CAS 652-67-5 Isosorbide (HCID 12597)

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Basic information

CAS: 652-67-5
Standard SMILES: O[C@@H]1CO[C@H]2[C@@H]1OC[C@@H]2O
InChIKey: KLDXJTOLSGUMSJ-JGWLITMVSA-N
Molecular formula: C6H10O4
Average molar mass: 146.14 g/mol
Monoisotopic mass: 146.0579088

Names & identifiers

Preferred name: Isosorbide
IUPAC: (3S,3aR,6R,6aR)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol
English name: Isosorbide
Molecular formula: C6H10O4
Molecular weight: 146.14

Names & synonyms

isosorbide652-67-5Isobide1,4:3,6-Dianhydro-D-glucitolDevicoran(3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diolHydronolIsmotic(+)-D-IsosorbideD-Glucitol, 1,4:3,6-dianhydro-1,4:3,6-Dianhydro-D-sorbitol1,4:3,6-Dianhydrosorbitol

Show more names

at101Isosorbide (75% solution, 1 g)ucitoLIsosorbidNSC 40725

DTXSID5046196NSC-40725Glucitol, 1,4:3,6-dianhydro-, D-WXR179L51SNSC40725DTXCID3026196(3R,3aR,6S,6aR)-hexahydrofuro(3,2-b)furan-3,6-diolRefChem:55420

Database identifiers

CAS: 652-67-5
PubChem CID: 12597
DTXSID: DTXSID5046196
ChEMBL: CHEMBL1200660
ChEBI: CHEBI:6060
UNII: WXR179L51S
EC Number: 211-492-3
Nikkaji: J7.077G

Properties

Computed structural properties

XLogP: -1.4
Topological polar surface area: 58.9 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 0
Heavy atoms: 10
Formal charge: 0
Complexity: 122

Physicochemical properties

Melting point: 60 · 60-63 °C (lit.)
alpha: 42 · 42 º (c=3, H2O)
Boiling point: 175 °C/2mmHg · 175°C/2mmHg(lit.)
Density: 1.0945 · 1.0945 (rough estimate)
vapor pressure: 0.007 Pa · 0.007Pa at 20℃
refractive index: 45 ° · 45 ° (C=5, H2O)
storage temp.: Inert atmosphere,Room Temperature
solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
form: Crystals, Crystalline Solid or Mass
pka: 13.17 · 13.17±0.40(Predicted)
color: Off-white to light yellow or beige
optical activity: 20 · [α]20/D +45.2°, c = 3 in H2O
Water Solubility: Soluble in alcohols, water and ketones.
Sensitive: Hygroscopic
Merck: 14 · 14,5224

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 2
tsca: TSCA listed
rtecs: LZ4380000
hs_code: 29349990
risk_code: 22
Signal word: Warning
Symbol(GHS): GHS05
safety_code: 24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H227
REACH Registrations: Active
Precautionary statements: P501-P210-P280-P370+P378-P403+P235
Hazardous Substances Data: 652-67-5(Hazardous Substances Data)

Chemistry & industry

Applications · 3 items

Usespharmaceutical intermediate for dimethyl ether and mono- and dinitrate derivatives; the nitrate esters find use as vasodilators and coronary disease therapeutics.

UsesD-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.

UsesIsosorbide is a reagent widely used to prepare detergents, cleansers, cosmetics, agrochemicals and vasodilators.