A Chemical Analysis of Flavor Differences in Chocolate Coconut Rum Porter

Total Page:16

File Type:pdf, Size:1020Kb

A Chemical Analysis of Flavor Differences in Chocolate Coconut Rum Porter A Chemical Analysis of Flavor Differences in Chocolate Coconut Rum Porter A Major Qualifying Project Report Submitted to the Faculty of WORCESTER POLYTECHNIC INSTITUTE In partial fulfillment of the requirements for the degree of Bachelor of Science in the field of Chemical Engineering Sponsored by: Purgatory Beer Company 670 Linwood Ave, Whitinsville, MA 01588 Authors: Joseph Crognale Tyler Donovan Shane O’Dell Advised by: Professor Stephen Kmiotek This report represents the work of WPI undergraduate students submitted to the faculty as evidence of completion of a degree requirement. WPI routinely publishes these reports on its website without editorial or peer review. For more information about the projects program at WPI, please see http://www.wpi.edu/academics/ugradstudies/project-learning.html Abstract The origin of the batch-to-batch inconsistency in flavor of Purgatory Beer Company’s Fiero Coconut Rum porter was investigated by extracting organic compounds from desirable and undesirable batches of porter and quantifying them using GC-MS. The concentration and occurrence of key flavor compounds were compared between the samples and showed that the undesirable batch contained more unpleasant organoleptic compounds and was more acidic. Based on the marked inconsistency in chemical profile between batches, the team recommended quality control be improved through more accurate monitoring and consistent control of the fermentation temperature, oxygenation of wort and beer, order of ingredient addition to the fermentation broth, reuse of yeast, and filtration of water. i Table of Contents Abstract ............................................................................................................................................ i Table of Contents ............................................................................................................................ ii List of Tables ................................................................................................................................. iv List of Figures ................................................................................................................................. v 1. Introduction ............................................................................................................................. 1 2. Background ................................................................................................................................. 2 2.1 Brewing Process .................................................................................................................... 2 2.1.1 Malt ................................................................................................................................. 3 2.1.2 Hops ................................................................................................................................ 4 2.1.3 Yeast ............................................................................................................................... 4 2.1.4 Specifics of Brewing Porters .......................................................................................... 5 2.2 Flavor Compounds ................................................................................................................ 6 2.2.1 Primary flavor compounds ............................................................................................. 7 2.2.2 Secondary flavor compounds ....................................................................................... 11 2.2.3 Tertiary flavor compounds ........................................................................................... 13 2.2.4 Off-flavors .................................................................................................................... 14 2.3 Reactions in Beer ................................................................................................................ 17 3. Methodology ............................................................................................................................. 20 3.1 Extraction ............................................................................................................................ 20 3.2 Observations During Extraction .......................................................................................... 20 4. Results and Analysis ................................................................................................................. 23 4.1 Overall Chemical Composition Comparison from DCM Extraction .................................. 23 4.2 Overall Chemical Composition Comparison from THF Extraction ................................... 24 4.3 Individual Flavor Compound Area Comparison ................................................................. 26 4.4 Comparison of Presence or Absence of Individual Flavor Compounds ............................. 29 5. Conclusions ............................................................................................................................... 32 6. Recommendations ..................................................................................................................... 33 6.1 Control of Fermentation Variables ...................................................................................... 33 6.1.1 Temperature Control..................................................................................................... 33 ii 6.1.2 Addition of Flavor Compounds During Secondary Fermentation ............................... 35 6.1.3 Control of Oxygenation and Aeration .......................................................................... 35 6.1.4 Controlled Yeast Reuse ................................................................................................ 36 6.1.5 Improved Fermentation Monitoring Tools ................................................................... 37 6.2 Use of Unsulfured Coconut ................................................................................................. 38 6.3 Filtration of Water ............................................................................................................... 38 6.4 Minimize Effects of Aging .................................................................................................. 40 6.5 Improvements for Future Studies ........................................................................................ 40 Bibliography ................................................................................................................................. 42 Appendices .................................................................................................................................... 45 Appendix A: GC-MS Method ................................................................................................... 45 Appendix B: Initial Ineffective Extraction Method .................................................................. 47 Appendix C: GC-MS Results .................................................................................................... 48 Appendix D: Example Organoleptic Compound Comparison .................................................. 74 Appendix E: Whitinsville Water Quality Testing Results25...................................................... 75 iii List of Tables Table 1. Primary flavor compounds in beer.................................................................................. 10 Table 2. Secondary flavor compounds in beer .............................................................................. 13 Table 3. Potential off-flavors in beer ............................................................................................ 16 Table 4. Overall Chemical Composition, DCM Extraction 2/17/19 ............................................ 23 Table 5. Overall Chemical Composition, DCM Extraction 3/19/19 ............................................ 23 Table 6. Overall Chemical Composition, THF Extraction 2/26/19 .............................................. 24 Table 7. Overall Chemical Composition, THF Extraction 3/19/19 .............................................. 24 Table 8. Acidic Compound Comparison ...................................................................................... 25 Table 9. Overall Chemical Composition, THF Extraction 3/19/19 .............................................. 27 Table 10. Fusel Alcohol Area Comparison, THF Extractions ...................................................... 27 Table 11. Acetic Acid Area Comparison, DCM Extraction 2/17/19 ............................................ 28 Table 12. Ethyl Acetate Area Comparison ................................................................................... 28 Table 13. Organochloride Area Comparison ................................................................................ 29 iv List of Figures Figure 1. Beer Composition ............................................................................................................ 2 Figure 2. Example of Typical Commercial Porter Recipe .............................................................. 5 Figure 3. Isohumulone production during wort boiling .................................................................. 8 Figure 4. Visible Difference Between Undesirable and Desirable Batches in DCM ................... 21 Figure 5. Visible Difference Between Undesirable and Desirable Batches in DCM after Two Months of Aging ..........................................................................................................................
Recommended publications
  • Hyperbranched Polyaspartate Esters and a Process for Their Preparation
    Europäisches Patentamt *EP000743335B1* (19) European Patent Office Office européen des brevets (11) EP 0 743 335 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: C08G 63/685 of the grant of the patent: 26.09.2001 Bulletin 2001/39 (21) Application number: 96107069.5 (22) Date of filing: 06.05.1996 (54) Hyperbranched polyaspartate esters and a process for their preparation Hyperverzweigte Polyaspartatester und Verfahren zu ihrer Herstellung Ester de polyaspartate hyperramifiés et procédé pour leur préparation (84) Designated Contracting States: (74) Representative: Pettrich, Klaus-Günter, Dr. AT BE CH DE ES FR GB IT LI NL SE c/o Bayer AG, Konzernbereich RP (30) Priority: 18.05.1995 US 443505 Patente und Lizenzen 51368 Leverkusen (DE) (43) Date of publication of application: 20.11.1996 Bulletin 1996/47 (56) References cited: US-A- 5 126 170 (73) Proprietor: Bayer Corporation Pittsburgh, PA 15205-9741 (US) • ISRA L JOURNAL OF CHEMISTRY, vol. 9, 1971, JERUSALEM, pages 105-109, XP000670606 A. (72) Inventors: SINGERMAN ET AL.: "Poly threo-beta-hydroxy • Yeske, Philip E. aspartic acid" Pittsburgh, PA 15228 (US) • Gindin, Lyuba K. Remarks: Pittsburgh, PA 15216 (US) The file contains technical information submitted • Wicks, Douglas A. after the application was filed and not included in this Mt. Lebanon, PA 15228 (US) specification • Jonsson, E. Haakan Coraopolis, PA 15108 (US) Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement.
    [Show full text]
  • Aldrich FT-IR Collection Edition I Library
    Aldrich FT-IR Collection Edition I Library Library Listing – 10,505 spectra This library is the original FT-IR spectral collection from Aldrich. It includes a wide variety of pure chemical compounds found in the Aldrich Handbook of Fine Chemicals. The Aldrich Collection of FT-IR Spectra Edition I library contains spectra of 10,505 pure compounds and is a subset of the Aldrich Collection of FT-IR Spectra Edition II library. All spectra were acquired by Sigma-Aldrich Co. and were processed by Thermo Fisher Scientific. Eight smaller Aldrich Material Specific Sub-Libraries are also available. Aldrich FT-IR Collection Edition I Index Compound Name Index Compound Name 3515 ((1R)-(ENDO,ANTI))-(+)-3- 928 (+)-LIMONENE OXIDE, 97%, BROMOCAMPHOR-8- SULFONIC MIXTURE OF CIS AND TRANS ACID, AMMONIUM SALT 209 (+)-LONGIFOLENE, 98+% 1708 ((1R)-ENDO)-(+)-3- 2283 (+)-MURAMIC ACID HYDRATE, BROMOCAMPHOR, 98% 98% 3516 ((1S)-(ENDO,ANTI))-(-)-3- 2966 (+)-N,N'- BROMOCAMPHOR-8- SULFONIC DIALLYLTARTARDIAMIDE, 99+% ACID, AMMONIUM SALT 2976 (+)-N-ACETYLMURAMIC ACID, 644 ((1S)-ENDO)-(-)-BORNEOL, 99% 97% 9587 (+)-11ALPHA-HYDROXY-17ALPHA- 965 (+)-NOE-LACTOL DIMER, 99+% METHYLTESTOSTERONE 5127 (+)-P-BROMOTETRAMISOLE 9590 (+)-11ALPHA- OXALATE, 99% HYDROXYPROGESTERONE, 95% 661 (+)-P-MENTH-1-EN-9-OL, 97%, 9588 (+)-17-METHYLTESTOSTERONE, MIXTURE OF ISOMERS 99% 730 (+)-PERSEITOL 8681 (+)-2'-DEOXYURIDINE, 99+% 7913 (+)-PILOCARPINE 7591 (+)-2,3-O-ISOPROPYLIDENE-2,3- HYDROCHLORIDE, 99% DIHYDROXY- 1,4- 5844 (+)-RUTIN HYDRATE, 95% BIS(DIPHENYLPHOSPHINO)BUT 9571 (+)-STIGMASTANOL
    [Show full text]
  • (12) Patent Application Publication (10) Pub. No.: US 2009/0156618 A1 Tollefson (43) Pub
    US 20090156618A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2009/0156618 A1 Tollefson (43) Pub. Date: Jun. 18, 2009 (54) 1-(1-(2-ETHOXYETHYL)-3-ETHYL-7- Related U.S. Application Data (4-METHYLPYRIDIN-2-YLAMINO) - 1H-PYRAZOLO 4.3-D PYRIMIDIN-5-YL) (60) Provisional application No. 60/735,320, filed on Nov. PPERDINE-4-CARBOXYLIC ACID AND 10, 2005. SALTS THEREOF Publication Classification (51) Int. Cl. (75) Inventor: Michael B. Tollefson, Dardenne A 6LX 3/59 (2006.01) Prairie, MO (US) C07D 487/04 (2006.01) A6IP 9/12 (2006.01) A6IP 25/00 (2006.01) Correspondence Address: A6IP 9/00 (2006.01) PFZER INC. PATENT DEPARTMENT, Bld 114 M/S 114, (52) U.S. Cl. ...................................... 514/262.1; 54.4/262 EASTERN PONT ROAD (57) ABSTRACT GROTON, CT 06340 (US) The present invention comprises 1-(1-(2-ethoxyethyl)-3- ethyl-7-(4-methylpyridin-2-ylamino)-1H-pyrazolo 4.3-d (73) Assignee: Pfizer Inc pyrimidin-5-yl)piperidine-4-carboxylic acid and its salts. The invention further comprises pharmaceutical composi tions, methods of treatment, and synthetic methods relating to (21) Appl. No.: 111558,306 1-(1-(2-ethoxyethyl)-3-ethyl-7-(4-methylpyridin-2- ylamino)-1H-pyrazolo 4.3-dipyrimidin-5-yl)piperidine-4- (22) Filed: Nov. 9, 2006 carboxylic acid and its salts. Patent Application Publication Jun. 18, 2009 Sheet 2 of 2 US 2009/0156618 A1 "SOIHZ US 2009/0156618 A1 Jun. 18, 2009 1-(1-(2-ETHOXYETHYL)-3-ETHYL-7- 1H-pyrazolo 4,3-dipyrimidin-5-yl)piperidine-4-carboxylic (4-METHYLPYRIDIN-2-YLAMINO) - acid and its pharmaceutically acceptable salts.
    [Show full text]
  • United States Patent Office Patented June 17, 1969
    3,450,782 United States Patent Office Patented June 17, 1969 2 1,3-dibromocyclobutane with sodium in refluxing dioxane, 3,450,782 PROCESS FOR THE PREPARATION OF K. B. Wiberg, G. M. Lampman, R. P. Ciula, D. S. Con CYCLICALKANES nor, P. Scherter, and J. Lavanesh, Tetrahedron, 21, 2749 Daniel S. Connor, Cincinnati, Ohio, assignor to The (1695), bicyclo[1.1.1 pentane by treatment of 3-(bromo Procter & Gamble Company, Cincinnati, Ohio, a cor methyl)-cyclobutyl bromide with sodium metal at a 0.5% poration of Ohio yield, with lithium amalgam in refluxing dioxane at a No Drawing. Filed Nov. 29, 1967, Ser. No. 686,738 4.2% yield and with sodium/naphtahalene at a 8% yield, Int, C. C07c I/28 K. B. Wiberg, D. S. Connor, and G. M. Lampman, Tetra U.S. C. 260-666 8 Claims hedron Letters, 531 (1964); K. B. Wiberg and D. S. Con 0 nor, J. Am. Chem. Soc., 88, 4437 (1966). On examination of the literature hereinbefore cited ABSTRACT OF THE DISCLOSURE on cyclization, it is apparent that the yields obtained were This invention concerns the preparation of cyclic al extremely low, that the conditions for reaction when it kanes from dihalogenated alkanes using lithium amalgam. did occur were quite severe, and that the starting materials 5 used were less than common. OBJECTS OF THE INVENTION SUMMARY OF THE INVENTION The use of the method of this invention to obtain cyclic The object of this invention is to prepare cyclic al compounds provides a valuable synthetic tool heretofore kanes from the halogenated straight chain starting ma 20 unknown to chemists, thus enabling the production of terials using lithium amalgam to remove the halogens valuable end products.
    [Show full text]
  • Safety Assessment of Alkyl Esters As Used in Cosmetics
    PINK Safety Assessment of Alkyl Esters as Used in Cosmetics CIR EXPERT PANEL MEETING DECEMBER 10-11, 2012 Memorandum To: CIR Expert Panel Members and Liaisons From: Monice M. Fiume MMF Senior Scientific Analyst/Writer Date: November 16, 2012 Subject: Amended Safety Assessment of Alkyl Esters as Used in Cosmetics Enclosed in the Amended Safety Assessment of Alkyl Esters as Used in Cosmetics. The status of this document is draft tentative amended report for CIR Expert Panel Review. This report was tabled at the September meeting so that historical use data from reports on ingredients previously reviewed by CIR could be added to the safety assessment. You will find these data incor- porated into Table 8. Incorporation of the historical data into the table allows the Panel a side-by-side comparison of the concentration reported when determining safety in the original safety assessments compared to the use data submitted with the current re-review. Increases in reported concentrations are highlighted. Also at the September meeting, the Panel deleted 16 alkyl ethylhexanoates from the report. Concern about the possible fetotoxicity of 2-ethylhexanoic acid, a possible metabolite of the ethylhexanoates, led to a determination that these ingredients are not “no brainers” and therefore, the ethylhexanoates should not be included in this review. The following unpublished data have been received since the last review. These data, which are included under the data tab of this submission, have been incorporated. 1. Personal Care Products Council. 2012. Updated concentration of use by FDA product category: alkyl esters and ethylhexanoates; 2. Personal Care Products Council.
    [Show full text]
  • The Alcohol Textbook 4Th Edition
    TTHEHE AALCOHOLLCOHOL TEXTBOOKEXTBOOK T TH 44TH EEDITIONDITION A reference for the beverage, fuel and industrial alcohol industries Edited by KA Jacques, TP Lyons and DR Kelsall Foreword iii The Alcohol Textbook 4th Edition A reference for the beverage, fuel and industrial alcohol industries K.A. Jacques, PhD T.P. Lyons, PhD D.R. Kelsall iv T.P. Lyons Nottingham University Press Manor Farm, Main Street, Thrumpton Nottingham, NG11 0AX, United Kingdom NOTTINGHAM Published by Nottingham University Press (2nd Edition) 1995 Third edition published 1999 Fourth edition published 2003 © Alltech Inc 2003 All rights reserved. No part of this publication may be reproduced in any material form (including photocopying or storing in any medium by electronic means and whether or not transiently or incidentally to some other use of this publication) without the written permission of the copyright holder except in accordance with the provisions of the Copyright, Designs and Patents Act 1988. Applications for the copyright holder’s written permission to reproduce any part of this publication should be addressed to the publishers. ISBN 1-897676-13-1 Page layout and design by Nottingham University Press, Nottingham Printed and bound by Bath Press, Bath, England Foreword v Contents Foreword ix T. Pearse Lyons Presient, Alltech Inc., Nicholasville, Kentucky, USA Ethanol industry today 1 Ethanol around the world: rapid growth in policies, technology and production 1 T. Pearse Lyons Alltech Inc., Nicholasville, Kentucky, USA Raw material handling and processing 2 Grain dry milling and cooking procedures: extracting sugars in preparation for fermentation 9 Dave R. Kelsall and T. Pearse Lyons Alltech Inc., Nicholasville, Kentucky, USA 3 Enzymatic conversion of starch to fermentable sugars 23 Ronan F.
    [Show full text]
  • Article Download
    wjpls, 2018, Vol. 4, Issue 8, 153-159 Research Article ISSN 2454-2229 Sathyamurthy et al. World Journal of Pharmaceutical World Journal and Lifeof Pharmaceutical Sciences and Life Sciences WJPLS www.wjpls.org SJIF Impact Factor: 5.088 GCMS AND FTIR ANALYSIS ON THE METHANOLIC EXTRACT OF RED VITIS VINIFERA PULP 1Naresh S., 1Sunil K. S., 1Akki Suma, 1Ashika B. D., 1Chitrali Laha Roy, *2Dr. Balasubramanian Sathyamurthy 1Department of Biochemistry, Ramaiah College of Arts, Science and Commerce, Bangalore – 560054. *2Professor, Department of Biochemistry, Ramaiah College of Arts, Science and Commerce, Bangalore – 560054. *Corresponding Author: Dr. Balasubramanian Sathyamurthy Department of Biochemistry, Ramaiah College of Arts, Science and Commerce, Bangalore – 560054. Article Received on 12/06/2018 Article Revised on 02/07/2018 Article Accepted on 23/07/2018 ABSTRACT Red Vitis Vinifera pulp has major components such as Organic acids, Malate, Tartrate and Sugars and contains higher moisture content. Our work is designed to identify the possible phytochemicals compounds present in the methanolic extract of red grape pulp by using GCMS along with functional group analysis through FTIR. From the GCMS analysis of red Vitis Vinifera pulp nearly 61 compounds were identified. By FTIR analysis, strong absorption band was found at 3400 cm–1, which represents the amine groups and ketones at a frequency of –1 1066.02 cm gave maximum peaks. Hence, we can conclude that the red Vitis Vinifera pulp extract is rich in amines, ether and ester groups. KEYWORDS: GCMS, FTIR, spectral analysis, NIST. 1. INTRODUCTION biochemical and organic mixtures and it is also highly compatible.[4] Infrared spectroscopy is most powerful Red Grapes or Vitis vinifera is a Berry fruit and belongs technique for materials analysis and used in the to the group of versatile fruits which are used in a wide laboratories.
    [Show full text]
  • Profiling Taste and Aroma Compound Metabolism During Apricot Fruit Development and Ripening
    Int. J. Mol. Sci. 2016, 17, 998; doi:10.3390/ijms17070998 S1 of S4 Supplementary Materials: Profiling Taste and Aroma Compound Metabolism during Apricot Fruit Development and Ripening Wanpeng Xi, Huiwen Zheng, Qiuyun Zhang and Wenhui Li Figure S1. Sugars HPLC chromatogram of apricot fruit. Peaks (1) Fructose (2) Glucose (3) Sucrose. (a) sugars mixture standards; (b) sugars for SG peel of S5; (c) sugars for SG pulp of S5. Int. J. Mol. Sci. 2016, 17, 998; doi:10.3390/ijms17070998 S2 of S4 Figure S2. Organic acids HPLC chromatogram of apricot fruit. Peaks (1) oxalic acid (2) tartaric acid (3) quininic acid (4) malic acid (5) citric acid (6) fumaric acid. (a) organic acids mixture standard; (b) organic acid for YC peel of S4; (c) organic acid for YC pulp of S4. Int. J. Mol. Sci. 2016, 17, 998; doi:10.3390/ijms17070998 S3 of S4 Table S1. Chroma values of apricot fruit during development and ripening. L* a* b* C* H Cultivars S1 S2 S3 S4 S5 S1 S2 S3 S4 S5 S1 S2 S3 S4 S5 S1 S2 S3 S4 S5 S1 S2 S3 S4 S5 DX 54.52 57.13 61.56 62.61 55.49 20.28 18.13 14.41 8.87 17.97 39.02 37.67 38.27 39.99 43.83 43.98 42.27 41.06 42.26 47.67 117.46 116.92 110.21 76.26 67.36 HY 54.97 55.83 61.53 65.08 65.11 −16.04 −14.77 −13.30 11.01 12.78 34.44 31.68 32.74 38.82 42.51 37.99 34.84 35.35 52.69 45.14 114.91 114.94 112.05 72.65 72.57 KE 47.02 47.00 48.32 60.11 60.66 −17.08 −17.37 −16.65 −0.36 8.20 30.83 29.09 29.08 48.23 48.48 35.26 33.88 33.51 48.33 49.33 118.94 120.86 119.85 90.67 118.02 AK 50.02 50.90 52.19 68.35 60.28 −21.98 −21.76 −19.02 -4.97 4.04 40.07 39.12 35.71
    [Show full text]
  • Recommended Methods for the Identification and Analysis of Fentanyl and Its Analogues in Biological Specimens
    Recommended methods for the Identification and Analysis of Fentanyl and its Analogues in Biological Specimens MANUAL FOR USE BY NATIONAL DRUG ANALYSIS LABORATORIES Laboratory and Scientific Section UNITED NATIONS OFFICE ON DRUGS AND CRIME Vienna Recommended Methods for the Identification and Analysis of Fentanyl and its Analogues in Biological Specimens MANUAL FOR USE BY NATIONAL DRUG ANALYSIS LABORATORIES UNITED NATIONS Vienna, 2017 Note Operating and experimental conditions are reproduced from the original reference materials, including unpublished methods, validated and used in selected national laboratories as per the list of references. A number of alternative conditions and substitution of named commercial products may provide comparable results in many cases. However, any modification has to be validated before it is integrated into laboratory routines. ST/NAR/53 Original language: English © United Nations, November 2017. All rights reserved. The designations employed and the presentation of 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. Mention of names of firms and commercial products does not imply the endorse- ment of the United Nations. This publication has not been formally edited. Publishing production: English, Publishing and Library Section, United Nations Office at Vienna. Acknowledgements The Laboratory and Scientific Section of the UNODC (LSS, headed by Dr. Justice Tettey) wishes to express its appreciation and thanks to Dr. Barry Logan, Center for Forensic Science Research and Education, at the Fredric Rieders Family Founda- tion and NMS Labs, United States; Amanda L.A.
    [Show full text]
  • APPENDIX G Acid Dissociation Constants
    harxxxxx_App-G.qxd 3/8/10 1:34 PM Page AP11 APPENDIX G Acid Dissociation Constants §␮ ϭ 0.1 M 0 ؍ (Ionic strength (␮ † ‡ † Name Structure* pKa Ka pKa ϫ Ϫ5 Acetic acid CH3CO2H 4.756 1.75 10 4.56 (ethanoic acid) N ϩ H3 ϫ Ϫ3 Alanine CHCH3 2.344 (CO2H) 4.53 10 2.33 ϫ Ϫ10 9.868 (NH3) 1.36 10 9.71 CO2H ϩ Ϫ5 Aminobenzene NH3 4.601 2.51 ϫ 10 4.64 (aniline) ϪO SNϩ Ϫ4 4-Aminobenzenesulfonic acid 3 H3 3.232 5.86 ϫ 10 3.01 (sulfanilic acid) ϩ NH3 ϫ Ϫ3 2-Aminobenzoic acid 2.08 (CO2H) 8.3 10 2.01 ϫ Ϫ5 (anthranilic acid) 4.96 (NH3) 1.10 10 4.78 CO2H ϩ 2-Aminoethanethiol HSCH2CH2NH3 —— 8.21 (SH) (2-mercaptoethylamine) —— 10.73 (NH3) ϩ ϫ Ϫ10 2-Aminoethanol HOCH2CH2NH3 9.498 3.18 10 9.52 (ethanolamine) O H ϫ Ϫ5 4.70 (NH3) (20°) 2.0 10 4.74 2-Aminophenol Ϫ 9.97 (OH) (20°) 1.05 ϫ 10 10 9.87 ϩ NH3 ϩ ϫ Ϫ10 Ammonia NH4 9.245 5.69 10 9.26 N ϩ H3 N ϩ H2 ϫ Ϫ2 1.823 (CO2H) 1.50 10 2.03 CHCH CH CH NHC ϫ Ϫ9 Arginine 2 2 2 8.991 (NH3) 1.02 10 9.00 NH —— (NH2) —— (12.1) CO2H 2 O Ϫ 2.24 5.8 ϫ 10 3 2.15 Ϫ Arsenic acid HO As OH 6.96 1.10 ϫ 10 7 6.65 Ϫ (hydrogen arsenate) (11.50) 3.2 ϫ 10 12 (11.18) OH ϫ Ϫ10 Arsenious acid As(OH)3 9.29 5.1 10 9.14 (hydrogen arsenite) N ϩ O H3 Asparagine CHCH2CNH2 —— —— 2.16 (CO2H) —— —— 8.73 (NH3) CO2H *Each acid is written in its protonated form.
    [Show full text]
  • 624 — 632 [1974] ; Received January 9, 1974)
    Some ab Initio Calculations on Indole, Isoindole, Benzofuran, and Isobenzofuran J. Koller and A. Ažman Chemical Institute “Boris Kidric” and Department of Chemistry, University of Ljubljana, P.O.B. 537, 61001 Ljubljana, Slovenia, Yugoslavia N. Trinajstić Institute “Rugjer Boskovic”, Zagreb, Croatia, Yugoslavia (Z. Naturforsch. 29 a. 624 — 632 [1974] ; received January 9, 1974) Ab initio calculations in the framework of the methodology of Pople et al. have been performed on indole, isoindole, benzofuran. and isobenzofuran. Several molecular properties (dipole moments, n. m. r. chemical shifts, stabilities, and reactivities) correlate well with calculated indices (charge densities, HOMO-LUMO separation). The calculations failed to give magnitudes of first ionization potentials, although the correct trends are reproduced, i. e. giving higher values to more stable iso­ mers. Some of the obtained results (charge densities, dipole moments) parallel CNDO/2 values. Introduction as positional isomers 4 because they formally differ Indole (1), benzofuran (3) and their isoconju­ only in the position of a heteroatom. Their atomic gated isomers: isoindole (2) and isobenzofuran (4) skeletal structures and a numbering of atoms are are interesting heteroaromatic molecules1-3 denoted given in Figure 1. 13 1 HtKr^nL J J L / t hü H 15 U (3) U) Fig. 1. Atomic skeletal structures and numbering of atoms for indole (1), isoindole (2), benzofuran (3), and isobenzofuran (4). Reprint requests to Prof. Dr. N. Trinajstic, Rudjer Boskovic Institute, P.O.B. 1016, 41001 Zagreb I Croatia, Yugoslavia. Dieses Werk wurde im Jahr 2013 vom Verlag Zeitschrift für Naturforschung This work has been digitalized and published in 2013 by Verlag Zeitschrift in Zusammenarbeit mit der Max-Planck-Gesellschaft zur Förderung der für Naturforschung in cooperation with the Max Planck Society for the Wissenschaften e.V.
    [Show full text]
  • Nirmalal FRONT PAGE
    SYNTHESIS AND EVALUATION OF IN-VITRO HEPATOPROTECTIVE ACTIVITY OF NOVEL 1,2,3,4- TETRAHYDRO QUINAZOLINE DERIVATIVES Dissertation submitted to The Tamil Nadu Dr. M.G.R. Medical University, Chennai-32. In partial fulfillment for the award of the Degree of MASTER OF PHARMACY IN PHARMACEUTICAL CHEMISTRY Submitted by Reg.No: 261215202 Under the Guidance of Dr. M. Vijayabasakaran, M.Pharm., Ph.D Department of Pharmaceutical Chemistry J.K.K. Nattraja college of Pharmacy Kumarapalayam – 638 183. Tamil Nadu. APRIL – 2014 CERTIFICATE This is to certify that the dissertation entitled “SYNTHESIS AND EVALUATION OF IN-VITRO HEPATOPROTECTIVE ACTIVITY OF NOVEL 1,2,3,4- TETRAHYDRO QUINAZOLINE DERIVATIVES ”, is a bonafide work done by Mrs.R.NIRMALA [Reg. No. 261215202], J.K.K. Nattraja College of Pharmacy, in partial fulfillment of the University rules and regulations for award of Master of Pharmacy in Pharmaceutial Chemsitry under my guidance and supervision during the academic year 2013-14. Dr.M.Vijayabasakaran M.Pharm., Ph.D., Dr.M.Vijayabasakaran M.Pharm., Ph.D., Guide HOD Dr.R.Sambath Kumar M.Pharm., Ph.D Principal CERTIFICATE This is to certify that the work embodied in this dissertation entitled “ SYNTHESIS AND EVALUATION OF IN-VITRO HEPATOPROTECTIVE ACTIVITY OF NOVEL 1,2,3,4- TETRAHYDRO QUINAZOLINE DERIVATIVES ”, submitted to “The Tamil Nadu Dr. M.G.R. Medical University”, Chennai, in partial fulfillment to the requirement for the award of Degree of Master of Pharmacy in Pharmaceutical Chemistry, is a bonafide work carried out by Mrs.R.NIRMALA [Reg.No.261215202] , during the academic year 2013- 2014 under the guidance and supervision of Dr.
    [Show full text]