関: magnesium levulinate

WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/04/29 10:39:14」(JST)

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Levulinic acid, or 4-oxopentanoic acid, is an organic compound with the formula CH₃C(O)CH₂CH₂CO₂H. It is classified as a keto acid. This white crystalline solid is soluble in water and polar organic solvents. It is derived from degradation of cellulose and is a potential precursor to biofuels.^[2]

Synthesis

Related to its original synthesis,^[3] levulinic acid is prepared by heating sucrose with concentrated acid.^[4] The process proceeds via the intermediacy of glucose, which isomerizes to fructose and then undergoes dehydration to hydroxymethylfurfural (HMF). Other sugar-derivatives can be used in this process including levulose (D-fructose), inulin and starch. HMF hydrolyzes to formic acid and levulinic acid:

HOCH₂C₄H₂OCHO + 2 H₂O → HCO₂H + CH₃C(O)CH₂CH₂CO₂H

Reactions and applications

Levulinic acid is the precursor to pharmaceuticals, plasticizers, and various other additives.^[5]

Potential biofuels can be prepared from levulinic acid including methyltetrahydrofuran, valerolactone, and ethyl levulinate. Dehydration of levulinic acid gives angelica lactone.^[6]

Other occurrence and niche uses

Levulinic acid is used in cigarettes to increase nicotine delivery in smoke and binding of nicotine to neural receptors.^[7]

Safety

Levulinic acid is relatively nontoxic, with an LD₅₀ of 1850 mg/kg.^[5]

References

^ The Merck Index, 15th Ed. (2013), p. 1018, Monograph 5526, O'Neil: The Royal Society of Chemistry. Available online at: http://www.rsc.org/Merck-Index/monograph/mono1500005526
^ Biorefineries – Industrial Processes and Products. Status Quo and Future Directions. Vol. 1, Edited by Birgit Kamm, Patrick R. Gruber, Michael Kamm. 2006, WILEY-VCH, Weinheim. ISBN 3-527-31027-4
^ A. Freiherrn, V. Grote, B. Tollens, "Untersuchungen über Kohlenhydrate. I. Ueber die bei Einwirkung von Schwefelsäure auf Zucker entstehende Säure (Levulinsäure)" Justus Liebigs Annalen der Chemie volume 175, pp. 181-204 (1875). doi: 10.1002/jlac.18751750113
^ B. F. McKenzie (1941). "Levulinic acid". Org. Synth. ; Coll. Vol. 1, p. 335
^ ^a ^b Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a18 313
^ George W. Huber, Sara Iborra, = Avelino Corma "Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering" Chemical Reviews 2006, vol. 106, 4044-4098. doi:10.1021/cr068360d
^ Doris Cullen et al., A Guide to Deciphering the Internal Codes Used by the Tobacco Industry, Report No. 03-05, Harvard School of Public Health, Division of Public Health Practice, Tobacco Research Program, August 2005, http://legacy.library.ucsf.edu/resources/harvard_monograph.pdf

This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.

UpToDate Contents

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English Journal

Highly efficient transformation of levulinic acid into pyrrolidinones by iridium catalysed transfer hydrogenation.

Wei Y, Wang C, Jiang X, Xue D, Li J, Xiao J.SourceKey Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, Department of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an, 710062, China. c.wang@snnu.edu.cn.
Chemical communications (Cambridge, England).Chem Commun (Camb).2013 May 9. [Epub ahead of print]
Levulinic acid (LA) is transformed into pyrrolidinones via iridium-catalysed reductive amination using formic acid as the hydrogen source under aqueous conditions. The catalytic system is the most active and performs under the mildest conditions ever reported for the reductive amination of LA.
PMID 23661188

Adsorption of the compounds encountered in monosaccharide dehydration in zeolite Beta.

Leon M, Swift TD, Nikolakis V, Vlachos DG.AbstractA comprehensive study of the adsorption of the compounds involved in the reaction of dehydration of fructose to 5-hydroxymethyl furfural (HMF) on the zeolite H-BEA with SiO2/Al2O3 =18 has been carried out. Furthermore, a method for the estimation of the real adsorption loading from the experimentally measured excess adsorption is developed and applied to calculate the adsorption isotherms both in the case of single-solute and multi-solute mixtures. It was found that zeolite H-BEA-18 adsorbs HMF and levulinic acid from water mixtures to greater extent than sugars and formic acid, which prefer to partition in the aqueous phase. HMF and levulinic acid adsorption isotherms could be fitted in a Redlich-Peterson isotherm model, whilst the adsorption of formic acid is better fitted using the Freundlich model and sugars via the Henry model. Adsorption loadings decreased with increasing temperature (0, 25 and 40 °C), which is characteristic of an exothermic process. From the temperature dependence of the isotherms, the limiting heat of adsorption at zero coverage was determined using van't Hoff equation. Given the importance and the complexity of multicomponent systems, several experiments of adsorption of multi-solute solutions have been carried out. In most of the cases, the Ideal Adsorbed Solution Theory (IAST) has been proven to satisfactorily predict adsorption from multisolute mixtures using as input the single-solute isotherms.
Langmuir : the ACS journal of surfaces and colloids.Langmuir.2013 May 3. [Epub ahead of print]
A comprehensive study of the adsorption of the compounds involved in the reaction of dehydration of fructose to 5-hydroxymethyl furfural (HMF) on the zeolite H-BEA with SiO2/Al2O3 =18 has been carried out. Furthermore, a method for the estimation of the real adsorption loading from the experimentall
PMID 23642168

A chemo-enzymatic route to synthesize (S)-γ-valerolactone from levulinic acid.

Götz K, Liese A, Ansorge-Schumacher M, Hilterhaus L.SourceInstitute of Technical Biocatalysis, Hamburg University of Technology, Denickestraße 15, 21073, Hamburg, Germany.
Applied microbiology and biotechnology.Appl Microbiol Biotechnol.2013 May;97(9):3865-73. doi: 10.1007/s00253-012-4652-5. Epub 2013 Jan 8.
Levulinic acid is a feasible platform chemical derived from acid-catalyzed hydrolysis of lignocellulose. The conversion of this substrate to (S)-γ-valerolactone ((S)-GVL) was investigated in a chemo-enzymatic reaction sequence that benefits from mild reaction conditions and excellent enantiomeric e
PMID 23296499

Japanese Journal

Straightforward Synthesis of Levulinic Acid Ester from Lignocellulosic Biomass Resources

Nemoto Koji,Tominaga Ken-ichi,Sato Kazuhiko
Chemistry Letters 43(8), 1327-1329, 2014
… Use of a combination of Brønsted acid and Lewis acid directly afforded methyl levulinate in good yield from various raw lignocellulosic biomass resources. …
NAID 130004427158

Isolation of an X-factor-dependent but porphyrin-positive Escherichia coli from urine of a patient with hemorrhagic cystitis

Matsumoto Takehisa,Kawakami Yoshiyuki,Sueki Akane,Kasuga Eriko,Oana Kozue,Horiuchi Kazuki,Kato Miyuki,Honda Takayuki
JOURNAL OF INFECTION AND CHEMOTHERAPY 19(4), 764-766, 2013-08
… This finding suggested that some pyrrol-ring-containing porphyrin compounds or fluorescent porphyrins had been produced as chemical intermediates in the synthetic pathway from delta-amino-levulinic acid (ALA), although the isolate should be devoid of synthesizing hems from ALA. …
NAID 120005366104

5-アミノレブリン酸による塩害の改善(談話室)

田中徹,渡辺圭太郎
植物の生長調節 48(1), 102-104, 2013-05-31
NAID 110009615975

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リンク元	「レブリン酸」「magnesium levulinate」

「レブリン酸」

Levulinic acid^[1]
Names
	IUPAC name 4-Oxopentanoic acid
	Other names Levulinic acid, Laevulinic acid, β-Acetylpropionic acid, 3-Acetopropionic acid, β-acetylpropionic acid, γ-ketovaleric acid, 4-oxopentanoic acid
Identifiers
CAS Registry Number	123-76-2
ChEBI	CHEBI:45630
ChEMBL	ChEMBL1235931
ChemSpider	11091
DrugBank	DB02239
	InChI InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8) ; Key: JOOXCMJARBKPKM-UHFFFAOYSA-N ; InChI=1/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8); Key: JOOXCMJARBKPKM-UHFFFAOYAR ;
Jmol-3D images	Image
PubChem	11579
	SMILES CC(=O)CCC(=O)O ;
UNII	RYX5QG61EI
Properties
Chemical formula	C5H8O3
Molar mass	116.11 g/mol
Density	1.1447 g/cm3
Melting point	33 to 35 °C (91 to 95 °F; 306 to 308 K)
Boiling point	245 to 246 °C (473 to 475 °F; 518 to 519 K)
	Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references