Record Information
Version2.0
Creation Date2012-05-31 13:54:55 -0600
Update Date2015-09-13 12:56:12 -0600
Secondary Accession Numbers
  • ECMDB01882
Identification
Name:Dihydroxyacetone
Description:Dihydroxyacetone or DHA, also known as glycerone, is a simple carbohydrate (a triose) with formula C3H6O3. It is an intermedate in the process of glycerolipid metabolism. It is converted from glycerol by glycerol dehydrogenase, NAD (EC:1.1.1.6) and converts to glycerone phosphate by dihydroxyacetone kinase (EC:2.7.1.-). (KEGG)
Structure
Thumb
Synonyms:
  • 1,3-Dihydroxy-2-propanone
  • 1,3-Dihydroxyacetone
  • 1,3-Dihydroxydimethyl ketone
  • 1,3-Dihydroxypropan-2-one
  • 1,3-Dihydroxypropanone
  • A,a'-Dihydroxyacetone
  • Aliphatic ketone
  • Bis(hydroxymethyl) ketone
  • Chromelin
  • Dihydroxy-acetone
  • Dihydroxyacetone
  • Dihyxal
  • Glycerone
  • Ketochromin
  • Otan
  • Oxantin
  • Oxatone
  • Protosol
  • Soleal
  • Triulose
  • Viticolor
Chemical Formula:C3H6O3
Weight:Average: 90.0779
Monoisotopic: 90.031694058
InChI Key:RXKJFZQQPQGTFL-UHFFFAOYSA-N
InChI:InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2
CAS number:96-26-4
IUPAC Name:1,3-dihydroxypropan-2-one
Traditional IUPAC Name:dihydroxyacetone
SMILES:OCC(=O)CO
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Glycerone or derivatives
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:90 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility838.0 mg/mLALOGPS
logP-1.6ALOGPS
logP-1.5ChemAxon
logS0.97ALOGPS
pKa (Strongest Acidic)13.49ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.6 m3·mol-1ChemAxon
Polarizability8.1 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Propanoate metabolismPW000940 Pw000940Pw000940 greyscalePw000940 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0w2j-1900000000-b3783d91181e1657545dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0wa0-5900000000-f95dddc55209203877e3View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0a59-9000000000-089abb74f439c9265bb6View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0gvk-1900000000-bd875a5207eb70c5beb8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0w2j-1900000000-b3783d91181e1657545dView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0wa0-5900000000-f95dddc55209203877e3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0w2j-2900000000-f84cc49dd11822409addView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00g0-9320000000-6bdc226e79d3bc473a66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-7bb646a5cb5ca825e7b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fu-9000000000-ab60a50ef2013d762751View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-ef7c943cff3a9adfd1edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-0e836f7fe0512bb62662View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-059i-9000000000-d1a13699d0d0cbea36b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-57da9a85ff22593c3ab3View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. Pubmed: 6321058
  • Blake SM, Treble NJ: Popliteus tendon tenosynovitis. Br J Sports Med. 2005 Dec;39(12):e42; discussion e42. Pubmed: 16306488
  • Forest SE, Grothaus JT, Ertel KD, Rader C, Plante J: Fluorescence spectral imaging of dihydroxyacetone on skin in vivo. Photochem Photobiol. 2003 May;77(5):524-30. Pubmed: 12812295
  • GOLDMAN L, WITTGENSTEIN E, BLANEY D, GOLDMAN J, SAWYER F: Studies of some physical properties of the dihydroxyacetone color complex. J Invest Dermatol. 1961 Apr;36:233-4. Pubmed: 13706567
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Kerr HH, Pantely GA, Metcalfe J, Welch JE: Reduction of human blood O2 affinity using dihydroxyacetone, phosphate, and pyruvate. J Appl Physiol. 1979 Sep;47(3):478-81. Pubmed: 118143
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Phillipou G, Seaborn CJ, Phillips PJ: Re-evaluation of the fructosamine reaction. Clin Chem. 1988 Aug;34(8):1561-4. Pubmed: 3402055
  • Taylor CR, Kwangsukstith C, Wimberly J, Kollias N, Anderson RR: Turbo-PUVA: dihydroxyacetone-enhanced photochemotherapy for psoriasis: a pilot study. Arch Dermatol. 1999 May;135(5):540-4. Pubmed: 10328194
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • WITTGENSTEIN E, BERRY HK: Staining of skin with dihydroxyacetone. Science. 1960 Sep 30;132(3431):894-5. Pubmed: 13845496
  • WITTGENSTEIN E, GUEST GM: Biochemical effects of dihydroxyacetone. J Invest Dermatol. 1961 Nov;37:421-6. Pubmed: 14007781
Synthesis Reference:Hochuli, Erich; Taylor, Keith E.; Dutler, Hans. Dihydroxyacetone reductase from Mucor javanicus. 2. Identification of the physiological substrate and reactivity towards related compounds. European Journal of Biochemistry (1977), 75(2), 433-9.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16016
HMDB IDHMDB01882
Pubchem Compound ID670
Kegg IDC00184
ChemSpider ID650
WikipediaDihydroxyacetone
BioCyc IDDIHYDROXYACETONE
EcoCyc IDDIHYDROXYACETONE
Ligand Expo2HA

Enzymes

General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
Gene Name:
ptsI
Uniprot ID:
P08839
Molecular weight:
63561
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NAD-dependent oxidation of glycerol to dihydroxyacetone (glycerone). Allows microorganisms to utilize glycerol as a source of carbon under anaerobic conditions. In E.coli, an important role of gldA is also likely to regulate the intracellular level of dihydroxyacetone by catalyzing the reverse reaction, i.e. the conversion of dihydroxyacetone into glycerol. Possesses a broad substrate specificity, since it is also able to oxidize 1,2-propanediol and to reduce glycolaldehyde, methylglyoxal and hydroxyacetone into ethylene glycol, lactaldehyde and 1,2-propanediol, respectively
Gene Name:
gldA
Uniprot ID:
P0A9S5
Molecular weight:
38712
Reactions
Glycerol + NAD(+) = glycerone + NADH.
General function:
Involved in glycerone kinase activity
Specific function:
Dihydroxyacetone binding subunit of the dihydroxyacetone kinase, which is responsible for phosphorylating dihydroxyacetone. Binds covalently dihydroxyacetone in hemiaminal linkage. Acts also as a corepressor of dhaR by binding to its sensor domain, in the absence of dihydroxyacetone
Gene Name:
dhaK
Uniprot ID:
P76015
Molecular weight:
38215
General function:
Involved in catalytic activity
Specific function:
D-fructose 6-phosphate = glycerone + D- glyceraldehyde 3-phosphate
Gene Name:
fsaB
Uniprot ID:
P32669
Molecular weight:
23555
Reactions
D-fructose 6-phosphate = glycerone + D-glyceraldehyde 3-phosphate.
General function:
Involved in glycerone kinase activity
Specific function:
ADP-binding subunit of the dihydroxyacetone kinase, which is responsible for phosphorylating dihydroxyacetone. DhaL- ADP receives a phosphoryl group from dhaM and transmits it to dihydroxyacetone. DhaL-ADP acts also as a coactivator by binding to the sensor domain of dhaR. DhaL-ATP is inactive
Gene Name:
dhaL
Uniprot ID:
P76014
Molecular weight:
22632
General function:
Involved in catalytic activity
Specific function:
D-fructose 6-phosphate = glycerone + D- glyceraldehyde 3-phosphate
Gene Name:
fsaA
Uniprot ID:
P78055
Molecular weight:
22997
Reactions
D-fructose 6-phosphate = glycerone + D-glyceraldehyde 3-phosphate.
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Phosphotransferase subunit of the dihydroxyacetone kinase, which is responsible for phosphorylating dihydroxyacetone. DhaM serves as the phosphoryl donor. It is phosphorylated by HPr, then it donates its phosphoryl group to dhaL-ADP, which eventually transmits it to dihydroxyacetone
Gene Name:
dhaM
Uniprot ID:
P37349
Molecular weight:
51448
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine.
Protein EIIA N(pi)-phospho-L-histidine + dhaL-ADP = protein EIIA + dhaL-ATP.
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
Gene Name:
ptsH
Uniprot ID:
P0AA04
Molecular weight:
9119
Reactions
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine.

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368