CHEBI:16016 - dihydroxyacetone

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ChEBI Name dihydroxyacetone
ChEBI ID CHEBI:16016
Definition A ketotriose consisting of acetone bearing hydroxy substituents at positions 1 and 3. The simplest member of the class of ketoses and the parent of the class of glycerones.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:39809, CHEBI:5453, CHEBI:14340, CHEBI:24354
Supplier Information ChemicalBook:CB6306814, eMolecules:979314, ZINC000084397769
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Wikipedia License
Dihydroxyacetone ( ; DHA), also known as glycerone, is a simple saccharide (a triose) with formula C3H6O3. DHA is primarily used as an ingredient in sunless tanning products. It is often derived from plant sources such as sugar beets and sugar cane, and by the fermentation of glycerin.
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Formula C3H6O3
Net Charge 0
Average Mass 90.078
Monoisotopic Mass 90.03169
InChI InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2
InChIKey RXKJFZQQPQGTFL-UHFFFAOYSA-N
SMILES C(CO)(CO)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing dihydroxyacetone (CHEBI:16016) has role Escherichia coli metabolite (CHEBI:76971)
dihydroxyacetone (CHEBI:16016) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
dihydroxyacetone (CHEBI:16016) has role antifungal agent (CHEBI:35718)
dihydroxyacetone (CHEBI:16016) has role human metabolite (CHEBI:77746)
dihydroxyacetone (CHEBI:16016) has role metabolite (CHEBI:25212)
dihydroxyacetone (CHEBI:16016) has role mouse metabolite (CHEBI:75771)
dihydroxyacetone (CHEBI:16016) is a ketotriose (CHEBI:24982)
dihydroxyacetone (CHEBI:16016) is a primary α-hydroxy ketone (CHEBI:139590)
Incoming 1-hydroxy-3-methoxyacetone (CHEBI:37551) has functional parent dihydroxyacetone (CHEBI:16016)
1-palmitoylglycerone 3-phosphate (CHEBI:17868) has functional parent dihydroxyacetone (CHEBI:16016)
1-stearoylglycerone 3-phosphate (CHEBI:36476) has functional parent dihydroxyacetone (CHEBI:16016)
dihydroxyacetone phosphate (CHEBI:16108) has functional parent dihydroxyacetone (CHEBI:16016)
glycerone derivative (CHEBI:24358) has functional parent dihydroxyacetone (CHEBI:16016)
glycerone phosphate(2−) (CHEBI:57642) has functional parent dihydroxyacetone (CHEBI:16016)
glycerone sulfate (CHEBI:27894) has functional parent dihydroxyacetone (CHEBI:16016)
IUPAC Name
1,3-dihydroxypropan-2-one
Synonyms Sources
1,3-Dihydroxy-2-propanone KEGG COMPOUND
1,3-Dihydroxyacetone KEGG COMPOUND
1,3-Dihydroxydimethyl ketone ChemIDplus
1,3-Dihydroxypropan-2-one KEGG COMPOUND
1,3-Dihydroxypropanone ChemIDplus
1,3-propanediol-2-one ChEBI
α,α'-dihydroxyacetone HMDB
Bis(hydroxymethyl) ketone HMDB
DHA ChEBI
Dihydroxyacetone KEGG COMPOUND
DIHYDROXYACETONE PDBeChem
dihydroxyacetone UniProt
Glycerone KEGG COMPOUND
Manual Xrefs Databases
2HA PDBeChem
C00184 KEGG COMPOUND
D07841 KEGG DRUG
DB01775 DrugBank
Dihydroxyacetone Wikipedia
DIHYDROXYACETONE MetaCyc
HMDB0001882 HMDB
View more database links
Registry Numbers Types Sources
1740268 Reaxys Registry Number Reaxys
96-26-4 CAS Registry Number KEGG COMPOUND
96-26-4 CAS Registry Number NIST Chemistry WebBook
96-26-4 CAS Registry Number ChemIDplus
Citations
Liu YP, Sun Y, Tan C, Li H, Zheng XJ, Jin KQ, Wang G (2013)
Efficient production of dihydroxyacetone from biodiesel-derived crude glycerol by newly isolated Gluconobacter frateurii.
Bioresource technology 142, 384-389 [PubMed:23748086]
[show Abstract]
Dapsens PY, Mondelli C, Pérez-Ramírez J (2013)
Highly selective Lewis acid sites in desilicated MFI zeolites for dihydroxyacetone isomerization to lactic acid.
ChemSusChem 6, 831-839 [PubMed:23554234]
[show Abstract]
Zhou YJ, Yang W, Wang L, Zhu Z, Zhang S, Zhao ZK (2013)
Engineering NAD+ availability for Escherichia coli whole-cell biocatalysis: a case study for dihydroxyacetone production.
Microbial cell factories 12, 103 [PubMed:24209782]
[show Abstract]
Chikazawa M, Otaki N, Shibata T, Miyashita H, Kawai Y, Maruyama S, Toyokuni S, Kitaura Y, Matsuda T, Uchida K (2013)
Multispecificity of immunoglobulin M antibodies raised against advanced glycation end products: involvement of electronegative potential of antigens.
The Journal of biological chemistry 288, 13204-13214 [PubMed:23543734]
[show Abstract]
Rasrendra CB, Fachri BA, Makertihartha IG, Adisasmito S, Heeres HJ (2011)
Catalytic conversion of dihydroxyacetone to lactic acid using metal salts in water.
ChemSusChem 4, 768-777 [PubMed:21598406]
[show Abstract]
Wu J, Li MH, Lin JP, Wei DZ (2011)
Determination of dihydroxyacetone and glycerol in fermentation process by GC after n-methylimidazole catalyzed acetylation.
Journal of chromatographic science 49, 375-378 [PubMed:21549029]
[show Abstract]
Stopiglia CD, Vieira FJ, Mondadori AG, Oppe TP, Scroferneker ML (2011)
In vitro antifungal activity of dihydroxyacetone against causative agents of dermatomycosis.
Mycopathologia 171, 267-271 [PubMed:20936361]
[show Abstract]
Last Modified
06 February 2018