Product Name

  • Name

    ADONITOL

  • EINECS 207-685-7
  • CAS No. 488-81-3
  • Article Data56
  • CAS DataBase
  • Density 1.526 g/cm3
  • Solubility Soluble in water (100 mg/ml).
  • Melting Point 102-105 °C
  • Formula C5H12O5
  • Boiling Point 494.527 °C at 760 mmHg
  • Molecular Weight 152.147
  • Flash Point 261.85 °C
  • Transport Information
  • Appearance White powder
  • Safety 24/25-36-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 488-81-3 (ADONITOL)
  • Hazard Symbols IrritantXi
  • Synonyms Adonitol(7CI);Adonit;Adonite;NSC 16868;ribo-Pentitol;Ribitol;
  • PSA 101.15000
  • LogP -2.94630

Synthetic route

C17H42O5Si4

C17H42O5Si4

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
Stage #1: C17H42O5Si4 With bis(pentafluorophenyl)borinic acid; 1,1,3,3-tetramethyldisilazane In 1,4-dioxane at 25℃; for 24h; Inert atmosphere; Glovebox;
Stage #2: In methanol Inert atmosphere; Glovebox; chemoselective reaction;
92%
DL-erythro-pentene-(1)-triol-(3.4.5)-triacetate
18524-23-7, 876594-33-1

DL-erythro-pentene-(1)-triol-(3.4.5)-triacetate

A

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With osmium(VIII) oxide; silver(I) chlorate und Acetylierung des erhaltenen Gemisches von Ribit-1.2.3-triacetat und D-Arabit-3.4.5-triacetat Verseifen des Pentaacetats mit methylalkoh.HCl;
D-ribose
50-69-1

D-ribose

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With sodium metaborate; water
With nickel; magnesium at 100℃; under 22065.2 Torr; Hydrogenation;
Yield given. Multistep reaction;
L-ribose
24259-59-4

L-ribose

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With sodium amalgam
1-bromo-DL-1-deoxy-ribitol-3.4.5-triacetate

1-bromo-DL-1-deoxy-ribitol-3.4.5-triacetate

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With potassium acetate; acetic anhydride; acetic acid und Verseifen des entstandenen Pentaacetats mit siedender methylalkoh.HCl;
D-Fructose
57-48-7

D-Fructose

A

Adonitol
488-81-3

Adonitol

B

(S)-3,4-dihydroxy-butyraldehyde
81893-52-9

(S)-3,4-dihydroxy-butyraldehyde

C

2,3-dideoxy-3-C-hydroxymethyltetrose
81539-41-5

2,3-dideoxy-3-C-hydroxymethyltetrose

D

2-deoxy-2-C-hydroxymethyltetrose
81539-40-4, 132215-58-8

2-deoxy-2-C-hydroxymethyltetrose

E

ethylene glycol
107-21-1

ethylene glycol

F

D-erythrose
583-50-6

D-erythrose

Conditions
ConditionsYield
In water Quantum yield; Irradiation; 254-nm photolysis in deoxigenated and oxygenated solutions;
D-xylose
58-86-6

D-xylose

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With sodium tetrahydroborate
D-erythro-pentos-2-ulose
3445-24-7

D-erythro-pentos-2-ulose

A

D-Arabitol
488-82-4

D-Arabitol

B

Adonitol
488-81-3

Adonitol

C

D-ribulose
488-84-6

D-ribulose

D

D-ribose
50-69-1

D-ribose

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In water at 80℃; for 0.5h;A n/a
B n/a
C 70 % Chromat.
D n/a
divinylcarbinol
922-65-6

divinylcarbinol

1,2,3,4,5-pentapentanol
6018-27-5

1,2,3,4,5-pentapentanol

B

XYLITOL
87-99-0

XYLITOL

C

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With 4-nitroperbenzoic acid In dichloromethane at 90℃;
4,5-O-isopropylidene-D-ribitol
81076-13-3

4,5-O-isopropylidene-D-ribitol

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With Dowex 50X8-200 resin In water at 25℃; for 3h;
With hydrogenchloride
(Z)-(4RS)-1,4,5-triacetoxypent-2-ene
85716-54-7

(Z)-(4RS)-1,4,5-triacetoxypent-2-ene

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With pyridine; hydrogenchloride; tert.-butylhydroperoxide; osmium(VIII) oxide; tetraethylammonium acetate; acetic anhydride Yield given. Multistep reaction;
(1R,2R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-propane-1,2,3-triol
81028-11-7, 81076-13-3, 81076-14-4, 81076-15-5, 92935-75-6, 92935-76-7, 92935-77-8, 92935-78-9

(1R,2R)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-propane-1,2,3-triol

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With hydrogenchloride In methanol Heating;
With hydrogenchloride In methanol Heating;
(1R,2R)-(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-propane-1,2,3-triol
88367-64-0, 88391-55-3, 88391-65-5, 88391-66-6

(1R,2R)-(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-propane-1,2,3-triol

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With hydrogenchloride In methanol Heating;
With hydrogenchloride In methanol Heating;
2,2-Dimethyl-propionic acid (2R,3R)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-propyl ester
88367-62-8, 88391-53-1, 88391-61-1, 88391-62-2

2,2-Dimethyl-propionic acid (2R,3R)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-propyl ester

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 0℃;
Multi-step reaction with 2 steps
1: 5 percent conc HCl / methanol / Heating
2: LiAlH4 / diethyl ether / 0 °C
View Scheme
(2R,3R,4S)-4,5-Bis-benzyloxy-pentane-1,2,3-triol
88367-65-1, 88391-56-4, 88391-67-7, 88391-68-8

(2R,3R,4S)-4,5-Bis-benzyloxy-pentane-1,2,3-triol

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol; acetic acid
With hydrogen; palladium on activated charcoal In methanol; acetic acid Ambient temperature;
(1S,2S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propane-1,2-diol
88367-63-9, 88391-54-2, 88391-63-3, 88391-64-4

(1S,2S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propane-1,2-diol

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 0℃;
Multi-step reaction with 2 steps
1: 5 percent conc HCl / methanol / Heating
2: (n-Bu)4N(+)F(-) / tetrahydrofuran / Ambient temperature
View Scheme
2,2-Dimethyl-propionic acid (2S,3R,4R)-2,3,4,5-tetrahydroxy-pentyl ester

2,2-Dimethyl-propionic acid (2S,3R,4R)-2,3,4,5-tetrahydroxy-pentyl ester

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 0℃;
(2R,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-pentane-1,2,3,4-tetraol

(2R,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-pentane-1,2,3,4-tetraol

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature;
C41H66O14

C41H66O14

A

Adonitol
488-81-3

Adonitol

B

(2R,4aS,5R,6aS,6bR,9R,10S,12aS)-5-Hydroxy-4a,9-bis-hydroxymethyl-2,6a,6b,9,12a-pentamethyl-10-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b-octadecahydro-picene-2-carboxylic acid

(2R,4aS,5R,6aS,6bR,9R,10S,12aS)-5-Hydroxy-4a,9-bis-hydroxymethyl-2,6a,6b,9,12a-pentamethyl-10-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b-octadecahydro-picene-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In water
scorzoneroside B

scorzoneroside B

A

D-Glucose
2280-44-6

D-Glucose

B

Adonitol
488-81-3

Adonitol

C

(2R,4aS,5R,6aS,6bR,9R,10S,12aS)-5-Hydroxy-4a,9-bis-hydroxymethyl-2,6a,6b,9,12a-pentamethyl-10-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b-octadecahydro-picene-2-carboxylic acid

(2R,4aS,5R,6aS,6bR,9R,10S,12aS)-5-Hydroxy-4a,9-bis-hydroxymethyl-2,6a,6b,9,12a-pentamethyl-10-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b-octadecahydro-picene-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In water
(2S,3S,4R)-5-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-pentane-1,2,3,4-tetraol
226089-02-7

(2S,3S,4R)-5-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-pentane-1,2,3,4-tetraol

A

D-Glucose
2280-44-6

D-Glucose

B

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane; water
D-ribitol 5-phosphate
35320-17-3

D-ribitol 5-phosphate

aqueous ammonium acetate

aqueous ammonium acetate

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
Hydrolysis;
arabinoic acid
488-30-2

arabinoic acid

A

meso-erythritol
909878-64-4

meso-erythritol

B

D-Arabitol
488-82-4

D-Arabitol

C

XYLITOL
87-99-0

XYLITOL

D

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With hydrogen; Ru-carbon In water at 80℃; under 45003.6 Torr; Product distribution; Further Variations:; Catalysts; pH-values; Temperatures; Reagents;
Glycolaldehyde
141-46-8

Glycolaldehyde

Glyceraldehyde
56-82-6

Glyceraldehyde

A

D-threitol
2418-52-2

D-threitol

B

D-Arabitol
488-82-4

D-Arabitol

C

XYLITOL
87-99-0

XYLITOL

D

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
Stage #1: Glycolaldehyde; Glyceraldehyde With zinc(II) bis(L-proline) In water at 20℃; for 168h;
Stage #2: With sodium tetrahydroborate for 3h; Further byproducts given. Title compound not separated from byproducts;
O-polysaccharide of the lipopolysaccharide from Proteus vulgaris strain TG 276-1

O-polysaccharide of the lipopolysaccharide from Proteus vulgaris strain TG 276-1

A

C6H12N2O2

C6H12N2O2

B

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
With trifluoroacetic acid at 120℃; for 2h;
Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((2R,3S,4S)-2,3,4,5-tetrahydroxy-pentyloxy)-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((2R,3S,4S)-2,3,4,5-tetrahydroxy-pentyloxy)-tetrahydro-pyran-4-yl ester

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOMe / methanol
2: 5percent H2SO4 / H2O; dioxane
View Scheme
(1R,4'R)-1-(2,2-dimethyl-1,3-dioxolane-4-yl)-2-trimethylsilylprop-2-en-1-ol
102419-56-7

(1R,4'R)-1-(2,2-dimethyl-1,3-dioxolane-4-yl)-2-trimethylsilylprop-2-en-1-ol

Adonitol
488-81-3

Adonitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 85 percent / TBHP-VO(acac)2
2: 80 percent / t-BuOK, n-Bu4NF
3: 70 percent / NaOH / 70 °C
4: HCl
View Scheme
Adonitol
488-81-3

Adonitol

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

bis(2,2-dimethyl-1,3-dioxolan-4-yl)methanol
3969-85-5, 73543-86-9, 88390-55-0

bis(2,2-dimethyl-1,3-dioxolan-4-yl)methanol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide Ambient temperature;99%
With hydrogen cation In acetone for 2h; Ambient temperature;95%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; acetone at 20℃; for 16h; Cyclization;85%
4,4-dimethyl-5-methylene-1,3-dioxolan-2-one
4437-80-3

4,4-dimethyl-5-methylene-1,3-dioxolan-2-one

Adonitol
488-81-3

Adonitol

C13H16O10

C13H16O10

Conditions
ConditionsYield
With 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine In N,N-dimethyl-formamide at 25℃; for 24h;99%
Adonitol
488-81-3

Adonitol

acetic anhydride
108-24-7

acetic anhydride

penta-O-acetylribitol
7208-42-6

penta-O-acetylribitol

Conditions
ConditionsYield
With Sulfuric acid immobilized on silica gel at 20℃; for 0.333333h; neat (no solvent);98%
With zinc(II) chloride anfangs unter Eiskuehlung;
With pyridine Ambient temperature;
Adonitol
488-81-3

Adonitol

(S)-((R)-2-Oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-((S)-2-oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-methanol

(S)-((R)-2-Oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-((S)-2-oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-methanol

Conditions
ConditionsYield
With 1H-imidazole; thionyl chloride In tetrahydrofuran at -10℃; for 0.5h;98%
Adonitol
488-81-3

Adonitol

LACTIC ACID
849585-22-4

LACTIC ACID

Conditions
ConditionsYield
With barium hydroxide octahydrate In methanol at 140℃; for 12h; Inert atmosphere; Sealed tube;93%
With H2O*Ba8H16O16 In methanol at 140℃; for 12h; Sealed tube;88 %Chromat.
Adonitol
488-81-3

Adonitol

ethyl fluoroformate
461-64-3

ethyl fluoroformate

Penta-O-(ethoxycarbonyl)adonitol
124781-65-3

Penta-O-(ethoxycarbonyl)adonitol

Conditions
ConditionsYield
With potassium fluoride In dimethyl sulfoxide 1) 60 deg C, 10 h; 2) 90 deg C, 10 h;91%
Conditions
ConditionsYield
With hydrogenchloride at 100℃; for 48h;90%
With pyridine hydrochloride at 150℃;70%
at 290℃; for 2h;45%
With hydrogenchloride at 110℃;
Conditions
ConditionsYield
With carbon tetrabromide; triphenylphosphine In N,N-dimethyl-formamide Ambient temperature;90%
In water at 249.84℃; Kinetics; Temperature; Inert atmosphere;
isocyanate de chlorosulfonyle
1189-71-5

isocyanate de chlorosulfonyle

Adonitol
488-81-3

Adonitol

d-ribitol pentacarbamate

d-ribitol pentacarbamate

Conditions
ConditionsYield
In acetonitrile at 20℃; for 1.5h; Cooling with ice;88%
Adonitol
488-81-3

Adonitol

trityl chloride
76-83-5

trityl chloride

1,5-Di-O-trityladonitol
96871-07-7

1,5-Di-O-trityladonitol

Conditions
ConditionsYield
With pyridine at 100℃; for 22h; Inert atmosphere;85%
With pyridine at 100℃;
With pyridine at 20℃;
With pyridine; dmap at 25℃; for 33h;
With pyridine; dmap at 20℃; for 30h; Inert atmosphere;
Conditions
ConditionsYield
With toluene-4-sulfonic acid In various solvent(s) Ambient temperature;85%
Adonitol
488-81-3

Adonitol

dichloromethylenedimethyliminium chloride
33842-02-3, 529510-96-1

dichloromethylenedimethyliminium chloride

1,5-dichloro-1,5-dideoxy-2,4-di-O--ribitol
143094-04-6, 143167-34-4, 143167-35-5

1,5-dichloro-1,5-dideoxy-2,4-di-O--ribitol

Conditions
ConditionsYield
In 1,4-dioxane at 25℃; for 2.5h;79%
In 1,4-dioxane at 23℃; for 2.5h;79%
Adonitol
488-81-3

Adonitol

p-formylacetophenone
3457-45-2

p-formylacetophenone

2,4-(4-methylcarbonylbenzylidene)-D-xylitol

2,4-(4-methylcarbonylbenzylidene)-D-xylitol

Conditions
ConditionsYield
With hydrogenchloride In methanol; water for 8h;70%
Adonitol
488-81-3

Adonitol

phenylcarbonochloridothioate
1005-56-7

phenylcarbonochloridothioate

ribitol-1,2:4,5-bis-thionocarbonate

ribitol-1,2:4,5-bis-thionocarbonate

Conditions
ConditionsYield
Stage #1: Adonitol With di(n-butyl)tin oxide In toluene
Stage #2: phenylcarbonochloridothioate In chloroform at 20℃; for 4h;
63%
Stage #1: Adonitol With di(n-butyl)tin oxide In toluene Heating;
Stage #2: phenylcarbonochloridothioate In chloroform at 20℃; for 4h;
63%
Adonitol
488-81-3

Adonitol

C22H22ClF3N2O4S

C22H22ClF3N2O4S

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

C30H32ClF3N2O8S

C30H32ClF3N2O8S

Conditions
ConditionsYield
Stage #1: Adonitol With pyridine hydrochloride at 150℃; for 4h;
Stage #2: 2,2-dimethoxy-propane With toluene-4-sulfonic acid In acetone at 20℃; for 0.5h;
Stage #3: C22H22ClF3N2O4S Further stages;
58%
Adonitol
488-81-3

Adonitol

ribitol 3-O-(dichlorophosphite) 1,2;4,5-bis-O-(chlorophosphite)
100664-93-5

ribitol 3-O-(dichlorophosphite) 1,2;4,5-bis-O-(chlorophosphite)

Conditions
ConditionsYield
With phosphorus trichloride In 1,4-dioxane at 60 - 65℃; for 30h;57%
Adonitol
488-81-3

Adonitol

acetic anhydride
108-24-7

acetic anhydride

benzyl bromide
100-39-0

benzyl bromide

A

penta-O-acetylribitol
7208-42-6

penta-O-acetylribitol

2,3,4,5-tetra-O-acetyl-1-O-benzyl-D,L-ribitol

2,3,4,5-tetra-O-acetyl-1-O-benzyl-D,L-ribitol

C

2,3,4-tri-O-acetyl-1,5-di-O-benzylribitol

2,3,4-tri-O-acetyl-1,5-di-O-benzylribitol

Conditions
ConditionsYield
Stage #1: Adonitol With bis(tri-n-butyltin)oxide In toluene for 5h; Heating;
Stage #2: benzyl bromide at 80℃; for 20h;
Stage #3: acetic anhydride With pyridine at 20℃;
A 23%
B 52%
C 16%
Adonitol
488-81-3

Adonitol

dichloromethylenedimethyliminium chloride
33842-02-3, 529510-96-1

dichloromethylenedimethyliminium chloride

A

1,5-dichloro-1,5-dideoxy-2,4-di-O--ribitol
143094-04-6, 143167-34-4, 143167-35-5

1,5-dichloro-1,5-dideoxy-2,4-di-O--ribitol

1,4,5-trichloro-1,4,5-trideoxy-2,3-di-O--DL-arabinitol

1,4,5-trichloro-1,4,5-trideoxy-2,3-di-O--DL-arabinitol

Conditions
ConditionsYield
In 1,4-dioxane at 23℃; for 26h;A 47%
B 20%
Adonitol
488-81-3

Adonitol

dichloromethylenedimethyliminium chloride
33842-02-3, 529510-96-1

dichloromethylenedimethyliminium chloride

A

1,5-dichloro-1,5-dideoxy-2,4-di-O--ribitol
143094-04-6, 143167-34-4, 143167-35-5

1,5-dichloro-1,5-dideoxy-2,4-di-O--ribitol

B

1,3,5-trichloro-1,3,5-trideoxy-2,4-di-O--ribitol or -xylitol

1,3,5-trichloro-1,3,5-trideoxy-2,4-di-O--ribitol or -xylitol

Conditions
ConditionsYield
In 1,4-dioxane at 23℃; for 26h;A 47%
B 21%
Adonitol
488-81-3

Adonitol

acetic anhydride
108-24-7

acetic anhydride

benzyl bromide
100-39-0

benzyl bromide

A

penta-O-acetylribitol
7208-42-6

penta-O-acetylribitol

2,3,4,5-tetra-O-acetyl-1-O-benzyl-D,L-ribitol

2,3,4,5-tetra-O-acetyl-1-O-benzyl-D,L-ribitol

C

2,3,4-tri-O-acetyl-1,5-di-O-benzylribitol

2,3,4-tri-O-acetyl-1,5-di-O-benzylribitol

2,3,5-tri-O-acetyl-1,4-di-O-benzyl-D,L-ribitol

2,3,5-tri-O-acetyl-1,4-di-O-benzyl-D,L-ribitol

Conditions
ConditionsYield
Stage #1: Adonitol With di(n-butyl)tin oxide In toluene for 16h; Heating;
Stage #2: benzyl bromide In chloroform at 65℃; for 65h;
Stage #3: acetic anhydride With pyridine at 20℃;
A 47%
B 10%
C n/a
D n/a
Stage #1: Adonitol With di(n-butyl)tin oxide In toluene for 16h; Heating;
Stage #2: benzyl bromide In chloroform at 50℃; for 40h;
Stage #3: acetic anhydride With pyridine at 20℃;
A 32%
B 31%
C 8%
D 17%
Stage #1: Adonitol With di(n-butyl)tin oxide In toluene for 16h; Heating;
Stage #2: benzyl bromide In chloroform at 65℃; for 65h;
Stage #3: acetic anhydride With pyridine at 20℃;
A 16%
B 26%
C 11%
D 20%
Adonitol
488-81-3

Adonitol

1-decanoic acid
334-48-5

1-decanoic acid

(±) ribitol monocaprate

(±) ribitol monocaprate

Conditions
ConditionsYield
With (1S)-10-camphorsulfonic acid; phenylboronic acid In toluene at 120 - 130℃; for 24h; Inert atmosphere; Dean-Stark;47%
Adonitol
488-81-3

Adonitol

stearic acid
57-11-4

stearic acid

(±) ribitol monostearate

(±) ribitol monostearate

Conditions
ConditionsYield
With (1S)-10-camphorsulfonic acid; phenylboronic acid In toluene at 120 - 130℃; for 24h; Inert atmosphere; Dean-Stark;44%
rac-3-octanol
589-98-0

rac-3-octanol

Adonitol
488-81-3

Adonitol

(E)-3-(penta-2,4-dienyloxy)octane
1402224-63-8

(E)-3-(penta-2,4-dienyloxy)octane

Conditions
ConditionsYield
With C13H21O3Re at 135℃; for 15h; Reagent/catalyst; Inert atmosphere;42%
Adonitol
488-81-3

Adonitol

triethyl phosphite
122-52-1

triethyl phosphite

3-O-(diethyl phosphite)-1,2:4,5-bis-O-(ethyl phosphite)ribitol
117562-69-3

3-O-(diethyl phosphite)-1,2:4,5-bis-O-(ethyl phosphite)ribitol

Conditions
ConditionsYield
at 115 - 130℃;38%
Adonitol
488-81-3

Adonitol

2-Methoxypropene
116-11-0

2-Methoxypropene

A

bis(2,2-dimethyl-1,3-dioxolan-4-yl)methanol
3969-85-5, 73543-86-9, 88390-55-0

bis(2,2-dimethyl-1,3-dioxolan-4-yl)methanol

1,4:2,3-di-O-isopropylidene-DL-ribitol
100423-71-0, 100484-25-1

1,4:2,3-di-O-isopropylidene-DL-ribitol

1,3:4,5-di-O-isopropylidene-DL-ribitol
131247-52-4

1,3:4,5-di-O-isopropylidene-DL-ribitol

1,3:2,5-di-O-isopropylidene-DL-ribitol
131247-54-6

1,3:2,5-di-O-isopropylidene-DL-ribitol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 0℃; for 0.0166667h;A 36%
B 3%
C 12%
D 5%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 0℃; for 0.0166667h; Product distribution;A 36%
B 3%
C 12%
D 5%
Adonitol
488-81-3

Adonitol

2-pentanol
584-02-1

2-pentanol

(E)-5-(pentan-3-yloxy)penta-1,3-diene
1402224-62-7

(E)-5-(pentan-3-yloxy)penta-1,3-diene

Conditions
ConditionsYield
With methyltrioxorhenium(VII) at 170℃; for 3h;33%
Adonitol
488-81-3

Adonitol

3,4-bis(decyloxy)benzoic acid
120878-42-4

3,4-bis(decyloxy)benzoic acid

Pentakis-O-(3,4-didecyloxybenzoyl)adonitol

Pentakis-O-(3,4-didecyloxybenzoyl)adonitol

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 72h; Esterification;8%

D-(+)-Arabitol Chemical Properties

Molecular Formula: C5H12O5
Molar mass: 152.15 g/mol
EINECS: 207-685-7
Density: 1.525 g/cm3
Flash Point: 261.9 °C
Index of Refraction: 1.57
Boiling Point: 494.5 °C at 760 mmHg
Vapour Pressure: 7.47E-12 mmHg at 25°C
Melting point: 102-105 °C
Storage temp: Store at RT.
Sensitive: Hygroscopic
Appearance: White powder
Product categories: Sugars, Carbohydrates & Glucosides;Biochemistry;Sugar Alcohols
Structure of Ribitol (488-81-3):
          
XLogP3-AA: -2.5
H-Bond Donor: 5
H-Bond Acceptor: 5
Systematic Name: Pentane-1,2,3,4,5-pentol 
SMILES: OC(CO)C(O)C(O)CO 
InChI: InChI=1/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2 
InChIKey: HEBKCHPVOIAQTA-UHFFFAOYAB 
Std. InChI: InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2 
Std. InChIKey: HEBKCHPVOIAQTA-UHFFFAOYSA-N

D-(+)-Arabitol Production

 Ribitol (488-81-3) is formed by the reduction of Ribose . It occurs naturally in the plant Adonis vernalis, as well as in the cell walls of Gram positive bacteria.

D-(+)-Arabitol Toxicity Data With Reference

1.    

ipr-mus LDLo:10 g/kg

    PSEBAA    Proceedings of the Society for Experimental Biology and Medicine. 35 (1936),98.

Carcinogenicity of Ribitol (488-81-3) hasn't been listed as a carcinogen by NTP, IARC,ACGIH, or CA Prop 65.You can see actual entry in RTECS for complete information.

D-(+)-Arabitol Consensus Reports

Reported in EPA TSCA Inventory.

D-(+)-Arabitol Safety Profile

Mildly toxic by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating fumes.
 

Hazard Codes: Xi
Risk Statements:
36:  Irritating to the eyes
37:  Irritating to the respiratory system
38:  Irritating to the skin
Safety Statements:
24:  Avoid contact with skin
25:  Avoid contact with eyes
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:  Wear suitable protective clothing

D-(+)-Arabitol Specification

 Ribitol (488-81-3) is a crystalline pentose alcohol, and also can be called adonitol  ; pentitol ; Pentane-1,2,3,4,5-pentaol ; 1,2,3,4,5-Pentanepentol ; 1,2,3,4,5-Pentahydroxypentane .It is hazardous,so the first aid measures and others should be known.Such as: When on the skin: should  flush skin with plenty of water immediatelyfor at least 15 minutes while removing contaminated clothing.Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Then you have the ingesting of the product : Do not induce vomiting.If victim is conscious and alert, give 2-4 cupfuls of milk or water.
In addition, Ribitol (488-81-3) can be stable under normal temperature and pressure conditions.It is not compatible with strong oxidizing agents, and you must not take it with strong oxidants and incompatible materials.And also prevent it to broken down into hazardous decomposition products: irritating and toxic fumes and gases, carbon dioxide, carbon monoxide.

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