29400

D-α,β-Cyclohexylideneglycerol

≥98.0% (sum of enantiomers, GC)

• Synonym(s): (S)-(+)-1,4-Dioxaspiro[4.5]decane-2-methanol
• Empirical Formula (Hill Notation): C₉H₁₆O₃
• CAS Number: 95335-91-4
• Molecular Weight: 172.22
• Beilstein/REAXYS Number: 108000
• MDL number: MFCD08276891
• UNSPSC Code: 12352005
• PubChem Substance ID: 24857694
• NACRES: NA.22

Properties

• assay: ≥98.0% (sum of enantiomers, GC)
• form: liquid
• optical activity: [α]20/D +5.9±0.5°, c = 5% in methanol
• refractive index: n20/D 1.477 (lit.); n20/D 1.480
• bp: 118-120 °C/5 mmHg (lit.)
• density: 1.096 g/mL at 25 °C (lit.)
• storage temp.: 2-8°C
• SMILES string: OC[C@H]1COC2(CCCCC2)O1
• InChI: 1S/C9H16O3/c10-6-8-7-11-9(12-8)4-2-1-3-5-9/h8,10H,1-7H2/t8-/m0/s1
• InChI key: XUGYZVQSZWPABZ-QMMMGPOBSA-N

Description

Application

D-α,β-Cyclohexylideneglycerol can be used:

• As an intermediate in the synthesis of antiarrhythmic oral drugs: (+)- and (−)-mexiletine.[1]
• As a precursor in the preparation of glycoglycerolipids.[2]
• As an intermediate in the synthesis of (S)-hydroxymethyl-1,4-benzodioxane, a key intermediate for the preparation of α-adrenergic receptor antagonists, and antidepressant drug doxazosin.[3]

Other Notes

Chiral building block; used e.g. in the synthesis of glycerides and carbohydrates[4]

Safety Information

• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves