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call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js Jmol JavaScript applet jmolApplet0_object__068506437510457__ initializing getValue debug = null getValue logLevel = null getValue allowjavascript = null AppletRegistry.checkIn(jmolApplet0_object__068506437510457__) call loadScript javascripts\jsmol\core\corestate.z.js viewerOptions: { "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15366","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__068506437510457__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"068506437510457","bgcolor":"#000" } (C) 2012 Jmol Development Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $ java.vendor: j2s java.version: 0.0 os.name: j2s Access: ALL memory: 0.0/0.0 processors available: 1 useCommandThread: false appletId:jmolApplet0_object (signed) starting HoverWatcher_1 getValue emulate = null defaults = "Jmol" getValue boxbgcolor = null getValue bgcolor = #000 backgroundColor = "#000" getValue ANIMFRAMECallback = null getValue APPLETREADYCallback = Jmol._readyCallback APPLETREADYCallback = "Jmol._readyCallback" getValue ATOMMOVEDCallback = null getValue CLICKCallback = null getValue ECHOCallback = null getValue ERRORCallback = null getValue EVALCallback = null getValue HOVERCallback = null getValue LOADSTRUCTCallback = null getValue MEASURECallback = null getValue MESSAGECallback = null getValue MINIMIZATIONCallback = null getValue PICKCallback = null getValue RESIZECallback = null getValue SCRIPTCallback = null getValue SYNCCallback = null getValue STRUCTUREMODIFIEDCallback = null getValue doTranslate = null language=en_US getValue popupMenu = null getValue script = null Jmol applet jmolApplet0_object__068506437510457__ ready call loadScript javascripts\jsmol\core\corescript.z.js call loadScript javascripts\jsmol\J\script\FileLoadThread.js starting QueueThread0_2 script 1 started starting HoverWatcher_3 starting HoverWatcher_4 The Resolver thinks Mol Marvin 11030523303D starting HoverWatcher_5 Time for openFile( Marvin 11030523303D 8 7 0 0 0 0 999 V2000 -0.8778 0.1263 -0.2641 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5300 0.1263 0.0396 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0124 -0.7782 0.7097 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2661 1.0166 -0.3588 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1580 0.9928 -0.8669 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1377 -0.7760 -0.8210 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4573 0.1513 0.6607 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8716 -0.7874 0.9008 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 2 4 2 0 0 0 0 5 1 1 0 0 0 0 6 1 1 0 0 0 0 7 1 1 0 0 0 0 8 3 1 0 0 0 0 M END): 18 ms reading 8 atoms ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false 1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them. Default Van der Waals type for model set to Babel 8 atoms created ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation Script completed Jmol script terminated
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| Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH (also written as CH3CO2H, C2H4O2, or HC2H3O2). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.
Acetic acid is the second simplest carboxylic acid (after formic acid). It is an important chemical reagent and industrial chemical across various fields, used primarily in the production of cellulose acetate for photographic film, polyvinyl acetate for wood glue, and synthetic fibres and fabrics. In households, diluted acetic acid is often used in descaling agents. In the food industry, acetic acid is controlled by the food additive code E260 as an acidity regulator and as a condiment. In biochemistry, the acetyl group, derived from acetic acid, is fundamental to all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.
The global demand for acetic acid as of 2023 is about 17.88 million metric tonnes per year (t/a). Most of the world's acetic acid is produced via the carbonylation of methanol. Its production and subsequent industrial use poses health hazards to workers, including incidental skin damage and chronic respiratory injuries from inhalation. |
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Read full article at Wikipedia
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| InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4) |
| QTBSBXVTEAMEQO-UHFFFAOYSA-N |
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protic solvent
A polar solvent that is capable of acting as a hydron (proton) donor.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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food acidity regulator
A food additive that is used to change or otherwise control the acidity or alkalinity of foods. They may be acids, bases, neutralising agents or buffering agents.
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
antimicrobial food preservative
A food preservative which prevents decomposition of food by preventing the growth of fungi or bacteria. In European countries, E-numbers for permitted food preservatives are from E200 to E299, divided into sorbates (E200-209), benzoates (E210-219), sulfites (E220-229), phenols and formates (E230-239), nitrates (E240-259), acetates (E260-269), lactates (E270-279), propionates (E280-289) and others (E290-299).
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food acidity regulator
A food additive that is used to change or otherwise control the acidity or alkalinity of foods. They may be acids, bases, neutralising agents or buffering agents.
protic solvent
A polar solvent that is capable of acting as a hydron (proton) donor.
antimicrobial food preservative
A food preservative which prevents decomposition of food by preventing the growth of fungi or bacteria. In European countries, E-numbers for permitted food preservatives are from E200 to E299, divided into sorbates (E200-209), benzoates (E210-219), sulfites (E220-229), phenols and formates (E230-239), nitrates (E240-259), acetates (E260-269), lactates (E270-279), propionates (E280-289) and others (E290-299).
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View more via ChEBI Ontology
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Outgoing
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acetic acid
(CHEBI:15366)
has role
Daphnia magna metabolite
(CHEBI:83056)
acetic acid
(CHEBI:15366)
has role
antimicrobial food preservative
(CHEBI:65256)
acetic acid
(CHEBI:15366)
has role
food acidity regulator
(CHEBI:64049)
acetic acid
(CHEBI:15366)
has role
protic solvent
(CHEBI:48356)
acetic acid
(CHEBI:15366)
is a
monocarboxylic acid
(CHEBI:25384)
acetic acid
(CHEBI:15366)
is conjugate acid of
acetate
(CHEBI:30089)
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Incoming
|
(1-hydroxycyclohexyl)acetic acid
(CHEBI:37276)
has functional parent
acetic acid
(CHEBI:15366)
(2,2,2-trifluoroethoxy)acetic acid
(CHEBI:60702)
has functional parent
acetic acid
(CHEBI:15366)
(2,2,3-trimethyl-5-oxocyclopent-3-en-1-yl)acetic acid
(CHEBI:28045)
has functional parent
acetic acid
(CHEBI:15366)
(2,6-dihydroxyphenyl)acetic acid
(CHEBI:952)
has functional parent
acetic acid
(CHEBI:15366)
(2-hydroxyphenyl)acetic acid
(CHEBI:28478)
has functional parent
acetic acid
(CHEBI:15366)
(2S)-({(5Z)-5-[(5-ethylfuran-2-yl)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl}amino)(4-fluorophenyl)acetic acid
(CHEBI:46520)
has functional parent
acetic acid
(CHEBI:15366)
(2S)-[(2S,3S,4S,5S)-1,3,4,5-tetrahydroxy-4-(hydroxymethyl)piperidin-2-yl](L-tyrosylamino)acetic acid
(CHEBI:40208)
has functional parent
acetic acid
(CHEBI:15366)
(3-amino-2,5-dioxopyrrolidin-1-yl)acetic acid
(CHEBI:45890)
has functional parent
acetic acid
(CHEBI:15366)
(3-chloro-4-hydroxyphenyl)acetic acid
(CHEBI:47106)
has functional parent
acetic acid
(CHEBI:15366)
(3-{(1R)-3-(3,4-dimethoxyphenyl)-1-[({(2S)-1-[(2S)-2-(3,4,5-trimethoxyphenyl)butanoyl]piperidin-2-yl}carbonyl)oxy]propyl}phenoxy)acetic acid
(CHEBI:40833)
has functional parent
acetic acid
(CHEBI:15366)
(3Z)-hex-3-en-1-yl acetate
(CHEBI:61316)
has functional parent
acetic acid
(CHEBI:15366)
(4-oxo-3-{[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]methyl}-3,4-dihydrophthalazin-1-yl)acetic acid
(CHEBI:46609)
has functional parent
acetic acid
(CHEBI:15366)
(5-fluoro-2-{[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]carbamoyl}phenoxy)acetic acid
(CHEBI:43373)
has functional parent
acetic acid
(CHEBI:15366)
1-O-palmityl-2-acetyl-sn-glycerol
(CHEBI:75936)
has functional parent
acetic acid
(CHEBI:15366)
1-alkyl-2-acetylglycerol
(CHEBI:75882)
has functional parent
acetic acid
(CHEBI:15366)
1-hexadecyl-2-acetyl-sn-glycero-3-phosphoethanolamine
(CHEBI:79280)
has functional parent
acetic acid
(CHEBI:15366)
1-methyl-4-imidazoleacetic acid
(CHEBI:1606)
has functional parent
acetic acid
(CHEBI:15366)
1-palmitoyl-2-acetyl-sn-glycero-3-phosphocholine
(CHEBI:75219)
has functional parent
acetic acid
(CHEBI:15366)
1-palmityl-2-acetyl-sn-glycero-3-phosphate
(CHEBI:79277)
has functional parent
acetic acid
(CHEBI:15366)
1-stearoyl-2-acetyl-sn-glycero-3-phosphocholine
(CHEBI:75220)
has functional parent
acetic acid
(CHEBI:15366)
2-acetyl-sn-glycero-3-phosphocholine
(CHEBI:78045)
has functional parent
acetic acid
(CHEBI:15366)
2-thienylacetic acid
(CHEBI:45807)
has functional parent
acetic acid
(CHEBI:15366)
2H-imidazol-4-ylacetic acid
(CHEBI:43615)
has functional parent
acetic acid
(CHEBI:15366)
3-hydroxyphenylacetic acid
(CHEBI:17445)
has functional parent
acetic acid
(CHEBI:15366)
3-methylphenylacetic acid
(CHEBI:88356)
has functional parent
acetic acid
(CHEBI:15366)
4-chlorophenylacetic acid
(CHEBI:30749)
has functional parent
acetic acid
(CHEBI:15366)
4-hydroxyphenylacetic acid
(CHEBI:18101)
has functional parent
acetic acid
(CHEBI:15366)
6-{[1-(benzylsulfonyl)piperidin-4-yl]amino}-3-(carboxymethoxy)thieno[3,2-b][1]benzothiophene-2-carboxylic acid
(CHEBI:40145)
has functional parent
acetic acid
(CHEBI:15366)
N-acetyl-amino acid
(CHEBI:21575)
has functional parent
acetic acid
(CHEBI:15366)
N-phenylacetamide
(CHEBI:28884)
has functional parent
acetic acid
(CHEBI:15366)
O-acetylcarnitine
(CHEBI:73024)
has functional parent
acetic acid
(CHEBI:15366)
[(1S)-4-hydroxy-2,2,3-trimethylcyclopent-3-enyl]acetic acid
(CHEBI:64899)
has functional parent
acetic acid
(CHEBI:15366)
[(2S,4S)-2-[(1R)-1-amino-2-hydroxyethyl]-4-(1H-imidazol-4-ylmethyl)-5-oxoimidazolidin-1-yl]acetic acid
(CHEBI:41707)
has functional parent
acetic acid
(CHEBI:15366)
[(2S,4S)-2-[(1R)-1-amino-2-hydroxyethyl]-4-(4-hydroxybenzyl)-5-oxoimidazolidin-1-yl]acetic acid
(CHEBI:41749)
has functional parent
acetic acid
(CHEBI:15366)
[(2S,4S)-2-[(1R)-1-amino-2-sulfanylethyl]-4-(4-hydroxybenzyl)-5-oxoimidazolidin-1-yl]acetic acid
(CHEBI:41383)
has functional parent
acetic acid
(CHEBI:15366)
[5-fluoro-1-(4-isopropylbenzylidene)-2-methylinden-3-yl]acetic acid
(CHEBI:59660)
has functional parent
acetic acid
(CHEBI:15366)
acetamidine
(CHEBI:38478)
has functional parent
acetic acid
(CHEBI:15366)
acetate ester
(CHEBI:47622)
has functional parent
acetic acid
(CHEBI:15366)
acetimidic acid
(CHEBI:49028)
has functional parent
acetic acid
(CHEBI:15366)
acetyl chloride
(CHEBI:37580)
has functional parent
acetic acid
(CHEBI:15366)
acetyl-CoA
(CHEBI:15351)
has functional parent
acetic acid
(CHEBI:15366)
arsenoacetic acid
(CHEBI:22634)
has functional parent
acetic acid
(CHEBI:15366)
biphenyl-4-ylacetic acid
(CHEBI:31597)
has functional parent
acetic acid
(CHEBI:15366)
bis(4-chlorophenyl)acetic acid
(CHEBI:28139)
has functional parent
acetic acid
(CHEBI:15366)
chloroacetic acid
(CHEBI:27869)
has functional parent
acetic acid
(CHEBI:15366)
cyanoacetic acid
(CHEBI:51889)
has functional parent
acetic acid
(CHEBI:15366)
cyclohexylacetic acid
(CHEBI:37277)
has functional parent
acetic acid
(CHEBI:15366)
dibromoacetic acid
(CHEBI:90124)
has functional parent
acetic acid
(CHEBI:15366)
dichloroacetic acid
(CHEBI:36386)
has functional parent
acetic acid
(CHEBI:15366)
diflorasone diacetate
(CHEBI:31483)
has functional parent
acetic acid
(CHEBI:15366)
difluoroacetic acid
(CHEBI:23716)
has functional parent
acetic acid
(CHEBI:15366)
diphenylacetic acid
(CHEBI:41967)
has functional parent
acetic acid
(CHEBI:15366)
etacrynic acid
(CHEBI:4876)
has functional parent
acetic acid
(CHEBI:15366)
glycolic acid
(CHEBI:17497)
has functional parent
acetic acid
(CHEBI:15366)
haloacetic acid
(CHEBI:16277)
has functional parent
acetic acid
(CHEBI:15366)
hydroxy(phenyl)2-thienylacetic acid
(CHEBI:64444)
has functional parent
acetic acid
(CHEBI:15366)
ibufenac
(CHEBI:76158)
has functional parent
acetic acid
(CHEBI:15366)
imidazol-1-ylacetic acid
(CHEBI:70801)
has functional parent
acetic acid
(CHEBI:15366)
imidazol-2-ylacetic acid
(CHEBI:70806)
has functional parent
acetic acid
(CHEBI:15366)
imidazol-4-ylacetic acid
(CHEBI:16974)
has functional parent
acetic acid
(CHEBI:15366)
imidazol-5-ylacetic acid
(CHEBI:70804)
has functional parent
acetic acid
(CHEBI:15366)
indole-1-acetic acid
(CHEBI:72814)
has functional parent
acetic acid
(CHEBI:15366)
indole-3-acetic acids
(CHEBI:24803)
has functional parent
acetic acid
(CHEBI:15366)
lonazolac
(CHEBI:76164)
has functional parent
acetic acid
(CHEBI:15366)
magnesium acetate
(CHEBI:62964)
has functional parent
acetic acid
(CHEBI:15366)
mandelic acid
(CHEBI:35825)
has functional parent
acetic acid
(CHEBI:15366)
methoxyacetic acid
(CHEBI:132098)
has functional parent
acetic acid
(CHEBI:15366)
naphthylacetic acid
(CHEBI:35629)
has functional parent
acetic acid
(CHEBI:15366)
peracetic acid
(CHEBI:42530)
has functional parent
acetic acid
(CHEBI:15366)
phenylacetic acid
(CHEBI:30745)
has functional parent
acetic acid
(CHEBI:15366)
phosphonoacetic acid
(CHEBI:15732)
has functional parent
acetic acid
(CHEBI:15366)
phosphonoacetohydroxamic acid
(CHEBI:44692)
has functional parent
acetic acid
(CHEBI:15366)
pirinixic acid
(CHEBI:32509)
has functional parent
acetic acid
(CHEBI:15366)
sulfoacetic acid
(CHEBI:50519)
has functional parent
acetic acid
(CHEBI:15366)
sulindac
(CHEBI:9352)
has functional parent
acetic acid
(CHEBI:15366)
triacetin
(CHEBI:9661)
has functional parent
acetic acid
(CHEBI:15366)
trichloroacetic acid
(CHEBI:30956)
has functional parent
acetic acid
(CHEBI:15366)
trifluoroacetic acid
(CHEBI:45892)
has functional parent
acetic acid
(CHEBI:15366)
uracil-6-ylacetic acid
(CHEBI:46371)
has functional parent
acetic acid
(CHEBI:15366)
zomepirac
(CHEBI:35859)
has functional parent
acetic acid
(CHEBI:15366)
{(2R)-2-[(1S)-1-aminoethyl]-2-hydroxy-4-methylidene-5-oxoimidazolidin-1-yl}acetic acid
(CHEBI:41608)
has functional parent
acetic acid
(CHEBI:15366)
{(2R)-2-[(1S,2R)-1-amino-2-hydroxypropyl]-2-hydroxy-4,5-dioxoimidazolidin-1-yl}acetic acid
(CHEBI:41360)
has functional parent
acetic acid
(CHEBI:15366)
{4-[(carboxymethoxy)carbonyl]-3,3-dioxido-1-oxonaphtho[1,2-d]-1,2-thiazol-2(1H)-yl}acetic acid
(CHEBI:43485)
has functional parent
acetic acid
(CHEBI:15366)
{[5-(3-{[1-(benzylsulfonyl)piperidin-4-yl]amino}phenyl)-4-bromo-2-(2H-tetrazol-5-yl)thiophen-3-yl]oxy}acetic acid
(CHEBI:47182)
has functional parent
acetic acid
(CHEBI:15366)
{[5-(5-nitro-2-furyl)-1,3,4-oxadiazol-2-yl]thio}acetic acid
(CHEBI:43741)
has functional parent
acetic acid
(CHEBI:15366)
acetate
(CHEBI:30089)
is conjugate base of
acetic acid
(CHEBI:15366)
acetyl group
(CHEBI:40574)
is substituent group from
acetic acid
(CHEBI:15366)
acetyloxy group
(CHEBI:48076)
is substituent group from
acetic acid
(CHEBI:15366)
carboxymethyl group
(CHEBI:41402)
is substituent group from
acetic acid
(CHEBI:15366)
methylenecarbonyl group
(CHEBI:43923)
is substituent group from
acetic acid
(CHEBI:15366)
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ACETIC ACID
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PDBeChem
|
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Acetic acid
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KEGG COMPOUND
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acide acétique
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ChemIDplus
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AcOH
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ChEBI
|
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CH3‒COOH
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IUPAC
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CH3CO2H
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ChEBI
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E 260
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ChEBI
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E-260
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ChEBI
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E260
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ChEBI
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Essigsäure
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ChEBI
|
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Ethanoic acid
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KEGG COMPOUND
|
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ethoic acid
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ChEBI
|
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Ethylic acid
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ChemIDplus
|
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HOAc
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ChEBI
|
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INS No. 260
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ChEBI
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MeCO2H
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ChEBI
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MeCOOH
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ChEBI
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Methanecarboxylic acid
|
ChemIDplus
|
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1333
|
PPDB
|
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4211
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DrugCentral
|
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ACET
|
MetaCyc
|
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Acetic_acid
|
Wikipedia
|
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ACT
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PDBeChem
|
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ACY
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PDBeChem
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C00001176
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KNApSAcK
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C00033
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KEGG COMPOUND
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D00010
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KEGG DRUG
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HMDB0000042
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HMDB
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LMFA01010002
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LIPID MAPS
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| View more database links |
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1380
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Gmelin Registry Number
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Gmelin
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506007
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Reaxys Registry Number
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Reaxys
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64-19-7
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CAS Registry Number
|
KEGG COMPOUND
|
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64-19-7
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CAS Registry Number
|
NIST Chemistry WebBook
|
|
64-19-7
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CAS Registry Number
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ChemIDplus
|
Zuo Z, Zhu Y, Bai Y, Wang Y (2012)
Acetic acid-induced programmed cell death and release of volatile organic compounds in Chlamydomonas reinhardtii.
Plant physiology and biochemistry : PPB 51, 175-184 [PubMed:22153255]
[show Abstract]
Acetic acid widely spreads in atmosphere, aquatic ecosystems containing residues and anoxic soil. It can inhibit aquatic plant germination and growth, and even cause programmed cell death (PCD) of yeast. In the present study, biochemical and physiological responses of the model unicellular green algae Chlamydomonas reinhardtii were examined after acetic acid stress. H(2)O(2) burst was found in C. reinhardtii after acetic acid stress at pH 5.0 for 10 min. The photosynthetic pigments were degraded, gross photosynthesis and respiration were disappeared gradually, and DNA fragmentation was also detected. Those results indicated that C. reinhardtii cells underwent a PCD but not a necrotic, accidental cell death event. It was noticed that C. reinhardtii cells in PCD released abundant volatile organic compounds (VOCs) upon acetic acid stress. Therefore, we analyzed the VOCs and tested their effects on other normal cells. The treatment of C. reinhardtii cultures with VOCs reduced the cell density and increased antioxidant enzyme activity. Therefore, a function of VOCs as infochemicals involved in cell-to-cell communication at the conditions of applied stress is suggested. | Aggrey A, Dare P, Lei R, Gapes D (2012)
Evaluation of a two-stage hydrothermal process for enhancing acetic acid production using municipal biosolids.
Water science and technology : a journal of the International Association on Water Pollution Research 65, 149-155 [PubMed:22173419]
[show Abstract]
A two-stage hydrothermal process aimed at improving acetic acid production using municipal biosolids was evaluated against thermal hydrolysis and conventional wet oxidation process in a 600 ml Parr batch reactor. Thermal hydrolysis was conducted at 140 °C, wet oxidation at 220 °C and the two-stage process, which acted as a series combination of thermal hydrolysis and wet oxidation, at 220 °C. Initial pressure of 1 MPa was maintained in all the three processes. The results indicated that the highest acetic acid production of up to 58 mg/g dry solids feed was achieved in the wet oxidation process followed by the two-stage process with 36 mg/g dry solids feed and 1.8 mg/g dry solids feed for thermal hydrolysis. The acetic acid yield obtained by the thermal processes increased from 0.4% in the thermal hydrolysis process to 12% during the single stage wet oxidation, with the two-stage process achieving 8%. The purity of the acetic acid improved from 1% in thermal hydrolysis to 38% in the wet oxidation process. The two-stage process achieved acetic acid purity of 25%. This work demonstrated no enhancement of acetic acid production by the two-stage concept compared with the single stage wet oxidation process. This is in contrast to similar work by other researchers, investigated on carbohydrate biomass and vegetable wastes using hydrogen peroxide as the oxidant. However, the data obtained revealed that substrate specificity, reaction severity or oxidant type is clearly important in promoting reaction mechanisms which support enhanced acetic acid production using municipal biosolids. | Bellissimi E, van Dijken JP, Pronk JT, van Maris AJ (2009)
Effects of acetic acid on the kinetics of xylose fermentation by an engineered, xylose-isomerase-based Saccharomyces cerevisiae strain.
FEMS yeast research 9, 358-364 [PubMed:19416101]
[show Abstract]
Acetic acid, an inhibitor released during hydrolysis of lignocellulosic feedstocks, has previously been shown to negatively affect the kinetics and stoichiometry of sugar fermentation by (engineered) Saccharomyces cerevisiae strains. This study investigates the effects of acetic acid on S. cerevisiae RWB 218, an engineered xylose-fermenting strain based on the Piromyces XylA (xylose isomerase) gene. Anaerobic batch cultures on synthetic medium supplemented with glucose-xylose mixtures were grown at pH 5 and 3.5, with and without addition of 3 g L(-1) acetic acid. In these cultures, consumption of the sugar mixtures followed a diauxic pattern. At pH 5, acetic acid addition caused increased glucose consumption rates, whereas specific xylose consumption rates were not significantly affected. In contrast, at pH 3.5 acetic acid had a strong and specific negative impact on xylose consumption rates, which, after glucose depletion, slowed down dramatically, leaving 50% of the xylose unused after 48 h of fermentation. Xylitol production was absent (<0.10 g L(-1)) in all cultures. Xylose fermentation in acetic -acid-stressed cultures at pH 3.5 could be restored by applying a continuous, limiting glucose feed, consistent with a key role of ATP regeneration in acetic acid tolerance. | Kondo T, Kishi M, Fushimi T, Kaga T (2009)
Acetic acid upregulates the expression of genes for fatty acid oxidation enzymes in liver to suppress body fat accumulation.
Journal of agricultural and food chemistry 57, 5982-5986 [PubMed:19469536]
[show Abstract]
We investigated the effect of acetic acid (AcOH) on the prevention of obesity in high-fat-fed mice. The mice were intragastrically administrated with water or 0.3 or 1.5% AcOH for 6 weeks. AcOH administration inhibited the accumulation of body fat and hepatic lipids without changing food consumption or skeletal muscle weight. Significant increases were observed in the expressions of genes for peroxisome-proliferator-activated receptor alpha (PPARalpha) and for fatty-acid-oxidation- and thermogenesis-related proteins: acetyl-CoA oxidase (ACO), carnitine palmitoyl transferase-1 (CPT-1), and uncoupling protein-2 (UCP-2), in the liver of the AcOH-treatment groups. PPARalpha, ACO, CPT-1, and UCP-2 gene expressions were increased in vitro by acetate addition to HepG2 cells. However, the effects were not observed in cells depleted of alpha2 5'-AMP-activated protein kinase (AMPK) by siRNA. In conclusion, AcOH suppresses accumulation of body fat and liver lipids by upregulation of genes for PPARalpha and fatty-acid-oxidation-related proteins by alpha2 AMPK mediation in the liver. | Salek RM, Maguire ML, Bentley E, Rubtsov DV, Hough T, Cheeseman M, Nunez D, Sweatman BC, Haselden JN, Cox RD, Connor SC, Griffin JL (2007)
A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human.
Physiological genomics 29, 99-108 [PubMed:17190852]
[show Abstract]
Type 2 diabetes mellitus is the result of a combination of impaired insulin secretion with reduced insulin sensitivity of target tissues. There are an estimated 150 million affected individuals worldwide, of whom a large proportion remains undiagnosed because of a lack of specific symptoms early in this disorder and inadequate diagnostics. In this study, NMR-based metabolomic analysis in conjunction with multivariate statistics was applied to examine the urinary metabolic changes in two rodent models of type 2 diabetes mellitus as well as unmedicated human sufferers. The db/db mouse and obese Zucker (fa/fa) rat have autosomal recessive defects in the leptin receptor gene, causing type 2 diabetes. 1H-NMR spectra of urine were used in conjunction with uni- and multivariate statistics to identify disease-related metabolic changes in these two animal models and human sufferers. This study demonstrates metabolic similarities between the three species examined, including metabolic responses associated with general systemic stress, changes in the TCA cycle, and perturbations in nucleotide metabolism and in methylamine metabolism. All three species demonstrated profound changes in nucleotide metabolism, including that of N-methylnicotinamide and N-methyl-2-pyridone-5-carboxamide, which may provide unique biomarkers for following type 2 diabetes mellitus progression. | Sakakibara S, Yamauchi T, Oshima Y, Tsukamoto Y, Kadowaki T (2006)
Acetic acid activates hepatic AMPK and reduces hyperglycemia in diabetic KK-A(y) mice.
Biochemical and biophysical research communications 344, 597-604 [PubMed:16630552]
[show Abstract]
Acetic acid (AcOH), which is a short-chain fatty acid, is reported to have some beneficial effects on metabolism. To test the hypothesis that feeding of AcOH exerts beneficial effects on glucose homeostasis in type 2 diabetes, we fed either a standard diet or one containing 0.3% AcOH to KK-A(y) mice for 8 weeks. Fasting plasma glucose and HbA1c levels were lower in mice fed AcOH for 8 weeks than in control mice. AcOH also reduced the expression of genes involved in gluconeogenesis and lipogenesis, which is in part regulated by 5'-AMP-activated protein kinase (AMPK) in the liver. Finally, sodium acetate, in the form of neutralized AcOH, directly activated AMPK and lowered the expression of genes such as for glucose-6-phosphatase and sterol regulatory element binding protein-1 in rat hepatocytes. These results indicate that the hypoglycemic effect of AcOH might be due to activation of AMPK in the liver. | Gilman JB, Vaida V (2006)
Permeability of acetic acid through organic films at the air-aqueous interface.
The journal of physical chemistry. A 110, 7581-7587 [PubMed:16774200]
[show Abstract]
Recent field studies of collected aerosol particles, both marine and continental, show that the outermost layers contain long-chain (C >or= 18) organics. The presence of these long-chain organics could impede the transport of gases and other volatile species across the interface. This could effect the particle's composition, lifetime, and heterogeneous chemistry. In this study, the uptake rate of acetic acid vapor across a clean interface and through films of long-chain organics into an aqueous subphase solution containing an acid-base indicator (bromocresol green) was measured under ambient conditions using visible absorption spectroscopy. Acetic acid is a volatile organic compound (VOC) and is an atmospherically relevant organic acid. The uptake of acetic acid through single-component organic films of 1-octadecanol (C(18)H(38)O), 1-triacontanol (C(30)H(62)O), cis-9-octadecen-1-ol (C(18)H(36)O), and nonacosane (C(29)H(60)) in addition to two mixed films containing equimolar 1-triacontanol/nonacosane and equimolar 1-triacontanol/cis-9-octadecen-1-ol was determined. These species represent long-chain organic compounds that reside at the air-aqueous interface of atmospheric aerosols. The cis-9-octadecen-1-ol film had little effect on the net uptake rate of acetic acid vapor into solution; however, the uptake rate was reduced by almost one-half by an interfacial film of 1-triacontanol. The measured uptake rates were used to calculate the permeability of acetic acid through the various films which ranged from 1.5 x 10(-3) cm s(-1) for 1-triacontanol, the least permeable film, to 2.5 x 10(-2) cm s(-1) for cis-9-octadecen-1-ol, the most permeable film. Both mixed films had permeabilities that were between that of the single-component films comprising the mixture. This shows that the permeability of a mixed film may not be solely determined by the most permeable species in the mixture. The permeabilities of all the films studied here are discussed in relation to their molecular properties, pressure-area isotherms, and atmospheric implications. | Lima LH, das Graças de Almeida Felipe M, Vitolo M, Torres FA (2004)
Effect of acetic acid present in bagasse hydrolysate on the activities of xylose reductase and xylitol dehydrogenase in Candida guilliermondii.
Applied microbiology and biotechnology 65, 734-738 [PubMed:15107950]
[show Abstract]
The first two steps in xylose metabolism are catalyzed by NAD(P)H-dependent xylose reductase (XR) (EC 1.1.1.21) and NAD(P)-dependent xylitol dehydrogenase (XDH) (EC 1.1.1.9), which lead to xylose-->xylitol-->xylulose conversion. Xylitol has high commercial value, due to its sweetening and anticariogenic properties, as well as several clinical applications. The acid hydrolysis of sugarcane bagasse allows the separation of a xylose-rich hemicellulosic fraction that can be used as a substrate for Candida guilliermondii to produce xylitol. However, the hydrolysate contains acetic acid, an inhibitor of microbial metabolism. In this study, the effect of acetic acid on the activities of XR and XDH and on xylitol formation by C. guilliermondii were studied. For this purpose, fermentations were carried out in bagasse hydrolysate and in synthetic medium. The activities of XR and XDH were higher in the medium containing acetic acid than in control medium. Moreover, none of the fermentative parameters were significantly altered during cell culture. It was concluded that acetic acid does not interfere with xylitol formation since the increase in XR activity is proportional to XDH activity, leading to a greater production of xylitol and its subsequent conversion to xylulose. | Gagnaire F, Marignac B, Hecht G, Héry M (2002)
Sensory irritation of acetic acid, hydrogen peroxide, peroxyacetic acid and their mixture in mice.
The Annals of occupational hygiene 46, 97-102 [PubMed:12005138]
[show Abstract]
The expiratory bradypnoea indicative of upper airway irritation in mice was evaluated during a period of 60 min of oronasal exposure to acetic acid, hydrogen peroxide and peroxyacetic acid vapours. The airborne concentration resulting in a 50% decrease in the respiratory rate of mice (RD50) was calculated for each chemical. The concentration-response curves of acetic acid, hydrogen peroxide and peroxyacetic acid had similar slopes. The results did however show that the three chemicals had different irritant potencies. The RD50 values of acetic acid, hydrogen peroxide and peroxyacetic acid were 227, 113 and 5.4 p.p.m. respectively. Moreover, a mixture containing 53% acetic acid, 11% hydrogen peroxide and 36% peroxyacetic acid had an RD50 of 10.6 ppm, 3.8 ppm being peroxyacetic acid, which is 1.4 times lower than the theoretical value estimated from the fractional concentrations and the respective RD50s of the individual components. On the basis of a TLV-STEL (threshold limit value for short-term exposure limit) equal to 0.1 RD50, the TLV-STELs for acetic acid, hydrogen peroxide and peroxyacetic acid should not exceed 20, 10 and 0.5 p.p.m. respectively. On the basis of a TLV-TWA (time-weighted average) equal to 0.03 RD50, the TLV-TWAs for these same chemicals should not exceed 5, 3 and 0.2 p.p.m. respectively. Finally, these values and existing TLVs in Europe and the USA are compared. |
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2011-03-25
