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87-99-0

Basic Information
CAS No.: 87-99-0
Name: Xylitol
Molecular Structure:
Molecular Structure of 87-99-0 (Xylitol)
Formula: C5H12O5
Molecular Weight: 152.17
Synonyms: Xylit;Klinit;Xylitol (JP14/NF);meso-xylitol;Xylite;(2S,4R)-pentane-1,2,3,4,5-pentol;Klinit (TN);Xylitol [USAN];Kannit;pentane-1,2,3,4,5-pentol;Eutrit;Newtol;Xyliton;1,2,3,4,5-Pentahydroxypentane;TORCH;Xylitol powder (food grade);Xylo-oligosaccharide;Acesulfame-K;Xylitol,food additive;Xylitol EP6;
EINECS: 201-788-0
Density: 1.525 g/cm3
Melting Point: 94-97 °C(lit.)
Boiling Point: 494.5 °C at 760 mmHg
Flash Point: 261.9 °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: 101.15000
LogP: -2.94630
Synthetic route
58-86-6

D-xylose

87-99-0

XYLITOL

Conditions
ConditionsYield
With hydrogen In water at 120℃; under 15001.5 Torr; for 0.166667h; Temperature; Pressure;100%
With sodium tetrahydroborate In water at 20℃; for 3h;88%
With hydrotalcite; Pt/γ-Al2O3; hydrogen In water at 60℃; under 12001.2 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Time; Green chemistry;79%

arabinose

87-99-0

XYLITOL

Conditions
ConditionsYield
With hydrogen; Ru(III) chloride, reduced with H2, inertated with N2, passivated with O2 In water at 80 - 130℃; under 67506.8 Torr;99.8%

C24H54O5Si3

87-99-0

XYLITOL

Conditions
ConditionsYield
With triethylsilane; tris(pentafluorophenyl)borate In toluene at 25℃; for 48h; Glovebox; Inert atmosphere;99%
609-06-3

L-xylose

87-99-0

XYLITOL

Conditions
ConditionsYield
With hydrogen In water at 150℃; under 37503.8 Torr; for 2h; Catalytic behavior; Solvent; Concentration; Reagent/catalyst; Temperature; Pressure; Sealed tube;98%
With sodium amalgam
With hydrogen; nickel In methanol; ethanol; water at 50℃; under 760.051 Torr; Product distribution / selectivity;
With Ru/TiO2; hydrogen In water at 120℃; under 15001.5 Torr; Temperature; Time; Autoclave;
551-84-8

xylulose

87-99-0

XYLITOL

Conditions
ConditionsYield
With NAD; hydrogen In water at 30℃; for 34h; hydrogenase, xylulose reductase, pH 8.0;98%
With NADred In water at 25℃; Equilibrium constant; Thermodynamic data; pH 7.43; biochemical reaction catalyzed by L-iditol 2-dehydrogenase; ΔH;
With D-ketopentoseoxidoreductase Kinetics; Reagent/catalyst; Enzymatic reaction;
at 30℃;
488-82-4

D-Arabitol

87-99-0

XYLITOL

Conditions
ConditionsYield
for 27h; Microbiological reaction;98%
With potassium phosphate buffer; Gluconobacter oxydans ATCC 621 membrane fraction; Gluconobacter oxydans phosphate buffer-soluble fraction; NAD at 30℃; for 40h; pH=6.0;
Conditions
ConditionsYield
In further solvent(s) argon-filled glovebox, durene, bibenzyl, heating 6h;A 59%
B 94%
C 1%
D 5%

C29H66O5Si4

87-99-0

XYLITOL

Conditions
ConditionsYield
With triethylsilane; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 48h;88%
With triethylsilane; tris(pentafluorophenyl)borate In toluene at 25℃; for 48h; Glovebox; Inert atmosphere;76%
Conditions
ConditionsYield
Stage #1: 1,2,3,4-tetra-O-trimethylsilyl-D-xylopyranose With bis(pentafluorophenyl)borinic acid; 1,1,3,3-tetramethyldisilazane In 1,4-dioxane at 25℃; for 72h; Inert atmosphere; Glovebox;
Stage #2: In methanol Inert atmosphere; Glovebox; chemoselective reaction;
85%
Stage #1: 1,2,3,4-tetra-O-trimethylsilyl-D-xylopyranose With tris(pentafluorophenyl)borate In dichloromethane-d2 at 23℃; for 1h; Inert atmosphere;
Stage #2: With methanol for 2h;
Stage #3: With water at 50℃; for 0.5h;
24%
hemicellulose

hemicellulose

87-99-0

XYLITOL

Conditions
ConditionsYield
With sulfuric acid; ruthenium-carbon composite In water; isopropyl alcohol at 140℃; for 3h; Reagent/catalyst; Solvent; Temperature; Time;83.03%
beechwood xylan

beechwood xylan

87-99-0

XYLITOL

Conditions
ConditionsYield
With 5 wt% ruthenium/carbon; sulfuric acid; water; isopropyl alcohol at 140℃; for 3h; pH=2; Inert atmosphere;83%
3370-86-3

methyl 2,3,4-tri-O-(trimethylsilyl)-α/β-D-xylopyranoside

87-99-0

XYLITOL

Conditions
ConditionsYield
Stage #1: methyl 2,3,4-tri-O-(trimethylsilyl)-α/β-D-xylopyranoside With bis(pentafluorophenyl)borinic acid; 1,1,3,3-tetramethyldisilazane In chloroform-d1 at 25℃; for 1h; Inert atmosphere; Glovebox;
Stage #2: In methanol Inert atmosphere; Glovebox; regioselective reaction;
79%
10323-20-3

D-Arabinose

A

488-82-4

D-Arabitol

B

87-99-0

XYLITOL

Conditions
ConditionsYield
With Butane-1,4-diol; Cu3Ni3Al2 In water at 149.84℃; pH=9 - 10;A 66%
B 8%
Conditions
ConditionsYield
With sodium dicyanodihydridoborate In trifluoroacetic acid at 100℃; for 40h;A 60%
B 34%
C 6%
58-86-6

D-xylose

A

488-82-4

D-Arabitol

B

87-99-0

XYLITOL

Conditions
ConditionsYield
With Butane-1,4-diol; Cu3Ni3Al2 In water at 149.84℃; pH=9 - 10;A 10%
B 60%
With hydrogen In water at 60℃; under 12001.2 Torr; for 4h; Catalytic behavior; Time; Green chemistry;A 6%
B 50%
With hydrogen In water at 120℃; under 41254.1 Torr; for 1h; Catalytic behavior; Reagent/catalyst; Temperature; Concentration; Pressure; Autoclave; Inert atmosphere; Green chemistry;
With hydrogen In water at 130℃; under 12001.2 Torr; for 2h; Autoclave;A 13 %Chromat.
B 66 %Chromat.
609-06-3

L-xylose

A

97-99-4

Tetrahydrofurfuryl alcohol

B

87-99-0

XYLITOL

Conditions
ConditionsYield
With 1% Pd on activated carbon; hydrogen In water at 140℃; under 37503.8 Torr; for 2h; Reagent/catalyst; Sealed tube;A n/a
B 58%
xylan from corncob

xylan from corncob

A

87-99-0

XYLITOL

B

50-70-4

D-sorbitol

C

107-21-1

ethylene glycol

Conditions
ConditionsYield
With hydrogen In water at 205℃; under 37503.8 Torr; for 0.5h; Reagent/catalyst; Autoclave;A 45.4%
B 5.9%
C 6.4%
Conditions
ConditionsYield
With hydrogenchloride In methanol for 16h; Ambient temperature;27%
xylan from corncob

xylan from corncob

A

58-86-6

D-xylose

B

87-99-0

XYLITOL

C

107-21-1

ethylene glycol

Conditions
ConditionsYield
With mesoporous carbon nanoparticles; hydrogen In water at 205℃; under 37503.8 Torr; for 0.5h; Autoclave;A 25.5%
B 11.8%
C 5.1%
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    87-99-0

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    CAS No.: 87-99-0 M.F.: C5H12O5 Molecular Weight:152.15 g·mol−1 Assay: 98.5%-101.0% Appearance: White fine or crystalline powder Spec: 30 mesh 80mesh 100mesh Solubility:Easily dissolve in water, sparingly soluble in etha

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Chemistry

Molecular Structure:

Molecular Formula: C5H12O5
Molecular Weight: 152.1458
IUPAC Name: Pentane-1,2,3,4,5-pentol
Classification Code: Flavoring Agents ; Food Additives ; Mutation data ; Pharmaceutic aid [vehicle, sweetened] ; Sweetening Agents
Melting point: 94-97 °C 
Index of Refraction: 1.57
Molar Refractivity: 32.76 cm3
Molar Volume: 99.7 cm3
Surface Tension: 89.6 dyne/cm
Density: 1.525 g/cm3
Flash Point: 261.9 °C
Enthalpy of Vaporization: 87.76 kJ/mol
Boiling Point: 494.5 °C at 760 mmHg
Vapour Pressure of Xylitol (CAS NO.87-99-0): 7.47E-12 mmHg at 25 °C

History

   In the 20th century, Xylitol (CAS NO.87-99-0) was first derived from birch trees in Finland  and was first popularised in Europe as a safe sweetener for people with diabetes that would not impact insulin levels. 

Uses

 Xylitol (CAS NO.87-99-0) is used as a naturally occurring sugar substitute found in the fibres of many fruits and vegetables, including various berries, oats, corn husks, and mushrooms. Many Finnish confectioneries employ Xylitol, or have a Xylitol version available. In Finland, Virtually all chewing gum sold  is sweetened with Xylitol.

Production

 Xylitol (CAS NO.87-99-0) is produced by hydrogenation of xylose, which converts the sugar (an aldehyde) into a primary alcohol.Today, using hardwood or maize sources, the largest manufacturer globally is the Danish company Danisco, with several other suppliers from China.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 10200mg/kg (10200mg/kg)   Drugs in Japan Vol. -, Pg. 297, 1990.
mouse LD50 intravenous 8500mg/kg (8500mg/kg)   Drugs in Japan Vol. -, Pg. 352, 1995.
mouse LD50 oral 12500mg/kg (12500mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH

LIVER: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 36(2), Pg. 25, 1971.
mouse LD50 subcutaneous 18300mg/kg (18300mg/kg)   Drugs in Japan Vol. -, Pg. 297, 1990.
mouse LDLo intraperitoneal 22100mg/kg (22100mg/kg)   Russian Pharmacology and Toxicology Vol. 34, Pg. 124, 1971.
rabbit LD50 intravenous 4gm/kg (4000mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 31, Pg. 726, 1972.
rabbit LD50 oral 25gm/kg (25000mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH

LIVER: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 36(2), Pg. 25, 1971.
rat LD50 intramuscular 15gm/kg (15000mg/kg)   Drugs in Japan Vol. -, Pg. 297, 1990.
rat LD50 intravenous 10800mg/kg (10800mg/kg)   Drugs in Japan Vol. -, Pg. 297, 1990.
rat LD50 oral 16500mg/kg (16500mg/kg)   Drugs in Japan Vol. -, Pg. 297, 1990.
rat LD50 subcutaneous > 25gm/kg (25000mg/kg)   Drugs in Japan Vol. -, Pg. 297, 1990.

Safety Profile

  Xylitol (CAS NO.87-99-0) was consumed as much as 400 grams daily for long periods with no toxicity . Like most sugar alcohols, it has a laxative effect because sugar alcohols are not fully broken down during digestion.
   Dogs that have ingested foods containing high levels of xylitol(87-99-0) (greater than 100 milligram of xylitol(87-99-0) consumed per kilogram of bodyweight) have presented with low blood sugar (hypoglycaemia) which can be life-threatening. Low blood sugar can result in a loss of coordination, depression, collapse and seizures in as soon as 30 minutes. Intake of very high doses of xylitol(87-99-0) (greater than 500 - 1000 mg/kg bwt) has also been implicated in liver failure in dogs, which can be fatal. These are points of controversy, however, as earlier World Health Organization studies using much higher doses on dogs for long periods showed no ill effect.  
Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26 
S24/25: Avoid contact with skin and eyes. 
S36: Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 2
RTECS: ZF0800000

Specification

  Xylitol (CAS NO.87-99-0), its Synonyms are Xylitol [USAN] ; Eutrit ; Kannit ; Klinit ; NSC 25283 ; Newtol ; UNII-VCQ006KQ1E ; Xylite ; Xylite (sugar) ; Xyliton .