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652-67-5

Basic Information
CAS No.: 652-67-5
Name: Isosorbide
Molecular Structure:
Molecular Structure of 652-67-5 (Isosorbide)
Formula: C6H10O4
Molecular Weight: 146.14 .
Synonyms: 1,4:3, 6-Dianhydro-D-glucitol;Hydronol;D-Glucitol, 1,4:3,6-dianhydro-;AT-101;Vascardin dinitrate;(1S,2S,5S,6R)-4,8-dioxabicyclo[3.3.0]octane-2,6-diol;Sorbid;(+)-D-Isosorbide;(1R,2S,5S,6R)-4,8-dioxabicyclo[3.3.0]octane-2,6-diol;Ismotic (TN);Devicoran;Glucitol, 1,4:3,6-dianhydro-, D-;Isosorbide (JP14/USP);D-Isosorbide;
EINECS: 211-492-3
Density: 1.475 g/cm3
Melting Point: 60-63 °C(lit.)
Boiling Point: 372.1 °C at 760 mmHg
Flash Point: 178.8 °C
Solubility: Soluble in alcohols, water and ketones.
Appearance: off-white to light yellow or beige crystal
Hazard Symbols:
Risk Codes: 22
Safety: 24/25
Transport Information:
PSA: 58.92000
LogP: -1.49420
Synthetic route
50-70-4

D-sorbitol

652-67-5

Isosorbide

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; carbonic acid dimethyl ester In methanol at 90℃; for 48h; Time; Large scale;98%
With sulfuric acid In water at 150℃; under 75.0075 Torr; for 3h; Reagent/catalyst;96.1%
With silica-alumina In water at 244.84℃; Inert atmosphere;95%
Conditions
ConditionsYield
With SA-SiO2-60.5 at 120℃; under 7.50075 Torr; for 10h; Reagent/catalyst;A n/a
B n/a
C 84%
Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; triethylamine In ethanol; water at 0℃; under 2250.23 Torr; for 12h; Autoclave;A 81.55%
B 16.1%
Conditions
ConditionsYield
zinc(II) chloride In 1-methyl-3-octylimidazol-3-ium chloride at 150℃; for 1h; Product distribution / selectivity;A 3.8%
B 76%
With zirconium phosphate In neat (no solvent) at 210℃; for 2h; Catalytic behavior; Temperature; Time; Reagent/catalyst; Inert atmosphere; Autoclave;A 73%
B n/a
With hydrogen; palladium on activated charcoal at 160℃; under 2311.54 Torr; for 6h; Product distribution / selectivity; Autoclave; Neat (no solvent);A 72.68%
B 2.1%
50-70-4

D-sorbitol

A

51607-79-5

2,5-anhydro-d-sorbitol

B

652-67-5

Isosorbide

Conditions
ConditionsYield
With H-beta zeolite In neat (no solvent) at 126.84℃; under 525.053 Torr; for 2h; Catalytic behavior; Reagent/catalyst;A n/a
B 76%
Conditions
ConditionsYield
sulfuric acid In water at 125 - 145℃; under 18 - 20 Torr; Industry scale;A n/a
B 75%
C n/a
D n/a
E n/a
50-70-4

D-sorbitol

A

1,5-sorbitan

B

652-67-5

Isosorbide

Conditions
ConditionsYield
With sulfuric acid In water at 200℃; under 30003 Torr; for 6h; Autoclave;A 8%
B 73%
50-70-4

D-sorbitol

A

51607-79-5

2,5-anhydro-d-sorbitol

B

652-67-5

Isosorbide

C

154-58-5

1,5-anhydro-D-glucitol

Conditions
ConditionsYield
With Amberlyst-15 at 120℃; under 7.50075 Torr; for 10h; Reagent/catalyst;A n/a
B 71%
C n/a
Conditions
ConditionsYield
With hydrogen; phosphotungstic acid; palladium on activated charcoal In water at 160℃; under 2311.54 Torr; for 20h; Product distribution / selectivity; Autoclave;A 13.06%
B 70.33%
C 5.73%
With hydrogen; palladium dichloride at 160℃; under 2311.54 Torr; for 6h; Product distribution / selectivity; Autoclave; Neat (no solvent);A 24.89%
B 55.76%
C 0.61%
Conditions
ConditionsYield
With pyridine hydrochloride at 185℃; for 10h;67%
With carbonic acid dimethyl ester In 1,4-dioxane; methanol at 120℃;1.07 g
With zinc(II) chloride at 300℃; under 71257.1 Torr; for 0.05h; Temperature; Pressure; Autoclave;
With 4-methyl-2-pentanone at 170℃; for 1h; Autoclave;97.5 %Chromat.
50-99-7

D-glucose

652-67-5

Isosorbide

Conditions
ConditionsYield
Stage #1: D-glucose With sulfuric acid; hydrogen In water at 170℃; under 15001.5 Torr; for 2h; Autoclave;
Stage #2: In water at 200℃; under 30003 Torr; for 6h; Reagent/catalyst; Temperature; Pressure; Time; Autoclave;
65%
Conditions
ConditionsYield
In water at 251.84℃; for 10h; Kinetics; Temperature;A n/a
B 64.6%
C n/a
With toluene-4-sulfonic acid at 180℃; Reagent/catalyst;
Conditions
ConditionsYield
With hydrogen; nickel In methanol at 70℃; under 22800 Torr; for 3h;A 62%
B 38%
50-99-7

D-glucose

A

1,5-sorbitan

B

652-67-5

Isosorbide

Conditions
ConditionsYield
Stage #1: D-glucose With sulfuric acid; hydrogen In water at 170℃; under 15001.5 Torr; for 2h; Autoclave;
Stage #2: In water at 200℃; under 30003 Torr; for 6h; Autoclave;
A 8%
B 62%
50-70-4

D-sorbitol

A

652-67-5

Isosorbide

B

154-58-5

1,5-anhydro-D-glucitol

Conditions
ConditionsYield
With toluene-4-sulfonic acid; N,N,N-trimethyl-N-propylammonium bis(trifluoromethanesulfonyl)imide at 180℃; for 0.166667h; Reagent/catalyst; Temperature; Time; Microwave irradiation;A 61%
B 5%
With toluene-4-sulfonic acid; N,N,N-trimethyl-N-propylammonium bis(trifluoromethanesulfonyl)imide at 130℃; for 0.5h; Microwave irradiation; Ionic liquid;A 22%
B 26%
With N,N,N-trimethyl-N-propylammonium bis(trifluoromethanesulfonyl)imide at 180℃; for 0.166667h; Catalytic behavior; Reagent/catalyst; Microwave irradiation; chemoselective reaction;A 50 %Chromat.
B 18 %Chromat.
50-70-4

D-sorbitol

A

51607-79-5

2,5-anhydro-d-sorbitol

B

652-67-5

Isosorbide

C

32742-35-1

1,4-anhydro-D-galactitol

D

41107-82-8

2,5-anhydro-D-mannitol

Conditions
ConditionsYield
With sulfuric acid at 129.84℃; for 0.75h; Kinetics; Mechanism;A n/a
B 16%
C 58%
D n/a
50-70-4

D-sorbitol

A

652-67-5

Isosorbide

B

28218-55-5

2,5-anhydro-D-iditol

C

41107-82-8

2,5-anhydro-D-mannitol

Conditions
ConditionsYield
With Amberlite IR-120 (H+) at 170℃; under 10 Torr; for 2h;A 57%
B 4 % Spectr.
C 3 % Spectr.
Conditions
ConditionsYield
With H-beta zeolite modified with triphenylsilane at 126.84℃; under 525.053 Torr; for 1h; Catalytic behavior; Reagent/catalyst;A n/a
B 57%
C 18%
milled cellulose

milled cellulose

652-67-5

Isosorbide

Conditions
ConditionsYield
With ruthenium on carbon; water; hydrogen at 189.84℃; under 37503.8 Torr; for 16h; Reagent/catalyst; Acidic conditions; Inert atmosphere;55.8%
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Specification

The Hydronol, with its CAS registry number 652-67-5, has the IUPAC name of (3S,3aR,6R,6aR)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol. This is a kind of off-white to light yellow or beige crystal, and it is often used as the diuretic. When you swallow it, it will be harmful, and you should avoid contacting skin and eyes.

The characteristics of Hydronol are as follows: (1)ACD/LogP: -1.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.75; (4)ACD/LogD (pH 7.4): -1.75; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 2.65; (8)ACD/KOC (pH 7.4): 2.65; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 36.92; (13)Index of Refraction: 1.562; (14)Molar Refractivity: 32.11 cm3; (15)Molar Volume: 99 cm3; (16)Polarizability: 12.73×10-24 cm3; (17)Surface Tension: 56.6 dyne/cm; (18)Density: 1.475 g/cm3; (19)Flash Point: 178.8 °C; (20)Enthalpy of Vaporization: 71.64 kJ/mol; (21)Boiling Point: 372.1 °C at 760 mmHg; (22)Vapour Pressure: 4.71E-07 mmHg at 25°C; (23)Exact Mass: 146.057909; (24)MonoIsotopic Mass: 146.057909; (25)Topological Polar Surface Area: 58.9; (26)Heavy Atom Count: 10; (27)Complexity: 122.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C1C(C2C(O1)C(CO2)O)O
(2)Isomeric SMILES: C1[C@H]([C@@H]2[C@H](O1)[C@H](CO2)O)O
(3)InChI: InChI=1S/C6H10O4/c7-3-1-9-6-4(8)2-10-5(3)6/h3-8H,1-2H2/t3-,4+,5-,6-/m1/s1
(4)InChIKey: KLDXJTOLSGUMSJ-JGWLITMVSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 13600mg/kg (13600mg/kg)   Drugs in Japan Vol. 6, Pg. 71, 1982.
mouse LD50 intravenous 6870mg/kg (6870mg/kg) BRAIN AND COVERINGS: CHANGES IN CEREBRAL SPINAL FLUID Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 15, 1969.
mouse LD50 oral 289mg/kg (289mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 187, 1969.
rat LD50 intravenous 11gm/kg (11000mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 158S, 1968.
rat LD50 oral 24150mg/kg (24150mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 15, 1969.