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551-68-8 Usage

Description

D-Psicose, the D-enantiomer of psicose, is a C3 epimer of L-fructose and a clear colorless to yellow liquid or powder. It is a naturally occurring sugar alcohol that has gained attention for its potential health benefits, particularly in the area of weight management and metabolism.

Uses

Used in the Food Industry:
D-Psicose is used as a low-calorie sweetener for its ability to provide sweetness without contributing significant calories. It is suitable for those looking to reduce their calorie intake while still enjoying a sweet taste.
Used in the Health and Nutrition Industry:
D-Psicose is used as a dietary supplement for its potential to reduce fat accumulation. It achieves this by inhibiting intestinal α-glucosidase, an enzyme involved in the breakdown of carbohydrates, thus helping to control blood sugar levels and support weight management.
Used in the Pharmaceutical Industry:
D-Psicose is used as an active ingredient in medications aimed at managing obesity and related metabolic disorders. Its ability to reduce fat accumulation and control blood sugar levels makes it a promising candidate for the development of new drugs targeting these health issues.
Used in the Cosmetics Industry:
D-Psicose may be used as an ingredient in cosmetics and personal care products for its potential skin health benefits. Its ability to support healthy blood sugar levels and reduce inflammation could contribute to improved skin health and appearance.

Enzyme inhibitor

This ketohexose (FW = 180.16 g/mol), also known as D-ribo-2-hexulose and reportedly fpound in cane molasses, has epimers of D-psicose are Dfructose, D-sorbose, and L-tagatose. D-Psicose is an alternative substrate for fructokinase. The structural composition of D-psicose at 27°C in D2O is 22% a-pyranose, 24% b-pyranose, 39% a-furanose, and 15% bfuranose. Target(s): ketohexokinase, or hepatic fructokinase; also alternative substrate.

Check Digit Verification of cas no

The CAS Registry Mumber 551-68-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 1 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 551-68:
(5*5)+(4*5)+(3*1)+(2*6)+(1*8)=68
68 % 10 = 8
So 551-68-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5-,6+/m1/s1

551-68-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name D-psicose

1.2 Other means of identification

Product number -
Other names D-PSICOSE

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:551-68-8 SDS

551-68-8Synthetic route

(S)-4-((R)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)(hydroxy)methyl)-2,2-dimethyl-1,3-dioxan-5-one
915947-48-7

(S)-4-((R)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)(hydroxy)methyl)-2,2-dimethyl-1,3-dioxan-5-one

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With Dowex 50W-X2-200 In water100%
D-Fructose
57-48-7

D-Fructose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With immobilized D-psicose epimerase from Corynebacterium glutamicum KCCM 11046 In water at 30 - 50℃; Enzymatic reaction;75%
With triethylamine In ethanol for 15h; Heating; Yield given;
With D-tagatose 3-epimerase at 25℃; Enzymatic reaction;
D-Glucose
2280-44-6

D-Glucose

D-Glyceraldehyde
453-17-8

D-Glyceraldehyde

A

D-psicose
551-68-8

D-psicose

B

D-Sorbose
3615-56-3

D-Sorbose

Conditions
ConditionsYield
With recombinant Escherichia coli strain RhuA-Y; isopropyl β-D-thiogalactopyranoside for 20h; Enzymatic reaction; Overall yield = 35.6 %; Overall yield = 960 mg; diastereoselective reaction;A 10.4%
B 10.6%
With recombinant Escherichia coli strain FucA-Y; isopropyl β-D-thiogalactopyranoside for 20h; Enzymatic reaction; Overall yield = 35.6 %; Overall yield = 960 mg; diastereoselective reaction;A n/a
B n/a
D-glucose
50-99-7

D-glucose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With ammonium hydroxide
D-Allose
2595-97-3

D-Allose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With pyridine
Penta-O-acetyl-keto-D-psicose
98574-01-7

Penta-O-acetyl-keto-D-psicose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With barium dihydroxide; water
O1,O2-isopropylidene-O3-methanesulfonyl-β-D-fructopyranose

O1,O2-isopropylidene-O3-methanesulfonyl-β-D-fructopyranose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With sulfuric acid Behandeln des (mit Hilfe von Bariumcarbonat) von Sulfat-Ionen befreiten Reaktionsgemisches mit wss.Natronlauge;
D-Mannose
3458-28-4

D-Mannose

A

glycolic Acid
79-14-1

glycolic Acid

B

LACTIC ACID
849585-22-4

LACTIC ACID

C

D-Fructose
57-48-7

D-Fructose

D

D-psicose
551-68-8

D-psicose

E

D-glucose
50-99-7

D-glucose

F

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 78℃; for 0.333333h; Rate constant; Product distribution; Mechanism; isomerization equilibrium; degradation to acids; varying time, OH(1-) concentration 0.001 M to O.1 M; also in presence of Ca(2+) up to 0.06 M;
D-glucose
50-99-7

D-glucose

A

glycolic Acid
79-14-1

glycolic Acid

B

LACTIC ACID
849585-22-4

LACTIC ACID

C

D-Fructose
57-48-7

D-Fructose

D

D-Mannose
3458-28-4

D-Mannose

E

D-psicose
551-68-8

D-psicose

F

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 78℃; for 0.333333h; Rate constant; Product distribution; Mechanism; isomerization equilibrium; degradation to acids; varying time, OH(1-) concentration 0.001 M to O.1 M; also in presence of Ca(2+) up to 0.06 M;
D-altrose
1990-29-0

D-altrose

A

D-psicose
551-68-8

D-psicose

B

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With potassium hydroxide In water at 25℃; for 336h; Product distribution; Kinetics;
D-Allose
2595-97-3

D-Allose

A

D-psicose
551-68-8

D-psicose

B

D-altrose
1990-29-0

D-altrose

Conditions
ConditionsYield
With potassium hydroxide In water at 25℃; for 336h; Product distribution; Kinetics;
3.4.5.6-Tetra-O-acetyl-D-psicose
97833-77-7, 121351-05-1

3.4.5.6-Tetra-O-acetyl-D-psicose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With barium dihydroxide Yield given;
sulfuric acid
7664-93-9

sulfuric acid

O1,O2-isopropylidene-O3-methanesulfonyl-β-D-fructopyranose

O1,O2-isopropylidene-O3-methanesulfonyl-β-D-fructopyranose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
Behandeln des von Sulfat befreiten Reaktionsgemisches mit wss. Natronlauge;
D-Fructose
57-48-7

D-Fructose

water
7732-18-5

water

D-psicose
551-68-8

D-psicose

D-Fructose
57-48-7

D-Fructose

aqueous lead (II)-hydroxide

aqueous lead (II)-hydroxide

D-psicose
551-68-8

D-psicose

D-Fructose
57-48-7

D-Fructose

water
7732-18-5

water

A

D-Mannose
3458-28-4

D-Mannose

B

D-psicose
551-68-8

D-psicose

C

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
Behandeln mit einem basischen Anionenaustauscher;
Behandeln mit einem basischen Anionenaustauscher, zeitlicher Verlauf dieser Reaktion;
D-Fructose
57-48-7

D-Fructose

aqueous calcium hydroxide

aqueous calcium hydroxide

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

D-psicose
551-68-8

D-psicose

C

D-glucose
50-99-7

D-glucose

D

2-methyl-D-ribonic acid

2-methyl-D-ribonic acid

Conditions
ConditionsYield
at 25℃; zeitlicher Verlauf unter Ausschluss von Sauerstoff;
D-glucose
50-99-7

D-glucose

water
7732-18-5

water

A

D-Fructose
57-48-7

D-Fructose

B

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
Beim Erwaermen einer gepufferten Loesung vom pH 7.5;
D-glucose
50-99-7

D-glucose

ammonium hydroxide

ammonium hydroxide

A

D-Fructose
57-48-7

D-Fructose

B

D-Mannose
3458-28-4

D-Mannose

C

D-psicose
551-68-8

D-psicose

D-glucose
50-99-7

D-glucose

aqueous calcium hydroxide (0.04n)

aqueous calcium hydroxide (0.04n)

A

D-Fructose
57-48-7

D-Fructose

B

D-Mannose
3458-28-4

D-Mannose

C

D-psicose
551-68-8

D-psicose

D

2-methyl-D-ribonic acid

2-methyl-D-ribonic acid

Conditions
ConditionsYield
at 25℃; Zeitlicher Verlauf; unter Ausschluss von Sauerstoff; Produkt 5: DL-Milchsaeure;
D-Fructose
57-48-7

D-Fructose

A

D-Mannose
3458-28-4

D-Mannose

B

D-psicose
551-68-8

D-psicose

C

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With sodium hydroxide In water at 80℃; for 2h; pH=8.3; Kinetics; Lobry de Brujn-Alberda van Ekenstein reaction;A n/a
B 6.46 % Chromat.
C n/a
Stage #1: D-Fructose With aluminum oxide In pyridine for 9h; Heating;
Stage #2: With sulfuric acid In acetone for 2h; Further stages.;
A 13 % Chromat.
B 10 % Chromat.
C 22 % Chromat.
D-glucose
50-99-7

D-glucose

A

D-Fructose
57-48-7

D-Fructose

B

D-Mannose
3458-28-4

D-Mannose

C

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
With sodium hydroxide In water at 80℃; for 2h; pH=8.3; Kinetics; Lobry de Brujn-Alberda van Ekenstein reaction;A n/a
B n/a
C 3.28 % Chromat.
D-Mannose
3458-28-4

D-Mannose

A

D-Fructose
57-48-7

D-Fructose

B

D-psicose
551-68-8

D-psicose

C

D-glucose
50-99-7

D-glucose

D

D-arabino-[3]hexulose
53989-88-1

D-arabino-[3]hexulose

Conditions
ConditionsYield
With sodium aluminate In water at 35℃; for 20h; Product distribution; Further Variations:; reaction times;
D-Allose
2595-97-3

D-Allose

A

D-Fructose
57-48-7

D-Fructose

B

D-psicose
551-68-8

D-psicose

C

D-altrose
1990-29-0

D-altrose

Conditions
ConditionsYield
Stage #1: D-Allose With aluminum oxide In pyridine for 2h; Heating;
Stage #2: With sulfuric acid In acetone for 2h; Further stages.;
A 2 % Chromat.
B 50 % Chromat.
C 2 % Chromat.
2,3,4,5-tetra-O-acetyl-aldehydo-D-ribose
30571-54-1

2,3,4,5-tetra-O-acetyl-aldehydo-D-ribose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / 3-ethylbenzothiazolium bromide / ethanol / 72 h / 70 °C
2: barium hydroxide
View Scheme
tetra-O-acetyl-D-ribonic acid
61212-28-0

tetra-O-acetyl-D-ribonic acid

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: diethyl ether; PCl5
2: diethyl ether
3: copper (II)-acetate
4: barium hydroxide; water
View Scheme
tetra-O-acetyl-D-ribonic acid chloride
18968-65-5

tetra-O-acetyl-D-ribonic acid chloride

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diethyl ether
2: copper (II)-acetate
3: barium hydroxide; water
View Scheme
tetra-O-acetyl-1-diazo-keto-D-1-deoxy-psicose
6632-53-7

tetra-O-acetyl-1-diazo-keto-D-1-deoxy-psicose

D-psicose
551-68-8

D-psicose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper (II)-acetate
2: barium hydroxide; water
View Scheme
D-psicose
551-68-8

D-psicose

acetone
67-64-1

acetone

1,2:3,4-di-O-isopropylidene-β-D-psicofuranose
34626-95-4

1,2:3,4-di-O-isopropylidene-β-D-psicofuranose

Conditions
ConditionsYield
With hydrogenchloride; copper(II) sulfate In water at 20℃;73%
With sulfuric acid for 2h; Ambient temperature;
D-psicose
551-68-8

D-psicose

sodium cyanide
143-33-9

sodium cyanide

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

acetone
67-64-1

acetone

A

2,2':5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-altrono-1,4-lactone

2,2':5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-altrono-1,4-lactone

B

6-O-tert-butyldimethylsilyl-2-C-tert-butyldimethylsilyloxymethyl-2,3-O-isopropylidene-L-allono-1,4-lactone

6-O-tert-butyldimethylsilyl-2-C-tert-butyldimethylsilyloxymethyl-2,3-O-isopropylidene-L-allono-1,4-lactone

Conditions
ConditionsYield
Multistep reaction;A 19%
B 71%
D-psicose
551-68-8

D-psicose

benzoyl chloride
98-88-4

benzoyl chloride

A

C34H28O10
1232836-56-4

C34H28O10

B

C34H28O10
1232836-55-3

C34H28O10

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 3h;A 12%
B 54%
D-psicose
551-68-8

D-psicose

sodium cyanide
143-33-9

sodium cyanide

acetone
67-64-1

acetone

A

2,2':5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-altrono-1,4-lactone

2,2':5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-altrono-1,4-lactone

B

2,3:5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-allono-1,4-lactone
864846-18-4

2,3:5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-allono-1,4-lactone

Conditions
ConditionsYield
Stage #1: D-psicose; sodium cyanide With water Kiliani reaction; Heating;
Stage #2: With Amberlite IR-120 H(1+); water at 20℃;
Stage #3: acetone With copper(I) sulfate; sulfuric acid; copper(II) sulfate
A n/a
B 38%
2-aminopyridine
504-29-0

2-aminopyridine

D-psicose
551-68-8

D-psicose

A

D-altrose
1990-29-0

D-altrose

B

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
Stage #1: D-psicose With 2-aminopyridine; acetic acid at 90℃; Lobry de Bruyn-van Ekenstein transformation; Sealed tube;
Stage #2: 2-aminopyridine With acetic acid at 90℃; Sealed tube;
Stage #3: With trifluoroacetic acid at 65℃; for 1h;
A 11%
B 32%
D-psicose
551-68-8

D-psicose

1,2:3,4-di-O-isopropylidene-D-psicofuranose
29474-80-4

1,2:3,4-di-O-isopropylidene-D-psicofuranose

Conditions
ConditionsYield
With sulfuric acid; copper(II) sulfate; acetone
D-psicose
551-68-8

D-psicose

phenylhydrazine
100-63-0

phenylhydrazine

D-allose osazone
6164-71-2

D-allose osazone

Conditions
ConditionsYield
With sodium hydrogensulfite; acetic acid
D-psicose
551-68-8

D-psicose

dimethyl sulfate
77-78-1

dimethyl sulfate

methyl-[tetra-O-methyl-psicofuranoside
23259-20-3, 94942-15-1

methyl-[tetra-O-methyl-psicofuranoside

Conditions
ConditionsYield
With sodium hydroxide (+)-methyl-O-methyl-ξ-D-psicofuranoside>;
D-psicose
551-68-8

D-psicose

2,2,2-trifluoro-N-methyl-N-(2,2,2-trifluoroacetyl)acetamide
685-27-8

2,2,2-trifluoro-N-methyl-N-(2,2,2-trifluoroacetyl)acetamide

N-benzyloxyamine
622-33-3

N-benzyloxyamine

trifluoroacetylated psicose-O-benzyloxime

trifluoroacetylated psicose-O-benzyloxime

Conditions
ConditionsYield
1.) NMP, 75 deg C, 30 min, 2.) NMP, RT, 3 h; Multistep reaction;
D-psicose
551-68-8

D-psicose

A

D-altrose
1990-29-0

D-altrose

B

D-Allose
2595-97-3

D-Allose

Conditions
ConditionsYield
With potassium hydroxide In water at 25℃; for 336h; Product distribution; Kinetics;
D-psicose
551-68-8

D-psicose

A

glycolic Acid
79-14-1

glycolic Acid

B

LACTIC ACID
849585-22-4

LACTIC ACID

C

D-Fructose
57-48-7

D-Fructose

D

D-Mannose
3458-28-4

D-Mannose

E

D-glucose
50-99-7

D-glucose

F

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 78℃; for 0.333333h; Rate constant; Product distribution; Mechanism; isomerization equilibrium; degradation to acids; varying time, OH(1-) concentration 0.001 M to O.1 M; also in presence of Ca(2+) up to 0.06 M;
O-Methylhydroxylamin
67-62-9

O-Methylhydroxylamin

D-psicose
551-68-8

D-psicose

1-(Trimethylsilyl)imidazole
18156-74-6

1-(Trimethylsilyl)imidazole

trimethylsilyl ether of psicose O-methyloxime
56196-14-6, 128705-57-7, 128705-81-7, 129445-30-3, 129445-32-5

trimethylsilyl ether of psicose O-methyloxime

Conditions
ConditionsYield
1.) NMP, 75 deg C, 30 min, 2.) NMP, RT, 5-10 min; Multistep reaction;
D-psicose
551-68-8

D-psicose

N-benzyloxyamine
622-33-3

N-benzyloxyamine

1-(Trimethylsilyl)imidazole
18156-74-6

1-(Trimethylsilyl)imidazole

trimethylsilyl ether of psicose-O-benzyloxime

trimethylsilyl ether of psicose-O-benzyloxime

Conditions
ConditionsYield
1.) NMP, 75 deg C, 30 min, 2.) NMP, RT, 5-10 min; Multistep reaction;

551-68-8Relevant articles and documents

Few-Unit-Cell MFI Zeolite Synthesized using a Simple Di-quaternary Ammonium Structure-Directing Agent

Abeykoon, Milinda,Al-Thabaiti, Shaeel,Bell, Alexis T.,Boscoboinik, J. Anibal,Dai, Heng,Dauenhauer, Paul,Dorneles de Mello, Matheus,Duan, Xuekui,Ghosh, Supriya,Kamaluddin, Huda Sharbini,Khan, Zaheer,Kumar, Gaurav,Li, Xinyu,Lu, Peng,Luo, Tianyi,Mkhoyan, K. Andre,Narasimharao, Katabathini,Qi, Liang,Rimer, Jeffrey D.,Tsapatsis, Michael

supporting information, p. 19214 - 19221 (2021/08/09)

Synthesis of a pentasil-type zeolite with ultra-small few-unit-cell crystalline domains, which we call FDP (few-unit-cell crystalline domain pentasil), is reported. FDP is made using bis-1,5(tributyl ammonium) pentamethylene cations as structure directing agent (SDA). This di-quaternary ammonium SDA combines butyl ammonium, in place of the one commonly used for MFI synthesis, propyl ammonium, and a five-carbon nitrogen-connecting chain, in place of the six-carbon connecting chain SDAs that are known to fit well within the MFI pores. X-ray diffraction analysis and electron microscopy imaging of FDP indicate ca. 10 nm crystalline domains organized in hierarchical micro-/meso-porous aggregates exhibiting mesoscopic order with an aggregate particle size up to ca. 5 μm. Al and Sn can be incorporated into the FDP zeolite framework to produce active and selective methanol-to-hydrocarbon and glucose isomerization catalysts, respectively.

Method for preparing fructose (by machine translation)

-

Paragraph 0070-0101, (2020/07/02)

The method comprises the following steps: (1) reacting glucose with a catalyst in the presence of alcohol and carrying out reaction to obtain fructose-containing product; wherein the weight ratio of the glucose to the mixture of the titanium silicalite molecular sieve and the tin-silicon molecular sieve 50 - 600 is below 30 °C: (100 °C 0.1 - 6 1 1 - 10h) The method disclosed by the invention has high glucose conversion rate and fructose yield. (by machine translation)

Bi-Functional Magnesium Silicate Catalyzed Glucose and Furfural Transformations to Renewable Chemicals

Kumar, Abhinav,Srivastava, Rajendra

, p. 4807 - 4816 (2020/08/24)

Bio-refinery is attracting significant interest to produce a wide range of renewable chemicals and fuels from biomass that are alternative to fossil fuel derived petrochemicals. Similar to petrochemical industries, bio-refinery also depends on solid zeolite catalysts. Acid-base catalysis plays pivotal role in producing a wide range of chemicals from biomass. Herein, the Mg framework substituted MTW zeolite is synthesized and explored in the valorisation of glucose and furfural. Bi-functional (acidic and basic) characteristics are confirmed using pyridine adsorbed FT?IR analysis and NH3 and CO2 temperature-programmed desorption techniques. Textural properties and morphological information are retrieved from N2-sorption, X-ray photoelectron spectroscopy, and electron microscopy. The activity of the catalyst is demonstrated in the selective isomerisation of glucose to fructose in ethanol. Glucose is converted to methyl lactate in high yield using the same catalyst. Further, the bi-functional activity of this catalyst is demonstrated in the production of fuel precursor by the reaction of furfural and isopropanol. Mg?MTW zeolite exhibits excellent activity in the production of all these chemicals and fuel derivative. The catalyst exhibits no significant loss in the activity even after five recycles. One simple catalyst affording three renewable synthetic intermediates from glucose and furfural will attract significant attention to catalysis researchers and industrialists.

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