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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H14O6
Molecular Weight 182.1718
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SORBITOL, L-

SMILES

OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO

InChI

InChIKey=FBPFZTCFMRRESA-FSIIMWSLSA-N
InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m0/s1

HIDE SMILES / InChI

Molecular Formula C6H14O6
Molecular Weight 182.1718
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Sorbitol 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. L-Sorbitol is a sugar alcohol also known as glucitol. Used as a non-stimulant laxative via an oral suspension or enema. Sorbitol exerts its laxative effect by drawing water into the large intestine, thereby stimulating bowel movements. Sorbitol plays a vital step in the 'polyol pathway'. The sudden injection of extra sorbitol can ruin the equilibrium of enzymes that regulate the conversion of glucose to fructose in a process associated with the onset of diabetes and its complications. Further, the polyol pathway is involved with a complex network of metabolic activities; disruption leads to a cascade of problems (citations here, here and here) such as mitochondrial failure, cell apoptosis (cell death), and DNA fragmentation. In general, sorbitol induces cell hyperosmotic stress resulting in phosphorylation (uptake of phosphorus into cell) — an important on/off switch regulating enzymes and signaling networks. Bradyrhizobium japonicum sorbitol dehydrogenase is NADH-dependent and is active at elevated temperatures. The best substrate is D-glucitol, although L-glucitol (L-glucitol) is also accepted, giving it particular potential in industrial applications.

Originator

Sources: Alternative Sweeteners, Third Edition, Revised and Expanded. Ed. Lyn O'Brien-Nabors. CRC Press, 2001, p. 572
Curator's Comment: Manufactured - Atlas Powder Company, Wilmington, Delaware, 1937

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:05:27 GMT 2023
Edited
by admin
on Sat Dec 16 10:05:27 GMT 2023
Record UNII
01Q0586BG1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SORBITOL, L-
Common Name English
L-GLUCITOL
Common Name English
D-GULITOL
Common Name English
GLUCITOL, L-
Common Name English
L-SORBITOL
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID4042096
Created by admin on Sat Dec 16 10:05:27 GMT 2023 , Edited by admin on Sat Dec 16 10:05:27 GMT 2023
PRIMARY
RXCUI
1742749
Created by admin on Sat Dec 16 10:05:27 GMT 2023 , Edited by admin on Sat Dec 16 10:05:27 GMT 2023
PRIMARY
CAS
6706-59-8
Created by admin on Sat Dec 16 10:05:27 GMT 2023 , Edited by admin on Sat Dec 16 10:05:27 GMT 2023
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FDA UNII
01Q0586BG1
Created by admin on Sat Dec 16 10:05:27 GMT 2023 , Edited by admin on Sat Dec 16 10:05:27 GMT 2023
PRIMARY
CHEBI
28789
Created by admin on Sat Dec 16 10:05:27 GMT 2023 , Edited by admin on Sat Dec 16 10:05:27 GMT 2023
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PUBCHEM
82170
Created by admin on Sat Dec 16 10:05:27 GMT 2023 , Edited by admin on Sat Dec 16 10:05:27 GMT 2023
PRIMARY
DAILYMED
01Q0586BG1
Created by admin on Sat Dec 16 10:05:27 GMT 2023 , Edited by admin on Sat Dec 16 10:05:27 GMT 2023
PRIMARY