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

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/07/24 16:12:05」(JST)

wiki en

[Wiki en表示]

Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C₂ carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially.

Structure and nomenclature[edit]

Glyoxylic acid is usually described with the chemical formula OCHCO₂H, i.e. containing an aldehyde functional group (see image in upper right). In fact the aldehyde is not observed in solution or as a solid. In general aldehydes with electron-withdrawing substituents often exist mainly as their hydrate. Thus, the formula for glyoxylic acid is really (HO)₂CHCO₂H, described as the "monohydrate." This diol exists in equilibrium with the dimeric hemiacetal in solution:^[4] Henry's law constant of glyoxylic acid is K_H = 1.09 × 10⁴ × exp[(40.0 × 10³/R) × (1/T − 1/298)].^[5]

2 (HO)₂CHCO₂H O[(HO)CHCO₂H]₂ + H₂O

Preparation[edit]

The compound is formed by organic oxidation of glyoxal with hot nitric acid, the main side product being oxalic acid. Ozonolysis of maleic acid is also effective.^[4]

The conjugate base of gloxylic acid is known as glyoxylate and is the form that the compound exists in solution at neutral pH. Glyoxylate is an intermediate of the glyoxylate cycle, which enables organisms, such as bacteria,^[6] fungi, and plants ^[7] to convert fatty acids into carbohydrates. Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides.

Reactions and uses[edit]

Glyoxylic acid is about 10x stronger acid than acetic acid, with an acid dissociation constant of 4.7 × 10⁻⁴ (pK_a = 3.32):

(HO)₂CHCOOH (HO)₂CHCO₂⁻ + H⁺

With base, glyoxylic acid disproportionates:

2 OCHCOOH + H₂O → HOCHCOOH + HOOC–COOH

Even though the aldehyde is a very minor component of its solutions, glyoxylic acid behaves as an aldehyde in its reactions. For example, it gives heterocycles upon condensation with urea and 1,2-diaminobenzene.

Phenol derivatives[edit]

Its condensation with phenols is versatile. The immediate product is 4-hydroxymandelic acid. This species reacts with ammonia to give hydroxyphenylglycine, a precursor to the drug amoxicillin. Reduction of the 4-hydroxymandelic acid gives 4-hydroxyphenylacetic acid, a precursor to the drug atenolol. Condensations with guaiacol in place of phenol provides a route to vanillin, a net formylation.^[4]

Safety[edit]

The compound is not very toxic with an LD₅₀ for rats of 2500 mg/kg.

References[edit]

^ Merck Index, 11th Edition, 4394
^ Dissociation Constants Of Organic Acids and Bases (600 compounds), http://zirchrom.com/organic.htm.
^ pKa Data Compiled by R. Williams, http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf.
^ ^a ^b ^c Georges Mattioda and Yani Christidis “Glyoxylic Acid” Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a12_495
^ Ip, H. S. Simon; Huang, X. H. Hilda, Yu, Jian Zhen. "Effective Henry's law constants of glyoxal, glyoxylic acid, and glycolic acid". Geophysical Research Letters 36 (1). doi:10.1029/2008GL036212.
^ Holms WH (1987). "Control of flux through the citric acid cycle and the glyoxylate bypass in Escherichia coli". Biochem Soc Symp. 54: 17–31. PMID 3332993.
^ Escher CL, Widmer F (1997). "Lipid mobilization and gluconeogenesis in plants: do glyoxylate cycle enzyme activities constitute a real cycle? A hypothesis". Biol Chem. 378 (8): 803–813. PMID 9377475.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 尿酸のバランス uric acid balance
2. 胎児の酸塩基の生理学 fetal acid base physiology
3. 妊娠中の葉酸補充 folic acid supplementation in pregnancy
4. ポルフィリン症：概要 porphyrias an overview
5. 疾患予防におけるビタミン補給 vitamin supplementation in disease prevention

English Journal

A kinetic study of the enhancement of solution chemiluminescence of glyoxylic acid oxidation by manganese species.

Otamonga JP1, Abdel-Mageed A1, Agater IB1, Jewsbury RA1.
Luminescence : the journal of biological and chemical luminescence.Luminescence.2015 Aug;30(5):507-11. doi: 10.1002/bio.2768. Epub 2014 Sep 16.
In order to study the mechanism of the enhancement of solution chemiluminescence, the kinetics of the decay of the oxidant and the chemiluminescence emission were followed for oxidations by permanganate, manganese dioxide sol and Mn(3+) (aq) of glyoxylic acid, using stopped-flow spectrophotometry. R
PMID 25223402

Functional differences between the arteries perfusing gas exchange and nutritional membranes in the late chicken embryo.

Mohammed R1, Cavallaro G, Kessels CG, Villamor E.
Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology.J Comp Physiol B.2015 Jun 29. [Epub ahead of print]
The chicken extraembryonic arterial system comprises the allantoic arteries, which irrigate the gas exchange organ (the chorioallantoic membrane, CAM) and the yolk sac (YS) artery, which irrigates the nutritional organ (the YS membrane). We compared, using wire myography, the reactivity of allantoic
PMID 26119481

One-pot laser-assisted synthesis of porous carbon with embedded magnetic cobalt nanoparticles.

Ghimbeu CM1, Sopronyi M, Sima F, Delmotte L, Vaulot C, Zlotea C, Paul-Boncour V, Le Meins JM.
Nanoscale.Nanoscale.2015 Jun 14;7(22):10111-22. doi: 10.1039/c5nr01687h. Epub 2015 May 18.
A novel one-pot laser-assisted approach is reported herein for the synthesis of ordered carbons with embedded cobalt nanoparticles. The process is based on a UV pulsed laser exposure of an ethanolic solution consisting of green carbon precursors, a structure directing agent and a cobalt salt. Very s
PMID 25981107

Japanese Journal

Determination of glyoxylic acid in urine by liquid chromatography with fluorescence detection, using a novel derivatization procedure based on the Petasis reaction

Chihara Kohki,Kishikawa Naoya,Ohyama Kaname,Nakashima Kenichiro,Kuroda Naotaka
Analytical and Bioanalytical Chemistry 403(9), 2765-2770, 2012-07-00
… The Petasis reaction is the multi-component reaction of a carbonyl compound, amine, and arylboronic acid to form an α-amino acid or a β-aminoalcohol. … In this work, as the first analytical application of the Petasis reaction, a highperformance liquid chromatographic (HPLC) method with fluorescence detection was developed for determination of glyoxylic acid. …
NAID 80022610844

Cloning and sequencing of a gene encoding of aldehyde oxidase in Pseudomonas sp. AIU 362(ENZYMOLOGY, PROTEIN ENGINEERING, AND ENZYME TECHNOLOGY)

Sasaki Yasutaka,Urano Nobuyuki,Kataoka Michihiko [他],Ogawa Jun,Iwasaki Akira,Hasegawa Junzo,Isobe Kimiyasu,Shimizu Sakayu
Journal of bioscience and bioengineering 114(1), 28-32, 2012-07-00
… We have cloned a gene encoding an aldehyde oxidase (ALOD) oxidized glyoxal but not glyoxylic acid from Pseudomonas sp. … The ALOD gene contained an open reading frame consisting of 888 nucleotides corresponding to 295 amino acid residues. … The deduced amino acid sequence exhibited a high similarity to those of 3-hydroxyisobutyrate dehydrogenases (3-HIBDHs). …
NAID 110009479360

Stable carbon isotopic compositions of total carbon, dicarboxylic acids and glyoxylic acid in the tropical Indian aerosols : Implications for sources and photochemical processing of organic aerosols

Pavuluri Chandra Mouli,Kawamura Kimitaka,Swaminathan T.,Tachibana Eri
Journal of Geophysical Research, Atmospheres 116, D18307, 2011-09-29
… 80.17°E) were studied for stable carbon isotopic compositions (δ13C) of total carbon (TC), individual dicarboxylic acids (C2-C9) and glyoxylic acid (ωC2). … Oxalic (C2) (-17.1 ± 2.5‰), malonic (C3) (-20.8 ± 1.8‰), succinic (C4) (-22.5 ± 1.5‰) and adipic (C6) (-20.6 ± 4.1‰) acids and ωC2 acid (-22.4 ± 5.5‰) were found to be more enriched with 13C compared to TC. …
NAID 120003918920

Related Pictures

★リンクテーブル★

リンク元	「グリオキシル酸」「glyoxalic acid」「glyoxylate」

「グリオキシル酸」

Glyoxylic acid
	IUPAC name oxoethanoic acid
	Other names formylformic acid; oxoethanoic acid
Identifiers
CAS number	298-12-4
PubChem	760
ChemSpider	740
DrugBank	DB04343
KEGG	C00048
ChEBI	CHEBI:16891
ChEMBL	CHEMBL1162545
Jmol-3D images	Image 1
	SMILES C(=O)C(=O)O ;
	InChI InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5) ; Key: HHLFWLYXYJOTON-UHFFFAOYSA-N InChI=1/C2H2O3/c3-1-2(4)5/h1H,(H,4,5); Key: HHLFWLYXYJOTON-UHFFFAOYAU ;
Properties
Molecular formula	C2H2O3
Molar mass	74.04 g mol−1
Density	1.384 g/mL
Melting point	80 °C
Boiling point	111 °C
Acidity (pKa)	3.18, 3.32
Related compounds
Other anions	glyoxylate
Related carboxylic acids	formic acid; acetic acid; glycolic acid; oxalic acid; propionic acid; pyruvic acid
Related compounds	acetaldehyde; glyoxal; glycolaldehyde
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references