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）』「2013/08/18 09:31:58」(JST)

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Glutaric acid is the organic compound with the formula C₃H₆(COOH)₂ . Although the related "linear" dicarboxylic acids adipic and succinic acids are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50%.

Biochemistry[edit source | edit]

Glutaric acid is naturally produced in the body during the metabolism of some amino acids, including lysine and tryptophan. Defects in this metabolic pathway can lead to a disorder called glutaric aciduria, where toxic byproducts build up and can cause severe encephalopathy.

Production[edit source | edit]

Glutaric acid can be prepared by the ring-opening of butyrolactone with potassium cyanide to give the mixed potassium carboxylate-nitrile that is hydrolyzed to the diacid.^[1] Alternatively hydrolysis, followed by oxidation of dihydropyran gives glutaric acid. It can also be prepared from reacting 1,3-dibromopropane with sodium or potassium cyanide to obtain the dinitrile, followed by hydrolysis.

Uses[edit source | edit]

1,5-Pentanediol, a common plasticizer and precursor to polyesters is manufactured by hydrogenation of glutaric acid and its derivatives.^[2]

Glutaric acid itself has been used in the production of polymers such as polyester polyols, polyamides. The odd number of carbon atoms (i.e. 5) is useful in decreasing polymer elasticity.^{[citation needed]}

References[edit source | edit]

^ G. Paris, L. Berlinguet, R. Gaudry, J. English, Jr. and J. E. Dayan (1963), "Glutaric Acid and Glutaramide", Org. Synth. ; Coll. Vol. 4: 496
^ Peter Werle and Marcus Morawietz "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry: 2002, Wiley-VCH: Weinheim. DOI 10.1002/14356007.a01_305

External links[edit source | edit]

Calculator: Water and solute activities in aqueous glutaric acid

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UpToDate Contents

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4. 乳児および小児における低血糖症の原因 causes of hypoglycemia in infants and children
5. 尿酸のバランス uric acid balance

English Journal

Co-crystallization of pyridine-2-carboxamide with a series of alkyl dicarboxylic acids with different carbon chain: Crystal structure, spectroscopy and Hirshfeld analysis.

Luo YH1, Sun BW2.Author information 1College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.2College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China. Electronic address: chmsunb@seu.edu.cn.AbstractThree new co-crystals: pyridine-2-carboxamide-succinic acid (1), pyridine-2-carboxamide-glutaric acid (2) and pyridine-2-carboxamide-adipic acid (3) have been synthesized and characterized by single-crystal X-ray diffraction, TGA/DSC measurements, solid-state vibrational spectroscopy (IR and Raman) in this work. The investigation revealed that the carbon chain length of these alkyl acids changed the connecting motif of co-crystals 1-3 from trimer to 1D chain, and the formation of hydrogen bond interaction of pyridine-2-carboxamide with these alkyl acids lead to red shift of stretching vibration of NH2 and OH groups in IR and Raman spectra. We also studied Hirshfeld surface and UV properties of co-crystals 1-3, and we found that the carbon chain length lead to decrease of close intermolecular interactions, and the formation of hydrogen bond interaction lead to red shift of UV spectra.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2014 Feb 24;120:228-36. doi: 10.1016/j.saa.2013.09.144. Epub 2013 Oct 9.
Three new co-crystals: pyridine-2-carboxamide-succinic acid (1), pyridine-2-carboxamide-glutaric acid (2) and pyridine-2-carboxamide-adipic acid (3) have been synthesized and characterized by single-crystal X-ray diffraction, TGA/DSC measurements, solid-state vibrational spectroscopy (IR and Raman)
PMID 24184625

Hygroscopic properties of internally mixed particles composed of NaCl and water soluble organic acids.

Ghorai S, Wang BB, Tivanski AV, Laskin A.AbstractAtmospheric aging of naturally emitted marine aerosol often leads to formation of internally mixed particles composed of sea salts and water soluble organic compounds of anthropogenic origin. Mixing of sea salt and organic components has profound effects on the evolving chemical composition and hygroscopic properties of the resulted particles, which are poorly understood. Here, we have studied chemical composition and hygroscopic properties of laboratory generated NaCl particles mixed with malonic acid (MA) and glutaric acid (GA) at different molar ratios using micro-FTIR spectroscopy and X-ray elemental microanalysis. Hygroscopic properties of internally mixed NaCl and organic acid particles were distinctly different from pure components and varied significantly with the type and amount of organic compound present. Experimental results were in a good agreement with the AIM modeling calculations of gas/liquid/solid partitioning in studied systems. X-ray elemental microanalysis of particles showed that Cl/Na ratio decreased with increasing organic acid component in the particles with MA yielding lower ratios relative to GA. We attribute the depletion of chloride to the formation of Na-malonate and Na-glutarate salts resulted by HCl evaporation from dehydrating particles.
Environmental science & technology.Environ Sci Technol.2014 Jan 17. [Epub ahead of print]
Atmospheric aging of naturally emitted marine aerosol often leads to formation of internally mixed particles composed of sea salts and water soluble organic compounds of anthropogenic origin. Mixing of sea salt and organic components has profound effects on the evolving chemical composition and hygr
PMID 24437520

Proofreading of noncognate acyl adenylates by an acyl-coenzyme a ligase.

Manandhar M1, Cronan JE2.Author information 1Department of Microbiology, University of Illinois at Urbana-Champaign, Urbana, IL 61801, USA.2Department of Microbiology, University of Illinois at Urbana-Champaign, Urbana, IL 61801, USA; Department of Biochemistry, University of Illinois at Urbana-Champaign, Urbana, IL 61801, USA. Electronic address: j-cronan@life.uiuc.edu.AbstractAminoacyl-tRNA synthetases remove (proofread) incorrect substrates and thereby prevent errors in protein synthesis. We report enzyme-catalyzed pretransfer editing by pimeloyl-coenzyme A (CoA) ligase (BioW), a biotin synthetic enzyme that converts pimelate, a seven-carbon dicarboxylic acid, to its CoA ester. The noncognate BioW substrate glutaric acid results in hydrolysis of ATP to AMP with formation of only trace amounts of glutaryl-CoA, thereby mimicking pretransfer editing of incorrect aminoacyl-adenylates by aminoacyl-tRNA synthetases.
Chemistry & biology.Chem Biol.2013 Dec 19;20(12):1441-6. doi: 10.1016/j.chembiol.2013.10.010. Epub 2013 Nov 21.
Aminoacyl-tRNA synthetases remove (proofread) incorrect substrates and thereby prevent errors in protein synthesis. We report enzyme-catalyzed pretransfer editing by pimeloyl-coenzyme A (CoA) ligase (BioW), a biotin synthetic enzyme that converts pimelate, a seven-carbon dicarboxylic acid, to its Co
PMID 24269150

Japanese Journal

Solubility and Solubility-Limiting Solid Phase in M(IV)-OH-Dicarboxylate Ternary Aqueous System

KOBAYASHI Taishi,SASAKI Takayuki,TAKAGI Ikuji,MORIYAMA Hirotake
Journal of nuclear science and technology 48(7), 993-1003, 2011-07-01
… In the presence of succinic, glutaric, and adipic acids, few Th colloidal species larger than 2 nm were observed, and the apparent solubility appeared to be controlled by thorium-dicarboxylate solid phases. … The Th solubility in the presence of fumaric (trans-butenedioic) acid was similar to that in the presence of succinic (butanedioic) acid, whereas no solid phase was observed under pHc 4 in the presence of maleic (cis-butenedioic) acid. …
NAID 10028154047

Anticholinesterase and Antioxidant Constituents from Gloiopeltis furcata

Fang Zhe,Jeong Su Yang,Jung Hyun Ah,Choi Jae Sue,Min Byung Sun,Woo Mi Hee
CHEMICAL & PHARMACEUTICAL BULLETIN 58(9), 1236-1239, 2010
… were elucidated as 2-(3-hydroxy-5-oxotetrahydrofuran-3-yl)acetic acid (1), glutaric acid (2), succinic acid (3), nicotinic acid (4), (E)-4-hydroxyhex-2-enoic acid (5), cholesterol (6), 7-hydroxycholesterol (7), uridine (8), glycerol (9), 5-(hydroxymethyl)-2-methoxybenzene-1,3-diol (10), (5E,7E)-9-oxodeca-5,7-dienoic acid (11), (Z)-3-ethylidene-4-methylpyrrolidine-2,5-dione (12), …
NAID 130000324602

Related Pictures

★リンクテーブル★

リンク元	「グルタル酸」「glutarate」
拡張検索	「ketoglutaric acid」「alpha-ketoglutaric acid」「β-methylglutaric aciduria」「hydroxyglutaric aciduria」「hydroxyglutaric acid」

「グルタル酸」

Glutaric acid
	IUPAC name pentanedioic acid
	Other names Propane-1,3-dicarboxylic acid; 1,3-propanedicarboxylic acid; pentanedioic acid; n-Pyrotartaric acid
Identifiers
CAS number	110-94-1
PubChem	743
ChemSpider	723
EC number	203-817-2
DrugBank	DB03553
KEGG	C00489
ChEBI	CHEBI:17859
ChEMBL	CHEMBL1162495
Jmol-3D images	Image 1
	SMILES C(CC(=O)O)CC(=O)O ;
	InChI InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9) ; Key: JFCQEDHGNNZCLN-UHFFFAOYSA-N InChI=1/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9); Key: JFCQEDHGNNZCLN-UHFFFAOYAU ;
Properties
Molecular formula	C5H8O4
Molar mass	132.12 g/mol
Melting point	95 to 98 °C
Boiling point	200 °C/20 mmHg
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: glutaric acid, glutarate
同: 1,3-プロパンジカルボン酸、n-ピロ酒石酸 n-pyrotartaric acid
関: glutaryl

name=グルタル酸
構造式=
IUPAC=1,5-ペンタン二酸
ペンタン-1,5-ジカルボン酸
別名=プロパン-1,3-ジカルボン酸
1,3-プロパンジカルボン酸
n-ピロ酒石酸
分子式=C₅H₈O₄
分子量=132.12
CAS登録番号=110-94-1
融点=95～98
沸点=200

グルタル酸(Glutaric acid)は示性式HOOC(CH₂)₃COOHで表されるカルボン酸の一つ。IUPAC命名法では1,5-ペンタン二酸(1,5-pentanedioic acid)またはペンタン-1,5-ジカルボン酸(pentane-1,5-dicarboxylic acid)である。無色からわずかに薄い黄色の結晶または結晶性粉末で、水に可溶、アルコール、エーテル (化学)に易溶。融点95～98℃、沸点302℃、分子量132.11。CAS登録番号は110-94-1。