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3458-28-4

Basic Information
CAS No.: 3458-28-4
Name: D-(+)-Mannose
Molecular Structure:
Molecular Structure of 3458-28-4 (D-(+)-Mannose)
Formula: C6H12 O6
Molecular Weight: 180.16
Synonyms: D-Mannose;
EINECS: 222-392-4
Density: 1,581 g/cm3
Melting Point: 133-140ºC
Boiling Point: 527.1 °C at 760 mmHg
Flash Point: 286.7 °C
Solubility: 2480 g/L (17 ºC)
Appearance: White powder
Hazard Symbols: Xi
Risk Codes: 36/37/38
Safety: 24/25-36-26
Transport Information:
PSA: 118.22000
LogP: -3.37880
Synthetic route
7296-15-3

alpha-D-mannopyranoside

107-11-9

1-amino-2-propene

A

3458-28-4

D-Mannose

B

1-(allylamino)-1-deoxy-α-D-mannopyranose

Conditions
ConditionsYield
In methanol at 60℃; for 0.166667h; Temperature; Time; Inert atmosphere;A n/a
B 98.6%

cellobiose

A

67-47-0

5-hydroxymethyl-2-furfuraldehyde

B

3458-28-4

D-Mannose

fructose

D-glucose

Conditions
ConditionsYield
With water at 150℃; for 24h; Autoclave; Green chemistry;A 8.4%
B 2.7%
C 2.2%
D 67.7%
50-99-7

D-glucose

A

57-48-7

D-Fructose

B

3458-28-4

D-Mannose

Conditions
ConditionsYield
Stage #1: D-glucose With zirconium metal organic framework UiO-66 In propan-1-ol at 90℃; for 24h; Sealed tube;
Stage #2: In water at 90℃; for 24h; Catalytic behavior; Mechanism; Solvent;
A 56%
B n/a
With SrO(SrTiO3)2 In water at 110℃; for 1h; Reagent/catalyst;A 34%
B 10%
With 5% LaOH/C In water at 100℃; under 15001.5 Torr; for 2h; Reagent/catalyst; Solvent; Autoclave; Inert atmosphere;A 25.97%
B 6.95%
cellulose

cellulose

A

67-47-0

5-hydroxymethyl-2-furfuraldehyde

B

3458-28-4

D-Mannose

C

cellobiose

fructose

D-glucose

Conditions
ConditionsYield
With water at 150℃; for 24h; Activation energy; Reagent/catalyst; Temperature; Autoclave; Green chemistry;A n/a
B n/a
C n/a
D n/a
E 49.9%
cellulose

cellulose

A

67-47-0

5-hydroxymethyl-2-furfuraldehyde

B

3458-28-4

D-Mannose

Conditions
ConditionsYield
With water; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride at 100℃; for 0.5h;A 41.1%
B 9.2%
13360-52-6

Cellobiose

A

3458-28-4

D-Mannose

B

50-99-7

D-glucose

Conditions
ConditionsYield
With water at 160℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Temperature; Microwave irradiation; Sealed tube;A 10.5%
B 32.6%
With water at 160℃; under 18751.9 Torr; for 1.5h; Reagent/catalyst; Autoclave; Inert atmosphere;A 8.8%
B 25.6%
13360-52-6

Cellobiose

A

3458-28-4

D-Mannose

B

50-99-7

D-glucose

C

141-46-8

Glycolaldehyde

Conditions
ConditionsYield
With water at 160℃; under 18751.9 Torr; for 1.5h; Reagent/catalyst; Autoclave; Inert atmosphere;A 20.6%
B 32%
C 7.1%
50-99-7

D-glucose

3458-28-4

D-Mannose

Conditions
ConditionsYield
With molybdic acid In water for 0.05h; Bilik reaction; microwave irradiation;27%
With water at 160℃; for 0.5h; Reagent/catalyst;22.8%
With triply sodium-exchanged zeolite tin-Beta In methanol at 79.84℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Solvent;7.9%
cellulose

cellulose

A

3458-28-4

D-Mannose

B

50-99-7

D-glucose

C

123-76-2

levulinic acid

Conditions
ConditionsYield
With H3N*2H(1+)*TeW6O21(2-); water at 175℃; for 2h; Autoclave;A 7.8%
B 25.8%
C 8.5%
50-99-7

D-glucose

A

67-47-0

5-hydroxymethyl-2-furfuraldehyde

B

57-48-7

D-Fructose

C

3458-28-4

D-Mannose

Conditions
ConditionsYield
With 0.06-Fe/β zeolite In water at 150℃; under 3750.38 Torr; for 1.5h; Autoclave; High pressure; Inert atmosphere; Green chemistry;A 6%
B 22%
C 7%
With water at 140℃; for 2h; Inert atmosphere;
With lithium bromide trihydrate In water at 130℃; for 1h; Green chemistry;
cellulose

cellulose

A

3458-28-4

D-Mannose

B

50-99-7

D-glucose

Conditions
ConditionsYield
With H3N*2H(1+)*TeW6O21(2-); water at 175℃; for 2h; Autoclave;A 7.2%
B 19%
13360-52-6

Cellobiose

A

3458-28-4

D-Mannose

B

50-99-7

D-glucose

C

glucopyranosyl-glucitol

Conditions
ConditionsYield
With water at 160℃; under 18751.9 Torr; for 1.5h; Reagent/catalyst; Autoclave; Inert atmosphere;A 6.9%
B 17.3%
C 6.8%
504-29-0

2-aminopyridine

57-48-7

D-Fructose

A

3458-28-4

D-Mannose

B

50-99-7

D-glucose

Conditions
ConditionsYield
Stage #1: D-Fructose 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 100℃; for 3h;
A 12%
B 8%
110-86-1

pyridine

50-99-7

D-glucose

A

57-48-7

D-Fructose

B

3458-28-4

D-Mannose

69-65-8

mannitol

A

57-48-7

D-Fructose

B

3458-28-4

D-Mannose

Conditions
ConditionsYield
With water; chlorine
bei Einw.von Acetobacter pasteurianum;
69-65-8

mannitol

3458-28-4

D-Mannose

Conditions
ConditionsYield
With para-xylene; water; oxygen im Sonnenlicht;
With bromine im Sonnenlicht(?);
With nitrogen oxides; water; iron(II)
3416-24-8

2-amino-2-deoxyglucose

3458-28-4

D-Mannose

14199-83-8

1-deoxy-1-nitro-D-manno-hexitol

3458-28-4

D-Mannose

Conditions
ConditionsYield
With sodium hydroxide anschliessend mit wss.Schwefelsaeure;
69-65-8

mannitol

106-51-4

p-benzoquinone

3458-28-4

D-Mannose

Conditions
ConditionsYield
bei gleichzeitiger Belichtung;
617-04-9

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

3458-28-4

D-Mannose

Conditions
ConditionsYield
With sulfuric acid
With hydrogenchloride
With CuGGH metallopeptide based glycosidase; dihydrogen peroxide; sodium L-ascorbate In methanol; aq. phosphate buffer; water at 37℃; for 8h; pH=7; Enzymatic reaction;
26301-79-1

D-mannono-1,4-lactone

3458-28-4

D-Mannose

Conditions
ConditionsYield
With sodium amalgam; water; benzoic acid
With sodium amalgam; water; sodium hydrogen oxalate
57-48-7

D-Fructose

A

3458-28-4

D-Mannose

B

50-99-7

D-glucose

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

D-psicose

A

79-14-1

glycolic Acid

B

849585-22-4

LACTIC ACID

C

57-48-7

D-Fructose

D

3458-28-4

D-Mannose

E

50-99-7

D-glucose

F

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;
50-99-7

D-glucose

A

79-14-1

glycolic Acid

B

849585-22-4

LACTIC ACID

C

57-48-7

D-Fructose

D

3458-28-4

D-Mannose

E

551-68-8

D-psicose

F

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;
3458-28-4

D-Mannose

69-65-8

mannitol

Conditions
ConditionsYield
With hydrogen In water at 120℃; under 15001.5 Torr; for 1h;100%
With sodium tetrahydroborate In water at 20℃; for 2h;78%
With water; hydrogen at 99.84℃; under 37503.8 Torr; for 0.5h;8.7%
75-77-4

chloro-trimethyl-silane

3458-28-4

D-Mannose

55529-69-6

trimethylsilyl 2,3,4,6-tetra-O-trimethylsilyl-D-mannopyranoside

Conditions
ConditionsYield
With pyridine at 20℃; for 4h; Inert atmosphere;100%
With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane at 20℃; for 0.583333h;
With triethylamine In N,N-dimethyl-formamide at 0 - 25℃; Inert atmosphere;
3458-28-4

D-Mannose

108-24-7

acetic anhydride

4163-65-9

per-O-acetyl-α-D-mannopyranose

Conditions
ConditionsYield
With iodine at 20℃; for 1h; optical yield given as %de;100%
With pyridine; dmap at 0 - 20℃;100%
With pyridine; dmap at 20℃; Inert atmosphere;100%
With pyridine; dmap at 0 - 20℃;100%
With sulfuric acid at 0 - 20℃; for 0.666667h;80.4%
75-77-4

chloro-trimethyl-silane

3458-28-4

D-Mannose

24707-99-1

1,2,3,4,6-penta-O-(trimethylsilyl)-α-D-mannopyranose

Conditions
ConditionsYield
With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane at 75℃; for 1.5h; Inert atmosphere;100%
With pyridine at 0 - 23℃; for 24h;64%
3458-28-4

D-Mannose

75-04-7

ethylamine

68045-28-3

N-ethyl-β-D-mannopyranosylamine

Conditions
ConditionsYield
In ethanol99%
71-23-8

propan-1-ol

3458-28-4

D-Mannose

118245-34-4

1-propyl D-mannopyranoside

Conditions
ConditionsYield
With Dowex-50W X-8H+-400 for 12h; Heating;97%
67-56-1

methanol

3458-28-4

D-Mannose

617-04-9

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
With acetyl chloride for 6h; Inert atmosphere; Reflux;97%
In dimethyl sulfoxide at 20℃; Reflux;

carbonic acid bis(1-isopropylhydrazide) dihydrochloride

3458-28-4

D-Mannose

1'R,2'R,3'R,4'R-2,4-diisopropyl-6-(1',2',3',4',5'-pentahydroxypentyl)-1,2,4,5-tetrazinan-3-one

Conditions
ConditionsYield
With sodium acetate In water at 20℃;97%
3458-28-4

D-Mannose

771-97-1

2,3-Diaminonaphthalene

1027103-24-7

(1'R,2'R,3'R,4'R)-2-[1',2',3',4',5'-pentahydroxypentyl]-1H-naphthimidazole

Conditions
ConditionsYield
With air; iodine; acetic acid at 20℃; for 18h;96%
3458-28-4

D-Mannose

D-mannonitrile

Conditions
ConditionsYield
With phenoxyamine hydrochloride In aq. phosphate buffer; water-d2 at 20℃; for 24h;96%
Conditions
ConditionsYield
With camphorsulfonic acid In acetone at 20℃;95%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20℃; Inert atmosphere;76%
With toluene-4-sulfonic acid In acetone73%
With toluene-4-sulfonic acid at 40℃; for 4h;
3458-28-4

D-Mannose

479-27-6

naphthalene-1,8-diamine

73858-36-3

(1R,2R,3R,4R)-1-(2,3-Dihydro-1H-perimidin-2-yl)-pentane-1,2,3,4,5-pentaol

Conditions
ConditionsYield
In ethanol; water; acetic acid for 2h; Heating;95%
In ethanol; water at 20℃;68%
120-72-9

indole

3458-28-4

D-Mannose

108-24-7

acetic anhydride

Acetic acid (1R,2R,3R,4R)-2,3,4,5-tetraacetoxy-1-[bis-(1H-indol-2-yl)-methyl]-pentyl ester

Conditions
ConditionsYield
Stage #1: indole; D-Mannose; scandium tris(trifluoromethanesulfonate) In ethanol; water at 50℃; for 48h;
Stage #2: acetic anhydride With pyridine; dmap at 20℃;
95%
3458-28-4

D-Mannose

98-88-4

benzoyl chloride

96996-90-6

1,2,3,4,6-penta-O-benzoyl-α,β-D-mannopyranoside

Conditions
ConditionsYield
With pyridine at 20℃; for 12h;95%
With pyridine at 0 - 20℃; Inert atmosphere;
With pyridine; dmap at 20℃; Cooling with ice;
With pyridine at 0 - 20℃;
3458-28-4

D-Mannose

77-76-9

2,2-dimethoxy-propane

78964-16-6

2,3;5,6-di-O-isopropylidene-β-D-mannofuranose

Conditions
ConditionsYield
Stage #1: D-Mannose; 2,2-dimethoxy-propane With sulfuric acid In acetone at 0 - 20℃; for 24h;
Stage #2: With triethylamine In acetone
95%
Conditions
ConditionsYield
With dmap In pyridine at 20℃;95%
With pyridine at 20℃; for 24h; Inert atmosphere;
Conditions
ConditionsYield
With sulfuric acid at 20℃; for 2h;95%
Acidic conditions;
With sulfuric acid; copper(II) sulfate
3458-28-4

D-Mannose

77-76-9

2,2-dimethoxy-propane

40036-82-6

[2,3:5,6]-di-O-isopropylidene-D-mannose

Conditions
ConditionsYield
With camphosulfonic acid In acetone at 0 - 20℃; Inert atmosphere;95%
With toluene-4-sulfonic acid In acetone at 0 - 20℃;
3458-28-4

D-Mannose

77-76-9

2,2-dimethoxy-propane

67-64-1

acetone

7757-38-2, 14131-84-1, 23262-78-4, 27108-13-0, 33823-04-0, 34685-42-2, 57819-52-0, 78039-08-4, 78039-12-0, 78964-16-6, 94842-76-9, 149342-31-4

(3aR,4R,6R,6aR)-6-(2,2-dimethyl-1,3-dioxolane-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol

Conditions
ConditionsYield
With sulfuric acid at 0 - 20℃; for 24h;95%
Conditions
ConditionsYield
With camphor-10-sulfonic acid at 0 - 20℃; for 24h; Inert atmosphere;95%
Conditions
ConditionsYield
With sulfuric acid; copper(II) sulfate93.5%
With sulfuric acid for 4h; Ambient temperature;90%
With sulfuric acid; copper(II) sulfate for 8h;85%
Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetone at 20℃; for 2h;93%
3458-28-4

D-Mannose

108-24-7

acetic anhydride

104-94-9

4-methoxy-aniline

123-54-6

acetylacetone

1020540-83-3

[(5R,6S)-3-acetyl-6-acetyloxy-1-(4-methoxyphenyl)-2-methyl-1,5,6,7-tetrahydropyrano[3,2-b]pyrrol-5-yl]methyl acetate

Conditions
ConditionsYield
Stage #1: D-Mannose; 4-methoxy-aniline; acetylacetone With indium(III) chloride In water at 80℃; for 6h;
Stage #2: acetic anhydride With dmap In dichloromethane at 20℃; for 1h; Further stages.;
93%
3458-28-4

D-Mannose

108-44-1

1-amino-3-methylbenzene

1096700-48-9

N-m-tolyl-β-D-mannopyranosylamine

Conditions
ConditionsYield
In water Reflux;93%
3458-28-4

D-Mannose

16596-41-1

N-aminopyrrolidine

(2R,3R,4R,5R)-6-(pyrrolidin-1-ylimino)hexane-1,2,3,4,5-pentol

Conditions
ConditionsYield
In methanol for 3.5h; Reflux;93%
Conditions
ConditionsYield
With malonic acid; choline chloride for 0.333333h; Reflux; Green chemistry;93%
3458-28-4

D-Mannose

95-53-4

o-toluidine

N-(o-tolyl)-β-D-mannopyranosylamine

Conditions
ConditionsYield
In water Reflux;92.8%
109-80-8

1.3-propanedithiol

3458-28-4

D-Mannose

173207-36-8

D-mannose propane-1,3-diyl dithioacetal

Conditions
ConditionsYield
With trifluoroacetic acid at 50 - 60℃; 30-50 min;92%
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    D-Mannose, Cas No.3458-28-4. Physical state and appearance: Solid. (Solid crystalline powder.) Odor: Odorless. Taste: Sweet. Molecular Weight: 180.16 g/mole Color: White color Melting Point: Decomposes. (132°C or 269.6°F)

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    D-(+)-Mannose

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Specification

The D-(+)-Mannose, with the CAS register number 3458-28-4, has other names as carubinose;d-mannopyranose;d-(+)-mannose;d-mannose;d-man;mannose, d-(+)-;seminose;d-mannos .Its product categories are including the following: Sugars, Carbohydrates & Glucosides. It is a kind of white crystalline powder and it is sweet with afteraste of bitter. And it is soluble in water and slightly soluble in ethanol but insoluble in diethyl [ethyl] ether. Besides, it has two types of α- and β-. The α- is the crystallize of methyl with the melting point of 133℃ while the β- is the crystallize of ethyl with the melting point of 132℃. As for its usage, it is usually used for being the biochemical reagents and sweet taste reagents. What's more, the simple way to get it is following:hydrolyze the cocoanut husk with sulfuric acid and then you could α- type of D-Mannose.

The physical properties of D-(+)-Mannose are as followings:
(1) ACD/LogP:  -2.49; (2)# of Rule of 5 Violations:  1; (3)ACD/LogD (pH 5.5):  -2.49; (4)ACD/LogD (pH 7.4):  -2.49; (5)ACD/BCF (pH 5.5):  1.00; (6)ACD/BCF (pH 7.4):  1.00; (7)ACD/KOC (pH 5.5):  1.05; (8)ACD/KOC (pH 7.4):  1.05; (9)#H bond acceptors:  6; (10)#H bond donors:  5; (11)#Freely Rotating Bonds:  6; (12)Index of Refraction:  1.635; (13)Molar Refractivity:  37.254 cm3; (14)Molar Volume:  104.015 cm3; (15)Surface Tension:  81.7509994506836 dyne/cm; (16)Density:  1.732 g/cm3; (17)Flash Point:  202.243 °C; (18)Enthalpy of Vaporization:  76.626 kJ/mol; (19)Boiling Point:  410.797 °C at 760 mmHg; (20)Vapour Pressure:  0 mmHg at 25°C.

Safety information of D-(+)-Mannose:
Being an irritant chemical to eyes, respiratory system and skin, it may cause inflammation to the skin or other mucous membranes. So while using this chemical, take the following instrction to protect your self: Wear suitable protective clothing and avoid contact with skin and eyes; If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And you could also obtain the safety information from WGK Germany  3. 

You can still convert the following datas into molecular structure:
(1)SMILES:O[C@H]1[C@H](O)[C@H](OC(O)[C@H]1O)CO;
(2)Std. InChI:InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6?/m1/s1;
(3)Std. InChIKey:WQZGKKKJIJFFOK-QTVWNMPRSA-N.

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