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.
|
Read full article at Wikipedia
|
InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2 |
RXKJFZQQPQGTFL-UHFFFAOYSA-N |
|
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
|
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
1,3-dihydroxypropan-2-one
|
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
|
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
|
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] The efficient production of dihydroxyacetone (DHA) on biodiesel-derived glycerol based media was developed. A newly isolated strain, Gluconobacter frateurii CGMCC 5397, could convert crude glycerol to DHA with high yield and productivity. In shake-flask fermentation, the DHA concentration of 73.1 gl(-1) was attained at 48 h using an optimum medium containing biodiesel-derived crude glycerol. When fed-batch fermentation was carried out in a 7-l stirred bioreactor with crude glycerol, the DHA concentration, productivity, and yield were 125.8 gl(-1), 2.6 gl(-1)h(-1), and 90.5% at 48 h, respectively. This study suggests that the inexpensive biodiesel-derived crude glycerol could be utilized for efficient production of DHA by G. frateurii. | 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] Desilication of commercial MFI-type (ZSM-5) zeolites in solutions of alkali metal hydroxides is demonstrated to generate highly selective heterogeneous catalysts for the aqueous-phase isomerization of biobased dihydroxyacetone (DHA) to lactic acid (LA). The best hierarchical ZSM-5 sample attains a LA selectivity exceeding 90 %, which is comparable to that of the state-of-the-art catalyst (i.e., the Sn-beta zeolite); this optimized hierarchical catalyst is recyclable over three runs. The Lewis acid sites, which are created through desilication along with the introduction of mesoporosity, are shown to play a crucial role in the formation of the desired product; these cannot be achieved by using other post-synthetic methods, such as steaming or impregnation of aluminum species. Desilication of other metallosilicates, such as Ga-MFI, also leads to high LA selectivity. In the presence of a soluble aluminum source, such as aluminum nitrate, alkaline-assisted alumination can introduce these unique Lewis acid centers in all-silica MFI zeolites. These findings highlight the potential of zeolites in the field of biomass-to-chemical conversion, and expand the applicability of desilication for the generation of selective catalytic centers. | 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]
BackgroundWhole-cell redox biocatalysis has been intensively explored for the production of valuable compounds because excellent selectivity is routinely achieved. Although the cellular cofactor level, redox state and the corresponding enzymatic activity are expected to have major effects on the performance of the biocatalysts, our ability remains limited to predict the outcome upon variation of those factors as well as the relationship among them.ResultsIn order to investigate the effects of cofactor availability on whole-cell redox biocatalysis, we devised recombinant Escherichia coli strains for the production of dihydroxyacetone (DHA) catalyzed by the NAD+-dependent glycerol dehydrogenase (GldA). In this model system, a water-forming NAD+ oxidase (NOX) and a NAD+ transporter (NTT4) were also co-expressed for cofactor regeneration and extracellular NAD+ uptake, respectively. We found that cellular cofactor level, NAD+/NADH ratio and NOX activity were not only strain-dependent, but also growth condition-dependent, leading to significant differences in specific DHA titer among different whole-cell biocatalysts. The host E. coli DH5α had the highest DHA specific titer of 0.81 g/gDCW with the highest NAD+/NADH ratio of 6.7 and NOX activity of 3900 U. The biocatalyst had a higher activity when induced with IPTG at 37°C for 8 h compared with those at 30°C for 8 h and 18 h. When cells were transformed with the ntt4 gene, feeding NAD+ during the cell culture stage increased cellular NAD(H) level by 1.44 fold and DHA specific titer by 1.58 fold to 2.13 g/gDCW. Supplementing NAD+ during the biotransformation stage was also beneficial to cellular NAD(H) level and DHA production, and the highest DHA productivity reached 0.76 g/gDCW/h. Cellular NAD(H) level, NAD+/NADH ratio, and NOX and GldA activity dropped over time during the biotransformation process.ConclusionsHigh NAD+/NADH ratio driving by NOX was very important for DHA production. Once cofactor was efficiently cycled, high cellular NAD(H) level was also beneficial for whole-cell redox biocatalysis. Our results indicated that NAD+ transporter could be applied to manipulate redox cofactor level for biocatalysis. Moreover, we suggested that genetically designed redox transformation should be carefully profiled for further optimizing whole-cell biocatalysis. | 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]
BackgroundAdvanced glycation end products (AGEs) can act as neoantigens to trigger immune responses.ResultsNatural IgM antibodies against AGEs recognize multiple molecules, including DNA and chemically modified proteins.ConclusionThere is a close relationship between the formation of AGEs and innate immune responses.SignificanceOur findings highlight AGEs and related modified proteins as a source of multispecific natural antibodies Advanced glycation end products (AGEs) are a heterogeneous and complex group of compounds that are formed when reducing sugars, such as dehydroascorbic acid, react in a nonenzymatic way with amino acids in proteins and other macromolecules. AGEs are prevalent in the diabetic vasculature and contribute to the development of atherosclerosis. The presence and accumulation of AGEs in many different cell types affect the extracellular and intracellular structure and function. In the present study, we studied the immune response to the dehydroascorbic acid-derived AGEs and provide multiple lines of evidence suggesting that the AGEs could be an endogenous source of innate epitopes recognized by natural IgM antibodies. Prominent IgM titers to the AGEs were detected in the sera of normal mice and were significantly accelerated by the immunization with the AGEs. Patients with systemic lupus erythematosus (SLE), a potentially fatal systemic autoimmune disease characterized by the increased production of autoantibodies, showed significantly higher serum levels of the IgM titer against the AGEs than healthy individuals. A progressive increase in the IgM response against the AGEs was also observed in the SLE-prone mice. Strikingly, a subset of monoclonal antibodies, showing a specificity toward the AGEs, prepared from normal mice immunized with the AGEs and from the SLE mice cross-reacted with the double-stranded DNA. Moreover, they also cross-reacted with several other modified proteins, including the acetylated proteins, suggesting that the multiple specificity of the antibodies might be ascribed, at least in part, to the increased electronegative potential of the proteins. These findings suggest that the protein modification by the endogenous carbonyl compounds, generating electronegative proteins, could be a source of multispecific natural antibodies. | 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] We herein present a study on the application of homogeneous catalysts in the form of metal salts on the conversion of trioses, such as dihydroxyacetone (DHA), and glyceraldehyde (GLY) to lactic acid (LA) in water. A wide range of metal salts (26 in total) were examined. Al(III) salts were identified as the most promising and essentially quantitative LA yields (>90 mol%) were obtained at 140 °C and a reaction time of 90 min. A reaction pathway is proposed and a kinetic model using the power law approach was developed for the conversion of DHA to LA with pyruvaldehyde (PRV) as the intermediate. Good agreement between experimental data and the model was obtained. Model predictions, supported by experiments, indicate that a high yield of LA is favoured in dilute solutions of DHA (0.1 M) at elevated temperatures (180 °C) and reaction times less than 10 min. | 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] A gas chromatographic method that accurately measures glycerol and dihydroxyacetone from a fermentation broth is described in this paper. The method incorporates a sample derivatization reaction using n-methylimidazole as catalyst in the presence of acetic anhydride. Resulting derivatives are separated on a DB-5 capillary column and flame ionization detector. Results show that 10 μL n-methylimidazole and 75 μL acetic anhydride are sufficient to complete the acetylation for glycerol and dihydroxyacetone at room temperature for 5 min. The present method exhibits good linearity at a concentration range of 1-100 g/L with excellent regression (R(2) > 0.9997). The limits of detection are 0.025 and 0.013 g/L for dihydroxyacetone and glycerol, respectively. The method has been successfully applied to the monitoring and control of the fermentation process, and recoveries are in the range of 95.5-98.8% with relative standard deviations below 1%. | 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] Dihydroxyacetone (DHA), a three-carbon sugar, is the browning ingredient in commercial sunless tanning formulations. DHA preparations have been used for more than 50 years and are currently highly popular for producing temporary pigmentation resembling an ultraviolet-induced tan. In this work, the in vitro antifungal activity of dihydroxyacetone was tested against causative agents of dermatomycosis, more specifically against dermatophytes and Candida spp. The antifungal activity was determined by the broth microdilution method according to the Clinical and Laboratory Standards Institute guidelines for yeasts and filamentous fungi. The data obtained show that the fungicidal activity varied from 1.6 to 50 mg ml(-1). DHA seems to be a promising substance for the treatment of dermatomycosis because it has antifungal properties at the same concentration used in artificial suntan lotions. Therefore, it is a potential low-toxicity antifungal agent that may be used topically because of its penetration into the corneal layers of the skin. |
|