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69-65-8

Basic Information
CAS No.: 69-65-8
Name: D-Mannitol
Molecular Structure:
Molecular Structure of 69-65-8 (D-Mannitol)
Formula: C6H14O6
Molecular Weight: 182.20
Synonyms: Resectisol;Osmitrol (TN);Mannistol;(2S,3S,4R,5R)-hexane-1,2,3,4,5,6-hexol;Mannitol, D-;Mannite;D(-)-Mannitol;Mannidex;Manna sugar;Maniton-S;Diosmol;Mannitol (USP);1,2,3,4,5,6-Hexanehexol;Osmosal;Cordycepic acid;NCI-C50362;Mannit;Mannazucker;Isotol;D-Mannit;Mannitol, Powder;Spray-dried mannitol;D-(-)-Mannitol;
EINECS: 200-711-8
Density: 1.596 g/cm3
Melting Point: 167-170 °C(lit.)
Boiling Point: 494.865 °C at 760 mmHg
Flash Point: 292.497 °C
Solubility: Soluble in water
Appearance: White crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-36-26
Transport Information:
PSA: 121.38000
LogP: -3.58540
Synthetic route
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%
28224-73-9

1,3:4,6-di-O-benzylidene-D-mannitol

A

2568-25-4

4-methyl-2-phenyl-1,3-dioxolane

B

69-65-8

mannitol

Conditions
ConditionsYield
With propylene glycol; toluene-4-sulfonic acid In dichloromethane for 1h;A n/a
B 99%
1707-77-3

1,2:5,6-di-O-isopropylidene-D-mannitol

A

1193-11-9, 116944-25-3

2,2,4-trimethyl-1,3-dioxolane

B

69-65-8

mannitol

Conditions
ConditionsYield
With propylene glycol; toluene-4-sulfonic acid; 1,1'-(1,2-ethanediyl)bisbenzene In dichloromethane for 1h;A n/a
B 99%
162956-98-1

(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

69-65-8

mannitol

Conditions
ConditionsYield
With dimethylbromosulphonium bromide In methanol at 20℃; for 1.5h;99%
1707-77-3

1,2:5,6-di-O-isopropylidene-D-mannitol

69-65-8

mannitol

Conditions
ConditionsYield
With H-Beta zeolite; water In methanol at 20℃; for 24h; Product distribution; Further Variations:; Reagents; Temperatures; reaction time;96%
55529-69-6

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

69-65-8

mannitol

Conditions
ConditionsYield
Stage #1: trimethylsilyl 2,3,4,6-tetra-O-trimethylsilyl-D-mannopyranoside With bis(pentafluorophenyl)borinic acid; 1,1,3,3-tetramethyldisilazane In 1,4-dioxane at 25℃; for 96h; Inert atmosphere; Glovebox;
Stage #2: In methanol Catalytic behavior; Time; Inert atmosphere; Glovebox; chemoselective reaction;
95%
57-48-7

D-Fructose

69-65-8

mannitol

Conditions
ConditionsYield
With hydrogen In butan-1-ol at 120℃; under 26252.6 Torr; for 10h; Reagent/catalyst; Pressure; Solvent;94%
With hydrogen In butan-1-ol at 120℃; under 18751.9 Torr; for 5h; Reagent/catalyst; Pressure; Solvent;50%
With hydrogen In water; isopropyl alcohol at 109.84℃; under 2400.24 Torr; for 3h; Autoclave;44%
57-48-7

D-Fructose

A

69-65-8

mannitol

B

50-70-4

D-sorbitol

Conditions
ConditionsYield
With hydrogen In butan-1-ol at 120℃; under 26252.6 Torr; for 10h; Reagent/catalyst; Pressure; Temperature; Solvent;A 93%
B 5%
With hydrogen In butan-1-ol at 120℃; under 18751.9 Torr; for 5h; Pressure; Reagent/catalyst; Temperature; Solvent;A 62%
B 14%
With Butane-1,4-diol; Cu3Ni3Al2 In water at 149.84℃; pH=9 - 10;A 60%
B 16%

D-(+)-cellobiose

A

69-65-8

mannitol

B

50-70-4

D-sorbitol

Conditions
ConditionsYield
With hydrogen In water at 19.84 - 189.84℃; under 37503.8 Torr; for 3h; Reagent/catalyst; Temperature; Time; Autoclave;A n/a
B 91.5%
19159-25-2

sucrose octakis(trimethylsilyl) ether

A

69-65-8

mannitol

B

50-70-4

D-sorbitol

C

154-58-5

1,5-anhydro-D-glucitol

Conditions
ConditionsYield
Stage #1: sucrose octakis(trimethylsilyl) ether With bis(pentafluorophenyl)borinic acid; 1,1,3,3-tetramethyldisilazane In chloroform-d1 at 25℃; for 3h; Inert atmosphere; Glovebox;
Stage #2: In methanol Inert atmosphere; Glovebox;
A n/a
B n/a
C 90%
50-99-7

D-glucose

A

69-65-8

mannitol

B

50-70-4

D-sorbitol

Conditions
ConditionsYield
With hydrogen; Ru/C In water at 120℃; under 15001.5 Torr; for 2h; Catalytic behavior; Inert atmosphere; Autoclave;A 12.6%
B 86.3%
With hydrotalcite; Pt/γ-Al2O3; hydrogen In water at 90℃; under 12001.2 Torr; for 4h; Catalytic behavior; Time; Green chemistry;A 14%
B 54%
With platinum Hydrogenation;
Conditions
ConditionsYield
With sodium dicyanodihydridoborate In trifluoroacetic acid at 100℃; for 40h;A 82%
B 11%
C 7%
3458-28-4

D-Mannose

1071-83-6

N-(phosphonemethyl)glycine

A

69-65-8

mannitol

B

1-deoxy-1-[[N-(phosphonomethyl)-2-oxoethyl]amino]-D-mannitol

Conditions
ConditionsYield
With sodium cyanoborohydride; triethylamine In methanol; water at 80℃; for 72h; pH=6.2; Reduction; amination;A n/a
B 81%
492-61-5

β-D-glucose

69-65-8

mannitol

Conditions
ConditionsYield
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); isopropyl alcohol In water at 120℃; for 12h; Inert atmosphere; Schlenk technique;80%
57-50-1

Sucrose

A

69-65-8

mannitol

B

50-70-4

D-sorbitol

Conditions
ConditionsYield
With hydrogen; Ru-carbon In water at 125℃; under 37503 Torr; for 1.5h;A 24.5%
B 75%
With hydrogen; ruthenium In water at 130℃; under 37503 Torr; for 2h;A 24.8%
B 75.2%
With hydrogen; Nafion; ruthenium In water at 125℃; under 37503 Torr; for 2.5h;A 30.5%
B 69.5%
50-70-4

D-sorbitol

A

57-55-6

propylene glycol

B

69-65-8

mannitol

Conditions
ConditionsYield
With 5% active carbon-supported ruthenium; water; zinc at 180℃; under 3750.38 Torr; for 20h; Autoclave; Inert atmosphere;A 11%
B 71%
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    Product Name: D-Mannitol Molecular formula: C6H14O6 Molecular weight: 182.17 CAS: 69-65-8 Melting point: 167-170ºC Boiling point: 295ºC Density: 1.52 g/cm3 D-Mannitol is colorless to white crystalline powder. It is od

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Consensus Reports

NTP Carcinogenesis Bioassay (feed); No Evidence: mouse, rat NTPTR*    National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. 206- NTP-TR-236 ,1982. . Reported in EPA TSCA Inventory.

Specification

The D-Mannitol is an organic compound with the formula C6H14O6. The systematic name of this chemical is D-mannitol. With the CAS registry number 69-65-8, it is also named as (2R,3R,4R,5R)-1,2,3,4,5,6-Hexanehexol. The product's categories are Substrates; Miscellaneous Natural Products; 13C & 2H Sugars; Biochemistry; Sugar Alcohols; Sugars; Dextrins, Sugar & Carbohydrates; Carbohydrates & Derivatives; Food & Flavor Additives. Besides, it is a white crystalline powder, which should be stored in a cool place.

The D-Mannitol is medically used as a dehydrating agent and diuretic drugs. It is used as analytical reagents and used in the synthesis of resins and synthetic drugs. It is also used as low calorie low-sweetness sweeteners, nutritional supplements, quality improver, anti-seize compound, insulation agent.

Physical properties about D-Mannitol are: (1)# of Rule of 5 Violations: 1; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 6; (7)#H bond donors: 6; (8)#Freely Rotating Bonds: 11; (9)Polar Surface Area: 121.38 Å2; (10)Index of Refraction: 1.597; (11)Molar Refractivity: 38.89 cm3; (12)Molar Volume: 114.118 cm3; (13)Polarizability: 15.417×10-24cm3; (14)Surface Tension: 99.896 dyne/cm; (15)Density: 1.596 g/cm3; (16)Flash Point: 292.497 °C; (17)Enthalpy of Vaporization: 87.805 kJ/mol; (18)Boiling Point: 494.865 °C at 760 mmHg.

Preparation: first, sucrose hydrolysis glucose and fructose, then they restore the generation sorbitol and mannitol, D-Mannitol is produced by bleaching, isolated and purified.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: C([C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)O
(2)InChI: InChI=1/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1
(3)InChIKey: FBPFZTCFMRRESA-KVTDHHQDBH
(4)Std. InChI: InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1
(5)Std. InChIKey: FBPFZTCFMRRESA-KVTDHHQDSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intravenous 17143mg/kg/2D (17143mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

GASTROINTESTINAL: NAUSEA OR VOMITING

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Archives of Internal Medicine. Vol. 144, Pg. 2053, 1984.
mouse LD50 intraperitoneal 14gm/kg (14000mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 35, Pg. 98, 1936.
mouse LD50 intravenous 7470mg/kg (7470mg/kg)   Yakkyoku. Pharmacy. Vol. 32, Pg. 1367, 1981.
mouse LD50 oral 22gm/kg (22000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE
FAO Nutrition Meetings Report Series. Vol. 40, Pg. 160, 1967.
rat LD50 intravenous 9690mg/kg (9690mg/kg)   Yakkyoku. Pharmacy. Vol. 32, Pg. 1367, 1981.
rat LD50 oral 13500mg/kg (13500mg/kg)   Yakkyoku. Pharmacy. Vol. 32, Pg. 1367, 1981.