Common NameD-sorbitol
DescriptionSorbitol is a polyhydric alcohol with about half the sweetness of sucrose. Sorbitol occurs naturally and is also produced synthetically from glucose. It was formerly used as a diuretic and may still be used as a laxative and in irrigating solutions for some surgical procedures. It is also used in many manufacturing processes, as a pharmaceutical aid, and in several research applications. Ascorbic acid fermentation; in solution form for moisture-conditioning of cosmetic creams and lotions, toothpaste, tobacco, gelatin; bodying agent for paper, textiles, and liquid pharmaceuticals; softener for candy; sugar crystallization inhibitor; surfactants; urethane resins and rigid foams; plasticizer, stabilizer for vinyl resins; food additive (sweetener, humectant, emulsifier, thickener, anticaking agent); dietary supplement. (Hawley's Condensed Chemical Dictionary) Biological Source: Occurs widely in plants ranging from algae to the higher orders. Fruits of the plant family Rosaceae, which include apples, pears, cherries, apricots, contain appreciable amounts. Rich sources are the fruits of the Sorbus and Crataegus species Use/Importance: Used for manufacturing of sorbose, propylene glycol, ascorbic acid, resins, plasticizers and as antifreeze mixtures with glycerol or glycol. Tablet diluent, sweetening agent and humectant, other food uses. Sorbitol is used in photometric determination of Ru(VI) and Ru(VIII); in acid-base titration of borate (Dictionary of Organic Compounds).
Structure
Molecular FormulaC6H14O6
Average Mass182.17180
Monoisotopic Mass182.07904
IUPAC Name(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
Traditional NameD-sorbitol
CAS Registry Number50-70-4
SMILESOC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO
InChI IdentifierInChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1
InChI KeyFBPFZTCFMRRESA-JGWLITMVSA-N
CHEBI IDCHEBI:17924
HMDB IDHMDB0000247
Pathways
NameSMPDB/PathBank
Fructose and mannose metabolism
Galactose Metabolism
Galactosemia
Fructosuria
Fructose intolerance, hereditary
StateNot Available
Water Solubility2.29e+02 g/l
logP-2.68
logS0.10
pKa (Strongest Acidic)12.59
pKa (Strongest Basic)-2.97
Hydrogen Acceptor Count6
Hydrogen Donor Count6
Polar Surface Area121.38 Ų
Rotatable Bond Count5
Physiological Charge0
Formal Charge0
Refractivity38.40 m³·mol⁻¹
Polarizability17.12

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