DOCSLIB.ORG

Deep Eutectic Solvents As Smart Cosubstrate in Alcohol Dehydrogenase-Catalyzed Reductions

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Deep Eutectic Solvents As Smart Cosubstrate in Alcohol Dehydrogenase-Catalyzed Reductions catalysts Communication Deep Eutectic Solvents as Smart Cosubstrate in Alcohol Dehydrogenase-Catalyzed Reductions 1,2, 1, 2 Santiago Nahuel Chanquia y , Lei Huang y, Guadalupe García Liñares , Pablo Domínguez de María 3 and Selin Kara 1,* 1 Department of Engineering, Biocatalysis and Bioprocessing Group, Aarhus University, 8000 Aarhus, Denmark; [email protected] (S.N.C.); [email protected] (L.H.) 2 Organic Chemistry Department, UMYMFOR-CONICET, Laboratory of Biocatalysis, Faculty of Exact and Natural Sciences, University of Buenos Aires, Buenos Aires C1428EGA, Argentina; [email protected] 3 Sustainable Momentum, SL. Av. Ansite 3, 4-6, Las Palmas de Gran Canaria, 35011 Canary Islands, Spain; [email protected] * Correspondence: [email protected]; Tel.: +45-2237-8964 The authors contributed equally. y Received: 20 July 2020; Accepted: 29 August 2020; Published: 3 September 2020 Abstract: Alcohol dehydrogenase (ADH) catalyzed reductions in deep eutectic solvents (DESs) may become efficient and sustainable alternatives to afford alcohols. This paper successfully explores the ADH-catalyzed reduction of ketones and aldehydes in a DES composed of choline chloride and 1,4-butanediol, in combination with buffer (Tris-HCl, 20% v/v). 1,4-butanediol (a DES component), acts as a smart cosubstrate for the enzymatic cofactor regeneration, shifting the thermodynamic equilibrium to the product side. By means of the novel DES media, cyclohexanone reduction was 1 1 optimized to yield maximum productivity with low enzyme amounts (in the range of 10 g L− d− ). Notably, with the herein developed reaction media, cinnamaldehyde was reduced to cinnamyl alcohol, an important compound for the fragrance industry, with promising high productivities of 1 1 ~75 g L− d− . Keywords: deep eutectic solvents; alcohol dehydrogenases; smart cosubstrate; reductions; cinnamyl alcohol 1. Introduction Oxidoreductases (EC1) are becoming increasingly important catalysts in organic synthesis given their high activity and selectivity when applied in redox processes. Reactions ranging from C = O and C = C reductions to hydroxylations, epoxidations, and Baeyer-Villiger reactions are catalyzed by these enzymes [1–5]. In particular, the application of alcohol dehydrogenases (ADHs, EC 1.1.1.1) represents a sustainable and efficient method for the synthesis of (optically active) alcohols starting from carbonyl compounds as inexpensive substrates [6,7]. ADHs are cofactor-dependent (nicotinamide cofactors (NAD(P)H)) and mediate as electron donors/acceptors in oxidations or reductions. For economic reasons, cofactors must be used in catalytic amounts combined with an in situ regeneration system [8], which normally implies a second enzymatic reaction, usually mediated by glucose dehydrogenase (GDH) [9] or formate dehydrogenase (FDH) and an adequate ancillary cosubstrate. Alternatively, chemical, electrochemical, or photochemical regeneration methods have been proposed [10–12], as well as synthetic nicotinamide cofactors in stoichiometric amounts [13]. In this area, the ADH mediated oxidation of simple alcohols for cofactor regenerations is a common and efficient approach, particularly useful when the same ADH is used in both reactions, conforming a biocatalytic version of the Meerwein–Ponndorf–Verley (MPV) Catalysts 2020, 10, 1013; doi:10.3390/catal10091013 www.mdpi.com/journal/catalysts Catalysts 2020, 10, x FOR PEER REVIEW 2 of 8 of the Meerwein–Ponndorf–Verley (MPV) reduction [14–17]. However, these combined cycles often present drawbacks related to their reversibility and poor thermodynamic driving force, which forces the use of a surplus of the cosubstrate or the carrying out of a coproduct removal. Using an excess amount of cosubstrate (e.g., isopropanol, ethanol, etc.) might enhance the solubility of a main substrate/product;Catalysts 2020, 10, 1013 nevertheless, it is still not an ideal approach in terms of atom economy. 2To of 8 overcome these issues, the use of smart cosubstrates has been put forth. The main concept behind this relatively new development consists of shifting the equilibrium of a certain reaction by transformingreduction [14 one–17]. of However, the substrates these combinedinto thermodynamically cycles often present and/or drawbacks kinetically related inert to coproducts their reversibility [18– 20].and poor thermodynamic driving force, which forces the use of a surplus of the cosubstrate or the carryingBiocatalysis out of in a coproductnon-conventional removal. reaction Using media, an excess such amountas solvent of-free cosubstrate systems, (e.g.,organic isopropanol, solvents, ionicethanol, liquids etc.) (ILs) might, or enhancesupercritical the solubility fluids, is of becoming a main substrate a well-established/product; nevertheless, strategy to cope it is stillwith not the an challengesideal approach that modern in terms synthesis of atom economy.entails [21]. To Herein, overcome deep these eutectic issues, solvents the use (DESs), of smart a new cosubstrates type of ILshas [22], been hold put promising forth. The features main concept as reaction behind solvents this relatively [23,24]. newA DES development is composed consists of a hydrogen of shifting bon thed donorequilibrium (HBD) ofand a certaina hydrogen reaction bond by acceptor transforming (HBA), one typically of the substrates a quaternary into ammonium thermodynamically salt. The and DES/or preparationkinetically inertis straightforward coproducts [18—–b20oth]. components must be gently mixed to form a liquid—which is advantageousBiocatalysis over in traditional non-conventional ILs both reactionin terms media, of simplicity such as and solvent-free environmental systems, impact. organic To solvents,reduce theionic inherent liquids high (ILs), viscosity or supercritical of DESs, the fluids, addition is becoming of water a as well-established cosolvent (up to strategy 20% v/v to) enables cope with a low the viscouschallenges media, that while modern keeping synthesis the non entails-conventional [21]. Herein, nature deep of eutecticit (i.e., a solvents substrate (DESs),-dissolving a new system) type of [25].ILs [These22], hold low promising viscous DES features-water as mixtures reaction solventsare particularly [23,24]. useful A DES when is composed continuous of a hydrogenprocesses bondare envisageddonor (HBD) [26,27 and]. a hydrogen bond acceptor (HBA), typically a quaternary ammonium salt. The DES preparationBased on is the straightforward—both recent work of us and components other groups must [20,28 be–30 gently], herein mixed the tocombination form a liquid—which of the smart is cosubstrateadvantageous concept over traditionalwith a DES, ILs to both set in up terms an ofefficient simplicity and andenviro environmentalnmentally-friendly impact. synthetic To reduce alternative,the inherent is addressed high viscosity for the of first DESs, time. the ADH addition from ofhorse water liver as (HLADH), cosolvent (upwhich to can 20% acceptv/v) enables a broad a rangelow viscousof diols media,as substrates while [31 keeping–34], was the selected non-conventional as the prototypical nature of enzyme, it (i.e., as a substrate-dissolvingit also can catalyze reactionssystem) [in25 DES]. These-aqueou lows viscous systems DES-water [35]. As reaction mixtures media, are particularly a DES consisting useful whenof choline continuous chloride processes (ChCl) andare 1,4 envisaged-butanediol [26, 27(1,4].-BD) was chosen. Acting as smart cosubstrate, 1,4-BD shifts the equilibrium of the MPVBased reduction on the when recent being work oxidized of us and to γ other-butyrolactone groups [20 (GBL),,28–30 a], thermodyn herein theamically combination stable of and the kineticallysmart cosubstrate inert coproduct concept (Scheme with a DES, 1). toThus, set upthe an reaction efficient solvent and environmentally-friendly becomes a part of the reaction, synthetic avoidingalternative, the addition is addressed of any for other the firstreagents, time. which ADH greatly from horse simplifies liver the (HLADH), process and which makes can it accept much a morebroad efficient range ofand diols sustainable. as substrates Analo [31gous–34], wasapproaches selected have as the been prototypical reported enzyme,in the literature as it also for can glycerolcatalyze [25] reactions and for inglucose DES-aqueous [30]. systems [35]. As reaction media, a DES consisting of choline chloride (ChCl) and 1,4-butanediol (1,4-BD) was chosen. Acting as smart cosubstrate, 1,4-BD shifts the 2.equilibrium Results and of Discussion the MPV reduction when being oxidized to γ-butyrolactone (GBL), a thermodynamically stable and kinetically inert coproduct (Scheme1). Thus, the reaction solvent becomes a part of the To validate the concept of using smart cosubstrates as part of the DES-water media, the HLADH- reaction, avoiding the addition of any other reagents, which greatly simplifies the process and makes it catalyzed reduction of cyclohexanone (CHO) to cyclohexanol (CHL) was chosen as model reaction much more efficient and sustainable. Analogous approaches have been reported in the literature for (Scheme 1). A choline chloride—1,4-butanediol DES was formed and mixed with 20% buffer (v/v) to glycerol [25] and for glucose [30]. decrease viscosity and to provide the enzyme with the necessary water for its activity [35]. SchemeScheme 1. 1. AlcoAlcoholhol dehydrogenase dehydrogenase from from horse horse liver liver (HLADH (HLADH)-catalyzed)-catalyzed reduction reduction of of cyclohexanone cyclohexanone (CHO)(CHO)
Load more

Recommended publications
  • Gc Applications
    gc applications Alcohols C1-C7 Alcohols C1-C6 Alcohols 1007 1255 1. Methanol 1. Methanol 4. 2-Methyl-2- 6. 2-Butanol 2. 2-Propanol 2. Ethanol propanol 7. 2-Methyl-1-propanol 3. 1-Propanol 3. 2-Propanol 5. 1-Propanol 8. 2-Methyl-2-butanol 4. 2-Butanol 9. 1-Butanol 5. 2-Methyl-1-propanol 10. 2,2-Dimethyl-1-propanol 6. 1-Butanol 11. 3-Methyl-2-butanol 7. 3-Methyl-1-butanol 12. 2-Pentanol + 3-Pentanol 8. 1-Pentanol 13. 3-Methyl-1-butanol 9. 2-Ethyl-1-butanol 14. 2-Methyl-1-butanol 10. 1-Hexanol 15. 4-Methyl-2-pentanol 11. Cyclohexanol 16. 1-Pentanol 12. 3-Methylcyclohexanol 17. 1-Hexanol 13. 1-Heptanol 18. Cyclohexanol å-IN Column: Econo-Cap™ EC™-1, 30m x 0.32mm x 0.25µm Column: Heliflex® AT™-1, 30m x 0.53mm x 5.00µm (Part No. 19651) (Part No. 16843) Temp: 40°C to 120°C at 10°C/min Temp: 35°C to 100°C at 5°C/min Carrier Gas: Helium at 1.09mL/min (26.7cm/sec) Carrier Gas: Helium at 3mL/min Detector: FID Detector: FID C1-C6 Alcohols Aromatic Alcohols 2596 1249 1. Methanol 1. A,A-Dimethylbenzyl Alcohol 2. Ethanol 2. DL-A-Methylbenzyl Alcohol 3. 1-Propanol 3. Benzyl Alcohol 4. 2-Methyl-1-propanol 4. 2-Phenylethyl Alcohol 5. 1-Butanol 5. 3-Phenyl-1-propanol 6. 4-Methyl-2-pentanol 6. Cinnamyl Alcohol 7. 1-Pentanol 7. Phenyl-1,2-ethanediol 8. 2-Ethyl-1-butanol 8.
    [Show full text]
  • A Practical and Stereoselective Synthesis of Cinnamyl Alcohols Bearing A-Cyano Or A-Ester Functional Group from Baylis-Hillman Adducts
    Notes Bull. Korean Chem. Soc. 2004, Vol. 25, No. 3 413 A Practical and Stereoselective Synthesis of Cinnamyl Alcohols Bearing a-Cyano or a-Ester Functional Group from Baylis-Hillman Adducts Ka Young Lee, Saravanan GowriSankar, and Jae Nyoung Kim Department of Chemistry and Institute of Basic Science, Chonnam National University, Gwangju 500-757, Korea Received December 18, 2003 Key Words : Cinnamyl alcohols, Baylis-Hillman adducts, Sulfuric acid, Acetic anhydride Cinnamyl alcohols bearing ester, acid, or nitrile functional Hillman alcohol into the primary acetate or eventually to group at the 2-position are very useful synthons for the primary alcohol (Scheme 1 and Table 1). synthesis of various biologically important compounds.1 The reaction of Baylis-Hillman adducts with acetic Synthesis of cinnamyl alcohol derivatives from the Baylis- anhydride (1.5 equiv.) in the presence of sulfuric acid (10 Hillman adducts has been reported by us and other groups.1-4 mol%) gave the corresponding rearranged cinnamyl acetates The conversion can be carried out directly by using 20% quantitatively in dichloromethane at room temperature aqueous sulfuric acid (for the Baylis-Hillman adducts within 30 min (Actually, the cinnamyl acetate derivatives derived from acrylonitrile)2 or trifluoroacetic acid (for the could be isolated in 92-95% yields.). In order to obtain the Baylis-Hillman adducts derived from acrylates).3 Recently, corresponding cinnamyl alcohols in a one-pot we tried some Basavaiah and coworkers have reported the two-step, one- reaction conditions for the next partial hydrolysis. Addition pot conversion method: TMSOTf-assisted conversion of of water to the reaction mixture (two-phase system) afforded Baylis-Hillman alcohol into the corresponding primary the hydrolyzed cinnamyl alcohols in trace amounts.
    [Show full text]
  • Food and Drug Administration, HHS § 172.515
    Food and Drug Administration, HHS § 172.515 Common name Scientific name Limitations Tolu ................................................................ Myroxylon balsamum (L.) Harms. Turpentine ...................................................... Pinus palustris Mill. and other Pinus spp. which yield terpene oils exclusively. Valerian rhizome and roots ............................ Valeriana officinalis L. Veronica ......................................................... Veronica officinalis L .................................................. Do. Vervain, European ......................................... Verbena officinalis L ................................................... Do. Vetiver ............................................................ Vetiveria zizanioides Stapf ......................................... Do. Violet, Swiss ................................................... Viola calcarata L. Walnut husks (hulls), leaves, and green nuts Juglans nigra L. or J. regia L. Woodruff, sweet ............................................. Asperula odorata L ..................................................... In alcoholic beverages only Yarrow ............................................................ Achillea millefolium L .................................................. In beverages only; fin- ished beverage thujone free1 Yerba santa .................................................... Eriodictyon californicum (Hook, et Arn.) Torr. Yucca, Joshua-tree ........................................ Yucca brevifolia Engelm. Yucca,
    [Show full text]
  • Nomination Background: Methyl Trans
    ' 7/?1 Methyl styryl ketone 122-57-6 NTP NOMINATION HISTORY AND REVIEW A. Nomination History 1. Nomination Source: NCI 2. Recommendations: -Comparative toxicity studies with methyl vinyl ketone -Metabolism -Carcinogenicity 3. Rationale/Remarks: -Potential for widespread human exposure -Nominated as a result of a class study of a,~-unsaturated ketones -Flavoring and fragrance additive -Natural product -Environmental pollutant -Mutagenic in Salmonella 4. Priority: -High for toxicity studies -Moderate for carcinogenicity s. Date of Nomination: July 1994 B. Interagency Committee for Chemical Evaluation and Coordination Review 1. Date of Review: 2. Recommendations: 3. Priority: 4. NTP Chemical Selection Principles: 5. Rationale/Remarks: 122-57-6 Methyl styryl ketone SUMMARY OF DATA FOR CHEMICAL SELECTION CHEMICAL IDENTIFICATION CAS Registry Number: 122-57-6 Chemical Abstracts Name: 3-Buten-2-one, 4-phenyl- (SCI, 9CI) Svnonvms and Trade Names: Acetocinnamone; benzalacetone; benzylideneacetone; methyl 2­ phenylvinyl ketone; methyl styryl ketone; methyl ~-styryl ketone; 4­ phenylbutenone; 4-phenyl-3-butene-2-one; 2-phenylvinyl methyl ketone; styryl methyl ketone; MSK FEMA Number: 2881 Related isomers CAS Registry Number: 937-53-1 Chemica] Abstracts Name: 3-Buten-2-one, 4-phenyl-, (Z)- (SCI, 9CI) Synonvms and Trade Names: cis -4-Phenyl-3-buten-2-one; cis -benzalacetone; cis­ benzylideneacetone; cis-methyl styryl ketone CAS Registry Number: 1896-62-4 Chemical Abstracts Name: 3-Buten-2-one, 4-phenyl-, (E)- (SCI, 9CI) Synonyms and Trade Names: trans-4-Phenyl-3-buten-2-one; trans-benzalacetone; trans­ benzylideneacetone; trans-methyl styryl ketone; TPBO Structure. Molecular Formula. and Molecular WeiKbt 0 II H•CHCCH3 Mol. wt.: 146.19 Chemical and Phvsical Properties (from Aldrich Chemical Co., 1993, 1994; Budavari, 1989) Description: White to yellow solid with a sweet, pungent, creamy, floral odor Prepared for NCI by Technical Resources, Inc.
    [Show full text]
  • Functional Expression of a Novel Methanol-Stable Esterase From
    Cai et al. BMC Biotechnology (2020) 20:36 https://doi.org/10.1186/s12896-020-00622-1 RESEARCH ARTICLE Open Access Functional expression of a novel methanol- stable esterase from Geobacillus subterraneus DSM13552 for biocatalytic synthesis of cinnamyl acetate in a solvent- free system Xianghai Cai1†, Lin Lin2,3†, Yaling Shen1, Wei Wei1* and Dong-zhi Wei1 Abstract Background: Esterases are widely distributed in nature and have important applications in medical, industrial and physiological. Recently, the increased demand for flavor esters has prompted the search of catalysts like lipases and esterases. Esterases from thermophiles also show thermal stability at elevated temperatures and have become enzymes of special interest in biotechnological applications. Although most of esterases catalyzed reactions are carried out in toxic and inflammable organic solvents, the solvent-free system owning many advantages such as low cost and easy downstream processing. Results: The gene estGSU753 from Geobacillus subterraneus DSM13552 was cloned, sequenced and overexpressed into Escherichia coli BL21 (DE3). The novel gene has an open reading frame of 753 bp and encodes 250-amino-acid esterase (EstGSU753). The sequence analysis showed that the protein contains a catalytic triad formed by Ser97, Asp196 and His226, and the Ser of the active site is located in the conserved motif Gly95-X-Ser97-X-Gly99 included in most esterases and lipases. The protein catalyzed the hydrolysis of pNP-esters of different acyl chain lengths, and the enzyme specific activity was 70 U/mg with the optimum substrate pNP-caprylate. The optimum pH and temperature of the recombinant enzyme were 8.0 and 60 °C respectively.
    [Show full text]
  • Proceedings of the Indiana Academy of Science
    The Reactions of Silicomolybdic Acid with Organic Compounds 1 John H. Billman, Donald B. Borders, and John A. Buehler, Indiana University, Hondo AFB, Texas, and Anderson College For many years the analytical and inorganic chemists have been seeking specific reagents to identify metallic ions. At the same time, the organic chemist has been interested in finding compounds that would be useful for spotting different types of functional groups commonly en- countered in organic compounds. A typical example of such a reagent is ferric chloride, which has found wide use with phenols. For several years we have been testing various compounds in an effort to find reagents that would be specific for metallic ions as well as organic functional groups. In the course of our investigation it was found that silicomolybdic acid (1), H 4 SiMo 12 O 40 .xH 2 O, would produce a dark blue mixture in the presence of aliphatic aldehydes, but would not give the same test with aromatic aldehydes. Further investigation indi- cated that only aldehydes that contain a hydrogen atom on the alpha carbon atom would give a positive test. On the basis of this work a more thorough study was undertaken of the reaction of silicomolybdic acid with various organic compounds containing different functional groups. Altogether the reagent has been tried with a one-hundred and forty-five organic compounds. Table 1 shows the aldehydes that have been tested. TABLE I Aldehydes — Formaldehyde — Benzaldehyde + Acetaldehyde — m-Nitrobenzaldehyde -f Phenylacetaldehyde — p-Nitrobenzaldehyde
    [Show full text]
  • Alcohol Dehydrogenase and Cinnamoyl-Coa Reductase (Monolignol͞genetic Modification͞antisense Rna͞coniferyl Alcohol͞feruloyl-Coa)
    Proc. Natl. Acad. Sci. USA Vol. 95, pp. 12803–12808, October 1998 Biochemistry NMR characterization of altered lignins extracted from tobacco plants down-regulated for lignification enzymes cinnamyl- alcohol dehydrogenase and cinnamoyl-CoA reductase (monolignolygenetic modificationyantisense RNAyconiferyl alcoholyferuloyl-CoA) JOHN RALPH*†‡,RONALD D. HATFIELD*, JOE¨L PIQUEMAL§,NABILA YAHIAOUI§,MICHEL PEAN¶, i CATHERINE LAPIERRE , AND ALAIN M. BOUDET§ *United States Dairy Forage Research Center, United States Department of Agriculture, Agricultural Research Service, Madison, WI 53706-1108; †Department of Forestry, University of Wisconsin, Madison, WI 53706-1598; §Unite´Mixte de Recherche, Centre National de la Recherche Scientifique 5546, Centre de Biologie et Physiologie Ve´ge´tale, Universite´Paul Sabatier Baˆt.4R1, 118 route de Narbonne, F-31062 Toulouse Cedex, France; ¶Commissariat a`l’Energie Atomique, De´partementd’Ecophysiologie Ve´ge´tale et Microbiologie, Cadarache, Baˆt.177, F-13108 Saint Paul lez Durance Cedex, France; and iInstitut National de la Recherche Agronomique, Laboratoire de Chimie Biologique, F-78850 Thiverval-Grignon, France Communicated by Ron Sederoff, North Carolina State University, Raleigh, NC, July 29, 1998 (received for review May 13, 1998) OHO OS OH OH ABSTRACT Homologous antisense constructs were CoA used to down-regulate tobacco cinnamyl-alcohol dehydro- CCL' CCR' CAD' p-Coumaryl genase (CAD; EC 1.1.1.195) and cinnamoyl-CoA reductase alcohol (CCR; EC 1.2.1.44) activities in the lignin monomer biosyn- OH OH OH OH 1) HYD1' 1) HYD2' 1) HYD3' 1) HYD4' thetic pathway. CCR converts activated cinnamic acids 2) OMT1' 2) OMT2' 2) OMT3' 2) OMT4' OHO OS OH OH (hydroxycinnamoyl–SCoAs) to cinnamaldehydes; cinnama- CoA CCR CAD ldehydes are then reduced to cinnamyl alcohols by CAD.
    [Show full text]
  • X-ADH Is the Sole Alcohol Dehydrogenase Isozyme of Mammalian Brains: Implications and Inferences (Class III Alcohol Dehydrogenase/Tissue-Specific Enzyme) THOMAS B
    Proc. Natl. Acad. Sci. USA Vol. 82, pp. 8369-8373, December 1985 Biochemistry X-ADH is the sole alcohol dehydrogenase isozyme of mammalian brains: Implications and inferences (class III alcohol dehydrogenase/tissue-specific enzyme) THOMAS B. BEISSWENGER, BARTON HOLMQUIST, AND BERT L. VALLEE* Center for Biochemical and Biophysical Sciences and Medicine, Harvard Medical School, 250 Longwood Avenue, Boston, MA 02115 Contributed by Bert L. Vallee, August 14, 1985 ABSTRACT Class m (X) is the only alcohol dehydrog- occurrence and function of ADH in that tissue has always enase (ADH) in human, equine, bovine, simian, canine, and been of particular interest, but efforts to uncover facts rodent brain and is the first to be identified, purified, and relevant to ethanol have been singularly disappointing. Most characterized from the brain of humans or other vertebrates. of those studies antedate the awareness of the remarkable Like the corresponding isozymes from human placenta and number and diversity of structure and specificity of ADH liver, the X-ADH isozymes purified from mammalian brain are isozymes (4), first noted much earlier (5). neither inhibited by nor do they bind to immobilized pyrazole, Experimental work failed to reveal any significant ADH and they oxidize ethanol only very poorly (Km > 2.5 M). activity in brain (6). The level ofethanol oxidation in rat brain Indeed, it would be incorrect to classify them as "ethanol is so vanishingly low that only assays of exceptionally high dehydrogenases." They contain 4 g.atom of zinc/mol, bind 2 sensitivity could detect it (7). A number of contemporaneous moles of NAD, and readily oxidize long-chain aliphatic and studies employing [14C]ethanol concluded that the perfused aromatic primary alcohols.
    [Show full text]
  • RIFM Fragrance Ingredient Safety Assessment, Α-Amylcinnamyl Alcohol, CAS T Registry Number 101-85-9 A.M
    Food and Chemical Toxicology 134 (2019) 110712 Contents lists available at ScienceDirect Food and Chemical Toxicology journal homepage: www.elsevier.com/locate/foodchemtox Short review RIFM fragrance ingredient safety assessment, α-amylcinnamyl alcohol, CAS T Registry Number 101-85-9 A.M. Apia, D. Belsitob, S. Bisertaa, D. Botelhoa, M. Bruzec, G.A. Burton Jr.d, J. Buschmanne, M.A. Cancellieria, M.L. Daglif, M. Datea, W. Dekantg, C. Deodhara, A.D. Fryerh, S. Gadhiaa, L. Jonesa, K. Joshia, A. Lapczynskia, M. Lavellea, D.C. Liebleri, M. Naa, D. O'Briena, A. Patela, T.M. Penningj, G. Ritaccoa, F. Rodriguez-Roperoa, J. Rominea, N. Sadekara, D. Salvitoa, ∗ T.W. Schultzk, F. Siddiqia, I.G. Sipesl, G. Sullivana, , Y. Thakkara, Y. Tokuram, S. Tsanga a Research Institute for Fragrance Materials, Inc, 50 Tice Boulevard, Woodcliff Lake, NJ, 07677, USA b Member Expert Panel, Columbia University Medical Center, Department of Dermatology, 161 Fort Washington Ave, New York, NY, 10032, USA c Member Expert Panel, Malmo University Hospital, Department of Occupational & Environmental Dermatology, Sodra Forstadsgatan 101, Entrance 47, Malmo SE, 20502, Sweden d Member Expert Panel, School of Natural Resources & Environment, University of Michigan, Dana Building G110, 440 Church St, Ann Arbor, MI, 58109, USA e Member Expert Panel, Fraunhofer Institute for Toxicology and Experimental Medicine, Nikolai-Fuchs-Strasse 1, 30625, Hannover, Germany f Member Expert Panel, University of Sao Paulo, School of Veterinary Medicine and Animal Science, Department of Pathology, Av. Prof. dr. Orlando Marques de Paiva, 87, Sao Paulo, CEP 05508-900, Brazil g Member Expert Panel, University of Wuerzburg, Department of Toxicology, Versbacher Str.
    [Show full text]
  • Safety Data Sheets
    SAFETY DATA SHEETS According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition Version: 1.0 Creation Date: Feb. 6, 2018 Revision Date: Feb. 6, 2018 1. Identification 1.1 GHS Product identifier Product name Cinnamyl alcohol 1.2 Other means of identification Product number A506174 Other names 3-Phenyl 1.3 Recommended use of the chemical and restrictions on use Identified uses Used for research and development only.Food additives -> Flavoring Agents Uses advised against no data available 1.4 Supplier's details Company Sangon Biotech (Shanghai) Co., Ltd. Address 698 Xiangmin Road, Songjiang, Shanghai 201611, China Telephone +86-400-821-0268 / +86-800-820-1016 Fax +86-400-821-0268 to 9 1.5 Emergency phone number Emergency phone +86-21-57072055 number Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours). 2. Hazard identification 2.1 Classification of the substance or mixture Skin irritation, Category 2 Eye irritation, Category 2 2.2 GHS label elements, including precautionary statements Pictogram(s) Signal word Warning Cinnamyl alcohol Page 1 of 8 Hazard statement(s) H315 Causes skin irritation H319 Causes serious eye irritation Precautionary statement(s) Prevention P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. Response P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes.
    [Show full text]
  • Arabidopsis Thaliana Defense-Related Protein ELI3 Is an Aromatic Alcohol:NADP؉ Oxidoreductase (Benzyl Alcohol Dehydrogenase͞disease Resistance͞fungal Elicitor)
    Proc. Natl. Acad. Sci. USA Vol. 93, pp. 14199–14203, November 1996 Plant Biology Arabidopsis thaliana defense-related protein ELI3 is an aromatic alcohol:NADP1 oxidoreductase (benzyl alcohol dehydrogenaseydisease resistanceyfungal elicitor) IMRE E. SOMSSICH*, PETRA WERNERT,SIEGRID KIEDROWSKI†, AND KLAUS HAHLBROCK Max Planck Institut fu¨r Zu¨chtungsforschung, Department of Biochemistry, D-50829 Ko¨ln, Germany Contributed by Klaus Hahlbrock, September 12, 1996 ABSTRACT We expressed a cDNA encoding the Arabi- presence of the RPMI resistance gene in A. thaliana (7). The dopsis thaliana defense-related protein ELI3-2 in Escherichia RPM1 locus confers resistance to Pseudomonas syringae strains coli to determine its biochemical function. Based on a protein carrying the corresponding avirulence (avr) gene avrRpm1 (8). database search, this protein was recently predicted to be a The ELI3 cDNAs from parsley and A. thaliana share 67% mannitol dehydrogenase [Williamson, J. D., Stoop, J. M. H., nucleotide and 70% deduced amino acid sequence identity (7). Massel, M. O., Conkling, M. A. & Pharr, D. M. (1995) Proc. At the time of their isolation, no related sequences were found Natl. Acad. Sci. USA 92, 7148–7152]. Studies on the substrate in the various data bases. Meanwhile, several plant cinnamyl- specificity now revealed that ELI3-2 is an aromatic alcohol: alcohol dehydrogenases (CAD) with similarity to the deduced NADP1 oxidoreductase (benzyl alcohol dehydrogenase). The ELI3 proteins have been reported (9). Based on this similarity, enzyme showed a strong preference for various aromatic it was possible that the eli3 gene encodes a CAD. Recently, aldehydes as opposed to the corresponding alcohols. Highest however, Williamson et al.
    [Show full text]
  • Selective Oxidation of Cinnamyl Alcohol to Cinnamaldehyde Over Functionalized Multi-Walled Carbon Nanotubes Supported Silver-Cobalt Nanoparticles
    catalysts Article Selective Oxidation of Cinnamyl Alcohol to Cinnamaldehyde over Functionalized Multi-Walled Carbon Nanotubes Supported Silver-Cobalt Nanoparticles Zahoor Iqbal 1,* , Muhammad Sufaid Khan 1,*, Rozina Khattak 2, Tausif Iqbal 3, Ivar Zekker 4, Muhammad Zahoor 5 , Helal F. Hetta 6 , Gaber El-Saber Batiha 7 and Eida M. Alshammari 8 1 Department of Chemistry, University of Malakand, Chakdara 18800, Pakistan 2 Department of Chemistry, Shaheed Benazir Bhutto Women University, Peshawar 25000, Pakistan; [email protected] 3 Center for Computational Materials Science, University of Malakand, Chakdara 18800, Pakistan; [email protected] 4 Institute of Chemistry, University of Tartu, 14a Ravila St., 50411 Tartu, Estonia; [email protected] 5 Department of Biochemistry, University of Malakand, Chakdara 18800, Pakistan; [email protected] 6 Department of Internal Medicine, University of Cincinnati College of Medicine, Cincinnati, OH 45267-0595, USA; [email protected] 7 Department of Pharmacology and Therapeutics, Faculty of Veterinary Medicine, Damanhour University, Damanhour 22511, El-Beheira, Egypt; [email protected] 8 Department of Chemistry, College of Sciences, University of Ha’il, Ha’il 81451, Saudi Arabia; Citation: Iqbal, Z.; Khan, M.S.; [email protected] Khattak, R.; Iqbal, T.; Zekker, I.; * Correspondence: [email protected] (Z.I.); [email protected] (M.S.K.) Zahoor, M.; Hetta, H.F.; El-Saber Batiha, G.; Alshammari, E.M. Abstract: The selective oxidation of alcohols to aldehydes has attracted a lot of attention because of Selective Oxidation of Cinnamyl its potential use in agrochemicals, fragrances, and fine chemicals. However, due to homogenous Alcohol to Cinnamaldehyde over catalysis, low yield, low selectivity, and hazardous oxidants, traditional approaches have lost their Functionalized Multi-Walled Carbon efficiency.
    [Show full text]