Synthesis and Solubility of Hydrophilic Derivatives of β- Sitosterol
|
|
- Benedict Ramsey
- 5 years ago
- Views:
Transcription
1 J. Ind. Eng. Chem., Vol. 13, No. 3, (2007) Synthesis and Solubility of Hydrophilic Derivatives of β- Sitosterol Dae-won Chung and Young Tai Choi Department of Polymer Engineering, College of Engineering, Suwon University, Suwon , Korea Received November 28, 2006; Accepted December 31, 2006 Abstract: In this study, hydrophilic derivatives of β-sitosterol, which is known to have potential to reduce blood cholesterol levels, were synthesized by the esterification of poly(ethylene glycol) (PEG) and β -sitosterol with carboxylic functionality in the presence of dehydrating agents and a basic catalyst. By adjusting the molar ratios of reactants in the esterification reaction, hydrophilic β-sitosterol derivatives (HPSs) with various degrees of substitution (DS, average molar number of β-sitosterol moieties per molecule of HPS) were synthesized. The chemical structure and the distribution of isomers in HPSs were characterized by 1 H-NMR spectroscopy and MALDI-TOF mass spectrometry, respectively. The solubility of HPS in water was significantly affected by the value of DS of HPS. Keywords: β-sitosterol, hydrophilic derivatives, poly(ethylene glycol), esterification Introduction 1) Phytosterols refer to all of the alcohol compounds with steroid moietics found in higher plant life. They can be classified as stigmasterol, spinasterol, campesterol, and sitosterol; for example, sitosterol has α, β, and γ- types. Among all the phytosterols, β-sitosterol (24-ethyl-5-cholestene-3-ol) has been acquiring greater importance for the production of steroidal drugs and as a food ingredient that functions as a cholesterol lowering agents. β-sitosterol lowers the serum cholesterol level by reducing the absorption of cholesterol in the intestines through competition with LDL-cholesterol [1-3]. However, the hydrophobic and lipophobic properties of β- sitosterol have prevented its widespread application; it can be formulated only as a tablet or capsule, making it difficult and inefficient as a food ingredient. To utilize β-sitosterol as a food ingredient, many studies have focused on the chemical modification of β -sitosterol, mainly using its 3-hydroxy group. The first approaches to increase the solubility of β-sitosterol in fats were carried out by esterification of the 3-hydroxy group with fatty acids in the presence of an acidic cata- To whom all correspondence should be addressed. ( dwchung@suwon.ac.kr) lyst such as sodium bisulfate [4]; many synthetic methods using fatty acid anhydride [5], acyl chloride [6], or a basic catalyst [2-(dimethylamino)pyridine] with an activator (dicy- clohexylcarbodiimide) [7] were investigated. Lipase-catalyzed syntheses of β-sitosterol esters were recently reported [8]. β-sitosterol ester compounds are reported as having the same cholesterol lowering effect. For example, when β-sitosteryl oleate was given to an adult at 2 g per day for 5 days, the serum cholesterol level was reduced by ca 33 % [9]. A margarine containing a β-sitosterol ester, produced by transesterification of β-sitosterol with a fatty acid methyl ester derived from canola oil in the presence of sodium ethoxide at o C under vacuum, finally entered the United States market in 1999 [10,11]. On the other hand, approaches to increase the water-solublility of β-sitosterol for potential application in nonlipid-based foods were carried out only by formulation with an emulsifier. Lecitine-emulsified micelles of β- sitosterol were reported as having the same cholesterol lowering effect [12]. However, no studies on the synthesis of hydrophilic derivatives of β-sitosterol have been reported. In the present studies, hydrophilic β-sitosterol derivatives (HPSs) were synthesized by two step reactions,
2 368 Dae-won Chung and Young Tai Choi TEA, the reaction mixture was heated for 2 h at 80 o C. After confirming the completion of the reaction with thin layer chromatography (TLC), the solvent was evaporated from the reaction mixture. The remaining solid residue was dissolved in 500 ml of ethyl alcohol and then 11 ml of concentrated HCl was added dropwise. A white precipitate was collected by filtration after adding 500 ml of water. Recrystallization from hexane afforded 56.8 g of the intermediate compound (yield; 92 %). The structure of CES was confirmed by 1 H-NMR spectroscopy in CDCl 3. Figure 1. Synthesis of HPS. as described in Figure 1. The first step was the synthesis of an intermediate (carboxyethyl-β-sitosterol, CES), which afforded carboxylic functionality to β-sitosterol; the second step was the coupling of a hydrophilic polymer (PEG) to CES in the presence of a basic catalyst and dehydrating agents. HPSs with various values of DS were synthesized by adjusting the molar ratios of CES to PEG in the second reaction. For comparison, an HPS with one sterol moiety per molecule of PEG (Mono) was also synthesized. The solubility of HPS in water and the effect of the value of DS on the solubility were also investigated. Experimental Materials β-sitosterol, PEG (MW = 1500), succinic anhydride, 1,3-dicyclohexylcarbodiimide (DCC), and 4-dimethylaminopyridine (DMAP) were purchased from Aldrich and used without further purification. β-sitosterol contains % of campersterol and % of dihydrobrassicasterol. Gas chromatography was performed using a capillary column [HP-1 (30 m 0.25 mm i.d µm)] and a M600D instrument (Young-Lin Instrument Co.). FT-IR spectroscopy was performed using a Nexus instrument (Nicolet Instrument Corp.). 1 H-NMR spectra were obtained using a Bruker FT-NMR spectrometer (500 MHz) and CDCl 3 as solvent. A Voyager Biospectrometry Workstation (Applied Biosystem Inc.) was used for the measurement of Matrix-Assisted Laser Desorption Ionization (MALDI-TOF) Mass Spectra. Preparation of HPS 15.0 g of PEG having a molecular weight of 1500, 2.7 g (13 mmol) of DCC, and 0.1 g (0.8 mmol) of DMAP were dissolved in 100 ml of methylene chloride (MC) at room temperature. 7.7 g (1.5 times the number of moles of PEG) of CES pre-dissolved in MC was then added dropwise to the reaction mixture at 30 o C. The reaction was continued at 30 o C until the CES peak disappeared (TLC). Dicyclohexylurea was removed by filtration, and then the filtrate was evaporated. Recrystallization in isopropyl alcohol afforded 20.6 g of HPS. The structure of HPS was confirmed by 1 H-NMR spectroscopy in CDCl 3. Preparation of Mono (R=H in Figure 1) 15.0 g (10 mmol) of PEG having a molecular weight of 1500, 0.58 g (2.8 mmol) of DCC, and 0.24 g (2.0 mmol) of DMAP were dissolved in 100 ml of MC at room temperature. 2.1 g (4 moles) of CES pre-dissolved in MC was then added dropwise at 30 o C to the reaction mixture. The reaction was continued at 30 o C until the CES peak disappeared in TLC. Dicyclohexylurea was removed by filtration, and then the filtrate was extracted with water four times to remove unreacted PEG. Recrystallization three times from isopropyl alcohol afforded 2.1 g of Mono. Solubility Test of HPS The solubility was determined visually after 600 mg of HPS in 1 ml of water was stirred at 35 o C for 2 h. After the solution became clear, it was kept at 25 or 4 o C for 48 h. If HPS was not soluble at 35 o C or the precipitation appeared during the storage at 25 or 4 o C, 1 ml of water was added, and the same procedure was repeated until the solution appeared clear. The critical concentration at each temperature was defined as the maximum concentration where the solution was visually clear. Preparation of CES 50.0 g (0.12 mol) of β-sitosterol and 24.1 g (0.24 mol) of succinic anhydride were dissolved in 250 ml of dichloroethane (DCE). After adding 16.7 ml (0.12 mol) of
3 Synthesis and Solubility of Hydrophilic Derivatives of β- Sitosterol H-NMR spectra for cholesterol and cholesterol acetate [17]. The absence of succinic anhydride in CES was confirmed by GC. Figure 2. 1 H-NMR spectra of β-sitosterol (A), CES (B), and HPS with DS=1.08 (C). Results and Discussion Preparation of CES Although the synthesis of CES has not been reported, previously the preparation of carboxyethyl-cholesterol (cholesteryl hemisuccinate), which acts as a stabilizer for phosphatidylcholine membranes [13] and an enhancer for the specific immunogenicity of tumor cell [14], is well known. In this paper, CES was synthesized according to the reported method [15,16] for preparing carboxyethylcholesterol, with a minor modification. The chemical structure of CES was confirmed by 1 H-NMR spectroscopy studies. As described in (A) and (B) of Figure 2, the proton of the 3-position at 3.5 ppm [b in (A)] of free β-sitosterol shifted to 4.6 ppm [b in (B)], as a result of the vicinal hydroxy group having changed into an ester group. Similar phenomena were observed in Preparation of HPS There are many known methods used to prepare ester compounds by coupling OH and COOH groups. The most common method is using an acidic catalyst, such as P-toluenesulfonic acid (PTSA) [18,19]; however, the ester group in CES can be cleaved under acidic conditions. In fact, the reaction between CES and PEG in the presence of PTSA in toluene afforded the target compound (HPS), but free β-sitosterol was also observed in TLC at the initial stage of reaction, suggesting that the ester group in CES was partially hydrolyzed under these conditions. DCC is a powerful dehydrating agent commonly used for the preparation of amides, esters, and anhydrides [20]. In general, ester formation reactions proceed reliably through O-acylurea or anhydride intermediates, but require the presence of an acylation catalyst [21]. When the combination of DCC and DMAP was applied for the esterification reactions between β-sitosterol and fatty acids, the yields were over 90 % and no side products were observed [7]. In this study, DMAP was also used as an acylation catalyst, and the reactions were completed during 6 8 h. As described in (C) of Figure 2, the 1 H-NMR spectrum of the product showed a remarkable peak at ppm (e), which is assigned to the methylene protons of PEG. The most characteristic peak appeared at 4.3 ppm (d). This triplet can be assigned to terminal methylene protons of PEG coupled with CES, and its appearance is considered to be direct evidence for the esterification of CES with PEG. The integration ratio of peaks a, b, c, and d corresponded to the ideal ratio (1:1:4:2), regardless of the DS value. Because one chain of PEG has -OH groups at both ends, two sterol moieties can be introduced into one PEG chain. However, HPS having two sterol moieties at both ends may not be soluble in water. Thus, HPSs with various DS were synthesized through coupling reactions under various molar ratios of CES to PEG, whose molecular weight was fixed at The results are summarized in Table 1. In Table 1, the reaction time is the time required for the CES peak to disappear completely in TLC, and the DS value of HPS was calculated, based on a 1 H-NMR spectrum, according to the following equation: DS = n*c /e, where n is the degree of polymerization of PEG (in this case, n=34), and c and e are the integrations of the peaks
4 370 Dae-won Chung and Young Tai Choi Table 1. Reaction Conditions and Results Feeding molar ratio (PEG : CES) Reaction time (hr) DS * Yield** (%) 1.00 : : : : : * Calculated from 1 H-NMR spectra. ** Yield was calculated according to the following equation: {weight of product/( *DS)}/moles of PEG reacted. assigned in (C) of Figure 2. As the ratio of CES increased, more time was required for the completion of the reaction. Good agreement between the DS values and the feeding molar ratios of CES to PEG and the high yield (over 86 %) suggest that the coupling reaction occurred quantitatively without any side reactions. Synthesis of Mono The coupling reaction between CES and PEG can produce three different compounds (unreacted PEG, Mono, and Di) because PEG is a di-functional compound and CES is mono-functional. As described in the experimental section, pure Mono was synthesized by coupling CES with an excess (5 equivalents) of PEG to prevent the formation of Di, with subsequent purification to remove unreacted PEG. No significant difference in the 1 H-NMR spectra of Mono and HPS with DS=1.08 was observed because DS obtained from the 1 H-NMR spectral data means the average number of sterol moieties in HPS. The distribution of isomers in pure Mono was investigated using MALDI-TOF mass spectrometry. Distribution of Isomers Figure 3 shows MALDI-TOF mass spectra of PEG and HPSs with various DS values. Each peak has intervals of 44, which is equivalent to the mass of a monomeric unit of PEG. As shown in (C) of Figure 3, HPS with DS=1.08 contained three groups in the peak pattern. The first group, with a range of mass (m/e), is considered to be unreacted PEG. The slightly higher and narrower range of the first group, compared to the spectrum (A in Figure 3) of PEG, suggests that PEG with a lower molecular weight reacted preferentially with CES so that the PEG with higher molecular weight remained unreacted. The second and third groups are equivalent to the spectra of pure Mono (B) and Di (E), as well as to the expected masses of Mono and Di (molecular weight of one sterol moiety is 515). HPS (D) with DS=1.59 shows a similar pattern, but with a significant decrease in the Figure 3. MALDI-TOF mass spectra of PEG (A), Mono (B), HPS with DS = 1.08 (C), HPS with DS = 1.59 (D), and Di (E). amount of unreacted PEG and an increase in Di compared to HPS with DS=1.08. On the other hand, in spectrum (E) of Di, no significant peaks assigned to PEG and Mono are observed.
5 Synthesis and Solubility of Hydrophilic Derivatives of β- Sitosterol 371 Table 2. Solubility of HPSs Critical Concentration * Critical Concentration * (g of HPS / ml of water) DS (mg of β-sitosterol moiety in HPS / ml of water) 4 o C 25 o C 35 o C 4 o C 25 o C 35 o C 1.00 (Mono) (Di) insoluble insoluble insoluble insoluble insoluble insoluble * Maximum concentration where the solution becomes visually clear. Solubility Test As more sterol moieties are introduced into PEG, the hydrophilicities of the HPSs decreased. Therefore, it is important to figure out relationships between the value of DS and the solubility of the products. As summarized in Table 2, the water-solubility of the HPSs decreased as the DS values increased and the temperature decreased; Di was not soluble in water, even at g/ml. It is clear that the introduction of bulky hydrophobic groups (β-sitosterol) at both ends of PEG limit the water-solubility of HPS. However, considering the application of HPS, it is also important to evaluate the solubility based on the β-sitosterol moiety in HPS, which can be calculated from the following equation: Weight ratio of β-sitosterol moiety in HPS = 515 DS / ( DS) where 515 is the molecular weight of CES and 1500 is the average molecular weight of PEG; thus, DS corresponds to the average molecular weight of HPS. The water-solubility based on the β-sitosterol moiety in HPSs also decreased as the DS values increased and the temperature decreased. It is remarkable that the water-solubility of Mono was higher than that of HPS with DS = 1.08, even though the contents of β-sitosterol moiety of both compounds were almost the same. This result strongly suggests that the absence of Di in HPS is desirable for potential application of HPS in non-lipid-based foods. Conclusion Hydrophilic β-sitosterol derivatives were synthesized through two-step reactions and their solubilities in water investigated. The following results are drawn: 1) In the presence of a basic catalyst and dehydrating agents, the coupling reactions of CES to PEG were accomplished without side reactions. HPSs with various DS values were obtained by adjusting the feeding molar ratios of CES to PEG in the coupling reaction. 2) Mono, with one sterol moiety per molecule of PEG, was synthesized by coupling CES with an excess of PEG, to prevent the formation of Di, and subsequent purification to remove unreacted PEG. 3) The distribution of isomers of HPSs, including Mono and Di, could be determined clearly through MALDI-TOF mass spectrometries studies. 4) The solubilities of HPSs decreased as the DS values increased and the temperature decreased. The solubility of Mono was higher than that of HPS with DS = 1.08, even though the content of β-sitosterol moieties of both compounds was almost identical. This result strongly suggests that absence of Di in HPS is desirable for the development of water-soluble β-sitosterol derivatives. References 1. H. T. Vanhanen and T. A. Miettinen, Clin. Chim. Acta, 205, 97 (1992). 2. H. Gylling and T. A. Miettinen, J. Lipid Res., 37, 1776 (1996). 3. P. J. H. Jones, D. E. MacDougall, F. Ntanios, and C. A. Vanstone, Can. J. Physiol. Pharmacol., 75, 217 (1997). 4. U. S. Patent 6,184,397 (2001). 5. F. H. Mattson, R. A. Volpenhein, and J. B. Martin, J. Lipid Res., 5, 374 (1964). 6. K. G. Pinter, J. G. Hamilton, and J. E. Muldrey, J. Lipid Res., 5, 273 (1964). 7. D.-W. Chung and Y. T. Cho, J. Korean Ind. Eng. Chem., 17, 375 (2006). 8. U. S. Patent 6,660,491 (2003). 9. P. J. H. Jones, D. E. MacDougall, F. Ntanios, and C. A. Vanstone, Can, J. Pharmacol., 75, 217 (1997). 10. U. S. Patent 5,502,045 (1996). 11. J. A. Weststrate and G. W. Meijer, Eur. J. Clin.
6 372 Dae-won Chung and Young Tai Choi Nutr., 52, 334 (1998). 12. U. S. Patent 5,215,759 (1993). 13. W.-X. Ding, X.-R. Qi, P. Li, Y. Maitani, and T. Nagai, Int. J. Pharm., 300, 38 (2005). 14. Y. G. Skornick, G. H. Rong, W. F. Sindelar, L. Richert, J. M. Klausner, R. R. Rozin, and M. Shinitzky, Cancer, 58, 650 (1986). 15. X.-B. Yuan, H. Li, and Y.-B. Yuan, Carbohydr. Polym., 65, 337 (2006). 16. R. W. Kuhn, W. T. Schrader, R. G. Smith, and B. W. O Malley, J. Biol. Chem., 250, 4220 (1975). 17. C. J. Pouchert and J. Behnke, The Aldrich Library of 13 C and 1 H FT NMR Spectra, Aldrich Chemical Company, Inc. (1993). 18. S. P. Mun, E. M. Hassan, and T. H. Yoon, J. Korean Ind. Eng. Chem., 7, 430 (2001). 19. S. P. Mun, I. A. Gilmour, and P. J. Jordan, J. Ind. Eng. Chem., 12, 720 (2006). 20. S. B. Lee, K. A. Park, and I. K. Hong, J. Korean Ind. Eng. Chem., 10, 438 (1999). 21. L. A. Paquette, Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Chichester (1995).
Student Handout. This experiment allows you to explore the properties of chiral molecules. You have
Student Handout This experiment allows you to explore the properties of chiral molecules. You have learned that some compounds exist as enantiomers non-identical mirror images, such as your left and right
More informationEsterification. Preparation of β-d-glucose pentaacetate. Dr. Zerong Wang at UHCL. Table of contents
Esterification Preparation of β-d-glucose pentaacetate Table of contents Ester eaction with carboxylic acids eaction with esters: transesterification eaction with acid anhydrides eaction with acid halides
More informationAll chemicals were obtained from Aldrich, Acros, Fisher, or Fluka and were used without
Supplemental Data Alexander et al. Experimental Procedures General Methods for Inhibitor Synthesis All chemicals were obtained from Aldrich, Acros, Fisher, or Fluka and were used without further purification,
More informationph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors
ph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors Jie Li, Chendong Ji, Wantai Yang, Meizhen Yin* State Key Laboratory of Chemical Resource Engineering,
More informationSupporting information
S1 Supporting information Biodegradable Injectable Polymer Systems Exhibiting Temperature-Responsive Irreversible Sol-to-Gel Transition by Covalent Bond Formation Yasuyuki YOSHIDA 1,2, Keisuke KAWAHARA
More informationCharacterization and Modification of Low Molecular Water-Soluble Chitosan for Pharmaceutical Application
Characterization and Modification of Low Molecular Water-Soluble Chitosan Bull. Korean Chem. Soc. 2003, Vol. 24, No. 9 1303 Characterization and Modification of Low Molecular Water-Soluble Chitosan for
More informationNovel D-erythro N-Octanoyl Sphingosine Analogs As Chemo- and Endocrine. Resistant Breast Cancer Therapeutics
Page 11 of 32 Cancer Chemotherapy and Pharmacology Novel D-erythro N-Octanoyl Sphingosine Analogs As Chemo- and Endocrine Resistant Breast Cancer Therapeutics James W. Antoon, Jiawang Liu, Adharsh P. Ponnapakkam,
More informationDivergent Construction of Pyrazoles via Michael Addition of N-Aryl Hydrazones to 1,2-Diaza-1,3-dienes
Divergent Construction of Pyrazoles via Michael Addition of N-Aryl Hydrazones to 1,2-Diaza-1,3-dienes Serena Mantenuto, Fabio Mantellini, Gianfranco Favi,* and Orazio A. Attanasi Department of Biomolecular
More informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Supporting Information Enantioselective Cu-catalyzed 1,4-Addition of Various Grignard Reagents to Cyclohexenone using Taddol-derived Phosphine-Phosphite
More informationCarboxylic Acid Derivatives Reading Study Problems Key Concepts and Skills Lecture Topics: Structures and reactivity of carboxylic acid derivatives
Carboxylic Acid Derivatives Reading: Wade chapter 21, sections 21-1- 21-16 Study Problems: 21-45, 21-46, 21-48, 21-49, 21-50, 21-53, 21-56, 21-58, 21-63 Key Concepts and Skills: Interpret the spectra of
More informationSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Supporting Information Facile Three-Step Synthesis and Photophysical Properties of [8]-, [9]-,
More informationSupporting Information
Supporting Information A single design strategy for dual sensitive ph probe with a suitable range to map ph in living cells Kang-Kang Yu, Ji-Ting Hou, Kun Li, * Qian Yao, Jin Yang, Ming-Yu Wu, Yong-Mei
More informationManganese powder promoted highly efficient and selective synthesis of fullerene mono- and biscycloadducts at room temperature
Supplementary Information Manganese powder promoted highly efficient and selective synthesis of fullerene mono- and biscycloadducts at room temperature Weili Si 1, Xuan Zhang 1, Shirong Lu 1, Takeshi Yasuda
More informationThiol-Ene Photoimmobilization of Chymotrypsin on Polysiloxane Gels for Enzymatic Peptide Synthesis
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Supporting information for: Thiol-Ene Photoimmobilization of Chymotrypsin on Polysiloxane Gels
More informationSupporting Information
Supporting Information Direct Synthesis of Benzimidazoles by Dehydrogenative Coupling of Aromatic Diamines and Alcohols Catalyzed by Cobalt Prosenjit Daw, Yehoshoa Ben-David, and David Milstein* Department
More informationEnantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction
Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction P. Veeraraghavan Ramachandran* and Prem B. Chanda Department of Chemistry, Purdue
More informationSupporting Information
Supporting Information Synthesis of N-Heteropolycyclic Compounds Including Quinazolinone Skeletons by Using Friedel-Crafts Alkylation Bu Keun Oh, Eun Bi Ko, Jin Wook Han* and Chang Ho Oh* Department of
More informationIdentification of Aromatic Fatty Acid Ethyl Esters
Chapter 3.2 Identification of Aromatic Fatty Acid Ethyl Esters The only use of gas chromatography is not sufficient to determine which compounds are eluting from the catalytic bed. At the beginning of
More informationElectronic Supplementary Material
Electronic Supplementary Material PAMAM Dendrimers Bearing Electron-Donating Chromophores: Fluorescence and Electrochemical Properties Bing-BingWang a, Xin Zhang a, Ling Yang a, Xin-Ru Jia* a, Yan Ji a,
More informationMasatoshi Shibuya,Takahisa Sato, Masaki Tomizawa, and Yoshiharu Iwabuchi* Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences,
Oxoammonium ion/naclo 2 : An Expedient, Catalytic System for One-pot Oxidation of Primary Alcohols to Carboxylic Acid with Broad Substrate Applicability Masatoshi Shibuya,Takahisa Sato, Masaki Tomizawa,
More informationCHAPTER - 2 SYNTHESIS AND CHARACTERIZATION
26 CHAPTER - 2 SYNTHESIS AND CHARACTERIZATION OF NOVEL ANTI-LIPIDEMIC AGENTS 27 2.1 - INTRODUCTION 2.1.1 - Drug Discovery and Anti-lipidemic agents: Anti-lipidemic agents are basic drugs for prevention
More informationBIOCATALYTIC CONVERSION OF OTHER LIPIDS
Chapter 6 BIOCATALYTIC CONVERSION OF OTHER LIPIDS In Chapters 4 and 5, lipase-mediated conversion of acylglycerols were presented. The Chapter 6 deals with biocatalytic modification of phospholipids, sphingolipids,
More informationSupporting Information for. Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of. 3,5-Disubstituted Pyridines: Mechanistic Studies
Supporting Information for Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of 3,5-Disubstituted Pyridines: Mechanistic Studies Ta-Hsien Chuang* a, Yu-Chi Chen b and Someshwar Pola
More informationElectronic Supporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 The First Peripherally Masked Thiol Dendrimers : A Facile and Highly Efficient Functionalization
More information22. The Fischer Esterification
22. The Fischer Esterification A. Background Esters are an incredibly important functional group in organic chemistry. Esters are typically very pleasant smelling molecules and are therefore frequently
More informationFactors to Consider in the Study of Biomolecules
Factors to Consider in the Study of Biomolecules What are the features of the basic building blocks? (ex: monosaccharides, alcohols, fatty acids, amino acids) 1) General structure and functional groups
More informationA New Design for Light-Breakable Polymer Micelles
Supporting Information A New Design for Light-Breakable Polymer Micelles 1. Synthesis and Characterization of Diblock Copolymer Materials. Dioxane and THF were purified by distillation from sodium with
More informationRameshwar Prasad Pandit and Yong Rok Lee * School of Chemical Engineering, Yeungnam University, Gyeongsan , Korea
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Novel ne-pot Synthesis of Diverse γ,δ-unsaturated β-ketoesters by Thermal
More informationPreparation, isolation and characterization of N α -Fmoc-peptide isocyanates: Solution synthesis of oligo-α-peptidyl ureas
SUPPORTING INFORMATION Preparation, isolation and characterization of N α -Fmoc-peptide isocyanates: Solution synthesis of oligo-α-peptidyl ureas Vommina V. Suresh Babu*, Basanagoud S. Patil, and Rao Venkataramanarao
More informationSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 Supporting Information General. NMR spectra for identification of intermediates and final compoundswere recorded
More informationAccessory Publication
10.1071/CH09088_AC CSIRO 2009 Accessory Publication: Australian Journal of Chemistry, 2009, 62(8), 790 793 Thermally Responsive Elastomeric Supramolecular Polymers Featuring Flexible Aliphatic Hydrogen
More informationCarboxylic Acid Derivatives
arboxylic Acid Derivatives The most important derivatives of carboxylic acids are l " ' ' acid halide acid anhydride an ester an amide Although not direct derivatives, nitriles, -, are related to carboxylic
More informationSupporting Information. for. Access to pyrrolo-pyridines by gold-catalyzed. hydroarylation of pyrroles tethered to terminal alkynes
Supporting Information for Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes Elena Borsini 1, Gianluigi Broggini* 1, Andrea Fasana 1, Chiara Baldassarri
More informationSupporting Information. Transformation of Framework Solids into Processible Metallo-polymers
Supporting Information Transformation of Framework Solids into Processible Metallo-polymers Eun-Young Choi, Chunji Gao, Hong-Jun Lee, O-Pil Kwon*, Suck-Hyun Lee* Department of Molecular Science and Technology,
More informationSynthesis and Evaluation of Esterified Estolide
Chapter 5 Synthesis and Evaluation of Esterified Estolide 5.1 Introduction Coconut oil has a very high congelation temperature precluding its use as base oil for industrial lubricants in temperate and
More informationNitro-Grela-type complexes containing iodides. robust and selective catalysts for olefin metathesis
Supporting Information for Nitro-Grela-type complexes containing iodides robust and selective catalysts for olefin metathesis under challenging conditions. Andrzej Tracz, 1,2 Mateusz Matczak, 1 Katarzyna
More informationChapter 18. Carboxylic Acids and Their Derivatives. Nucleophilic Addition-Elimination at the Acyl Carbon
Chapter 18 Carboxylic Acids and Their Derivatives. Nucleophilic Addition-Elimination at the Acyl Carbon Carboxylic Acids Organic compounds characterized by their acidity Contains COOH group (must be at
More informationAnalysis of fatty acid metabolism using Click-Chemistry and HPLC-MS
Analysis of fatty acid metabolism using Click-Chemistry and HPLC-MS Alexander J. Pérez and Helge B. Bode -Supporting Information- Contents Experimental section Supplementary figures NMR spectra Page S2
More informationBio Ionic Liquids: Room Temperature Ionic Liquids Composed Wholly of Biomaterials
SUPPORTING INFORMATION Bio Ionic Liquids: Room Temperature Ionic Liquids Composed Wholly of Biomaterials Yukinobu Fukaya a, Yoshiki Iizuka a, Kenta Sekikawa a, and Hiroyuki Ohno a * a Department of Biotechnology,
More informationSYNTHESIS AND CHARACTERIZATION OF SEVERAL AMPHIPHILIC CHITOSAN DERIVATIVES NADHRATUN NAIIM MOBARAK & MD. PAUZI ABDULLAH
SYNTHESIS AND CHARACTERIZATION OF SEVERAL AMPHIPHILIC CHITOSAN DERIVATIVES NADHRATUN NAIIM MOBARAK & MD. PAUZI ABDULLAH School of Chemistry Science and Food Technology, Faculty of Science and Technology,
More informationSupplementary Figures
Supplementary Figures Absorption 4 3 2 1 Intensity Energy U(R) relaxation ~~~ ~~~~~~ 2 3 4 1 S S 1 2 3 4 1 Fluoescence 4 3 2 1 Intensity H-aggregation ~~~~ J-aggregation Absorption Emission Vibrational
More informationCatalytic decarboxylative alkylation of β-keto acids with sulfonamides via the cleavage of carbon nitrogen and carbon carbon bonds
Catalytic decarboxylative alkylation of β-keto acids with sulfonamides via the cleavage of carbon nitrogen and carbon carbon bonds Cui-Feng Yang, Jian-Yong Wang and Shi-Kai Tian* Joint Laboratory of Green
More informationSupporting Information. for. Pd-catalyzed decarboxylative Heck vinylation of. 2-nitro-benzoates in the presence of CuF 2
Supporting Information for Pd-catalyzed decarboxylative Heck vinylation of 2-nitro-benzoates in the presence of CuF 2 Lukas J. Gooßen*, Bettina Zimmermann, Thomas Knauber Address: Department of Chemistry,
More informationRuthenium-Catalyzed C H Oxygenation on Aryl Weinreb Amides
Supporting Information Ruthenium-Catalyzed C H xygenation on Aryl Weinreb Amides Fanzhi Yang and Lutz Ackermann* Institut für rganische und Biomolekulare Chemie Georg-August-Universität Tammannstrasse
More informationSupplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2008
Experimental Details Unless otherwise noted, all chemicals were purchased from Sigma-Aldrich Chemical Company and were used as received. 2-DOS and neamine were kindly provided by Dr. F. Huang. Paromamine
More informationAn Orthogonal Array Optimization of Lipid-like Nanoparticles for. mrna Delivery in Vivo
Supporting Information An rthogonal Array ptimization of Lipid-like Nanoparticles for mrna Delivery in Vivo Bin Li, Xiao Luo, Binbin Deng, Junfeng Wang, David W. McComb, Yimin Shi, Karin M.L. Gaensler,
More informationSupporting Information. for. Synthesis of 2,1-benzisoxazole-3(1H)-ones by basemediated. photochemical N O bond-forming
Supporting Information for Synthesis of 2,1-benzisoxazole-3(1H)-ones by basemediated photochemical N O bond-forming cyclization of 2-azidobenzoic acids Daria Yu. Dzhons and Andrei V. Budruev* Address:
More informationBase-promoted acetal formation employing aryl salicylates
Base-promoted acetal formation employing aryl salicylates Pinmanee Boontheung, Patrick Perlmutter*, and Evaloni Puniani School of Chemistry, Monash University, PO Box 23, Victoria 3800 Australia E-mail:
More informationTest Bank for Lehninger Principles of Biochemistry 5th Edition by Nelson
Test Bank for Lehninger Principles of Biochemistry 5th Edition by Nelson Link download full: http://testbankair.com/download/test-bank-forlehninger-principles-of-biochemistry-5th-edition-by-nelson/ Chapter
More informationZillillah, a Guowei Tan, a,b and Zhi Li* a,b. 4 Engineering Drive 4, Singapore Fax: ; Tel:
Highly Active, Stable, and Recyclable Magnetic Nano-size Solid Acid Catalysts: Efficient Esterification of Free Fatty Acid in Grease to Produce Biodiesel Zillillah, a Guowei Tan, a,b and Zhi Li* a,b a
More informationSynthesis and Blastocyst Implantation Inhibition Potential of Lupeol Derivatives in Female Mice
Supporting Information Rec. Nat. Prod. 9:4 (2015) 561-566 Synthesis and Blastocyst Implantation Inhibition Potential of Lupeol Derivatives in Female Mice Anita Mahapatra 1*, Purvi Shah 1, Mehul Jivrajani
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information ovel pseudo[2]rotaxanes constructed by selfassembly of dibenzyl
More information4.2 Aims and Objectives
4.1 Introduction The reaction between the products of interaction of halogens and silver salts of carboxylic acids and olefns forms the basis of the Woodward and Prevost methods of cis- and trans- hydroxylations
More informationSupporting Information for. Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the. analysis of Glucose in Whole Blood
Supporting Information for Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the analysis of Glucose in Whole Blood Yueling Liu, Jingwei Zhu, Yanmei Xu, Yu Qin*, Dechen Jiang*
More informationConcentrating Alpha-tocopherol from Oil Byproduct with Supercritical Methanol and CO 2
Concentrating Alpha-tocopherol from Oil Byproduct with Supercritical Methanol and CO 2 Tao Fang, Wahyudiono, Motonobu Goto *, Mitsuru Sasaki Department of Applied Chemistry and Biochemistry, Kumamoto University,
More informationSupporting Information
Supporting Information Polymer Micelles Stabilization-n-Demand through Reversible Photocrosslinking 1. Synthesis and Characterization of Diblock Copolymers Materials. Cu(I)Br, 2-Bromo-2-methylpropionyl
More informationCopper(II) Ionic Liquid Catalyzed Cyclization-Aromatization of. Hydrazones with Dimethyl Acetylenedicarboxylate: A Green Synthesis
Copper(II) Ionic Liquid Catalyzed Cyclization-Aromatization of Hydrazones with Dimethyl Acetylenedicarboxylate: A Green Synthesis of Fully Substituted Pyrazoles Shirin Safaei, Iraj Mohammadpoor-Baltork,*
More informationSupporting Materials. Experimental Section. internal standard TMS (0 ppm). The peak patterns are indicated as follows: s, singlet; d,
CuBr-Catalyzed Efficient Alkynylation of sp 3 C-H Bonds Adjacent to a itrogen Atom Zhiping Li and Chao-Jun Li* Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec H3A
More informationHiroya Hidaka *1), Masaki Takiwaki 2), Mine Yamashita 2), Shinya Otsuki 1), Kenji Kawasaki 3), Mitsutoshi Sugano 3) and Takayuki Honda 4)
Mild acid hydrolysis of sphingolipids yields lysosphingolipids: a matrix-assisted laser desorption and ionization time-of-flight mass spectrometry study Hiroya Hidaka *1), Masaki Takiwaki 2), Mine Yamashita
More informationIntroduction to the Study of Lipids
Introduction to the Study of Lipids Factors to Consider in the Study of Biomolecules What are the features of the basic building blocks? (ex: monosaccharides, alcohols, fatty acids, amino acids) 1) General
More informationPreparation of Stable Aziridinium Ions and Their Ring Openings
Supplementary Information Preparation of Stable Aziridinium Ions and Their Ring Openings Yongeun Kim a Hyun-Joon Ha*, a Sae Young Yun b and Won Koo Lee,*,b a Department of Chemistry and Protein Research
More information1/3/2011. Chapter 17 Carboxylic Acids and Their Derivatives. Nucleophilic Addition- Elimination at the Acyl Carbon
Introduction The carboxyl group (-CO 2 H) is the parent group of a family of compounds called acyl compounds or carboxylic acid derivatives Chapter 17 Carboxylic Acids and Their Derivatives. Nucleophilic
More information# Supplementary Material (ESI) for Molecular BioSystems # This journal is The Royal Society of Chemistry 2005
Supporting Information Multifunctional Polymeric Micelles with Folate-Mediated Cancer Cell Targeting and ph-triggered Drug Releasing Properties for Active Intracellular Drug Delivery Younsoo Bae, Woo-Dong
More informationp-toluenesulfonic Acid-Mediated 1,3-Dipolar Cycloaddition of
Supporting Information for: p-toluenesulfonic Acid-Mediated 1,3-Dipolar Cycloaddition of Nitroolefins with NaN 3 for Synthesis of 4-Aryl-NH-1,2,3-triazoles Xue-Jing Quan, Zhi-Hui Ren, Yao-Yu Wang, and
More informationFatty Acid Methylation Kits
Methyl esterification kit for fatty acids analysis Fatty Acid Methylation Kits Below are two methods for efficiently preparing fatty acid samples for GC analysis. Neither method requires high temperatures,
More informationSupporting Information. Radical fluorination powered expedient synthesis of 3 fluorobicyclo[1.1.1]pentan 1 amine
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Radical fluorination powered expedient synthesis
More informationSupporting Information. Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base
Supporting Information Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base Feng Wang, a Haijun Yang, b Hua Fu, b,c * and Zhichao Pei a * a College
More informationThermal shift binding experiments were carried out using Thermofluor 384 ELS system. Protein
Supplementary Methods Thermal shift assays Thermal shift binding experiments were carried out using Thermofluor 384 ELS system. Protein unfolding was examined by monitoring the fluorescence of ANS (1-anilinonaphthalene-8-
More informationLipids are used to store and excess energy from extra carbohydrates in animals
Lipids Lipids are a major source of energy used by cells, however lipids are more difficult for your body to break down. They produce nearly twice the amount of energy than proteins or carbohydrates. Lipids
More informationChristophe Lincheneau, Bernard Jean-Denis and Thorfinnur Gunnlaugsson* Electronic Supplementary Information
Self-assembly formation of mechanically interlocked [2]- and [3]catenanes using lanthanide ion [Eu(III)] templation and ring closing metathesis reactions Christophe Lincheneau, Bernard Jean-Denis and Thorfinnur
More informationSupporting information for
Supporting information for A Coordination Gelator that Shows a Reversible Chromatic Change and a Sol-Gel Phase Transition Behavior upon xidative / Reductive Stimuli Shin-ichiro Kawano, orifumi Fujita,
More informationSUPPORTING INFORMATION. Transition metal-promoted synthesis of 2-aryl/heteroaryl-thioquinazoline: C-S
1 SUPPORTING INFORMATION Transition metal-promoted synthesis of 2-aryl/heteroaryl-thioquinazoline: C-S Bond formation by Chan-Lam Cross-Coupling Reaction SATYA KARUNA PULAKHANDAM a, NARESH KUMAR KATARI
More informationZinc Chloride Promoted Formal Oxidative Coupling of Aromatic Aldehydes and Isocyanides to α- Ketoamides
Supporting information for Zinc Chloride Promoted Formal xidative Coupling of Aromatic Aldehydes and Isocyanides to α- Ketoamides Marinus Bouma, Géraldine Masson* and Jieping Zhu* Institut de Chimie des
More informationSupplementary Figures
Supplementary Figures Supplementary Figure 1. 1 H NMR (400 MHz, CDCl3) spectrum of 3a Supplementary Figure 2. 13 C NMR (75 MHz, CDCl3) spectrum of 3a 1 Supplementary Figure 3. 1 H NMR (400 MHz, CDCl3)
More informationTunable Hydrophobicity in DNA Micelles Anaya, Milena; Kwak, Minseok; Musser, Andrew J.; Muellen, Klaus; Herrmann, Andreas; Müllen, Klaus
University of Groningen Tunable Hydrophobicity in DNA Micelles Anaya, Milena; Kwak, Minseok; Musser, Andrew J.; Muellen, Klaus; Herrmann, Andreas; Müllen, Klaus Published in: Chemistry DOI: 10.1002/chem.201001816
More informationSupporting Information. were prepared from commercially available ethyl acetoacetate by alkylation with the
ighly Stereoselective Reductions of α-alkyl-1,3-diketones and α- Alkyl-β-keto esters Catalyzed by Isolated NADP-dependent Ketoreductases Dimitris Kalaitzakis, a David J. Rozzell b, Spiros Kambourakis *b
More informationDual-Responsive Polymer Micelles for. Target-Cell-Specific Anticancer Drug Delivery
Dual-Responsive Polymer Micelles for Target-Cell-Specific Anticancer Drug Delivery Xing Guo, Chunli Shi, Guang Yang, Jie Wang, Zhenghong Cai, and Shaobing Zhou,, * Key Laboratory of Advanced Technologies
More informationElectronic Supplementary Information
Electronic Supplementary Information ~ Experimental Procedures and Spectral/Analytical Data ~ Use of Dimethyl Carbonate as a Solvent Greatly Enhances the Biaryl Coupling of Aryl Iodides and Organoboron
More informationDirect Regioselective Esterification at O-2 of β- Cyclodextrin and Hydrolysis by Neighboring-group Participation
ISSN: 0973-4945; CDEN ECJHA E- Chemistry http://www.ejchem.net 2012, 9(3), 1562-1568 Direct Regioselective Esterification at -2 of β- Cyclodextrin and Hydrolysis by Neighboring-group Participation ZHI-ZHNG
More informationSynthesis, Characterization and Application Study of Two Glycosides as Flavour Precursors
Asian Journal of Chemistry Vol. 22, No. 9 (2010), 6647-6651 Synthesis, Characterization and Application Study of Two Glycosides as Flavour Precursors JI-BAO CAI*, LI HUI, XIA SHEN and QING-DE SU Center
More informationChapter 18 Carboxylic Acids and Their Derivatives. Nucleophilic Addition- Elimination at the Acyl Carbon
Chapter 18 Carboxylic Acids and Their Derivatives. Nucleophilic Addition- Elimination at the Acyl Carbon Introduction The carboxyl group (-CO 2 H) is the parent group of a family of compounds called acyl
More informationREACTIONS OF CARBOXYLIC ACID DERIVATIVES WITH NUCLEOPHILES A. Reactions of Acid Chlorides with Nucleophiles
1016 CHAPTER 1 THE CHEMITRY F CARBXYLIC ACID DERIVATIVE 1.8 REACTI F CARBXYLIC ACID DERIVATIVE WITH UCLEPHILE ection 1.7 showed that all carboxylic acid derivatives hydrolyze to carboxylic acids. Water
More informationL-Carnosine-Derived Fmoc-Tripeptides Forming ph- Sensitive and Proteolytically Stable Supramolecular
Supporting Information: L-Carnosine-Derived Fmoc-Tripeptides Forming ph- Sensitive and Proteolytically Stable Supramolecular Hydrogels Rita Das Mahapatra, a Joykrishna Dey* a, and Richard G. Weiss b a
More informationLOCALISATION, IDENTIFICATION AND SEPARATION OF MOLECULES. Gilles Frache Materials Characterization Day October 14 th 2016
LOCALISATION, IDENTIFICATION AND SEPARATION OF MOLECULES Gilles Frache Materials Characterization Day October 14 th 2016 1 MOLECULAR ANALYSES Which focus? LOCALIZATION of molecules by Mass Spectrometry
More informationCharacterizing fatty acids with advanced multinuclear NMR methods
Characterizing fatty acids with advanced multinuclear NMR methods Fatty acids consist of long carbon chains ending with a carboxylic acid on one side and a methyl group on the other. Most naturally occurring
More informationSupporting Information
Supporting Information An Amphiphilic Pillar[5]arene as Efficient and Substrate-Selective Phase-Transfer Catalyst Tomoki Ogoshi*, Naosuke Ueshima and Tada-aki Yamagishi Table of Contents Experimental Section
More informationExperiment 15: Fischer Esterification and Combinatorial Chemistry Phill Rasnick Introduction
28 November 2012 Experiment 15: Fischer Esterification and Combinatorial Chemistry Phill Rasnick Introduction Esterification reactions, which produce esters, have proven to have great importance in organic
More informationEUDRAGIT L 100 and EUDRAGIT S 100
Technical Information EUDRAGIT L 100 and EUDRAGIT S 100 Specification and Test Methods Ph. Eur. Methacrylic Acid - Methyl Methacrylate Copolymer (1:1) Methacrylic Acid - Methyl Methacrylate Copolymer (1:2)
More informationFundamentals of Organic Chemistry CHEM 109 For Students of Health Colleges Credit hrs.: (2+1)
Fundamentals of Organic Chemistry CHEM 109 For Students of Health Colleges Credit hrs.: (2+1) King Saud University College of Science, Chemistry Department CHEM 109 CHAPTER 7. CARBOXYLIC ACIDS AND THEIR
More informationSimple copper/tempo catalyzed aerobic dehydrogenation. of benzylic amines and anilines
Simple copper/tempo catalyzed aerobic dehydrogenation of benzylic amines and anilines Zhenzhong Hu and Francesca M. Kerton,* Department of Chemistry, Memorial University of Newfoundland, St. John s, NL,
More informationSupporting Information
Supporting Information Unconventional Passerini Reaction towards α-aminoxyamides Ajay L. Chandgude, Alexander Dömling* Department of Drug Design, University of Groningen, Antonius Deusinglaan 1, 9713 AV
More informationKeywords: Cholesteryl ester; Plant sterol ester; Cholesterol esterase; Trichoderma sp. Stigmasterol
Novel process for enzymatic production of sterol esters in microaqueous solution with cholesterol esterase from Trichoderma sp. AS59 Atsushi Maeda a, Norihumi Hashitani a, Takayuki Mizuno a, Masanori Bunya
More informationDirect Aerobic Carbonylation of C(sp 2 )-H and C(sp 3 )-H Bonds through Ni/Cu Synergistic Catalysis with DMF as the Carbonyl Source
Direct Aerobic Carbonylation of C(sp 2 )-H and C(sp 3 )-H Bonds through Ni/Cu Synergistic Catalysis with DMF as the Carbonyl Source Xuesong Wu, Yan Zhao, and Haibo Ge* Table of Contents General Information...
More informationSupporting Information
Notes Bull. Korean Chem. Soc. 2013, Vol. 34, No. 1 1 http://dx.doi.org/10.5012/bkcs.2013.34.1.xxx Supporting Information Chemical Constituents of Ficus drupacea Leaves and their α-glucosidase Inhibitory
More informationFacile Cu(II) mediated conjugation of thioesters and thioacids to peptides and proteins under mild conditions
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Facile Cu(II) mediated conjugation of thioesters and thioacids to peptides
More informationPractice Questions for Biochemistry Test A. 1 B. 2 C. 3 D. 4
Practice Questions for Biochemistry Test 1. The quaternary structure of a protein is determined by: A. interactions between distant amino acids of the same polypeptide. B.interactions between close amino
More informationSalenCo(OAc)/chiral ionic liquid catalyzed the asymmetric cycloaddition of CO 2 to epoxides
Supporting information SalenCo(OAc)/chiral ionic liquid catalyzed the asymmetric cycloaddition of CO 2 to epoxides Suling Zhang, Yongzhong Huang, Huanwang Jing*, Weixuan Yao, Peng Yan State Key Laboratory
More informationCHAPTER 3 REACTIONS BETWEEN EPOXIDIZED NATURAL RUBBER AND PALM OIL-BASED ALKYDS
CHAPTER 3 REACTIONS BETWEEN EPOXIDIZED NATURAL RUBBER AND PALM OIL-BASED ALKYDS Alkyds are polyfunctional vegetable oil-modified polyesters, produced through esterification reaction between the natural
More informationNOTE: For studying for the final, you only have to worry about those with an asterix (*)
NOTE: For studying for the final, you only have to worry about those with an asterix (*) (*)1. An organic compound is one that: a. contains carbon b. is slightly acidic c. forms long chains d. is soluble
More informationAllenylphosphine oxides as simple scaffolds for. phosphinoylindoles and phosphinoylisocoumarins
Supporting Information for Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins G. Gangadhararao, Ramesh Kotikalapudi, M. Nagarjuna Reddy and K. C. Kumara Swamy*
More information