Record Information
Version1.0
Creation date2010-04-08 22:09:46 UTC
Update date2020-09-17 15:42:12 UTC
Primary IDFDB011676
Secondary Accession Numbers
  • FDB030799
Chemical Information
FooDB NameD-Glucitol
DescriptionSorbitol, also known as D-glucitol or L-gulitol, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of sugars in which the carbonyl group (aldehyde or ketone from the reducing sugar) has been reduced to a primary or secondary hydroxyl group. Sorbitol is a polyhydric alcohol with about half the sweetness of sucrose. Sorbitol occurs naturally in many plants and plant products and is also produced synthetically from glucose. As an industrial chemical, sorbitol is used in the manufacturing of sorbose, propylene glycol and ascorbic acid. It is also used as a plasticizer and stabilizer for vinyl resins, urethane resins and for other rigid foams. Sorbitol also has some pharmaceutical utility. It was formerly used as a diuretic and may still be used as a laxative and in irrigating solutions for some surgical procedures. Sorbitol is also used as a pharmaceutical or cosmetic aid. Sorbitol is used in solution form for moisture-conditioning of cosmetic creams and lotions, toothpaste, gelatins and liquid pharmaceuticals. As a food additive sorbitol functions as a sweetener, humectant, emulsifier, thickener and anticaking agent. Sorbitol is also used as a softener for candy as it acts as a sugar crystallization inhibitor (Hawley's Condensed Chemical Dictionary). As a research chemical, sorbitol is used in photometric determination of Ru (VI) and Ru(VIII) and in acid-base titration of borate (Dictionary of Organic Compounds). Sorbitol occurs widely in nature and is found in simple plants such as algae to higher order plants. Fruits of the plant family Rosacea, which include apples, pears, cherries, apricots, contain appreciable amounts of sorbitol. Particularly rich sources of sorbitol are the fruits of the Sorbus and Crataegus species.
CAS Number50-70-4
Structure
Thumb
Synonyms
SynonymSource
(-)-SorbitolChEBI
(2R,3R,4R,5S)-Hexane-1,2,3,4,5,6-hexolChEBI
D-(-)-SorbitolChEBI
D-SorbitChEBI
D-SORBITOLChEBI
e 420ChEBI
e-420ChEBI
e420ChEBI
g-OlChEBI
GLC-OlChEBI
L-GulitolChEBI
D-GlucitolKegg
Sorbitol 3% in plastic containerKegg
D-SorbolHMDB
DiakarmonHMDB
EsasorbHMDB
Foodol D 70HMDB
GlucarineHMDB
GlucitolHMDB
KarionHMDB
Karion instantHMDB
Kyowa powder 50mHMDB
MultitolHMDB
NeosorbHMDB
Neosorb 20/60dCHMDB
Neosorb 70/02HMDB
Neosorb 70/70HMDB
Neosorb p 20/60HMDB
Neosorb p 60HMDB
Neosorb p 60WHMDB
NivitinHMDB
ResulaxHMDB
SionitHMDB
Sionit KHMDB
SioniteHMDB
SiononHMDB
SiosanHMDB
Sorbex mHMDB
Sorbex RHMDB
Sorbex RPHMDB
Sorbex SHMDB
Sorbex XHMDB
SorbilandeHMDB
SorbilaxHMDB
SorbitHMDB
Sorbit D 70HMDB
Sorbit D-powderHMDB
Sorbit DPHMDB
Sorbit DP 50HMDB
Sorbit kyowa powder 50mHMDB
Sorbit L 70HMDB
Sorbit SHMDB
Sorbit T 70HMDB
Sorbit W 70HMDB
Sorbit W-powderHMDB
Sorbit W-powder 50HMDB
Sorbit WPHMDB
SorbiteHMDB
Sorbitol FHMDB
Sorbitol FKHMDB
Sorbitol FPHMDB
Sorbitol SHMDB
Sorbitol syrup CHMDB
SorbiturHMDB
SorboHMDB
Sorbogem 712HMDB
SorbolHMDB
SorbostylHMDB
Medefield brand OF sorbitolHMDB
Sorbitol pfizer brandHMDB
YalHMDB
Klysma sorbitHMDB
MedevacHMDB
Trommsdorff brand OF sorbitolHMDB
Baxter brand OF sorbitolHMDB
Pfizer brand OF sorbitolHMDB
(-)-sorbitolbiospider
(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexolbiospider
FEMA 3029db_source
Glc-olChEBI
Neosorb 20/60dcHMDB
Neosorb P 20/60HMDB
Neosorb P 60HMDB
Neosorb P 60WHMDB
Sionit kHMDB
Sorbex rpHMDB
Sorbit dpHMDB
Sorbit dp 50HMDB
Sorbit t 70HMDB
Sorbitol fkHMDB
Predicted Properties
PropertyValueSource
Water Solubility229 g/LALOGPS
logP-2.7ALOGPS
logP-3.7ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.4 m³·mol⁻¹ChemAxon
Polarizability17.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H14O6
IUPAC name(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
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
Isomeric SMILESOC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
Average Molecular Weight182.1718
Monoisotopic Molecular Weight182.07903818
Classification
Description belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 39.56%; H 7.75%; O 52.70%DFC
Melting PointMp 110-112° (anhyd.)DFC
Boiling PointNot Available
Experimental Water Solubility2750 mg/mL at 30 oCMULLIN,JW (1972)
Experimental logP-2.20SANGSTER (1994)
Experimental pKapKa 13 (60°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +31 (molybdate)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0ldj-0941000000-19d96a9ba7ba0c482c83JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-014i-1973000000-d907b75f68a7927501a7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ldj-0941000000-19d96a9ba7ba0c482c83JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1973000000-d907b75f68a7927501a7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ktb-0931000000-4ffadb4b25e8e2510d93JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03k9-9500000000-97c5853d3e9b96f9d054JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positivesplash10-0a6s-7141193000-dcd9245e12314ee0ced4JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-017j-8900000000-700285f86eac0a3501d1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-066r-9000000000-84676b839b145250d67dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052f-9000000000-dce72cab270c488d65daJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0ik9-2900000000-26a16e983791be7818f2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0ik9-2900000000-6513771e890cbff9c402JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-0900000000-58e6917626e28d1830a2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-83169b2192f847cc0636JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0900000000-4cd721d87e359527adf3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0900000000-b44f68c64bc74e79e9fcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-bbb5e957a9e67ddc411eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-772c3052966c05f29842JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-d1fbea514e7f1c1628f2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0790000000-b5b098cd5b4b4ec10821JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0690000000-41d4e48d49836c63485cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-ef92b9091ecf5d15cdeeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-47f19bd4e51bff726536JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9100000000-60d5147d8e349337fe97JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-07ju-8900000000-36f0fe0f346a6424162aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0c0c-9200000000-36e85b5ec098a45204c3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-9000000000-77703ee971336704163fJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID5576
ChEMBL IDCHEMBL1682
KEGG Compound IDC00794
Pubchem Compound ID5780
Pubchem Substance IDNot Available
ChEBI ID17924
Phenol-Explorer IDNot Available
DrugBank IDDB01638
HMDB IDHMDB00247
CRC / DFC (Dictionary of Food Compounds) IDBTN67-X:GXX95-H
EAFUS ID3491
Dr. Duke IDSORBITOL|D-SORBITOL
BIGG ID36018
KNApSAcK IDC00001173
HET IDSOR
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1034721
SuperScent IDNot Available
Wikipedia IDSorbitol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ketoticDUKE
cataractagenicDUKE
cathartic75325 Any substance that accelerates defecation. Compare with laxatives, which are substances that ease defecation (usually by softening faeces). A substance can be both a laxative and a cathartic.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
humectant77969 A humectant that is used as a food additive to prevent foodstuffs from drying out.DUKE
laxative50503 An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.DUKE
purgative50503 An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.DUKE
sweetener50505 Substance that sweeten food, beverages, medications, etc.DUKE
Enzymes
NameGene NameUniProt ID
Alpha-galactosidase AGLAP06280
Glycophorin-BGYPBP06028
GlucokinaseGCKP35557
Hexokinase-3HK3P52790
Hexokinase-2HK2P52789
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064 map00051
Galactose MetabolismSMP00043 map00052
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramel
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).