- CYP505E3: A Novel Self-Sufficient ω-7 In-Chain Hydroxylase
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The self-sufficient cytochrome P450 monooxygenase CYP505E3 from Aspergillus terreus catalyzes the regioselective in-chain hydroxylation of alkanes, fatty alcohols, and fatty acids at the ω-7 position. It is the first reported P450 to give regioselective in-chain ω-7 hydroxylation of C10–C16 n-alkanes, thereby enabling the one step biocatalytic synthesis of rare alcohols such as 5-dodecanol and 7-tetradecanol. It shows more than 70 percent regioselectivity for the eighth carbon from one methyl terminus, and displays remarkably high activity towards decane (TTN≈8000) and dodecane (TTN≈2000). CYP505E3 can be used to synthesize the high-value flavour compound δ-dodecalactone via two routes: 1) conversion of dodecanoic acid into 5-hydroxydodecanoic acid (24 percent regioselectivity), which at low pH lactonises to δ-dodecalactone, and 2) conversion of 1-dodecanol into 1,5-dodecanediol (55 percent regioselectivity), which can be converted into δ-dodecalactone by horse liver alcohol dehydrogenase.
- Maseme, Mpeyake Jacob,Opperman, Diederik Johannes,Pennec, Alizé,Smit, Martha Sophia,van Marwijk, Jacqueline
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supporting information
p. 10359 - 10362
(2020/04/23)
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- Photocatalytic atom transfer radical addition to olefins utilizing novel photocatalysts
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Photocatalysis is a rapidly evolving area of research in modern organic synthesis. Among the traditional photocatalysts, metal-complexes based on ruthenium or iridium are the most common. Herein, we present the synthesis of two photoactive, ruthenium-based complexes bearing pyridine-quinoline or terpyridine ligands with extended aromatic conjugation. Our complexes were utilized in the atom transfer radical addition (ATRA) of haloalkanes to olefins, using bromoacetonitrile or bromotrichloromethane as the source of the alkyl group. The tailor-made ruthenium-based catalyst bearing the pyridine-quinoline bidentate ligand proved to be the best-performing photocatalyst, among a range of metal complexes and organocatalysts, efficiently catalyzing both reactions. These photocatalytic atom transfer protocols can be expanded into a broad scope of olefins. In both protocols, the photocatalytic reactions led to products in good to excellent isolated yields.
- Voutyritsa, Errika,Triandafillidi, Ierasia,Tzouras, Nikolaos V.,Nikitas, Nikolaos F.,Pefkianakis, Eleftherios K.,Vougioukalakis, Georgios C.,Kokotos, Christoforos G.
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supporting information
(2019/05/24)
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- Photocatalytic Synthesis of γ-Lactones from Alkenes: High-Resolution Mass Spectrometry as a Tool to Study Photoredox Reactions
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A mild photocatalytic manifold for the synthesis of γ-lactones has been developed. Utilizing Ru(bpy)3Cl2 as the photocatalyst, a cheap and reproducible synthetic protocol for γ-lactones has been introduced. Mechanistic studies revealed the successful monitoring of photocatalytic reactions and radical intermediates via high-resolution mass spectrometry.
- Triandafillidi, Ierasia,Kokotou, Maroula G.,Kokotos, Christoforos G.
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supporting information
p. 36 - 39
(2018/01/17)
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- W(OTf)6-Catalyzed Synthesis of Γ-Lactones by Ring Contraction of Macrolides or Ring Closing of Terminal Hydroxyfatty Acids in Ionic Liquid
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γ-Lactones are an important class of fine chemical products and are widely used in perfumes, medicines, pesticides, dyes, and other fields. Herein, a new method for γ-lactones preparation based on ring contraction was developed. Starting from macrolides, W(OTf)6 was used to catalyze the ring-opening polymerization then depolymerization. The depolymerization step was not a common ring-closing process, and the carbon number of the ring was reduced one by one by rearrangement to form the most thermodynamically stable five-membered ring compounds. γ-Caprolactone (180 °C for 10 h) was obtained in a yield of 94 % when [EMIM]OTf was used as the solvent, and the yield of isolated product was up to 85 %. The interaction of various components and the reaction mechanism were studied by FTIR spectroscopy and 1H NMR spectroscopy, respectively. Furthermore, γ-lactones could be produced when the substrate was extended to terminal hydroxyfatty acids. Unexpectedly, the catalyst was poisoned by 1 equivalent of H2O added during the process and thus the yield decreased greatly. The reaction is green and simple, and proceeds in one pot with high atom economy (100 % for macrolides and with water as the only byproduct for terminal hydroxyfatty acid), which provides a promising approach to synthesizing γ-lactones.
- Xie, Zhong-Yu,Deng, Jin,Fu, Yao
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p. 2332 - 2339
(2018/07/31)
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- MnO2-promoted carboesterification of alkenes with anhydrides: A facile approach to γ-lactones
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An efficient carboesterification of alkenes with anhydrides promoted by MnO2 has been developed to afford functionalized γ-lactones in good to excellent yields. This method shows a broad substrate scope and provides a valuable and convenient synthetic tool for constructing γ-lactones.
- Wu, Lihuan,Zhang, Zhenming,Liao, Jianhua,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 2628 - 2631
(2016/02/18)
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- 1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents
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The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.
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- Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents
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The present invention primarily relates to imidazo[1,2-a]pyridine-ylmethyl-derivatives of Formula (I) wherein R1, R2, X, W e J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.
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- Biotransformation of linoleic acid into hydroxy fatty acids and carboxylic acids using a linoleate double bond hydratase as key enzyme
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Hydroxy fatty acids are used as starting materials for the production of secondary metabolites and signalling molecules as well as in the manufacture of industrial fine chemicals. However, these compounds are usually difficult to produce from renewable biomass by chemical means. In this study, linoleate double bond hydratases of Lactobacillus acidophilus NBRC 13951 were cloned for the first time. These enzymes were highly specific for the hydration of the C-9 or the C-12 double bond of unsaturated fatty acids (e.g., linoleic acid). Thereby, the enzymes allowed the selective production of hydroxy fatty acids such as 13-hydroxy- cis -9-octadecenoic acid and 10-hydroxy- cis -12-octadecenoic acid from linoleic acid. In addition, the hydroxy fatty acids were further converted into industrially relevant carboxylic acids (e.g., 12-hydroxy-cis-9-dodecenoic acid, a, w-tridec-9-enedioic acid) and lactones (i.e., d-decalactone, g-dodecelactone) via whole-cell biocatalysis using an enzyme cascade. This study thus contributes to the preparation of hydroxy fatty acids, unsaturated carboxylic acids, and lactones from renewable unsaturated fatty acids.
- Oh, Hye-Jin,Kim, Sae-Um,Song, Ji-Won,Lee, Jung-Hoo,Kang, Woo-Ri,Jo, Ye-Seul,Kim, Kyoung-Rok,Bornscheuer, Uwe T.,Oh, Deok-Kun,Park, Jin-Byung
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p. 408 - 416
(2015/03/05)
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- The absolute configuration of (+)- And (-)-1-phenylundec-4-yn-3-ols. Synthesis of (R)-4-dodecanolide, a component of the defensive secretion of rove beetle Bledius mandibullaris
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Hydrogenation of the triple bond of (+)-1-phenylundec-4-yn-3-ol (obtained from (+)[η6 (3-hydroxyundec-4-yn-1-yl)benzene]chromium tricarbonyl) with the NaBH4-NiCl2?6H2O reagent system in MeOH leads to (-)1-phenylundecan-3-ol. Ozonolysis of the phenyl ring in the corresponding acetate gives (R)-(-)acetoxydodecanoic acid, lactonization of which leads to the known (R)-(+)-4dodecanolide. The starting (+)-1phenylundec-4-yn-3-ol was thus shown to have the Sconfiguration.
- Vlasyuk,Voblikova,Gamalevich,Serebryakov
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p. 2032 - 2036
(2014/07/07)
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- A novel synthesis of γ,δ-unsaturated aldehydes from α-formyl-γ-lactones
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A preparatively useful one-step transformation of γ,γ- disubstituted α-formyl-γ-lactones into trisubstituted γ,δ-unsaturated aldehydes is described, by means of catalytic amounts of either AcOH or AcOEt in the vapor phase over a glass support. A mechanistic rationale is proposed. Copyright
- Snowden, Roger L.,Brauchli, Robert,Linder, Simon
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experimental part
p. 1216 - 1225
(2011/09/16)
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- INFANT FORMULA CONTAINING AN AROMA COMPOSITION FOR USE AS FRAGRANCE
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The invention relates to a nutraceutical composition such as infant formula or infant food comprising a) a defined aroma composition; b) a methodology for developing, maintaining certain aroma constituents in the infant formula and an aroma or fragrance composition to be used to increase the acceptance of a person or an object by the baby or new born.
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- Silver triflate-catalysed synthesis of γ-lactones from fatty acids
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A silver(i)-based catalytic system was found to efficiently promote the double-bond isomerization of unsaturated fatty acids and at the same time to mediate the intramolecular addition of the carboxylate group to the isomerized double bond under selective formation of five-ring lactones. The resulting one-step isomerization-γ-lactonization process allows the direct conversion of unsaturated fatty acids into the corresponding γ-lactones in good yields.
- Goossen, Lukas J.,Ohlmann, Dominik M.,Dierker, Markus
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supporting information; experimental part
p. 197 - 200
(2011/02/27)
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- Synthesis of (±)-4-alkanolides from pent-4-enoic acid
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Synthesis of (±)-4-hexanolide, (±)-4-nonanolide, and (±)-4-dodecanolide, racemic forms of the insect signal substances, has been accomplished by cationic cyclization of pent-4-enoic acid and its amide in the key step.
- Ugurchieva,Lozanova,Zlokazov,Veselovsky
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experimental part
p. 657 - 659
(2009/05/16)
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- Synthesis of deuterated γ-lactones for use in stable isotope dilution assays
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Two syntheses of deuterated γ-lactones for use as internal standards in stable isotope dilution assays (SIDA) were developed. [2,2,3,3- 2H4]-γ-Octa-, -γ-deca-, and -γ-dodecalactones with >89% deuterium incorporation were prepared in 27, 17, and 19% overall yields, respectively, by the reduction of a doubly protected hydroxypropiolic acid with deuterium gas. [3,3,4-2H 3]-γ-Octa- and -γ-dodecalactones were prepared in 6 and 23% yields with >92% deuterium incorporation by the free radical addition of 2-iodoacetamide to [1,1,2-2H3]-1-hexene and [1,1,2- 2H3]-1-decene, respectively. Reaction yields were highly dependent upon the purity of the 1-alkene starting material. The deuterated γ-lactones were evaluated as internal standards for SIDA.
- Hislop, J.O.-Anna,Hunt, Martin B.,Fielder, Simon,Rowan, Daryl D.
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p. 7075 - 7083
(2007/10/03)
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- Compounds having protected hydroxy groups
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The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.
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- Compounds having protected hydroxy groups
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The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.
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- Homoaldol and aldol reactions from common enolates and oxirance: Reaction of reductively generated chromium enolates through cationic rearrangement
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Enolates generated from α-bromo esters by the reduction with Bu6CrLi3 react with oxiranes to afford γ-hydroxy esters and β-hydroxy esters, depending on the Lewis acid used as a promoter.
- Hojo, Makoto,Sakata, Kyosuke,Maimaiti, Xiamuxikamaer,Ueno, Junya,Nishikori, Hisashi,Hosomi, Akira
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p. 142 - 143
(2007/10/03)
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- A direct method for the conversion of terminal epoxides into γ-butanolides
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A new and efficient process for the conversion of terminal epoxides to γ-butanolides is described involving Lewis acid promoted epoxide ring-opening by 1-morpholino-2-trimethylsilyl acetylene. Addition of a terminal epoxide to a solution of the ynamine an
- Movassaghi, Mohammad,Jacobsen, Eric N.
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p. 2456 - 2457
(2007/10/03)
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- Precursor compounds
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The compounds of the formula I are precursors for organoleptic and antimicrobial compounds. The latter are generated in the presence of skin bacteria, enzymes or acidic or alkaline conditions. One precursor molecule can provide one or more different compounds.
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- Beta-ketoester compounds
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The beta-ketoesters of formula I are useful as precursors for organoleptic compounds, especially for flavors, fragrances and masking agents and antimicrobial compounds.
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- Ruthenium-catalyzed cycloisomerization - Oxidation of homopropargyl alcohols. A new access to γ-butyrolactones
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Vinylidenemetal species, which readily form from terminal alkynes under mild conditions, have rarely been utilized as reactive intermediates in a catalytic cycle. The conversion of homopropargyl alcohols via such intermediates to metal-complexed oxacarbenes led to the development of an oxidant compatible with a ruthenium complex capable of performing the cycloisomerization, that would convert them to lactones. None of the oxidants known to stoichiometrically convert isolated metallooxacarbenes to esters are effective. The unconventional oxidants , N-hydroxyimides, proved to be capable of effecting the desired transformation, with N-hydroxysuccinimide being the oxidant of choice. The procedure of choice employs cyclopentadienyl (1,4-cyclooctadiene) ruthenium chloride and trifuryl phosphine as the precatalyst in the presence of tetra-n-butylammonium bromide or hexafluorophosphate with N-hydroxysuccinimide as the oxidant in DMF-water at 95°. In this way, a wide diversity of homopropargyl alcohols were converted to γ-butyrolactones with excellent chemoselectivity. Lactones synthesized include an intermediate toward a platelet aggregation inhibitor, a fruit flavor principle, an inhibitor of binding of phorbol esters to PKC-α, a tobacco constituent, a wood constituent (quercus lactone), an aldosterone antagonist (spironolactone) precursor, and an acetogenin known for pesticidal and antitumor activities (muricatacin).
- Trost, Barry M.,Rhee, Young H.
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p. 11680 - 11683
(2007/10/03)
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- Syntheses of rac- and optically active 2-alkyl-γ-butyrolactones and 2- alkyl-cyclobutanones
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γ-Butyrolactones have been produced in good yield from alkylidene cyclopropanes, as racemates or as an enantiomerically enriched mixture of stereoisomers (e.e.>60%) depending upon the method used. Optically active cyclobutanones which are intermediate in the process have been in some cases isolated. We show the limitations of a competitive method previously described and point out its weak step.
- Krief, Alain,Ronvaux, Alain,Tuch, Arounarith
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p. 6903 - 6908
(2007/10/03)
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- Synthesis and absolute stereochemistry of Hagen's-Gland lactones in some parasitic wasps (Hymenoptera:Braconidae)
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Efficient syntheses and enantioselective gas chromatography have confirmed the structures and established the absolute stcreochemistry of some novel bicyclic lactones (tetrahydrofurofuranones) in species of parasitic wasps (Hymenoptera:Braconidae). The co-occurring γ-lactones, octan-4-olide and dodecan-4-olide, have the (R)-configuation.
- Paddon-Jones, Gregory C.,Moore, Christopher J.,Brecknell, Douglas J.,Koenig, Wilfried A.,Kitching, William
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p. 3479 - 3482
(2007/10/03)
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- Direct Oxidation of Acetals and Aldehydes to Esters
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One step conversion of acetals and aldehydes to esters was achieved with hydrogen peroxide (35wt% solution in water) and hydrochloric acid in alcohol. This procedure was proved to be simple and effective.
- Takeda, Takanobu,Watanabe, Hidenori,Kitahara, Takeshi
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p. 1149 - 1150
(2007/10/03)
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- A convenient synthesis of pheromones (Z)-7-Nonadecen-11-one, (Z)-7-eicosen-11-one and γ-dodecanolide
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Friedel-Crafts acylation of acetylene with acid chloride (ROCl, R = C8, C9) provides a key synthon, β-chlorovinyl ketone (Ia,b) that on cyanation, ketalization followed by hydrogenation with Pd/C and DIBAL-H reduction furnishes γ-ketoaldehyde (Va,b).Wittig olefination of V(a,b) with n-heptyltriphenylphosphonium bromide, provides stereoselectively (Z)-7-nonadecen-11-one (1) and (Z)-7-eicosen-11-one (2), respectively.The β-ketovinyl cyanide IIa on hydrogenation and reduction with baker's yeast gives (S)-(-)-4-hydroxydodecanonitrile (VII), which on alkaline hydrolysisand subsequent acidification with HCl furnishes (R)-(+)-γ-n-dodecanolactone (3).
- Bhalerao, U T,Devalla, Sridhar,Rao, Vittal
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p. 266 - 268
(2007/10/02)
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- A NEW ROUTE TO γ-SUBSTITUTED γ-LACTONES AND δ-SUBSTITUTED δ-LACTONES BASED ON THE REGIOSELECTIVE β-SCISSION OF ALKOXY RADICALS GENERATED FROM TRANSANNULAR HEMIACETALS
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A new general synthesis of γ-substituted γ-lactones and δ-substituted δ-lactones including dihydro-5-octyl-2(3H)-furanone, a natural pheromone, is described.The synthesis involves the regioselective β-scission of alkoxy radicals generated from transannular hemiacetals as the key step. Key Words: γ-Lactones; δ-Lactones; Mercury(II) Oxide-Iodine Reagent; Photolysis; β-Scission of Alkoxyl Radicals
- Kobayashi, Kazuhiro,Sasaki, Akiyoshi,Kanno, Yoshikazu,Suginome, Hiroshi
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p. 7245 - 7258
(2007/10/02)
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- COBALT-MEDIATED ALKYLATION OF SILOXY FURANS
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Dicobalt hexacarbonyl complexes of propargylium and α-vinylpropargylium cations couple efficiently with 2-trimethylsiloxyfuran (5), 4-trimethylsilyloxy-2-benzyloxymethylfuran (15) and 2-trimethylsilyl-3-trimethylsilyloxy-4-ethylbenzofuran (20) to produce the corresponding complexed furan derivatives in good yields.A convenient procedure for introducing the 2,4-enyne moiety regio- and stereoselectively into the above heterocycles using this methodology is described.
- Stuart, John G.,Nicholas, Kenneth M.
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p. 949 - 963
(2007/10/02)
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- N-Benzyl-3-(tri-n-butylstannyl)thiopropionamide as Thiohomoenolatesynthon. Application to a Synthesis of Some Heterocycles
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N-Benzyl-3-(tri-n-butylstannyl)thiopropionamide undergoes metalexchange with n-butyllithium.The resulting thiohomoenolate dianion reacts with elestrophiles (aldehydes and ketones) to give the γ-hydroxythioamides, which are transformed into lactones, iminothiolactones, and thiolactams with simple elaboration.
- Takahata, Hiroki,Ohkura, Etsuko,Ikuro, Kazumi,Yamazaki, Takao
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p. 285 - 292
(2007/10/02)
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- SYNTHETIC INVESTIGATIONS IN THE REGION OF INSECT ATTRACTANTS (SEX ATTRACTANTS). IX. SYNTHESIS OF cis-7-NONADECEN-11-ONE AND cis-7-EICOSEN-11-ONE - COMPONENTS OF THE SEX PHEROMONE OF THE PEACH FRUIT MOTH Carposina niponensis W.
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The synthesis of cis-7-nonadecen-11-one and cis-7-eicosen-11-one, components of the sex pheromone of the peach fruit moth Carposina niponensis W., from furfural is described.
- Sorochinskaya, A. M.,Kovalev, B. G.,Avdeeva, L. A.
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p. 277 - 283
(2007/10/02)
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- Free Radical Addition of 2-Bromoalkanoic Acids to Alkenes
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The benzoyl peroxide-catalyzed reaction of 2-bromoalkanoic acids such as bromoacetic, 2-bromopropionic, and 2-bromobutyric acid with 1-alkenes was found to proceed thorough the addition of the C-Br bond across the double bond followed by cyclization affording 4-alkanolides in good yields.
- Nakano, Taichi,Kayama, Mikio,Nagai, Yoichiro
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p. 1049 - 1052
(2007/10/02)
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- Manganese(III)-Mediated γ-Lactone Annulation
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The annulation of a γ-lactone ring onto an alkene by manganese(III) acetate oxidation of acetic acid was investigated.The regioselectivity of addition to unsymmetrically substituted alkenes is reported along with the stereoselectivity of addition to various acyclic and cyclic alkenes.Alkenes with ionization potentials above 8.2 eV were found to react in good yield.The role of acetic anhydride in these reactions was studied, and it was shown to be oxidized faster than acetic acid and also led to different products.The fate of oxidized acetic acid or anhydridein the absence of suitable acceptor molecule has also been quantitatively identified.The relationship of enolizability, or C-H acidity, of the carboxylic acid being oxidized was established quantitatively.
- Fristad, William E.,Peterson, John R.
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- STANNYL ESTER CYCLIZATIONS
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Alpha halo stannyl esters react with alkenes to afford lactones.The reaction is catalyzed by AIBN.The reaction proceeds best with electron rich alkenes.The mechanistic aspects of this novel reaction are discussed.This reaction can also be conducted intramolecularly to produce bicyclic lactones.An approach to the lignan system is presented.
- Kraus, George A.,Landgrebe, Kevin
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p. 4039 - 4046
(2007/10/02)
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- THE TRANSFORMATION OF ALKENES INTO γ-LACTONES USING α-IODOESTERS
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Iodostannyl esters react with alkenes in the presence of AIBN to afford γ-lactones.
- Kraus, George A.,Landgrebe, Kevin
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p. 3939 - 3942
(2007/10/02)
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- Methyl 5-(Triphenylphosphoranylidene)levulinate: A Reagent for Homologation of Aldehydes to δ-Ene γ-Keto Esters
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Methyl 5-(triphenylphosphoranylidene)levulinate has been synthesized and shown to condense with aldehydes to afford E δ-ene γ-keto esters in good yield.
- Ronald, Robert C.,Wheeler, Carl J.
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p. 138 - 139
(2007/10/02)
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- Synthesis of Racemates and (+)-Enantiomers of γ-Caprolactone, γ-Dodecanolactone and δ-Hexadecanolactone, Lactonic Sex Pheromones of the Dermestid Beetle, Rove Beetle and Oriental Hornet
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A simple method based on regioselective two-step alkylation of easily-available diethyl 3-oxoglutarate (2) is described for the synthesis of racemates of the lactonic pheromones, 1a, 1b, and 1c.Their (+)-enantiomers were also synthesized by means of microbiological reduction of the intermediary keto acids.
- Naoshima, Yoshinobu,Ozawa, Hiroshi,Kondo, Hirokiyo,Hayashi, Shuichi
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p. 1431 - 1434
(2007/10/02)
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- FREE RADICAL ADDITION OF α-BROMOCARBOXYLIC ACIDS TO OLEFINS LEADING TO γ-BUTYROLACTONES
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Benzoyl peroxide-catalyzed free radical addition of bromoacetic, α-bromopropionic, and α-bromobutyric acids to olefins took place under mild conditions to afford γ-alkyl-, γ-alkyl-α-methyl-, and γ-alkyl-α-ethyl-γ-butyrolactones in good yields.
- Nakano, Taichi,Kayama, Mikio,Matsumoto, Hideyuki,Nagai, Yoichiro
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p. 415 - 418
(2007/10/02)
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- Biodegradable hard water detergents
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A novel class of biodegradable detergents having improved resistance to precipitation in hard water are the water-soluble ionic salts or nonionic esters or amides of alkanoic acids which are substituted by at least one group containing an electronegative
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