dodecyltrimethylammonium chloride: large effects from small changes." Langmuir : the ACS journal of surfaces and colloids vol. 29,14 (2013): 4460-9. doi: https://doi.org/10.1021/la400161n
Šarac B, Mériguet G, Ancian B, Bešter-Rogač M. Salicylate isomer-specific effect on the micellization of dodecyltrimethylammonium chloride: large effects from small changes. Langmuir. 2013 Apr 09;29(14):4460-9. doi: 10.1021/la400161n. Epub 2013 Mar 25. PMID: 23477611.
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