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96-26-4

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96-26-4 Usage

Description

1,3-Dihydroxyacetone (DHA) is a colorless compound that is commonly used as an artificial tanning agent in cosmetics. It is also a UV protector and a color additive. DHA is known for its ability to react with amino acids found on the skin's epidermal layer, providing a temporary tanned appearance without the need for sun exposure.

Uses

Used in Cosmetics Industry:
1,3-Dihydroxyacetone is used as a self-tanning agent for providing a tanned appearance without the need for sun exposure. It reacts with amino acids on the skin's epidermal layer, and its effects last only a few days as the color fades with the natural shedding of the stained cells. It works best on slightly acidic skin.
Used in UV Protection:
1,3-Dihydroxyacetone, when combined with lawsone, becomes an FDA Category I (approved) UV protectant. This combination provides protection against harmful UV rays, reducing the risk of skin damage and premature aging.
Used in Pharmaceutical Industry:
1,3-Dihydroxyacetone is used as a certified reference material in several analytical applications, including pharmaceutical release testing and method development for qualitative and quantitative analyses. It helps ensure the quality and accuracy of pharmaceutical products.
Used in Food and Beverage Industry:
1,3-Dihydroxyacetone is also used in food and beverage quality control testing. It serves as a reference material for calibration requirements, ensuring the safety and quality of food and beverage products.

Preparation

Usually produced commercially from Bacillus macerans or Bacillus circulans fermentation of starch or starch hydrolysate

Check Digit Verification of cas no

The CAS Registry Mumber 96-26-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 6 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 96-26:
(4*9)+(3*6)+(2*2)+(1*6)=64
64 % 10 = 4
So 96-26-4 is a valid CAS Registry Number.
InChI:InChI=1/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2

96-26-4 Well-known Company Product Price

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  • Sigma-Aldrich

  • (PHR1430)  Dihydroxyacetone  pharmaceutical secondary standard; traceable to USP

  • 96-26-4

  • PHR1430-1G

  • 791.15CNY

  • Detail
  • USP

  • (1204102)  Dihydroxyacetone  United States Pharmacopeia (USP) Reference Standard

  • 96-26-4

  • 1204102-250MG

  • 4,326.66CNY

  • Detail

96-26-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name glycerone

1.2 Other means of identification

Product number -
Other names 2-Propanone, 1,3-dihydroxy-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:96-26-4 SDS

96-26-4Synthetic route

benzaldehyde
100-52-7

benzaldehyde

glycerol
56-81-5

glycerol

A

dihydroxyacetone
96-26-4

dihydroxyacetone

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With potassium hydroxide at 120℃; for 7h; Inert atmosphere;A n/a
B 99%
With C40H50IrNP2 at 100℃; for 3h; Inert atmosphere; chemoselective reaction;A 24 %Chromat.
B 46 %Chromat.
2-phenyl-1,3-dioxan-5-one
52941-82-9

2-phenyl-1,3-dioxan-5-one

dihydroxyacetone
96-26-4

dihydroxyacetone

Conditions
ConditionsYield
With hydrogenchloride In water at 80℃; for 2h; Reagent/catalyst; Inert atmosphere;96%
glycerol
56-81-5

glycerol

dihydroxyacetone
96-26-4

dihydroxyacetone

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water; acetonitrile at 60℃; under 760.051 Torr; for 12h;95%
With C32H30N4O4Pd2(2+); p-benzoquinone In water; acetonitrile at 23℃; for 4h; chemoselective reaction;92%
With C30H42N4O6Pd2(2+)*2CF3O3S(1-); p-benzoquinone In water; acetonitrile at 55℃; for 24h; Darkness; chemoselective reaction;87%
glycerol
56-81-5

glycerol

A

glycolic Acid
79-14-1

glycolic Acid

B

glyceric acid
473-81-4

glyceric acid

C

dihydroxyacetone
96-26-4

dihydroxyacetone

Conditions
ConditionsYield
With oxygen In water at 60℃; Catalytic behavior; Reagent/catalyst; Autoclave; chemoselective reaction;A 8.9%
B 89.9%
C 6.8%
With oxygen In water at 80℃; under 7500.75 Torr; for 2h; pH=6.7; Reagent/catalyst; Autoclave;
With oxygen In water at 60℃; under 3750.38 Torr; for 24h; Catalytic behavior; Kinetics; Reagent/catalyst; Time; High pressure;A 7.8 %Chromat.
B 55.4 %Chromat.
C 7.7 %Chromat.
glycerol
56-81-5

glycerol

A

formaldehyd
50-00-0

formaldehyd

B

tartronic acid
80-69-3

tartronic acid

C

glyceric acid
473-81-4

glyceric acid

D

dihydroxyacetone
96-26-4

dihydroxyacetone

Conditions
ConditionsYield
With oxygen In water at 60℃; Catalytic behavior; Reagent/catalyst; Autoclave; chemoselective reaction;A n/a
B n/a
C 84.9%
D 6.5%
glycerol
56-81-5

glycerol

A

glyceric acid
473-81-4

glyceric acid

B

dihydroxyacetone
96-26-4

dihydroxyacetone

C

Glyceraldehyde
56-82-6

Glyceraldehyde

Conditions
ConditionsYield
With oxygen In water at 60℃; Catalytic behavior; Reagent/catalyst; Autoclave; chemoselective reaction;A 84.2%
B 9.5%
C 6.3%
With oxygen In water at 60℃; under 760.051 Torr; for 4h; Catalytic behavior;
With Pt-MCM-41 catalyst; oxygen In water at 69.84℃; under 760.051 Torr; pH=Ca. 7; Kinetics; Catalytic behavior; Reagent/catalyst; Temperature;
formaldehyd
50-00-0

formaldehyd

dihydroxyacetone
96-26-4

dihydroxyacetone

Conditions
ConditionsYield
With Thiamine hydrochloride; triethylamine In N,N-dimethyl-formamide at 75℃;80%
With 3-hexylbenzothiazolium bromide; triethylamine In ethanol at 100℃; for 0.5h; Temperature; Reagent/catalyst; Inert atmosphere;63.5%
With triethylamine; 3-ethylbenzothiazolium bromide In ethanol at 100℃; for 0.5h; Product distribution; Mechanism; different reagents, solvents catalysts, reaction time and temperature;
1,3-Dichloroacetone
534-07-6

1,3-Dichloroacetone

dihydroxyacetone
96-26-4

dihydroxyacetone

Conditions
ConditionsYield
With Amberlyst A26-OH- form resin In acetonitrile at 20℃; for 3h; Solvent;80%
With sodium hydroxide; ethanol; water at -22℃;
With sodium hydroxide at 50℃; for 1h; Temperature; Reagent/catalyst;15.35 g
acetophenone
98-86-2

acetophenone

glycerol
56-81-5

glycerol

A

dihydroxyacetone
96-26-4

dihydroxyacetone

B

1-Phenylethanol
98-85-1, 13323-81-4

1-Phenylethanol

Conditions
ConditionsYield
With [IrCl(COD)(C3H2N2(3,4,5-trimethoxybenzyl)(n-Bu))]; potassium hydroxide at 120℃; for 7h; Inert atmosphere;A n/a
B 80%
With C40H50IrNP2 at 120℃; for 1h; Inert atmosphere; chemoselective reaction;A 6 %Chromat.
B 8 %Chromat.
glycerol
56-81-5

glycerol

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

dihydroxyacetone
96-26-4

dihydroxyacetone

C

Glyceraldehyde
56-82-6

Glyceraldehyde

Conditions
ConditionsYield
With silver dodecamolybdophosphate; oxygen In water at 60℃; under 3750.38 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Autoclave;A 72%
B n/a
C n/a
With phosphomolybdic acid; dihydrogen peroxide at 60℃; for 0.133333h; Catalytic behavior;A 42%
B n/a
C n/a
With MoO40W12(3-)*Cr(3+); oxygen In water at 60℃; under 7500.75 Torr; for 20h; Autoclave;A 12.9%
B 8.6%
C 5.9%
1,3-diiodopropan-2-one
6305-40-4

1,3-diiodopropan-2-one

dihydroxyacetone
96-26-4

dihydroxyacetone

Conditions
ConditionsYield
With Amberlyst A26-OH- form resin In acetonitrile at 20℃; for 3h;66%
1,3-dibromoroacetone
816-39-7

1,3-dibromoroacetone

dihydroxyacetone
96-26-4

dihydroxyacetone

Conditions
ConditionsYield
With Amberlyst A26-OH- form resin In acetonitrile at 20℃; for 3h;64%
Glyceraldehyde
56-82-6

Glyceraldehyde

dihydroxyacetone
96-26-4

dihydroxyacetone

Conditions
ConditionsYield
With D-glucose; chromium(III) chloride hexahydrate In water at 110℃; for 0.5h;60.2%
In aq. phosphate buffer59%
With pyridine
glycerol
56-81-5

glycerol

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

glyceric acid
473-81-4

glyceric acid

C

dihydroxyacetone
96-26-4

dihydroxyacetone

D

acetic acid
64-19-7

acetic acid

E

Glyceraldehyde
56-82-6

Glyceraldehyde

Conditions
ConditionsYield
With oxygen In water at 60℃; under 3750.38 Torr; for 5h; Catalytic behavior; Autoclave;A 45%
B n/a
C n/a
D n/a
E n/a
2-C-(hydroxymethyl)-D-glycero-D-gulo-heptose
367261-89-0

2-C-(hydroxymethyl)-D-glycero-D-gulo-heptose

A

D-Arabinose
10323-20-3

D-Arabinose

B

dihydroxyacetone
96-26-4

dihydroxyacetone

C

D-glycero-D-ido-oct-2-ulose
1016606-96-4

D-glycero-D-ido-oct-2-ulose

Conditions
ConditionsYield
With molybdic acid In water at 85℃; for 8h;A n/a
B n/a
C 40%
glycerol
56-81-5

glycerol

A

glycolic Acid
79-14-1

glycolic Acid

B

LACTIC ACID
849585-22-4

LACTIC ACID

C

dihydroxyacetone
96-26-4

dihydroxyacetone

D

Glyceraldehyde
56-82-6

Glyceraldehyde

Conditions
ConditionsYield
With dihydrogen peroxide In water at 60℃; for 1h; Reagent/catalyst; Temperature; Time;A n/a
B 36%
C n/a
D n/a
glycerol
56-81-5

glycerol

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

dihydroxyacetone
96-26-4

dihydroxyacetone

C

2-oxopropanal
78-98-8

2-oxopropanal

Conditions
ConditionsYield
With MoO40W12(3-)*Al(3+); oxygen In water at 60℃; under 7500.75 Torr; for 20h; Kinetics; Autoclave;A 25%
B 14.5%
C 6.2%
Glyceraldehyde
56-82-6

Glyceraldehyde

A

dihydroxyacetone
96-26-4

dihydroxyacetone

B

2-oxopropanal
78-98-8

2-oxopropanal

Conditions
ConditionsYield
With MoO40W12(3-)*Al(3+) In water at 60℃; under 7500.75 Torr; for 20h; Autoclave; Inert atmosphere;A 25%
B 9%
glycerol
56-81-5

glycerol

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

dihydroxyacetone
96-26-4

dihydroxyacetone

Conditions
ConditionsYield
With MoO40W12(3-)*Fe(3+); oxygen In water at 60℃; under 7500.75 Torr; for 20h; Autoclave;A 19.8%
B 13.9%
glycerol
56-81-5

glycerol

A

dihydroxyacetone
96-26-4

dihydroxyacetone

B

Glyceraldehyde
56-82-6

Glyceraldehyde

C

2-oxopropanal
78-98-8

2-oxopropanal

Conditions
ConditionsYield
With 3H(1+)*MoO40W12(3-); oxygen In water at 60℃; under 7500.75 Torr; for 20h; Autoclave;A 16%
B 14.9%
C 8.4%
glycerol
56-81-5

glycerol

A

glycolic Acid
79-14-1

glycolic Acid

B

3-hydroxy-2-oxopropionic acid
1113-60-6

3-hydroxy-2-oxopropionic acid

C

dihydroxyacetone
96-26-4

dihydroxyacetone

Conditions
ConditionsYield
With pyridine; dodecacarbonyl triosmium; dihydrogen peroxide In acetonitrile at 60℃; for 13h; Kinetics; Temperature;A 8%
B 1.5%
C 7.5%
With pyridine; dodecacarbonyl triosmium; dihydrogen peroxide In acetonitrile at 60℃; for 5h; Kinetics; Temperature;A 4%
B 2.7%
C 8.3%
pyridine
110-86-1

pyridine

Glyceraldehyde
56-82-6

Glyceraldehyde

dihydroxyacetone
96-26-4

dihydroxyacetone

D-glucose
50-99-7

D-glucose

A

dihydroxyacetone
96-26-4

dihydroxyacetone

B

Glyceraldehyde
56-82-6

Glyceraldehyde

Conditions
ConditionsYield
With sodium carbonate; sodium sulfite bei der Destillation;
With sodium carbonate; sodium sulfite
D-glucose
50-99-7

D-glucose

dihydroxyacetone
96-26-4

dihydroxyacetone

Conditions
ConditionsYield
Einw. von Tyrothrix tenuis;
dihydroxyacetone
96-26-4

dihydroxyacetone

dihydroxyacetone phosphate
57-04-5

dihydroxyacetone phosphate

Conditions
ConditionsYield
With phosphoenolpyruvic acid; ATP for 0.75h; Enzymatic reaction;100%
With sodium hydroxide; acetic acid phosphoric acid-anhydride; PAN-immobilized acetate kinase; PAN-immobilized glycerol kinase; ATP; 2-hydroxyethanethiol; magnesium chloride for 16h; Ambient temperature; pH=6.7-7.0;98%
With pyridine; trichlorophosphate In acetonitrile 1) 0-5 degC, 20 min, 2) room temp., 20 min;60 % Turnov.
dihydroxyacetone
96-26-4

dihydroxyacetone

benzyl (S)-1-oxopropan-2-ylcarbamate
82353-55-7, 105499-10-3, 141884-07-3, 111955-03-4

benzyl (S)-1-oxopropan-2-ylcarbamate

(3R,4S,5S)-PhCH2OC(O)NHCH(Me)CH(OH)CH(OH)C(O)CH2OH
1274764-14-5

(3R,4S,5S)-PhCH2OC(O)NHCH(Me)CH(OH)CH(OH)C(O)CH2OH

Conditions
ConditionsYield
With L-rhamnulose-1-phosphate aldolase at 25℃; for 24h; pH=7; Kinetics; Reagent/catalyst; aq. sodium borate buffer; Enzymatic reaction; stereoselective reaction;100%
With L-rhamnulose-1-phosphate aldolase In N,N-dimethyl-formamide at 25℃; for 24h; pH=7.5; Aldol reaction; aq. buffer; Enzymatic reaction; optical yield given as %de; stereoselective reaction;99 %Chromat.
dihydroxyacetone
96-26-4

dihydroxyacetone

2(S)-hydroxypropanal
3913-64-2

2(S)-hydroxypropanal

6-deoxy-L-arabino-2-hexulose
14807-05-7

6-deoxy-L-arabino-2-hexulose

Conditions
ConditionsYield
With L-rhamnulose-1-phosphate aldolase at 25℃; for 24h; pH=7; aq. sodium borate buffer; Enzymatic reaction; stereoselective reaction;100%
dihydroxyacetone
96-26-4

dihydroxyacetone

ethyl tetrahydro-2H-pyran-4-carbimidate hydrochloride
1210226-49-5

ethyl tetrahydro-2H-pyran-4-carbimidate hydrochloride

(2-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)methanol

(2-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)methanol

Conditions
ConditionsYield
With ammonium hydroxide at 90℃; for 4h; Sealed tube;100%
dihydroxyacetone
96-26-4

dihydroxyacetone

tert-butyl 3-carbamimidoylazetidine-1-carboxylate

tert-butyl 3-carbamimidoylazetidine-1-carboxylate

tert-butyl 3-(5-(hydroxymethyl)-1H-imidazol-2-yl)azetidine-1-carboxylate

tert-butyl 3-(5-(hydroxymethyl)-1H-imidazol-2-yl)azetidine-1-carboxylate

Conditions
ConditionsYield
With ammonium hydroxide at 90℃; for 4h;100%
dihydroxyacetone
96-26-4

dihydroxyacetone

LACTIC ACID
849585-22-4

LACTIC ACID

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 24h; Catalytic behavior; Reagent/catalyst; Green chemistry;99.7%
With tin containing MWW type β-zeolite In water at 109.84℃; for 6h; Reagent/catalyst;96%
With indium(III) triflate In water at 109.84℃; for 2h; Time; Reagent/catalyst;95%
methanol
67-56-1

methanol

dihydroxyacetone
96-26-4

dihydroxyacetone

methyl lactate
547-64-8

methyl lactate

Conditions
ConditionsYield
With tin containing MWW type β-zeolite In decane at 119.84℃; for 24h; Reagent/catalyst;99%
With Y-zeolite H-USY-6 In water at 115℃; for 24h; Inert atmosphere;96%
With Sn(salen) functionalized [OMIm]Br at 160℃; under 15001.5 Torr; for 2h; Inert atmosphere; Autoclave; chemoselective reaction;95.5%
dihydroxyacetone
96-26-4

dihydroxyacetone

p-toluidine
106-49-0

p-toluidine

N-(4-methylphenyl)formamide
3085-54-9

N-(4-methylphenyl)formamide

Conditions
ConditionsYield
With Cu/Al2O3; dihydrogen peroxide In water at 50℃; for 12h; Green chemistry;99%
dihydroxyacetone
96-26-4

dihydroxyacetone

2,5-dihydro-2,2,4-tri-(hydroxymethyl)-1,3-oxazole

2,5-dihydro-2,2,4-tri-(hydroxymethyl)-1,3-oxazole

Conditions
ConditionsYield
With ammonium hydroxide In methanol; chloroform at 22℃; for 18h;98%
With ammonia In methanol at 20 - 24℃;
dihydroxyacetone
96-26-4

dihydroxyacetone

dibutylamine
111-92-2

dibutylamine

N,N-dibutylformamide
761-65-9

N,N-dibutylformamide

Conditions
ConditionsYield
With Cu/Al2O3; dihydrogen peroxide In water at 25℃; for 24h; Green chemistry;98%
dihydroxyacetone
96-26-4

dihydroxyacetone

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

(3R,4S)-1,3,4-trihydroxy-4-(2-nitrophenyl)butan-2-one
1114542-27-6

(3R,4S)-1,3,4-trihydroxy-4-(2-nitrophenyl)butan-2-one

Conditions
ConditionsYield
With (+)-(S)-2-amino-1-phenyl-3-(pyrrolidin-1-yl)propane; phosphotungstic acid In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Aldol reaction; optical yield given as %ee; enantioselective reaction;97%
dihydroxyacetone
96-26-4

dihydroxyacetone

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

1,3-dipalmitoyloxy-2-propanone
24472-45-5

1,3-dipalmitoyloxy-2-propanone

Conditions
ConditionsYield
With pyridine In chloroform at 20℃; for 48h;96%
With pyridine In dichloromethane at 20℃; for 16h; Inert atmosphere;95%
With pyridine In dichloromethane at 20℃; for 16h; Inert atmosphere;95%
dihydroxyacetone
96-26-4

dihydroxyacetone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1,3-bis-O-(tert-butyldimethylsilyl)-1,3-dihydroxy-2-propanone
127382-65-4

1,3-bis-O-(tert-butyldimethylsilyl)-1,3-dihydroxy-2-propanone

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 30℃;96%
With triethylamine In dichloromethane at 20℃; for 24h; silylation;95%
With dmap; triethylamine In dichloromethane at 25℃;92%
dihydroxyacetone
96-26-4

dihydroxyacetone

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

(3R,4S)-1,3,4-trihydroxy-4-(4-nitrophenyl)butan-2-one

(3R,4S)-1,3,4-trihydroxy-4-(4-nitrophenyl)butan-2-one

Conditions
ConditionsYield
With (2S,3R)-O-(n-octanoyl)-L-threonine In 1-methyl-pyrrolidin-2-one; water at 20℃; for 30h; Aldol addition; optical yield given as %ee; enantioselective reaction;96%
With (+)-(S)-2-amino-1-phenyl-3-(pyrrolidin-1-yl)propane; phosphotungstic acid In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Aldol reaction; optical yield given as %ee; enantioselective reaction;95%
dihydroxyacetone
96-26-4

dihydroxyacetone

dimethyl amine
124-40-3

dimethyl amine

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

Conditions
ConditionsYield
With Cu/Al2O3; dihydrogen peroxide In water at 25℃; for 24h; Green chemistry;96%
Wilkinson's catalyst
14694-95-2

Wilkinson's catalyst

dihydroxyacetone
96-26-4

dihydroxyacetone

A

chlorocarbonylbis(triphenylphosphine)rhodium(I)
15318-33-9, 16353-77-8, 13938-94-8

chlorocarbonylbis(triphenylphosphine)rhodium(I)

B

methane
34557-54-5

methane

Conditions
ConditionsYield
In further solvent(s) argon-filled glovebox, heating 7.5h at 130°C, cooling to room temp.; gas phase was sampled and analyzed by GC and GC-MS, liquid phase was analyzed by IR;A 85%
B 95%
dihydroxyacetone
96-26-4

dihydroxyacetone

N-methylaniline
100-61-8

N-methylaniline

N-methyl-N-phenylformamide
93-61-8

N-methyl-N-phenylformamide

Conditions
ConditionsYield
With Cu/Al2O3; dihydrogen peroxide In water at 50℃; for 12h; Green chemistry;95%
dihydroxyacetone
96-26-4

dihydroxyacetone

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

2-oxopropane-1,3-diyl dioctanoate
59925-18-7

2-oxopropane-1,3-diyl dioctanoate

Conditions
ConditionsYield
With pyridine In chloroform at 20℃; for 48h;94%
Stage #1: dihydroxyacetone With pyridine; dmap In dichloromethane for 0.0833333h;
Stage #2: n-octanoic acid chloride In dichloromethane at 0 - 20℃; for 16h;
73%
Stage #1: dihydroxyacetone With pyridine; dmap In dichloromethane for 0.0833333h; Cooling with ice;
Stage #2: n-octanoic acid chloride In dichloromethane at 0 - 20℃; for 16h;
73%
With pyridine In chloroform at 25℃; for 3h; Inert atmosphere;
dihydroxyacetone
96-26-4

dihydroxyacetone

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

rac-(2R,6R)-2,6-dicyclohexyl-4-hydroxymethyl-(1,3)-dioxane-(4S,5S)-4,5-diol

rac-(2R,6R)-2,6-dicyclohexyl-4-hydroxymethyl-(1,3)-dioxane-(4S,5S)-4,5-diol

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine at 20℃;94%
dihydroxyacetone
96-26-4

dihydroxyacetone

4-chloro-aniline
106-47-8

4-chloro-aniline

N-(4-chlorophenyl)formamide
2617-79-0

N-(4-chlorophenyl)formamide

Conditions
ConditionsYield
With Cu/Al2O3; dihydrogen peroxide In water at 50℃; for 12h; Green chemistry;94%
dihydroxyacetone
96-26-4

dihydroxyacetone

dimethoxyacetaldehyde
51673-84-8

dimethoxyacetaldehyde

C7H13O9P(1-)

C7H13O9P(1-)

Conditions
ConditionsYield
With acetic acid phosphoric acid-anhydride; fuculose-1-phosphate aldolase; ATP; acetate kinase; Citrobacter freundii dihydroxyacetone kinase In various solvent(s) pH=7.5;93.5%
dihydroxyacetone
96-26-4

dihydroxyacetone

4-Nitrophenylene-1,2-diamine
99-56-9

4-Nitrophenylene-1,2-diamine

2,2-bis(hydroxymethyl)-5-nitro-2,3-dihydro-1H-benzo[d]imidazole
1292785-77-3

2,2-bis(hydroxymethyl)-5-nitro-2,3-dihydro-1H-benzo[d]imidazole

Conditions
ConditionsYield
at 50℃; for 0.5h; Neat (no solvent); grinding;93%
dihydroxyacetone
96-26-4

dihydroxyacetone

aniline
62-53-3

aniline

Formanilid
103-70-8

Formanilid

Conditions
ConditionsYield
With Cu/Al2O3; dihydrogen peroxide at 50℃; for 12h; Catalytic behavior; Reagent/catalyst; Green chemistry;93%
Conditions
ConditionsYield
With E. coli BL21 (DE3) cells harboring pETDRhaD aldolase; sodium borate buffer In water; toluene at 37℃; for 16h; pH=7.6;A n/a
B 92%
dihydroxyacetone
96-26-4

dihydroxyacetone

isobutyraldehyde
78-84-2

isobutyraldehyde

rac-4-hydroxymethyl-(2R,6R)-2,6-diisopropyl-(1,3)-dioxane-(4S,5S)-4,5-diol

rac-4-hydroxymethyl-(2R,6R)-2,6-diisopropyl-(1,3)-dioxane-(4S,5S)-4,5-diol

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine at 20℃;92%
dihydroxyacetone
96-26-4

dihydroxyacetone

(E)-3-(4-methoxyphenyl)propenoyl chloride
34446-64-5, 42996-84-9

(E)-3-(4-methoxyphenyl)propenoyl chloride

1,3-bis-[(E)-3-(4-methoxyphenyl)-2-propenoyloxy]-2-oxopropane

1,3-bis-[(E)-3-(4-methoxyphenyl)-2-propenoyloxy]-2-oxopropane

Conditions
ConditionsYield
With dmap In pyridine at 20 - 100℃; for 1h; Product distribution / selectivity;92%
4-Trifluoromethylbenzaldehyde
455-19-6

4-Trifluoromethylbenzaldehyde

dihydroxyacetone
96-26-4

dihydroxyacetone

(3R,4S)-4-(4-(trifluoromethyl)phenyl)-1,3,4-trihydroxybutan-2-one
1114542-29-8

(3R,4S)-4-(4-(trifluoromethyl)phenyl)-1,3,4-trihydroxybutan-2-one

Conditions
ConditionsYield
With (+)-(S)-2-amino-1-phenyl-3-(pyrrolidin-1-yl)propane; phosphotungstic acid In 1-methyl-pyrrolidin-2-one at 20℃; for 36h; Aldol reaction; optical yield given as %ee; enantioselective reaction;92%

96-26-4Relevant articles and documents

One-pot biotransformation of glycerol into serinol catalysed by biocatalytic composites made of whole cells and immobilised enzymes

Ripoll, Magdalena,Velasco-Lozano, Susana,Jackson, Erienne,Diamanti, Eleftheria,Betancor, Lorena,López-Gallego, Fernando

supporting information, p. 1140 - 1146 (2021/02/26)

Biocatalytic cascades afford the development of economically sustainable and green processes. Herein we examined the unprecedented coupling of co-immobilisedGluconobacter oxydansand an isolated transaminase to synthesise serinol from glycerol. Through this approach, we manufactured up to 36 mM serinol, the highest titer ever reported for a non-fermentative biosynthesis. More importantly, similar productivities are obtained starting from the industrial by-product crude glycerol, demonstrating the possibilities of this hybrid heterogenenous biocatalyst for valorising bio-based raw materials.

Assembly of platinum nanoparticles and single-atom bismuth for selective oxidation of glycerol

Huang, Ning,Jiang, Dong,Jiang, Pingping,Leng, Yan,Lu, Yubing,Tian, Jinshu,Yue, Chenguang,Zhang, Pingbo,Zhang, Zihao

supporting information, p. 25576 - 25584 (2021/12/07)

Selective oxidation of the secondary hydroxyl group of glycerol to dihydroxyacetone (DHA) is an extremely challenging yet important reaction. The main difficulty is that the three hydroxyl groups in glycerol are prone to randomly oxidize, resulting in an unsatisfactory DHA selectivity. We show here that an assembly of platinum nanoparticles (NPs, ~2 nm) and N-stabilized single-atom bismuth (Bi), namely Pt/Bi@NC, shows a record-high DHA selectivity of ~95.0% towards glycerol oxidation under optimized reaction conditions. Characterization and theoretical calculations confirm that single-atom Bi in the vicinity of Pt NPs provides a preferred site to chelate with the primary -OH of glycerol, and its secondary -OH is prone to bind to a surface Pt atom of a Pt NP with a shorter Pt-H bond length. This as-formed unique adsorption configuration of glycerol on the Pt-Bi dual site significantly facilitates the oxidation of the secondary -OH of glycerol, thus contributing to a record-high selectivity to DHA. This journal is

Earth-abundant manganese oxide nanoneedle as highly efficient electrocatalyst for selective glycerol electro-oxidation to dihydroxyacetone

Chiang, Chia-Ying,Tran, Giang-Son,Vo, Truong-Giang

, p. 139 - 148 (2021/10/07)

In this study, earth-abundant manganese oxide (MnO2) was used as a catalyst for the electrocatalytic glycerol oxidation with a satisfactory yield and high selectivity under mild pH media; that is, the high current density of 6.0 mA cm?2 and selectivity of ca. 46% for dihydroxyacetone (DHA). MnO2 also exhibited reasonable durability without considerable changes for 3 h. More importantly, by combination of operando Raman and electrochemical studies, a tentative reaction pathway was also proposed. It is found that high selectivity of formic acid at low potential was due to predominant coverage of α-MnO2 on catalyst surface. Meanwhile, at high applied potential, partial transformation of α-MnO2 to δ-MnO2 causes decreasing C-C bond cleavage, leading to high DHA selectivity. The results of this work not only demonstrate that MnO2 holds promise as an efficient electrocatalyst for selectively producing DHA but also provides realistic details on electrochemically generated species under working condition.

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