Methyleugenol (4-Allyl-1,2-Dimethoxybenzene)
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Retention Indices for Frequently Reported Compounds of Plant Essential Oils
Retention Indices for Frequently Reported Compounds of Plant Essential Oils V. I. Babushok,a) P. J. Linstrom, and I. G. Zenkevichb) National Institute of Standards and Technology, Gaithersburg, Maryland 20899, USA (Received 1 August 2011; accepted 27 September 2011; published online 29 November 2011) Gas chromatographic retention indices were evaluated for 505 frequently reported plant essential oil components using a large retention index database. Retention data are presented for three types of commonly used stationary phases: dimethyl silicone (nonpolar), dimethyl sili- cone with 5% phenyl groups (slightly polar), and polyethylene glycol (polar) stationary phases. The evaluations are based on the treatment of multiple measurements with the number of data records ranging from about 5 to 800 per compound. Data analysis was limited to temperature programmed conditions. The data reported include the average and median values of retention index with standard deviations and confidence intervals. VC 2011 by the U.S. Secretary of Commerce on behalf of the United States. All rights reserved. [doi:10.1063/1.3653552] Key words: essential oils; gas chromatography; Kova´ts indices; linear indices; retention indices; identification; flavor; olfaction. CONTENTS 1. Introduction The practical applications of plant essential oils are very 1. Introduction................................ 1 diverse. They are used for the production of food, drugs, per- fumes, aromatherapy, and many other applications.1–4 The 2. Retention Indices ........................... 2 need for identification of essential oil components ranges 3. Retention Data Presentation and Discussion . 2 from product quality control to basic research. The identifi- 4. Summary.................................. 45 cation of unknown compounds remains a complex problem, in spite of great progress made in analytical techniques over 5. -
The Following Carcinogenic Essential Oils Should Not Be Used In
Aromatherapy Undiluted- Safety and Ethics Copyright © Tony Burfield and Sylla Sheppard-Hanger (2005) [modified from a previous article “A Brief Safety Guidance on Essential Oils” written for IFA, Sept 2004]. Intro In the last 20 years aromatherapy has spread its influence to the household, toiletries and personal care areas: consumer products claiming to relax or invigorate our psyche’s have invaded our bathrooms, kitchen and living room areas. The numbers of therapists using essential oils in Europe and the USA has grown from a handful in the early 1980’s to thousands now worldwide. We have had time to add to our bank of knowledge on essential oils from reflecting on many decades of aromatherapeutic development and history, the collection of anecdotal information from practicing therapists, as well as from clinical & scientific investigations. We have also had enough time to consider the risks in employing essential oils in therapy. In the last twenty years, many more people have had accidents, been ‘burnt’, developed rashes, become allergic, and become sensitized to our beloved tools. Why is this? In this paper, we hope to shed light on this issue, clarify current safety findings, and discuss how Aromatherapists and those in the aromatherapy trade (suppliers, spas, etc.) can interpret this data for continued safe practice. After a refresher on current safety issues including carcinogenic and toxic oils, irritant and photo-toxic oils, we will look at allergens, oils without formal testing, pregnancy issues and medication interactions. We will address the increasing numbers of cases of sensitization and the effect of diluting essential oils. -
Sassafras Tea: Using a Traditional Method of Preparation to Reduce the Carcinogenic Compound Safrole Kate Cummings Clemson University, [email protected]
Clemson University TigerPrints All Theses Theses 5-2012 Sassafras Tea: Using a Traditional Method of Preparation to Reduce the Carcinogenic Compound Safrole Kate Cummings Clemson University, [email protected] Follow this and additional works at: https://tigerprints.clemson.edu/all_theses Part of the Forest Sciences Commons Recommended Citation Cummings, Kate, "Sassafras Tea: Using a Traditional Method of Preparation to Reduce the Carcinogenic Compound Safrole" (2012). All Theses. 1345. https://tigerprints.clemson.edu/all_theses/1345 This Thesis is brought to you for free and open access by the Theses at TigerPrints. It has been accepted for inclusion in All Theses by an authorized administrator of TigerPrints. For more information, please contact [email protected]. SASSAFRAS TEA: USING A TRADITIONAL METHOD OF PREPARATION TO REDUCE THE CARCINOGENIC COMPOUND SAFROLE A Thesis Presented to the Graduate School of Clemson University In Partial Fulfillment of the Requirements for the Degree Master of Science Forest Resources by Kate Cummings May 2012 Accepted by: Patricia Layton, Ph.D., Committee Chair Karen C. Hall, Ph.D Feng Chen, Ph. D. Christina Wells, Ph. D. ABSTRACT The purpose of this research is to quantify the carcinogenic compound safrole in the traditional preparation method of making sassafras tea from the root of Sassafras albidum. The traditional method investigated was typical of preparation by members of the Eastern Band of Cherokee Indians and other Appalachian peoples. Sassafras is a tree common to the eastern coast of the United States, especially in the mountainous regions. Historically and continuing until today, roots of the tree are used to prepare fragrant teas and syrups. -
Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances 2017
INTERNATIONAL NARCOTICS CONTROL BOARD Precursors and chemicals frequently used in the illicit manufacture of narcotic drugs and psychotropic substances 2017 EMBARGO Observe release date: Not to be published or broadcast before Thursday, 1 March 2018, at 1100 hours (CET) UNITED NATIONS CAUTION Reports published by the International Narcotics Control Board in 2017 The Report of the International Narcotics Control Board for 2017 (E/INCB/2017/1) is supplemented by the following reports: Narcotic Drugs: Estimated World Requirements for 2018—Statistics for 2016 (E/INCB/2017/2) Psychotropic Substances: Statistics for 2016—Assessments of Annual Medical and Scientific Requirements for Substances in Schedules II, III and IV of the Convention on Psychotropic Substances of 1971 (E/INCB/2017/3) Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances: Report of the International Narcotics Control Board for 2017 on the Implementation of Article 12 of the United Nations Convention against Illicit Traffic in Narcotic Drugs and Psychotropic Substances of 1988 (E/INCB/2017/4) The updated lists of substances under international control, comprising narcotic drugs, psychotropic substances and substances frequently used in the illicit manufacture of narcotic drugs and psychotropic substances, are contained in the latest editions of the annexes to the statistical forms (“Yellow List”, “Green List” and “Red List”), which are also issued by the Board. Contacting the International Narcotics Control Board The secretariat of the Board may be reached at the following address: Vienna International Centre Room E-1339 P.O. Box 500 1400 Vienna Austria In addition, the following may be used to contact the secretariat: Telephone: (+43-1) 26060 Fax: (+43-1) 26060-5867 or 26060-5868 Email: [email protected] The text of the present report is also available on the website of the Board (www.incb.org). -
Safrole and the Versatility of a Natural Biophore Lima, L
Artigo Safrole and the Versatility of a Natural Biophore Lima, L. M.* Rev. Virtual Quim., 2015, 7 (2), 495-538. Data de publicação na Web: 31 de dezembro de 2014 http://www.uff.br/rvq Safrol e a Versatilidade de um Biofóro Natural Resumo: Safrol (1) obtido de óleos essenciais de diferentes espécies vegetais tem ampla aplicação na indústria química como precursor sintético do butóxido de piperonila, piperonal e de fármacos como a tadalafila, cinoxacina e levodopa. Do ponto vista toxicológico, é considerado uma hepatotoxina por mecanismo de bioativação metabólica conduzindo a formação de intermediários eletrofílicos, e tem sido descrito como inibidor de diferentes isoenzimas da família CYP450. A versatilidade de sua estrutura, permitindo várias transformações químicas, e a natureza biofórica de sua unidade benzodioxola ou metilenodioxifenila conferem-lhe características singulares, que o tornam atrativo material de partida para a síntese de compostos com distintas atividades farmacológicas. Exemplos selecionados de compostos bioativos, naturais e sintéticos, contendo o sistema benzodioxola serão comentados, incluindo aqueles provenientes de contribuição específica do LASSBio®. Palavras-chave: Safrol; benzodioxola; metilenodioxi; CYP450; bióforo; compostos bioativos. Abstract Safrole (1), obtained from essential oils from different plant species, has wide application in the chemical industry as a synthetic precursor of piperonyl butoxide, piperonal and drugs such as tadalafil, cinoxacin and levodopa. From the toxicological point of view, it is considered a hepatotoxin through metabolic bioactivation, leading to the formation of electrophilic metabolites, and has been described as an inhibitor of different CYP450 isoenzymes. The versatility of its structure, allowing various chemical transformations, and the biophoric nature of its benzodioxole or methylenedioxy subunit, give it unique features and make it an attractive starting material for the synthesis of compounds with different pharmacological activities. -
Extraction of Safrole from Essential Oils with Ionic Liquids
João Miguel Pinheiro Pinto Burguete Cardoso Bachelor degree in Chemical and Biochemical Engineering Extraction of safrole from essential oils with ionic liquids Dissertation submitted in partial fulfillment of the requirements for the degree of Master of Science in Chemical and Biochemical Engineering Adviser: Ewa Bogel-Łukasik, Auxiliary Researcher, Faculdade de Ciências e Tecnologia da Universidade Nova de Lisboa Co-adviser: Urszula Domanska-´ Zelazna,˙ Department of Physical Chemistry, Faculty of Chemistry, Warsaw University of Technology Examination Committee Chairperson: Mário Fernando José Eusébio Members: Luís Alexandre Almeida Fernandes Cobra Branco Ewa Bogel-Łukasik March, 2017 Extraction of safrole from essential oils with ionic liquids Copyright © João Miguel Pinheiro Pinto Burguete Cardoso, Faculty of Sciences and Tech- nology, NOVA University of Lisbon. The Faculty of Sciences and Technology and the NOVA University of Lisbon have the right, perpetual and without geographical boundaries, to file and publish this disserta- tion through printed copies reproduced on paper or on digital form, or by any other means known or that may be invented, and to disseminate through scientific reposito- ries and admit its copying and distribution for non-commercial, educational or research purposes, as long as credit is given to the author and editor. This document was created using the (pdf)LATEX processor, based in the “unlthesis” template[1], developed at the Dep. Informática of FCT-NOVA [2]. [1] https://github.com/joaomlourenco/unlthesis [2] http://www.di.fct.unl.pt Acknowledgements I am grateful to FCT/UNL and the Physical Chemistry department at Warsaw University of Technology for providing me the opportunity to study abroad as well as their staff for its continuous collaboration on this research work. -
Gas Chromatographic and Mass Spectrometric Analysis of N-Methyl-1-Aryl-2-Propanamines Synthesized from the Substituted Allylbenzenes Present in Sassafras Oil
Journal of Chromatographic Science, Vol. 29, June 1991 Gas Chromatographic and Mass Spectrometric Analysis of N-Methyl-1-aryl-2-propanamines Synthesized from the Substituted Allylbenzenes Present in Sassafras Oil F.T. Noggle, Jr. Alabama Department of Forensic Sciences, Wire Road, Auburn, Alabama 36830 C. Randall Clark and Jack DeRuiter Department of Pharmacal Sciences, School of Pharmacy, Auburn University, Auburn, Alabama 36849 A variety of methods have been reported for the synthesis of I Abstract I MDA, MDMA, and related compounds (5,6). The most direct One method used for the synthesis of the illicit drug N-methyl- approach involves treatment of the commercially available 1-(3,4-methylenedioxyphenyl)-2-propanami ne (methylene- ketone 1-(3,4-methylenedioxyphenyl)-2-propanone (3,4- dioxymethamphetamine, MDMA) involves the treatment of methylenedioxyphenylacetone) with ammonia or methylamine safrole with HBr to form the intermediate 2-bromosafrole, under reducing conditions as shown in Scheme 1. Based on this followed by bromide displacement with methylamine. The synthetic strategy, the availability of the ketone was controlled by starting material required for this synthesis, safrole, may be the Drug Enforcement Administration under the Chemical Di- obtained from sassafras oil which is isolated from the roots of version and Trafficking Act in March of 1989. The restricted the sassafras plant. In addition to safrole, sassafras oil availability of the key ketone precursor has forced clandestine contains other allyl benzenes such as eugenol and 4-allyl-1 ,2- laboratory operators to seek alternative approaches for the syn- dimethoxybenzene. Gas chromatography-mass spectrometric thesis of MDA and MDMA. One such alternate method em- (GC-MS) studies show that these allyl benzenes may also be ploys the natural product safrole, which is commercially avail- brominated and undergo amine displacement to yield the able or can be obtained by extraction or distillation of the corresponding N-methyl-1-aryl-2-propanamines. -
HM-08-026 Appendix B
Appendix B to HM-08-026 UNIVERSITY OF TOLEDO LABORATORY SAFETY AND HEALTH MANUAL AND INSTITUTIONAL CHEMICAL HYGIENE PLAN Environmental Health and Radiation Safety Department Effective Date: 07/01/1995 Revised: 12/20/05 2/23/09 2/1/10 6/28/10 2/1/11 2/1/12 4/10/12 2/1/2013 2/1/2014 1/30/15 1/29/16 1/27/17 1/25/18 1/22/19 1/20/20 1/20/21 EMERGENCY PHONE NUMBERS: Fire Pull Station / 911 Hazardous Matrerials Spills 419-530-2600 (MC) or 419-383-2600 (HSC) Environmental Health and Radiation Safety Department 419-530-3600 Radiation Safety Office 419-383-4301 TABLE OF CONTENTS SECTION I - FORWARD .................................................................................................................................................................. 3 SECTION II - PUBLIC EMPLOYEES RISK REDUCTION PROGRAM (PERRP) OSHA ................................................................. 4 SECTION III - LAB EQUIPMENT ..................................................................................................................................................... 5 SECTION IV - GENERAL SAFETY GUIDELINES…………………………………………………………………………………………..11 A. GENERAL PROCEDURES AND PRECAUTIONS FOR WORKING WITH SUBSTANCES OF MODERATE CHRONIC OR ACUTE HIGH TOXICITY* ....................................................................................................... 10 B. GENERAL PROCEDURES AND PRECAUSTIONS FOR WORKING WITH ALLERGENS AND EMBRYOTOXINS .......................................................................................................................................... -
Myristica Fragrans Houtt.) That Inhibit Locomotor Activity in Mice
Int. J. Mol. Sci. 2010, 11, 4771-4781; doi:10.3390/ijms11114771 OPEN ACCESS International Journal of Molecular Sciences ISSN 1422-0067 www.mdpi.com/journal/ijms Article Identification of Compounds in the Essential Oil of Nutmeg Seeds (Myristica fragrans Houtt.) That Inhibit Locomotor Activity in Mice Muchtaridi 1,*, Anas Subarnas 1, Anton Apriyantono 2 and Resmi Mustarichie 1 1 Faculty of Pharmacy, Universitas Padjadjaran, Jl KM 21.5 Bandung-Sumedang, Jatinangor, Indonesia; E-Mails: [email protected] (A.S.); [email protected] (R.M.) 2 Department of Food Technology and Human Nutrition, Bogor Agricultural University, Jl. Darmaga, Bogor, Indonesia; E-Mail: [email protected] * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +62-22-7796200; Fax: +62-22-7796200. Received: 11 October 2010; in revised form: 8 November 2010 / Accepted: 15 November 2010 / Published: 23 November 2010 Abstract: The present study was designed to evaluate the inhibitory effect of nutmeg (Myristica fragrans Houtt.) seed essential oil on the locomotor activity of mice in a wheel cage. Active compounds in the essential oil were identified by off-line solid phase extraction (SPE-C18) and GC/MS analysis. The essential oil was administered by inhalation at doses of 0.1, 0.3, and 0.5 mL/cage. The results showed that inhalation of nutmeg seed essential oil at a dose of 0.5 mL/cage decreased locomotion by 68.62%; and inhalation of 0.1 and 0.3 mL/cage inhibited locomotion by 62.81% and 65.33%, respectively. Generally, larger doses and longer administrations of nutmeg seed essential oil exhibited greater locomotor inhibition. -
Volatile Oil from the Aerial Parts of Tagetes Lucida (Asteraceae) Cultivated in Costa Rica
A source of almost pure methyl chavicol: volatile oil from the aerial parts of Tagetes lucida (Asteraceae) cultivated in Costa Rica José F. Cicció Centro de Investigaciones en Productos Naturales (CIPRONA) y Escuela de Química, Universidad de Costa Rica, 2060 San José, Costa Rica; [email protected] Received 28-XI-2003. Corrected 25-II-2003. Accepted 30-III-2004. Abstract: The plant Tagetes lucida Cav. (syn. T. florida Sweet, T. schiedeana Less.) is an aromatic herb dis- tributed naturally from Mexico to Honduras, at elevations between 1 000 and 2 000 m. It is used as a spice, for medicine, as insecticide and as ornamental plant. It is cultivated commercially in Costa Rica as a spice herb; it contains an oil having an anise-like odor, and the fresh aerial parts of this plant are sold in the supermarket as a substitute of tarragon (Artemisia dracunculus L.). The essential oils isolated from aerial parts bought, at May and October, in a supermarket in San José (Costa Rica). Fresh flowering aerial parts, flowers and leaves plus stems, were subjected to hydrodistillation for 3 hr using a modified Clevenger-type apparatus. The distilled oils were collected and dried over anhydrous sodium sulphate and stored in a freezer (0-10°C). The light yellow green oil yield was about 0.07% (v/w). GC/MS analyses were performed using a Shimadzu GCMS-QP5050 apparatus and CLASS 5000 software with Wiley 139 computer database. Identification of the components of the oil was performed using the retention indices, which were calculated in relation to a homologous series of hydrocarbons, and by comparison of their mass spectra with those published in the literature or those of our own database. -
Chemicals Required for the Illicit Manufacture of Drugs Table 1 SUBSTANCES in TABLES I and II of the 1988 CONVENTION
Chemicals Required 1. A variety of chemicals are used in the illicit manufacture of for the Illicit drugs. The United Nations Convention against Illicit Traffic in Manufacture of Drugs Narcotic Drugs and Psychotropic Substances of 1988 (1988 Convention) refers to “substances frequently used in the illicit manufacture of narcotic drugs and psychotropic substances”. Twenty-two such substances are listed in Tables I and II of the 1988 Convention as in force on 1st May, 1998. (See Table1) Table 1 Table I Table II SUBSTANCES IN N-Acetylanthranilic acid. Acetic anhydride TABLES I AND II OF Ephedrine Acetone THE 1988 Ergometrine Anthranilic acid CONVENTION Ergotamine Ethyl ether Isosafrole Hydrochloric acid* Lysergic acid Methyl ethyl ketone 3,4-methylenedioxyphenyl-2-propanone Phenylacetic acid 1-phenyl-2-propanone Piperidine Piperonal Potassium permanganate Pseudoephedrine Sulphuric acid* Safrole Toluene The salts of the substances in this Table The salts of the substances whenever the existence of such salts is in this Table whenever the possible. existence of such salts is possible. * The salts of hydrochloric acid and sulphuric acid are specifically excluded from Table II. U N D C P 11 The term “precursor” is used to indicate any of these substances in the two Tables. Chemicals used in the illicit manufacture of narcotic drugs and psychotropic substances are often described as precursors or essential chemicals, and these include true precursors, solvents, oxidising agents and other Chemicals used in the illicit manufacture of narcotic substances. Although the term is not drugs and psychotropic substances are often technically correct, it has become common described as precursors or essential chemicals, and practice to refer to all such substances as these include true precursors, solvents, oxidising “precursors”. -
Biomolecules of Interest Present in the Main Industrial Wood Species Used in Indonesia-A Review
Tech Science Press DOI: 10.32604/jrm.2021.014286 REVIEW Biomolecules of Interest Present in the Main Industrial Wood Species Used in Indonesia-A Review Resa Martha1,2, Mahdi Mubarok1,2, Wayan Darmawan2, Wasrin Syafii2, Stéphane Dumarcay1, Christine Gérardin Charbonnier1 and Philippe Gérardin1,* 1Université de Lorraine, Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement, Laboratoire d'Etudes et de Recherche sur le Matériau Bois, Nancy, France 2Department of Forest Products, Faculty of Forestry and Environment, Institut Pertanian Bogor, Bogor University, Bogor, Indonesia *Corresponding Author: Philippe Gérardin. Email: [email protected] Received: 17 September 2020 Accepted: 20 October 2020 ABSTRACT As a tropical archipelagic country, Indonesia’s forests possess high biodiversity, including its wide variety of wood species. Valorisation of biomolecules released from woody plant extracts has been gaining attractive interests since in the middle of 20th century. This paper focuses on a literature review of the potential valorisation of biomole- cules released from twenty wood species exploited in Indonesia. It has revealed that depending on the natural origin of the wood species studied and harmonized with the ethnobotanical and ethnomedicinal knowledge, the extractives derived from the woody plants have given valuable heritages in the fields of medicines and phar- macology. The families of the bioactive compounds found in the extracts mainly consisted of flavonoids, stilbenes, stilbenoids, lignans, tannins, simple phenols, terpenes, terpenoids, alkaloids, quinones, and saponins. In addition, biological or pharmacological activities of the extracts/isolated phytochemicals were recorded to have antioxidant, antimicrobial, antifungal, anti-inflammatory, anti-diabetes, anti-dysentery, anticancer, analgesic, anti-malaria, and anti-Alzheimer activities.