372:
247:
746:
44:
730:
931:
829:
770:
35:
927:, removing toxic phosphoglycolate, and initiating defense mechanisms. In photorespiration, glyoxylate is converted from glycolate through the activity of glycolate oxidase in the peroxisome. It is then converted into glycine through parallel actions by SGAT and GGAT, which is then transported into the mitochondria. It has also been reported that the pyruvate dehydrogenase complex may play a role in glycolate and glyoxylate metabolism.
950:
619:
1083:(commonly known as kidney stones). Glyoxylate is both a substrate and inductor of sulfate anion transporter-1 (sat-1), a gene responsible for oxalate transportation, allowing it to increase sat-1 mRNA expression and as a result oxalate efflux from the cell. The increased oxalate release allows the buildup of calcium oxalate in the urine, and thus the eventual formation of kidney stones.
894:
881:. The glyoxylate cycle is also important for induction of plant defense mechanisms in response to fungi. The glyoxylate cycle is initiated through the activity of isocitrate lyase, which converts isocitrate into glyoxylate and succinate. Research is being done to co-opt the pathway for a variety of uses such as the biosynthesis of succinate.
934:
Basic overview of photorespiration in
Arabidopsis. GGAT, glyoxylate:glutamate aminotransferase; GLYK, glycerate kinase; GO, glycolate oxidase; HPR, hydroxypyruvate reductase; PGLP, phosphoglycolate phosphatase; Rubisco, RuBP carboxylase/oxygenase; SGAT, serine:glyoxylate aminotransferase; SHM, serine
889:
Glyoxylate is produced via two pathways: through the oxidation of glycolate in peroxisomes or through the catabolism of hydroxyproline in mitochondria. In the peroxisomes, glyoxylate is converted into glycine by AGT1 or into oxalate by glycolate oxidase. In the mitochondria, glyoxylate is converted
1067:. In a study, glyoxylate levels were found to be significantly increased in patients who were later diagnosed with Type II diabetes. The elevated levels were found sometimes up to three years before the diagnosis, demonstrating the potential role for glyoxylate to be an early predictive marker.
1753:
Dubey, Mukesh K.; Broberg, Anders; Sooriyaarachchi, Sanjeewani; Ubhayasekera, Wimal; Jensen, Dan Funck; Karlsson, Magnus (September 2013). "The glyoxylate cycle is involved in pleotropic phenotypes, antagonism and induction of plant defence responses in the fungal biocontrol agent
Trichoderma
1090:
gene leads to a loss of the 4-hydroxy-2-oxoglutarate aldolase, an enzyme in the hydroxyproline to glyoxylate pathway. The glyoxylate resulting from this pathway is normally stored away to prevent oxidation to oxalate in the cytosol. The disrupted pathway, however, causes a buildup of
1793:
Zhu, Li-Wen; Li, Xiao-Hong; Zhang, Lei; Li, Hong-Mei; Liu, Jian-Hua; Yuan, Zhan-Peng; Chen, Tao; Tang, Ya-Jie (November 2013). "Activation of glyoxylate pathway without the activation of its related gene in succinate-producing engineered
Escherichia coli".
2032:
Zhang, Zhisheng; Mao, Xingxue; Ou, Juanying; Ye, Nenghui; Zhang, Jianhua; Peng, Xinxiang (January 2015). "Distinct photorespiratory reactions are preferentially catalyzed by glutamate:glyoxylate and serine:glyoxylate aminotransferases in rice".
1091:
4-hydroxy-2-oxoglutarate which can also be transported to the cytosol and converted into glyoxylate through a different aldolase. These glyoxylate molecules can be oxidized into oxalate increasing its concentration and causing hyperoxaluria.
2076:
Blume, Christian; Behrens, Christof; Eubel, Holger; Braun, Hans-Peter; Peterhansel, Christoph (November 2013). "A possible role for the chloroplast pyruvate dehydrogenase complex in plant glycolate and glyoxylate metabolism".
897:
Oxalate and glyoxylate metabolism in hepatocytes. AGT1 and 2, alanine:glyoxylate aminotransferase 1 and 2; GO, glycolate oxidase; GR, glyoxylate reductase; HKGA, 4-hydroxy-2-ketoglutarate lyase; LDH, lactate dehydrogenase
1063:. AGEs can lead to further complications of diabetes, such as tissue damage and cardiovascular disease. They are generally formed from reactive aldehydes, such as those present on reducing sugars and
1904:
Schnedler, Nina; Burckhardt, Gerhard; Burckhardt, Birgitta C. (March 2011). "Glyoxylate is a substrate of the sulfate-oxalate exchanger, sat-1, and increases its expression in HepG2 cells".
2131:
Nikiforova, Victoria J.; Giesbertz, Pieter; Wiemer, Jan; Bethan, Bianca; Looser, Ralf; Liebenberg, Volker; Ruiz
Noppinger, Patricia; Daniel, Hannelore; Rein, Dietrich (2014).
1840:
Belostotsky, Ruth; Pitt, James
Jonathon; Frishberg, Yaacov (2012-12-01). "Primary hyperoxaluria type III—a model for studying perturbations in glyoxylate metabolism".
890:
into glycine by AGT2 or into glycolate by glyoxylate reductase. A small amount of glyoxylate is converted into oxalate by cytoplasmic lactate dehydrogenase.
1726:
Escher CL, Widmer F (1997). "Lipid mobilization and gluconeogenesis in plants: do glyoxylate cycle enzyme activities constitute a real cycle? A hypothesis".
971:
964:
632:
696:. The aldehyde is only a minor component of the form most prevalent in some situations. Instead, glyoxalic acid often exists as a hydrate or a cyclic
1947:
923:. While at first considered a waste of energy and resources, photorespiration has been shown to be an important method of regenerating carbon and CO
1975:
Peterhansel, Christoph; Horst, Ina; Niessen, Markus; Blume, Christian; Kebeish, Rashad; KĂĽrkcĂĽoglu, Sophia; Kreuzaler, Fritz (2010-03-23).
421:
846:
to glyoxylic; however this reaction is highly exothermic and prone to thermal runaway. In addition, oxalic acid is the main side product.
1086:
The disruption of glyoxylate metabolism provides an additional mechanism of hyperoxaluria development. Loss of function mutations in the
1423:
1392:
1519:
Georges
Mattioda and Yani Christidis “Glyoxylic Acid” Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim.
2399:
1683:
1362:
1014:
2369:
1307:
986:
1288:
oxidation. Several different reaction pathways can ensue, leading to various other carboxylic acid and aldehyde products.
627:
1207:
993:
1033:
386:
639:
1699:
Holms WH (1987). "Control of flux through the citric acid cycle and the glyoxylate bypass in
Escherichia coli".
1280:
Glyoxylic acid is one of several ketone- and aldehyde-containing carboxylic acids that together are abundant in
1000:
1056:
1653:
1572:
2469:
68:
982:
329:
242:
184:
132:
1951:
350:
1346:
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1104:
800:
and is the form that the compound exists in solution at neutral pH. Glyoxylate is the byproduct of the
515:
17:
1536:
Redington, Richard L.; Liang, Chin-Kang Jim (1984). "Vibrational spectra of glyoxylic acid monomers".
1281:
1265:
254:
2474:
1343:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1052:
753:
367:
960:
1222:
1673:
1457:"Kinetics and equilibria for the reversible hydration of the aldehyde group in glyoxylic acid"
2389:
1187:
721:
1399:
1007:
2428:
2086:
1623:"Elektrolytische Reduction von Carbonsäuren und Carbonsäureestern in schwefelsaurer Lösung"
1587:
1545:
1080:
709:
338:
56:
8:
1225:. This species reacts with ammonia to give hydroxyphenylglycine, a precursor to the drug
1143:
204:
108:
98:
2432:
2251:"Glyco-oxidation and cardiovascular complications in type 2 diabetes: a clinical update"
2090:
1591:
1549:
1308:
https://karger.com/cnd/article/12/2/112/827730/Acute-Kidney-Injury-following-Exposure-to
371:
246:
164:
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2191:
2167:
2132:
2009:
1976:
1883:
1603:
1297:
1195:
1147:
1139:
893:
144:
745:
2446:
2395:
2347:
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2231:
2213:
2172:
2154:
2110:
2102:
2058:
2050:
2046:
2014:
1996:
1929:
1921:
1875:
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1811:
1775:
1767:
1735:
1708:
1679:
1607:
1557:
1473:
1456:
1417:
1358:
1064:
840:
697:
2098:
1887:
1488:
Czapik, Agnieszka; Gdaniec, Maria (2007). "Quinoxaline–dihydroxyacetic acid (1/1)".
2436:
2337:
2327:
2278:
2262:
2221:
2203:
2162:
2144:
2094:
2042:
2004:
1988:
1913:
1857:
1849:
1803:
1759:
1634:
1595:
1553:
1520:
1497:
1468:
1350:
912:
908:
866:
812:
693:
659:
444:
930:
1245:
678:
555:
273:
1807:
1354:
318:
1917:
1573:"Effective Henry's law constants of glyoxal, glyoxylic acid, and glycolic acid"
793:
777:
610:
601:
577:
2266:
1853:
1763:
1638:
1501:
681:. It is a colourless solid that occurs naturally and is useful industrially.
43:
2463:
2441:
2416:
2274:
2217:
2208:
2192:"Inflammation in the pathogenesis of microvascular complications in diabetes"
2158:
2106:
2054:
2000:
1925:
1871:
1815:
1771:
1524:
1285:
1076:
1060:
757:
667:
569:
505:
495:
235:
915:
pathway. Photorespiration is a result of the side reaction of RuBisCO with O
2450:
2365:
2351:
2292:
2235:
2176:
2114:
2062:
2018:
1933:
1879:
1823:
1779:
1319:
878:
816:
729:
705:
593:
581:
2332:
2249:
Piarulli, Francesco; Sartore, Giovanni; Lapolla, Annunziata (April 2013).
2149:
1739:
1712:
828:
769:
1599:
1438:
1253:
1226:
1151:
1100:
854:
836:
820:
671:
663:
573:
565:
561:
1862:
811:
For the historical record, glyoxylic acid was prepared from oxalic acid
224:
1752:
1269:
1055:. One of the key conditions of diabetes pathology is the production of
874:
850:
736:
In aqueous solution, this monohydrate exists in equilibrium with a hemi
546:
472:
255:
195:
1992:
801:
720:
at room temperature: Dihydroxyacetic acid has been characterized by
1622:
1284:. In the presence of water and sunlight, glyoxylic acid can undergo
949:
609:
Except where otherwise noted, data are given for materials in their
1377:
Dissociation
Constants Of Organic Acids and Bases (600 compounds),
1249:
1241:
1234:
870:
761:
701:
690:
293:
215:
2305:
1378:
131:
2320:
Journal of
Research of the National Bureau of Standards Section A
1570:
1211:
843:
805:
597:
485:
305:
34:
2371:
Manufacture of vanillin and its homologues U.S. Patent 2,640,083
1214:, a versatile step in the synthesis of several other compounds.
2130:
1620:
1240:
The sequence of reactions, in which glyoxylic acid reacts with
1218:
760:
structure with the aldehyde carbonyl in close proximity to the
737:
175:
2190:
Nguyen, Dung V.; Shaw, Lynn C.; Grant, Maria B. (2012-12-21).
1903:
1087:
155:
121:
2415:
Eugene, Alexis J.; Xia, Sha-Sha; Guzman, Marcelo I. (2016).
2364:
1974:
355:
1571:
Ip, H. S. Simon; Huang, X. H. Hilda; Yu, Jian Zhen (2009).
1191:
284:
1490:
Acta Crystallographica Section E: Structure Reports Online
1051:
Glyoxylate is thought to be a potential early marker for
540:
2133:"Glyoxylate, a New Marker Metabolite of Type 2 Diabetes"
1839:
1099:
Glyoxylic acid is about ten times stronger an acid than
819:
cathodes were applied for preparing glyoxylic acid from
2248:
2075:
1661:. London: Macmillan and Co. Limited. pp. 102–104.
911:, glyoxylate is also an important intermediate in the
689:
The structure of glyoxylic acid is shown as having an
2035:
Journal of Photochemistry and Photobiology B: Biology
1454:
1306:
But a recent experiment shows that it is toxic. See
752:
In isolation, the aldehyde structure has as a major
1719:
1671:
873:, such as bacteria, fungi, and plants to convert
1455:Sørensen, P. E.; Bruhn, K.; Lindeløv, F. (1974).
1244:the phenolic component followed by oxidation and
2461:
1229:. Reduction of the 4-hydroxymandelic acid gives
317:
2414:
2189:
1675:Materials Handbook: A Concise Desktop Reference
107:
1627:Berichte der Deutschen Chemischen Gesellschaft
1535:
2306:Fatiadi, Alexander; Schaffer, Robert (1974).
1487:
1075:Glyoxylate is involved in the development of
700:. For example, in the presence of water, the
684:
2031:
1792:
1725:
907:In addition to being an intermediate in the
804:process in biosynthesis of several amidated
1336:
1334:
2417:"Aqueous Photochemistry of Glyoxylic Acid"
2387:
1621:Tafel, Julius; Friedrichs, Gustav (1904).
1275:
370:
245:
203:
2440:
2341:
2331:
2282:
2225:
2207:
2166:
2148:
2008:
1861:
1472:
1034:Learn how and when to remove this message
337:
2308:"An Improved Procedure for Synthesis of
1698:
1331:
1259:
1206:In general, glyoxylic acid undergoes an
929:
892:
1296:The compound is not very toxic with an
1186:Glyoxylic acid gives heterocycles upon
1138:With concentrated base, glyoxylic acid
366:
223:
14:
2462:
1422:: CS1 maint: archived copy as title (
970:Please improve this article by adding
708:(described as the "monohydrate"). The
510:111 °C (232 °F; 384 K)
395:InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
236:
2394:. New Age International. p. 64.
2126:
2124:
1970:
1968:
1899:
1897:
1835:
1833:
1692:
1651:
1515:
1513:
1511:
1264:Glyoxylic acid is a component of the
1201:
1094:
865:Glyoxylate is an intermediate of the
500:80 °C (176 °F; 353 K)
405:InChI=1/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
398:Key: HHLFWLYXYJOTON-UHFFFAOYSA-N
183:
163:
1431:
1268:, used to check for the presence of
943:
939:
2312:-4-Hydroxy-3-methoxymandelic Acid (
1208:electrophilic aromatic substitution
408:Key: HHLFWLYXYJOTON-UHFFFAOYAU
308:
292:
24:
2121:
1965:
1894:
1830:
1655:Practical Organic Chemistry 2nd Ed
1508:
1390:pKa Data Compiled by R. Williams,
1070:
860:
25:
2486:
1538:Journal of Molecular Spectroscopy
2316:-"Vanillyl"-mandelic Acid, VMA)"
2047:10.1016/j.jphotobiol.2014.11.009
1474:10.3891/acta.chem.scand.28a-0162
948:
827:
823:in a sulfuric acid electrolyte.
768:
744:
728:
674:, glyoxylic acid is one of the C
617:
456:
42:
33:
2408:
2381:
2358:
2299:
2242:
2183:
2099:10.1016/j.phytochem.2013.07.009
2069:
2025:
1940:
1786:
1746:
1665:
1645:
1614:
1379:http://zirchrom.com/organic.htm
1057:advanced glycation end-products
787:
780:constant of glyoxylic acid is K
613:(at 25 °C , 100 kPa).
1564:
1529:
1481:
1448:
1384:
1371:
1347:The Royal Society of Chemistry
796:of glyoxylic acid is known as
716:) is 300 for the formation of
462:
450:
13:
1:
2391:Question Bank of Biochemistry
1842:Journal of Molecular Medicine
1325:
1303:for rats of 2500 mg/kg.
972:secondary or tertiary sources
935:hydroxymethyltransferase
2137:Journal of Diabetes Research
1672:François Cardarelli (2008).
1580:Geophysical Research Letters
1558:10.1016/0022-2852(84)90242-X
902:
884:
7:
1808:10.1016/j.ymben.2013.07.004
1756:Fungal Genetics and Biology
1355:10.1039/9781849733069-FP001
1313:
1217:The immediate product with
1046:
10:
2491:
2368:; Mathieson, Olin (1953).
2196:Frontiers in Endocrinology
1918:10.1016/j.jhep.2010.07.036
1282:secondary organic aerosols
1233:, a precursor to the drug
1231:4-hydroxyphenylacetic acid
1105:acid dissociation constant
685:Structure and nomenclature
2267:10.1007/s00592-012-0412-3
1854:10.1007/s00109-012-0930-z
1764:10.1016/j.fgb.2013.06.008
1678:. Springer. p. 574.
1639:10.1002/cber.190403703116
1502:10.1107/S1600536807025792
1291:
607:
532:
437:
417:
382:
91:
79:
67:
55:
50:
41:
32:
2442:10.1021/acs.jpca.6b00225
2209:10.3389/fendo.2012.00170
1525:10.1002/14356007.a12_495
1107:of 4.7 Ă— 10 (p
815:: in organic synthesis,
1276:Environmental chemistry
1652:Cohen, Julius (1920).
1248:, provides a route to
1223:4-hydroxymandelic acid
959:relies excessively on
936:
899:
704:rapidly converts to a
2377:. U.S. Patent Office.
2333:10.6028/jres.078A.024
1906:Journal of Hepatology
1796:Metabolic Engineering
1349:. 2014. p. 748.
1266:Hopkins–Cole reaction
1260:Hopkins Cole reaction
1059:(AGEs) caused by the
933:
896:
722:X-ray crystallography
69:Systematic IUPAC name
2470:Conjugated aldehydes
1981:The Arabidopsis Book
1600:10.1029/2008GL036212
813:electrosynthetically
718:dihydroxyacetic acid
710:equilibrium constant
57:Preferred IUPAC name
2433:2016JPCA..120.3817E
2388:R.A. Joshi (2006).
2150:10.1155/2014/685204
2091:2013PChem..95..168B
1592:2009GeoRL..36.1802I
1550:1984JMoSp.104...25R
1144:Cannizzaro reaction
784:= 1.09 Ă— 10 Ă— exp.
480: g·mol
145:Beilstein Reference
29:
2255:Acta Diabetologica
1977:"Photorespiration"
1948:"photorespiration"
1202:Phenol derivatives
1196:1,2-diaminobenzene
1148:hydroxyacetic acid
1095:Reactions and uses
1065:alpha-oxoaldehydes
937:
900:
640:Infobox references
533:Related compounds
27:
2427:(21): 3817–3826.
2401:978-81-224-1736-4
2315:
2311:
1848:(12): 1497–1504.
1685:978-1-84628-668-1
1364:978-0-85404-182-4
1140:disproportionates
1079:, a key cause of
1044:
1043:
1036:
1018:
940:Disease relevance
648:Chemical compound
646:
645:
589:Related compounds
351:CompTox Dashboard
133:Interactive image
86:Formylformic acid
16:(Redirected from
2482:
2455:
2454:
2444:
2421:J. Phys. Chem. A
2412:
2406:
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2066:
2029:
2023:
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2012:
1993:10.1199/tab.0130
1972:
1963:
1962:
1960:
1959:
1950:. Archived from
1944:
1938:
1937:
1901:
1892:
1891:
1865:
1837:
1828:
1827:
1790:
1784:
1783:
1758:. 58–59: 33–41.
1750:
1744:
1743:
1723:
1717:
1716:
1701:Biochem Soc Symp
1696:
1690:
1689:
1669:
1663:
1662:
1660:
1649:
1643:
1642:
1633:(3): 3187–3191.
1618:
1612:
1611:
1577:
1568:
1562:
1561:
1533:
1527:
1517:
1506:
1505:
1485:
1479:
1478:
1476:
1461:Acta Chem. Scand
1452:
1446:
1441:, 11th Edition,
1435:
1429:
1427:
1421:
1413:
1411:
1410:
1404:
1398:. Archived from
1397:
1388:
1382:
1375:
1369:
1368:
1341:"Front Matter".
1338:
1133:
1132:
1131:
1053:Type II diabetes
1039:
1032:
1028:
1025:
1019:
1017:
983:"Glyoxylic acid"
976:
952:
944:
913:photorespiration
909:glyoxylate cycle
869:, which enables
867:glyoxylate cycle
831:
772:
748:
732:
694:functional group
679:carboxylic acids
662:. Together with
660:organic compound
630:
624:
621:
620:
556:carboxylic acids
479:
464:
458:
452:
445:Chemical formula
375:
374:
359:
357:
341:
321:
310:
296:
274:Gmelin Reference
257:
249:
238:
227:
207:
187:
167:
135:
111:
84:2-Oxoacetic acid
73:Oxoethanoic acid
46:
37:
30:
26:
21:
2490:
2489:
2485:
2484:
2483:
2481:
2480:
2479:
2475:Aldehydic acids
2460:
2459:
2458:
2413:
2409:
2402:
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2374:
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2359:
2304:
2300:
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1902:
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1569:
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1509:
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1482:
1453:
1449:
1436:
1432:
1415:
1414:
1408:
1406:
1402:
1395:
1393:"Archived copy"
1391:
1389:
1385:
1376:
1372:
1365:
1340:
1339:
1332:
1328:
1316:
1301:
1294:
1278:
1262:
1246:decarboxylation
1204:
1181:
1177:
1173:
1169:
1165:
1161:
1130:
1127:
1126:
1125:
1123:
1121:
1113:
1097:
1081:nephrolithiasis
1073:
1071:Nephrolithiasis
1049:
1040:
1029:
1023:
1020:
977:
975:
969:
965:primary sources
953:
942:
926:
922:
918:
905:
887:
863:
861:Biological role
790:
783:
758:hydrogen-bonded
687:
677:
649:
642:
637:
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626:
622:
618:
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190:
170:
147:
138:
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83:
75:
74:
63:
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28:Glyoxylic acid
23:
22:
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12:
11:
5:
2488:
2478:
2477:
2472:
2457:
2456:
2407:
2400:
2380:
2357:
2326:(3): 411–412.
2298:
2261:(2): 101–110.
2241:
2182:
2120:
2079:Phytochemistry
2068:
2024:
1964:
1939:
1912:(3): 513–520.
1893:
1829:
1785:
1745:
1734:(8): 803–813.
1718:
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1613:
1563:
1528:
1507:
1480:
1447:
1430:
1383:
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1324:
1323:
1322:
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1299:
1293:
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1277:
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1210:reaction with
1203:
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1167:
1163:
1159:
1136:
1135:
1128:
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1069:
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938:
924:
920:
916:
904:
901:
886:
883:
862:
859:
857:is effective.
833:
832:
794:conjugate base
789:
786:
781:
774:
773:
750:
749:
734:
733:
686:
683:
675:
656:oxoacetic acid
652:Glyoxylic acid
647:
644:
643:
638:
616:
615:
611:standard state
608:
605:
604:
602:glycolaldehyde
591:
588:
585:
584:
578:propionic acid
559:
553:
550:
549:
544:
538:
535:
534:
530:
529:
526:
522:
512:
511:
508:
502:
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363:
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128:
126:
119:
116:
115:
113:
112:
104:
102:
97:
94:
93:
89:
88:
82:Glyoxylic acid
81:
77:
76:
72:
71:
65:
64:
61:Oxoacetic acid
60:
59:
53:
52:
48:
47:
39:
38:
9:
6:
4:
3:
2:
2487:
2476:
2473:
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2468:
2467:
2465:
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2448:
2443:
2438:
2434:
2430:
2426:
2422:
2418:
2411:
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2393:
2392:
2384:
2373:
2372:
2367:
2366:Kamlet, Jonas
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2325:
2321:
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2302:
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2290:
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2272:
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2264:
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2256:
2252:
2245:
2237:
2233:
2228:
2223:
2219:
2215:
2210:
2205:
2201:
2197:
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2178:
2174:
2169:
2164:
2160:
2156:
2151:
2146:
2142:
2138:
2134:
2127:
2125:
2116:
2112:
2108:
2104:
2100:
2096:
2092:
2088:
2084:
2080:
2072:
2064:
2060:
2056:
2052:
2048:
2044:
2040:
2036:
2028:
2020:
2016:
2011:
2006:
2002:
1998:
1994:
1990:
1986:
1982:
1978:
1971:
1969:
1954:on 2006-12-11
1953:
1949:
1943:
1935:
1931:
1927:
1923:
1919:
1915:
1911:
1907:
1900:
1898:
1889:
1885:
1881:
1877:
1873:
1869:
1864:
1859:
1855:
1851:
1847:
1843:
1836:
1834:
1825:
1821:
1817:
1813:
1809:
1805:
1801:
1797:
1789:
1781:
1777:
1773:
1769:
1765:
1761:
1757:
1754:atroviride".
1749:
1741:
1737:
1733:
1729:
1722:
1714:
1710:
1706:
1702:
1695:
1687:
1681:
1677:
1676:
1668:
1657:
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1636:
1632:
1628:
1624:
1617:
1609:
1605:
1601:
1597:
1593:
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1585:
1581:
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1567:
1559:
1555:
1551:
1547:
1543:
1539:
1532:
1526:
1522:
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1475:
1470:
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1462:
1458:
1451:
1445:
1444:
1440:
1434:
1425:
1419:
1405:on 2010-06-02
1401:
1394:
1387:
1380:
1374:
1366:
1360:
1356:
1352:
1348:
1345:. Cambridge:
1344:
1337:
1335:
1330:
1321:
1318:
1317:
1311:
1309:
1304:
1302:
1289:
1287:
1286:photochemical
1283:
1273:
1272:in proteins.
1271:
1267:
1257:
1255:
1251:
1247:
1243:
1238:
1236:
1232:
1228:
1224:
1220:
1215:
1213:
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1197:
1193:
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1117:
1116:
1115:
1110:
1106:
1102:
1092:
1089:
1084:
1082:
1078:
1077:hyperoxaluria
1068:
1066:
1062:
1061:hyperglycemia
1058:
1054:
1038:
1035:
1027:
1016:
1013:
1009:
1006:
1002:
999:
995:
992:
988:
985: –
984:
980:
979:Find sources:
973:
967:
966:
962:
957:This article
955:
951:
946:
945:
932:
928:
919:instead of CO
914:
910:
895:
891:
882:
880:
879:carbohydrates
876:
872:
868:
858:
856:
852:
847:
845:
842:
838:
830:
826:
825:
824:
822:
818:
814:
809:
807:
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799:
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785:
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771:
767:
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743:
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726:
725:
723:
719:
715:
711:
707:
703:
699:
695:
692:
682:
680:
673:
669:
668:glycolic acid
665:
661:
657:
653:
641:
634:
629:
612:
606:
603:
599:
595:
592:
587:
586:
583:
579:
575:
571:
570:glycolic acid
567:
563:
560:
557:
552:
551:
548:
545:
542:
537:
536:
531:
527:
521:
517:
514:
513:
509:
507:
506:Boiling point
504:
503:
499:
497:
496:Melting point
494:
493:
489:
487:
484:
483:
476:
474:
471:
470:
449:
446:
442:
441:
436:
427:
426:
423:
416:
402:
392:
391:
388:
381:
373:
369:
368:DTXSID5021594
365:
364:
362:
352:
348:
347:
340:
336:
335:
333:
331:
328:
327:
320:
316:
315:
313:
307:
303:
302:
295:
291:
290:
288:
286:
283:
282:
278:
275:
271:
270:
263:
262:
260:
258:
253:
252:
248:
244:
241:
239:
237:ECHA InfoCard
234:
233:
226:
222:
221:
219:
217:
214:
213:
206:
202:
201:
199:
197:
194:
193:
186:
185:ChEMBL1162545
182:
181:
179:
177:
174:
173:
166:
162:
161:
159:
157:
154:
153:
149:
146:
142:
141:
134:
130:
129:
127:
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118:
117:
110:
106:
105:
103:
100:
96:
95:
90:
78:
70:
66:
58:
54:
49:
45:
40:
36:
31:
19:
2424:
2420:
2410:
2390:
2383:
2370:
2360:
2323:
2319:
2301:
2258:
2254:
2244:
2199:
2195:
2185:
2140:
2136:
2082:
2078:
2071:
2038:
2034:
2027:
1984:
1980:
1956:. Retrieved
1952:the original
1942:
1909:
1905:
1863:11343/220107
1845:
1841:
1799:
1795:
1788:
1755:
1748:
1731:
1727:
1721:
1704:
1700:
1694:
1674:
1667:
1654:
1647:
1630:
1626:
1616:
1583:
1579:
1566:
1544:(1): 25–39.
1541:
1537:
1531:
1496:(7): o3081.
1493:
1489:
1483:
1464:
1460:
1450:
1442:
1437:
1433:
1407:. Retrieved
1400:the original
1386:
1373:
1342:
1320:Semialdehyde
1305:
1295:
1279:
1263:
1239:
1216:
1205:
1188:condensation
1185:
1166:O → HOCH
1137:
1108:
1098:
1085:
1074:
1050:
1030:
1021:
1011:
1004:
997:
990:
978:
958:
906:
888:
864:
848:
834:
817:lead dioxide
810:
797:
791:
788:Preparations
775:
751:
740:dimer form:
735:
717:
713:
706:geminal diol
688:
655:
651:
650:
594:acetaldehyde
582:pyruvic acid
528:3.18, 3.32
519:
92:Identifiers
80:Other names
2085:: 168–176.
2041:: 110–117.
1467:: 162–168.
1439:Merck Index
1254:formylation
1227:amoxicillin
1152:oxalic acid
1101:acetic acid
875:fatty acids
855:maleic acid
837:nitric acid
821:oxalic acid
778:Henry's law
672:oxalic acid
664:acetic acid
574:oxalic acid
566:acetic acid
562:formic acid
490:1.384 g/mL
438:Properties
429:C(=O)C(=O)O
243:100.005.508
165:CHEBI:16891
2464:Categories
2143:: 685204.
1958:2017-03-09
1728:Biol. Chem
1409:2010-06-02
1326:References
1270:tryptophan
1221:itself is
1146:, forming
1103:, with an
1024:March 2017
994:newspapers
961:references
851:ozonolysis
798:glyoxylate
764:hydrogen:
547:glyoxylate
473:Molar mass
339:JQ39C92HH6
196:ChemSpider
120:3D model (
99:CAS Number
18:Glyoxylate
2275:0940-5429
2218:1664-2392
2159:2314-6745
2107:0031-9422
2055:1011-1344
2001:1543-8120
1987:: e0130.
1926:0168-8278
1872:0946-2716
1816:1096-7176
1772:1087-1845
1707:: 17–31.
1608:129747490
1256:process.
1252:as a net
1114:= 3.32):
903:In plants
885:In humans
871:organisms
802:amidation
756:a cyclic
754:conformer
264:206-058-5
256:EC Number
2451:27192089
2352:32189791
2293:22763581
2236:23267348
2177:25525609
2115:23916564
2063:25528301
2019:22303256
1934:21093948
1888:11549218
1880:22729392
1824:23876414
1802:: 9–19.
1780:23850601
1418:cite web
1314:See also
1250:vanillin
1242:guaiacol
1235:atenolol
1174:H + HO
1047:Diabetes
806:peptides
762:carboxyl
702:carbonyl
691:aldehyde
554:Related
216:DrugBank
109:298-12-4
2429:Bibcode
2343:6742820
2284:3634985
2227:3527746
2202:: 170.
2168:4265698
2087:Bibcode
2010:3244903
1740:9377475
1713:3332993
1588:Bibcode
1546:Bibcode
1212:phenols
1162:H + H
1158:2 OCHCO
1008:scholar
844:glyoxal
841:oxidize
633:what is
631: (
598:glyoxal
516:Acidity
486:Density
306:PubChem
225:DB04343
150:741891
2449:
2398:
2350:
2340:
2291:
2281:
2273:
2234:
2224:
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2175:
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2017:
2007:
1999:
1932:
1924:
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1878:
1870:
1822:
1814:
1778:
1770:
1738:
1711:
1682:
1606:
1361:
1292:Safety
1219:phenol
1142:via a
1122:H ⇌
1010:
1003:
996:
989:
981:
849:Also,
738:acylal
670:, and
658:is an
628:verify
625:
541:anions
539:Other
478:74.035
422:SMILES
294:C00048
279:25752
176:ChEMBL
51:Names
2375:(PDF)
1884:S2CID
1659:(PDF)
1604:S2CID
1576:(PDF)
1403:(PDF)
1396:(PDF)
1190:with
1124:OCHCO
1118:OCHCO
1088:HOGA1
1015:JSTOR
1001:books
877:into
698:dimer
387:InChI
156:ChEBI
122:JSmol
2447:PMID
2396:ISBN
2348:PMID
2289:PMID
2271:ISSN
2232:PMID
2214:ISSN
2173:PMID
2155:ISSN
2141:2014
2111:PMID
2103:ISSN
2059:PMID
2051:ISSN
2015:PMID
1997:ISSN
1930:PMID
1922:ISSN
1876:PMID
1868:ISSN
1820:PMID
1812:ISSN
1776:PMID
1768:ISSN
1736:PMID
1709:PMID
1680:ISBN
1443:4394
1424:link
1359:ISBN
1194:and
1192:urea
1150:and
1134:+ H
987:news
839:can
835:Hot
792:The
776:The
330:UNII
285:KEGG
2437:doi
2425:120
2338:PMC
2328:doi
2324:78A
2279:PMC
2263:doi
2222:PMC
2204:doi
2163:PMC
2145:doi
2095:doi
2043:doi
2039:142
2005:PMC
1989:doi
1914:doi
1858:hdl
1850:doi
1804:doi
1760:doi
1732:378
1635:doi
1596:doi
1554:doi
1542:104
1521:doi
1498:doi
1469:doi
1351:doi
1178:CCO
963:to
853:of
654:or
356:EPA
319:760
309:CID
205:740
2466::
2445:.
2435:.
2423:.
2419:.
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2314:DL
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523:a
520:K
466:3
463:O
460:2
457:H
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354:(
124:)
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
