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MetaCyc Compound: (R)-acetoin

Synonyms: (R)-2-acetoin, (R)-3-hydroxy-2-butanone, (R)-3-hydroxybutan-2-one, (R)-dimethylketol, (3R)-3-hydroxybutan-2-one, (-)-acetoin, D-(-)-acetoin, levorotatory acetoin, (R)-acetylmethylcarbinol

Superclasses: an aldehyde or ketonea ketoneacetoin

Chemical Formula: C4H8O2

Molecular Weight: 88.106 Daltons

Monoisotopic Molecular Weight: 88.05242950099999 Daltons

(R)-acetoin compound structure


InChI: InChI=1S/C4H8O2/c1-3(5)4(2)6/h3,5H,1-2H3/t3-/m1/s1


Unification Links: ChEBI:15686, ChemSpider:388445, KEGG:C00810, PubChem:439314

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 10.048964Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

acetoin degradation :
acetoin + coenzyme A + NAD+ → acetaldehyde + acetyl-CoA + NADH + H+

Reactions known to produce the compound:

(R)-acetoin biosynthesis I :
(R)-acetoin + NAD+ ← diacetyl + NADH + H+

(R)-acetoin biosynthesis II :
(S)-2-acetolactate + H+(R)-acetoin + CO2

acetoin biosynthesis III :
2 acetaldehyde → acetoin
pyruvate + acetaldehyde + H+acetoin + CO2

Not in pathways:
acetoin + NAD+ ← diacetyl + NADH + H+

cuticular wax biosynthesis :
a secondary alcohol + an oxidized unknown electron acceptor → a ketone + an reduced unknown electron acceptor

Not in pathways:
a secondary alcohol + oxygen → a ketone + hydrogen peroxide

Not in pathways:
a nitroalkane + oxygen + H2O → an aldehyde or ketone + nitrite + hydrogen peroxide + H+

Reactions known to both consume and produce the compound:

(R,R)-butanediol biosynthesis , (R,R)-butanediol degradation :
(R,R)-2,3-butanediol + NAD+(R)-acetoin + NADH + H+

meso-butanediol biosynthesis I :
(R,S)-2,3-butanediol + NAD+(R)-acetoin + NADH + H+

In Reactions of unknown directionality:

Not in pathways:
(S)-acetoin = (R)-acetoin

Not in pathways:
D-ribose 5-phosphate + acetoin = 1-deoxy-D-altro-heptulose 7-phosphate + acetaldehyde
acetoin + NADP+ = diacetyl + NADPH + H+

Not in pathways:
a ketone + NADP+ = an enone + NADPH + H+
a secondary alcohol + an oxidized coenzyme F420 = a ketone + a reduced coenzyme F420
a secondary alcohol + NADP+ = a ketone + NADPH + H+
a secondary alcohol + NAD+ = a ketone + NADH + H+


Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Oppermann94: Oppermann FB, Steinbuchel A (1994). "Identification and molecular characterization of the aco genes encoding the Pelobacter carbinolicus acetoin dehydrogenase enzyme system." J Bacteriol 176(2);469-85. PMID: 8110297

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Mon May 2, 2016, biocyc13.