Isosorbide

Iupac Name：(3S,3aR,6R,6aR)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol

Molecular Weight：146.14

Modify Date.: 2022-11-29 08:04

Introduction: Isosorbide is a reagent widely used to prepare detergents, cleansers, cosmetics, agrochemicals and vasodilators. View more+

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1. Names and Identifiers

1.1 Name: Isosorbide
1.2 Synonyms: (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furane-3,6-diol 1,4:3,6-DIANHYDRO-D-GLUCITOL 1,4:3,6-DIANHYDRO-D-SORBITOL 1,4:3,6-DIANHYDROGLUCITOL 1,4:3,6-dianhydrogluticol 1,4:3,6-Dianhydro-L-glucitol 1,4:3,6-DIANHYDROSORBITOL at101 D-1,4:3,6-Dianhydroglucitol devicoran D-Glucitol, 1,4:3,6-dianhydro- DIANHYDRO-D-GLUCITOL DIANHYDRO-D-SORBITOL D-ISOSORBIDE EINECS 211-492-3 hydronol IsMotic isobide Isosorbid L-Glucitol, 1,4:3,6-dianhydro- MFCD00064827

1.3 CAS No.: 652-67-5

1.4 CID: 12597

1.5 EINECS(EC#): 211-492-3

1.6 Molecular Formula: C6H10O4 (isomer)

1.7 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

1.8 InChkey: KLDXJTOLSGUMSJ-JGWLITMVSA-N

1.9 Canonical Smiles: C1C(C2C(O1)C(CO2)O)O

1.10 Isomers Smiles: C1[C@H]([C@@H]2[C@H](O1)[C@H](CO2)O)O

2. Properties

2.1 Density: 1.0945 (rough estimate)

2.1 Melting point: 60-63 °C(lit.)

2.1 Boiling point: 175°C/2mmHg(lit.)

2.1 Refractive index: 45 ° (C=5, H2O)

2.1 Flash Point: 372.1 oC at 760 mmHg

2.1 Precise Quality: 146.05800

2.1 PSA: 58.92000

2.1 logP: -1.49420

2.1 Appearance: Off-white to light yellow or beige Crystals, Crystalline Solid or Mass

2.2 Storage: Hygroscopic. Ambient temperatures.

2.3 Chemical Properties: off-white to light yellow or beige crystals,

2.4 Color/Form: CRYSTALS

2.5 pKa: 13.17±0.40(Predicted)

2.6 Water Solubility: Soluble in alcohols, water and ketones.

2.7 Spectral Properties: SPECIFIC OPTICAL ROTATION: +44 DEG/D

2.8 StorageTemp: Refrigerator

3. Use and Manufacturing

3.1 Definition: A polyol with a hydroxyl group attached to each oftwo cis-oriented saturated furan rings. Intermediatefor pharmaceuticals. Combustible.

3.2 Methods of Manufacturing: PREPARED BY ACID DEHYDRATION OF D-GLUCITOL: HAWORTH, WIGGINS, BRITISH PATENT 600,870 (1948). PURIFICATION: HARTMANN, US PATENT 3,160,641 (1964 TO ATLAS CHEM INDUSTRIES).

3.3 Usage: Isosorbide is a reagent widely used to prepare detergents, cleansers, cosmetics, agrochemicals and vasodilators.

4. Safety and Handling

4.1 Risk Statements: 22

4.1 Safety Statements: 24/25

4.1 Formulations/Preparations: ISMOTIC (ALCON), ORAL AS 45% SOLUTION.

4.2 WGK Germany: 2

4.2 RTECS: LZ4380000

4.2 Safety: Risk Statements:22
22:Harmful if swallowed
Safety Statements:24/25
24/25:Avoid contact with skin and eyes
WGK Germany:2

4.3 Sensitive: Hygroscopic

4.4 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.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

652-67-5Total: 33 Synthesis Route

50-70-4 553 Suppliers

652-67-5 164 Suppliers

Literatures:
Li, Ning; Huber, George W. Journal of Catalysis, 2010 , vol. 270, # 1 p. 48 - 59
Yield: ~96%

57-50-1 349 Suppliers

652-67-5 164 Suppliers

Literatures:
Journal of the Chemical Society, , p. 433,435 Journal of the Chemical Society, , p. 2204,2206
Yield: null

50-70-4 553 Suppliers

488-81-3 83 Suppliers

652-67-5 164 Suppliers

Literatures:
US2008/249323 A1, ; Page/Page column 2 ;
Yield: null

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8. Precursor and Product

precursor:

470-15-5

53648-56-9

492-61-5

133-99-3

50-70-4

7726-97-8

641-74-7

1072106-21-8

87-33-2

13042-38-1

7625-23-2

64-19-7

57-50-1

View all

product :

5306-85-4

16051-77-7

185756-31-4

1235553-24-8

162426-86-0

50-70-4

6941-54-4

65940-93-4

1235553-25-9

84207-82-9

24808-20-6

226709-43-9

87-33-2

13042-38-1

1235553-26-0

13042-39-2

6338-38-1

399534-53-3

View all

9. Other Information

9.0 Usage: D-Isosorbide is used as a reagent in the preparation of detergents, agrochemicals, cleansers, cosmetics and vasodilators. It is also employed as a pharmaceutical intermediate for dimethyl ether and mono- and dinitrate derivatives, which is used as vasodilators and coronary disease therapeutics. It is used in the treatment of hydrocephalus and glaucoma. It finds application as a building block for polymers like polycarbonates and polyesters.

9.1 Storage Conditions: PREPARED BY ACID DEHYDRATION OF D-GLUCITOL: HAWORTH, WIGGINS, BRITISH PATENT 600,870 (1948). PURIFICATION: HARTMANN, US PATENT 3,160,641 (1964 TO ATLAS CHEM INDUSTRIES).

9.2 Therapeutic Uses: Diuretics, Osmotic|...IS ORAL OSMOTIC AGENT USED FOR EMERGENCY TREATMENT OF ACUTE ANGLE-CLOSURE GLAUCOMA & OTHER CONDITIONS IN WHICH RAPID REDUCTION IN INTRAOCULAR PRESSURE & VITREOUS VOLUME IS INDICATED.|ISOSORBIDE PRODUCES MORE SIGNIFICANT DIURESIS THAN GLYCERIN & CATHETERIZATION MAY BE NECESSARY.|USE OF ISOSORBIDE STUDIED IN 23 CHILDREN WITH MYELODYSPLASIA & HYDROCEPHALUS. HEAD GROWTH RATE SIGNIFICANTLY DECR IN 18 PATIENTS. CEREBROSPINAL FLUID FLOW DECR BY 50% IN 12 ISOSORBIDE TRIALS. DRUG IS OF BENEFIT FOR TEMPORARY USE PRIOR TO INSERTION OF MECHANICAL SHUNT SYSTEM.|For more Therapeutic Uses (Complete) data for ISOSORBIDE (8 total), please visit the HSDB record page.

9.3 Mesh: Compounds that increase urine volume by increasing the amount of osmotically active solute in the urine. Osmotic diuretics also increase the osmolarity of plasma. (See all compounds classified as Diuretics, Osmotic.)

9.4 Absorption: IN DOGS, 5.5 MILLIMOLES/KG IV CAUSED LESS SOLUTE EXCRETION THAN AN EQUIMOLAR DOSE OF MANNITOL. THE DISTRIBUTION SPACE OF LABELED ISOSORBIDE WAS 54% OF BODY WT IN INTACT & NEPHRECTOMIZED DOGS. PROXIMAL TUBULAR REABSORPTION OF ISOSORBIDE WAS PROBABLY PASSIVE.

9.5 Biological Half Life: TEN NORMAL MALES RECEIVED 0.25-1.5 G/KG ISOSORBIDE. DOSE RESPONSE EFFECTS ON WATER & OSMOLAR EXCRETION STATISTICALLY SIGNIFICANT. IN 9 VOLUNTEERS, ORALLY ADMIN ISOSORBIDE APPEARED RAPIDLY IN PLASMA & EXCRETED IN URINE WITH MEAN DISAPPEARANCE HALF-LIFE OF 8 HR.|ISOSORBIDE WAS RAPIDLY ABSORBED BY HUMANS FOLLOWING ORAL ADMIN & WAS EXCRETED UNCHANGED VIA KIDNEY WITH A MEAN DISAPPEARANCE T/2 OF APPROX 7 HR. IT INCREASED URINE VOLUME, CREATININE CLEARANCE, & SODIUM & CHLORIDE EXCRETION.|RABBITS GIVEN ORAL DOSES OF 2 G/KG FOR 1-7 DAYS HAD EST EXCRETION T/2 OF LESS THAN 6 HR IN ALL EYE TISSUE. PEAK LEVEL & EXCRETION T/2 WAS SIMILAR IN DAMAGED & UNDAMAGED EYE TISSUE, EXCEPT IN LENS OF DAMAGED EYES IN WHICH EXCRETION T/2 WAS SHORTER THAN OF NORMAL EYES.

9.6 Human Toxicity Excerpts: UNTOWARD EFFECTS ARE...SIMILAR /TO GLYCERIN/, ALTHOUGH ISOSORBIDE DOES NOT ADVERSELY AFFECT BLOOD GLUCOSE LEVELS & MAY CAUSE LESS NAUSEA & VOMITING /ORAL ADMIN/.|USE OF ISOSORBIDE STUDIED IN 23 CHILDREN WITH MYELODYSPLASIA & HYDROCEPHALUS. REVERSIBLE MILD TOXICITY INCLUDED LOOSE STOOLS, PALLOR, IRRITABILITY, HYPERNATREMIA, & DOUGHY SKIN.|ISOSORBIDE ADMIN ORALLY IN DAILY DOSES AVG 10 G/KG FOR A MEAN DURATION OF 4 DAYS NOTED ELEVATED SERUM SODIUM OR BLOOD UREA NITROGEN LEVELS, AS OBSERVED IN 26 TRIALS. TOXICITY WAS ALWAYS REVERSED BY DOSAGE ADJUSTMENTS.

9.7 Mesh Entry Terms: Dianhydrosorbitol

9.8 Production: 1,000,000 - 10,000,000 lb

9.9 Formulations: ISMOTIC (ALCON), ORAL AS 45% SOLUTION.

9.10 Manufacturing Info: All other chemical product and preparation manufacturing|D-Glucitol, 1,4:3,6-dianhydro-: ACTIVE|PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.|A POLYOL WITH HYDROXYL GROUP ATTACHED TO EACH OF TWO CIS-ORIENTED SATURATED FURAN RINGS.

9.11 Use Classification: Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

10. Computational chemical data

Molecular Weight: 146.14g/mol
Molecular Formula: C₆H₁₀O₄
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 146.05790880
Monoisotopic Mass: 146.05790880
Complexity: 122
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 58.9
Heavy Atom Count: 10
Defined Atom Stereocenter Count: 4
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBgOAAAAAAAAAAAAAAAAAAAASJAAAAAAAAAAAASAAAAAAAAGgAACAAACBSggAIAAAAABgAAAAAAAAAAAAAAAAAAAAAAAAABEAIAAAACQAAFAAADAAHAYAQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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