What's in Your Beer? Part 2: GC/MS Static Head Space with a Highly
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Chapter 21 the Chemistry of Carboxylic Acid Derivatives
Instructor Supplemental Solutions to Problems © 2010 Roberts and Company Publishers Chapter 21 The Chemistry of Carboxylic Acid Derivatives Solutions to In-Text Problems 21.1 (b) (d) (e) (h) 21.2 (a) butanenitrile (common: butyronitrile) (c) isopentyl 3-methylbutanoate (common: isoamyl isovalerate) The isoamyl group is the same as an isopentyl or 3-methylbutyl group: (d) N,N-dimethylbenzamide 21.3 The E and Z conformations of N-acetylproline: 21.5 As shown by the data above the problem, a carboxylic acid has a higher boiling point than an ester because it can both donate and accept hydrogen bonds within its liquid state; hydrogen bonding does not occur in the ester. Consequently, pentanoic acid (valeric acid) has a higher boiling point than methyl butanoate. Here are the actual data: INSTRUCTOR SUPPLEMENTAL SOLUTIONS TO PROBLEMS • CHAPTER 21 2 21.7 (a) The carbonyl absorption of the ester occurs at higher frequency, and only the carboxylic acid has the characteristic strong, broad O—H stretching absorption in 2400–3600 cm–1 region. (d) In N-methylpropanamide, the N-methyl group is a doublet at about d 3. N-Ethylacetamide has no doublet resonances. In N-methylpropanamide, the a-protons are a quartet near d 2.5. In N-ethylacetamide, the a- protons are a singlet at d 2. The NMR spectrum of N-methylpropanamide has no singlets. 21.9 (a) The first ester is more basic because its conjugate acid is stabilized not only by resonance interaction with the ester oxygen, but also by resonance interaction with the double bond; that is, the conjugate acid of the first ester has one more important resonance structure than the conjugate acid of the second. -
Transport of Dangerous Goods
ST/SG/AC.10/1/Rev.16 (Vol.I) Recommendations on the TRANSPORT OF DANGEROUS GOODS Model Regulations Volume I Sixteenth revised edition UNITED NATIONS New York and Geneva, 2009 NOTE The designations employed and the presentation of the material in this publication do not imply the expression of any opinion whatsoever on the part of the Secretariat of the United Nations concerning the legal status of any country, territory, city or area, or of its authorities, or concerning the delimitation of its frontiers or boundaries. ST/SG/AC.10/1/Rev.16 (Vol.I) Copyright © United Nations, 2009 All rights reserved. No part of this publication may, for sales purposes, be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic, electrostatic, magnetic tape, mechanical, photocopying or otherwise, without prior permission in writing from the United Nations. UNITED NATIONS Sales No. E.09.VIII.2 ISBN 978-92-1-139136-7 (complete set of two volumes) ISSN 1014-5753 Volumes I and II not to be sold separately FOREWORD The Recommendations on the Transport of Dangerous Goods are addressed to governments and to the international organizations concerned with safety in the transport of dangerous goods. The first version, prepared by the United Nations Economic and Social Council's Committee of Experts on the Transport of Dangerous Goods, was published in 1956 (ST/ECA/43-E/CN.2/170). In response to developments in technology and the changing needs of users, they have been regularly amended and updated at succeeding sessions of the Committee of Experts pursuant to Resolution 645 G (XXIII) of 26 April 1957 of the Economic and Social Council and subsequent resolutions. -
R Graphics Output
Dexamethasone sodium phosphate ( 0.339 ) Melengestrol acetate ( 0.282 ) 17beta−Trenbolone ( 0.252 ) 17alpha−Estradiol ( 0.24 ) 17alpha−Hydroxyprogesterone ( 0.238 ) Triamcinolone ( 0.233 ) Zearalenone ( 0.216 ) CP−634384 ( 0.21 ) 17alpha−Ethinylestradiol ( 0.203 ) Raloxifene hydrochloride ( 0.203 ) Volinanserin ( 0.2 ) Tiratricol ( 0.197 ) trans−Retinoic acid ( 0.192 ) Chlorpromazine hydrochloride ( 0.191 ) PharmaGSID_47315 ( 0.185 ) Apigenin ( 0.183 ) Diethylstilbestrol ( 0.178 ) 4−Dodecylphenol ( 0.161 ) 2,2',6,6'−Tetrachlorobisphenol A ( 0.156 ) o,p'−DDD ( 0.155 ) Progesterone ( 0.152 ) 4−Hydroxytamoxifen ( 0.151 ) SSR150106 ( 0.149 ) Equilin ( 0.3 ) 3,5,3'−Triiodothyronine ( 0.256 ) 17−Methyltestosterone ( 0.242 ) 17beta−Estradiol ( 0.24 ) 5alpha−Dihydrotestosterone ( 0.235 ) Mifepristone ( 0.218 ) Norethindrone ( 0.214 ) Spironolactone ( 0.204 ) Farglitazar ( 0.203 ) Testosterone propionate ( 0.202 ) meso−Hexestrol ( 0.199 ) Mestranol ( 0.196 ) Estriol ( 0.191 ) 2,2',4,4'−Tetrahydroxybenzophenone ( 0.185 ) 3,3,5,5−Tetraiodothyroacetic acid ( 0.183 ) Norgestrel ( 0.181 ) Cyproterone acetate ( 0.164 ) GSK232420A ( 0.161 ) N−Dodecanoyl−N−methylglycine ( 0.155 ) Pentachloroanisole ( 0.154 ) HPTE ( 0.151 ) Biochanin A ( 0.15 ) Dehydroepiandrosterone ( 0.149 ) PharmaCode_333941 ( 0.148 ) Prednisone ( 0.146 ) Nordihydroguaiaretic acid ( 0.145 ) p,p'−DDD ( 0.144 ) Diphenhydramine hydrochloride ( 0.142 ) Forskolin ( 0.141 ) Perfluorooctanoic acid ( 0.14 ) Oleyl sarcosine ( 0.139 ) Cyclohexylphenylketone ( 0.138 ) Pirinixic acid ( 0.137 ) -
Estimation of Hydrolysis Rate Constants of Carboxylic Acid Ester and Phosphate Ester Compounds in Aqueous Systems from Molecular Structure by SPARC
Estimation of Hydrolysis Rate Constants of Carboxylic Acid Ester and Phosphate Ester Compounds in Aqueous Systems from Molecular Structure by SPARC R E S E A R C H A N D D E V E L O P M E N T EPA/600/R-06/105 September 2006 Estimation of Hydrolysis Rate Constants of Carboxylic Acid Ester and Phosphate Ester Compounds in Aqueous Systems from Molecular Structure by SPARC By S. H. Hilal Ecosystems Research Division National Exposure Research Laboratory Athens, Georgia U.S. Environmental Protection Agency Office of Research and Development Washington, DC 20460 NOTICE The information in this document has been funded by the United States Environmental Protection Agency. It has been subjected to the Agency's peer and administrative review, and has been approved for publication. Mention of trade names of commercial products does not constitute endorsement or recommendation for use. ii ABSTRACT SPARC (SPARC Performs Automated Reasoning in Chemistry) chemical reactivity models were extended to calculate hydrolysis rate constants for carboxylic acid ester and phosphate ester compounds in aqueous non- aqueous and systems strictly from molecular structure. The energy differences between the initial state and the transition state for a molecule of interest are factored into internal and external mechanistic perturbation components. The internal perturbations quantify the interactions of the appended perturber (P) with the reaction center (C). These internal perturbations are factored into SPARC’s mechanistic components of electrostatic and resonance effects. External perturbations quantify the solute-solvent interactions (solvation energy) and are factored into H-bonding, field stabilization and steric effects. These models have been tested using 1471 reliable measured base, acid and general base-catalyzed carboxylic acid ester hydrolysis rate constants in water and in mixed solvent systems at different temperatures. -
Expanding the Modular Ester Fermentative Pathways for Combinatorial Biosynthesis of Esters from Volatile Organic Acids
ARTICLE Expanding the Modular Ester Fermentative Pathways for Combinatorial Biosynthesis of Esters From Volatile Organic Acids Donovan S. Layton,1,2 Cong T. Trinh1,2,3 1 Department of Chemical and Biomolecular Engineering, University of Tennessee, Knoxville, Tennessee 2 BioEnergy Science Center (BESC), Oak Ridge National Laboratory, Oak Ridge, Tennessee 3 Bredesen Center for Interdisciplinary Research and Graduate Education, University of Tennessee, Knoxville, Tennessee; telephone: þ865-974-8121; fax: 865-974-7076; e-mail: [email protected] Biotechnol. Bioeng. 2016;113: 1764–1776. ABSTRACT: Volatile organic acids are byproducts of fermentative ß 2016 Wiley Periodicals, Inc. metabolism, for example, anaerobic digestion of lignocellulosic KEYWORDS: modular chassis cell; carboxylate; ester; acyl acetate; biomass or organic wastes, and are often times undesired inhibiting acyl acylate; ester fermentative pathway cell growth and reducing directed formation of the desired products. Here, we devised a general framework for upgrading these volatile organic acids to high-value esters that can be used as flavors, fragrances, solvents, and biofuels. This framework employs the acid-to-ester modules, consisting of an AAT (alcohol Introduction acyltransferase) plus ACT (acyl CoA transferase) submodule and an alcohol submodule, for co-fermentation of sugars and organic Harnessing renewable or waste feedstocks (e.g., switchgrass, corn acids to acyl CoAs and alcohols to form a combinatorial library of stover, agricultural residue, or municipal solid waste) -
Comprehensive Characterization of Toxicity of Fermentative Metabolites on Microbial Growth Brandon Wilbanks1 and Cong T
Wilbanks and Trinh Biotechnol Biofuels (2017) 10:262 DOI 10.1186/s13068-017-0952-4 Biotechnology for Biofuels RESEARCH Open Access Comprehensive characterization of toxicity of fermentative metabolites on microbial growth Brandon Wilbanks1 and Cong T. Trinh1,2* Abstract Background: Volatile carboxylic acids, alcohols, and esters are natural fermentative products, typically derived from anaerobic digestion. These metabolites have important functional roles to regulate cellular metabolisms and broad use as food supplements, favors and fragrances, solvents, and fuels. Comprehensive characterization of toxic efects of these metabolites on microbial growth under similar conditions is very limited. Results: We characterized a comprehensive list of thirty-two short-chain carboxylic acids, alcohols, and esters on microbial growth of Escherichia coli MG1655 under anaerobic conditions. We analyzed toxic efects of these metabo- lites on E. coli health, quantifed by growth rate and cell mass, as a function of metabolite types, concentrations, and physiochemical properties including carbon number, chemical functional group, chain branching feature, energy density, total surface area, and hydrophobicity. Strain characterization revealed that these metabolites exert distinct toxic efects on E. coli health. We found that higher concentrations and/or carbon numbers of metabolites cause more severe growth inhibition. For the same carbon numbers and metabolite concentrations, we discovered that branched chain metabolites are less toxic than the linear chain ones. Remarkably, shorter alkyl esters (e.g., ethyl butyrate) appear less toxic than longer alkyl esters (e.g., butyl acetate). Regardless of metabolites, hydrophobicity of a metabolite, gov- erned by its physiochemical properties, strongly correlates with the metabolite’s toxic efect on E. coli health. -
Wo 2011/015417 A2
(12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date 10 February 2011 (10.02.2011) WO 2011/015417 A2 (51) International Patent Classification: Road East, Bebington, Wirral Merseyside CH63 3JW A61K 8/11 (2006.01) A61Q 15/00 (2006.01) (GB). A61Q 13/00 (2006.01) (74) Agent: WHALEY, Christopher; Unilever PLC, Unilever (21) International Application Number: Patent Group, Colworth House, Sharnbrook, Bedford PCT/EP2010/059736 Bedfordshire MK44 ILQ (GB). (22) International Filing Date: (81) Designated States (unless otherwise indicated, for every 7 July 2010 (07.07.2010) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, English (25) Filing Language: CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, (26) Publication Language: English DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, (30) Priority Data: KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, 09167370.7 6 August 2009 (06.08.2009) EP ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (71) Applicant (for AE, AG, AU, BB, BH, BW, BZ, CA, CY, NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, EG, GB, GD, GH, GM, IE, IL, KE, KN, LC, LK, LS, MT, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, MW, MY, NA, NG, NZ, OM, PG, SC, SD, SG, SL, SZ, TT, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. -
Microbial Synthesis of a Branched-Chain Ester Platform from Organic Waste Carboxylates
Metabolic Engineering Communications 3 (2016) 245–251 Contents lists available at ScienceDirect Metabolic Engineering Communications journal homepage: www.elsevier.com/locate/mec Microbial synthesis of a branched-chain ester platform from organic waste carboxylates Donovan S. Layton a,c, Cong T. Trinh a,b,c,n a Department of Chemical and Biomolecular Engineering, The University of Tennessee, Knoxville, The United States of America b Bredesen Center for Interdisciplinary Research and Graduate Education, The University of Tennessee, Knoxville, The United States of America c Bioenergy Science Center (BESC), Oak Ridge National Laboratory, Oak Ridge, The United States of America article info abstract Article history: Processing of lignocellulosic biomass or organic wastes produces a plethora of chemicals such as short, Received 6 June 2016 linear carboxylic acids, known as carboxylates, derived from anaerobic digestion. While these carbox- Received in revised form ylates have low values and are inhibitory to microbes during fermentation, they can be biologically 15 July 2016 upgraded to high-value products. In this study, we expanded our general framework for biological up- Accepted 5 August 2016 grading of carboxylates to branched-chain esters by using three highly active alcohol acyltransferases Available online 6 August 2016 (AATs) for alcohol and acyl CoA condensation and modulating the alcohol moiety from ethanol to iso- Keywords: butanol in the modular chassis cell. With this framework, we demonstrated the production of an ester Carboxylate platform library comprised of 16 out of all 18 potential esters, including acetate, propionate, butanoate, pen- Ester platform tanoate, and hexanoate esters, from the 5 linear, saturated C -C carboxylic acids. -
Comprehensive Overview of Common E-Liquid Ingredients and How They Can Be Used to Predict an E-Liquid's Flavour Category
Original research Tob Control: first published as 10.1136/tobaccocontrol-2019-055447 on 10 February 2020. Downloaded from Comprehensive overview of common e- liquid ingredients and how they can be used to predict an e- liquid’s flavour category Erna J Z Krüsemann ,1,2 Anne Havermans ,1 Jeroen L A Pennings,1 Kees de Graaf,2 Sanne Boesveldt,2 Reinskje Talhout1 10–14 ► Additional material is ABSTRact cigarette smoking. In line with this, the use and published online only. To view Objectives Flavours increase e- cigarette attractiveness marketing of e- liquid flavours that are appealing to please visit the journal online (http:// dx. doi. org/ 10. 1136/ and use and thereby exposure to potentially toxic smokers may contribute to public health benefits. tobaccocontrol- 2019- 055447). ingredients. An overview of e- liquid ingredients is needed However, flavours may also stimulate vaping among to select target ingredients for chemical analytical and non- users, in particular young people.15–17 This is 1 Centre for Health toxicological research and for regulatory approaches concerning, as e- cigarettes are not safe10 18 19 That Protection, Rijksinstituut voor aimed at reducing e- cigarette attractiveness. Using is, chemicals in e- cigarette emissions (eg, tobacco- Volksgezondheid en Milieu, Bilthoven, The Netherlands information from e- cigarette manufacturers, we aim to specific nitrosamines, metals, aldehydes and other 2Division of Human Nutrition identify the flavouring ingredients most frequently added flavourings) can be toxic and thus harmful to and Health, Wageningen to e- liquids on the Dutch market. Additionally, we used consumers’ health.20–22 In addition, e- cigarettes University, Wageningen, The flavouring compositions to automatically classify e-liquids may facilitate smoking initiation among never- Netherlands into flavour categories, thereby generating an overview smokers.23 As a consequence, e- liquid flavours are that can facilitate market surveillance. -
Supplemental Figure
● Agonist ● Antagonist ● Interference AR AUC 0.0 0.2 0.4 0.6 0.8 1.0 1.2 1.4 1.6 17beta−Trenbolone 5alpha−Dihydrotestosterone 17−Methyltestosterone Testosterone propionate Norethindrone Norgestrel GSK232420A 4−Androstene−3,17−dione Progesterone 17beta−Estradiol Mifepristone 17alpha−Ethinylestradiol Hydroxyflutamide 17alpha−Hydroxyprogesterone Corticosterone Nilutamide Basic Blue 7 Triphenyltin hydroxide Bicalutamide Tributyltin benzoate 17alpha−Estradiol Gentian Violet Equilin Zinc pyrithione Triticonazole Fenitrothion Mestranol Tributyltin methacrylate 2,2−Bis(4−hydroxyphenyl)−1,1,1 Dibutyltin dichloride Flutamide Methyltrioctylammonium chlorid Rhodamine 6G Tributyltetradecylphosphonium Emamectin benzoate Phenylmercuric acetate Cyproterone acetate Chlorothalonil 9−Phenanthrol 2,2',4,4'−Tetrahydroxybenzophe Melengestrol acetate Dehydroepiandrosterone 1−Chloro−2,4−dinitrobenzene SSR240612 Methylbenzethonium chloride Vinclozolin Tetraconazole Ziram Didecyldimethylammonium chlori Econazole nitrate Myristyltrimethylammonium chlo Clorophene Abamectin Octyl gallate 2−Chloro−4−phenylphenol Bisphenol A Propanil Dexamethasone sodium phosphate meso−Hexestrol Dichlorophen Hydroxyprogesterone caproate SSR241586 Bisphenol AF Prednisone Dichlone Reserpine Chlorobenzilate Diethylstilbestrol 3−Hydroxyfluorene Procymidone 4−Cumylphenol 4−Hydroxytamoxifen Napropamide PharmaGSID_48519 Clomiphene citrate (1:1) Chlorhexidine diacetate Tebuconazole Imazalil Dinocap PharmaGSID_48513 Linuron Prochloraz Zoxamide TDCPP Captan 3,3'−Dimethoxybenzidine dihydr 4−Phenylphenol -
Evaluation of Perceptual Interactions Between Ester Aroma Components in Langjiu by GC-MS, GC-O, Sensory Analysis, and Vector Model
foods Article Evaluation of Perceptual Interactions between Ester Aroma Components in Langjiu by GC-MS, GC-O, Sensory Analysis, and Vector Model Yunwei Niu 1, Ying Liu 1 and Zuobing Xiao 1,2,* 1 School of Perfume and Aroma Technology, Shanghai Institute of Technology, No.100 Haiquan Road, Shanghai 201418, China; [email protected] (Y.N.); [email protected] (Y.L.) 2 Beijing Advanced Innovation Center for Food Nutrition and Human Health, No. 11/33, Fucheng Road, Haidian District, Beijing 100048, China * Correspondence: [email protected]; Tel.: +86-21-60873511 Received: 3 January 2020; Accepted: 11 February 2020; Published: 13 February 2020 Abstract: The volatile compounds of three Langjiu (“Honghualangshi, HHL”, “Zhenpinlang, ZPL”, and “Langpailangjiu, LPLJ”) were studied by gas chromatography-olfactometry (GC-O) and gas chromatography-mass spectrometry (GC-MS). The results showed that a total of 31, 30, and 30 ester compounds making a contribution to aroma were present in the HHL, ZPL, and LPLJ samples, respectively. From these esters, 16 compounds were identified as important odour substances, and their odour activity values (OAVs) were greater than 1. The key ester components were selected as: ethyl acetate, ethyl 2-methylbutyrate, ethyl 3-methyl butyrate, ethyl hexanoate, and ethyl phenylacetate by aroma extract dilution analysis (AEDA), odour activity value (OAV), and omission testing. Five esters were studied for perceptual interactions while using Feller’s additive model, OAV, and a vector model. Among these mixtures, they all have an enhancing or synergistic effect. Among these mixtures, one mixture presented an additive effect and nine mixtures showed a synergistic effect. -
Supplemental Material
Haddad Supp pp 1 Supplementary materials for: Global features of neural activity in the olfactory system form a parallel code that predicts olfactory behavior and perception Rafi Haddad1,2#, Tali Weiss1, Rehan Khan1σ, Boaz Nadler2, Nathalie Mandairon3, 3 1* 1*# Moustafa Bensafi , Elad Schneidman and Noam Sobel . Section 1: PCA analysis We provide a step by step example of how we conducted the PCA analysis. Assume we have 8 odors, each located on the vertexes of a 3 dimensional unit cube. Each odor can thus be represented by the exact binary code of the numbers 0 to 7. We can represent these odors in the following binary code matrix: Odor ID Pattern code: 1 0 0 0 2 0 0 1 3 0 1 0 4 0 1 1 5 1 0 0 6 1 0 1 7 1 1 0 8 1 1 1 1 Haddad Supp pp 2 Using any available mathematical tool (we used Matlab 'princomp' method) we can calculate the principle components scores of this matrix. In this case the values of the PC1 scores are: [1 0 0]. The PC1 projection value of each row is the projection of each row by the PC1 weight vector. For example the PC1 value of the first row is [0,0,0]X[1,0,0] = 0X1 + 0X0 + 0X0 = 0. (this is a vector multiplication). Thus the PC1 value of each row of this matrix is: 0,0,0,0,1,1,1,1. Note that usually the PC1 is calculated on a centered matrix (the columns of the matrix have zero mean) and thus the PC1 value might be shifted by some value.