AFCDB: D-Glucitol (FDB011676)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:46 UTC

Update date

2020-09-17 15:42:12 UTC

Primary ID

FDB011676

Secondary Accession Numbers

FDB030799

Chemical Information

FooDB Name

D-Glucitol

Description

Sorbitol, 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 Number

50-70-4

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	229 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-3.7	ChemAxon
logS	0.1	ALOGPS
pKa (Strongest Acidic)	12.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	121.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	38.4 m³·mol⁻¹	ChemAxon
Polarizability	17.12 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H14O6

IUPAC name

(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol

InChI Identifier

InChI=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 Key

FBPFZTCFMRRESA-JGWLITMVSA-N

Isomeric SMILES

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

Average Molecular Weight

182.1718

Monoisotopic Molecular Weight

182.07903818

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar alcohols

Alternative Parents

Substituents

Sugar alcohol
Monosaccharide
Secondary alcohol
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glucitol (CHEBI:17924 )

Ontology

Physiological effect

Health effect:

Health condition:

Uremia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 39.56%; H 7.75%; O 52.70%	DFC
Melting Point	Mp 110-112° (anhyd.)	DFC
Boiling Point	Not Available
Experimental Water Solubility	2750 mg/mL at 30 oC	MULLIN,JW (1972)
Experimental logP	-2.20	SANGSTER (1994)
Experimental pKa	pKa 13 (60°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D +31 (molybdate)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	D-Glucitol, non-derivatized, GC-MS Spectrum	splash10-0ldj-0941000000-19d96a9ba7ba0c482c83	Spectrum
GC-MS	D-Glucitol, 6 TMS, GC-MS Spectrum	splash10-014i-1973000000-d907b75f68a7927501a7	Spectrum
GC-MS	D-Glucitol, non-derivatized, GC-MS Spectrum	splash10-0ldj-0941000000-19d96a9ba7ba0c482c83	Spectrum
GC-MS	D-Glucitol, non-derivatized, GC-MS Spectrum	splash10-014i-1973000000-d907b75f68a7927501a7	Spectrum
GC-MS	D-Glucitol, non-derivatized, GC-MS Spectrum	splash10-0ktb-0931000000-4ffadb4b25e8e2510d93	Spectrum
Predicted GC-MS	D-Glucitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03k9-9500000000-97c5853d3e9b96f9d054	Spectrum
Predicted GC-MS	D-Glucitol, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a6s-7141193000-dcd9245e12314ee0ced4	Spectrum
Predicted GC-MS	D-Glucitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Glucitol, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-017j-8900000000-700285f86eac0a3501d1	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-066r-9000000000-84676b839b145250d67d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052f-9000000000-dce72cab270c488d65da	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0ik9-2900000000-26a16e983791be7818f2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0ik9-2900000000-6513771e890cbff9c402	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014j-0900000000-58e6917626e28d1830a2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0900000000-83169b2192f847cc0636	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03di-0900000000-4cd721d87e359527adf3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03di-0900000000-b44f68c64bc74e79e9fc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0900000000-bbb5e957a9e67ddc411e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0900000000-772c3052966c05f29842	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0900000000-d1fbea514e7f1c1628f2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0790000000-b5b098cd5b4b4ec10821	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0690000000-41d4e48d49836c63485c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0002-9200000000-9b9f891e480758a7d333	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0900000000-6ed9009701977f0a1c00	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-1900000000-7cc0793661b053aaf61e	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-ef92b9091ecf5d15cdee	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9300000000-47f19bd4e51bff726536	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9100000000-60d5147d8e349337fe97	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-07ju-8900000000-36f0fe0f346a6424162a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0c0c-9200000000-36e85b5ec098a45204c3	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btc-9000000000-77703ee971336704163f	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-3900000000-6801fbed6b67e0df2d20	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-9000000000-4454dcd4b817c183328b	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17924

Phenol-Explorer ID

Not Available

DrugBank ID

DB01638

HMDB ID

HMDB00247

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1034721

SuperScent ID

Not Available

Wikipedia ID

Sorbitol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti ketotic			DUKE
cataractagenic			DUKE
cathartic	75325	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
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
humectant	77969	A humectant that is used as a food additive to prevent foodstuffs from drying out.	DUKE
laxative	50503	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
purgative	50503	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
sweetener	50505	Substance that sweeten food, beverages, medications, etc.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Alpha-galactosidase A	GLA	P06280
Glycophorin-B	GYPB	P06028
Glucokinase	GCK	P35557
Hexokinase-3	HK3	P52790
Hexokinase-2	HK2	P52789

Pathways

Name	SMPDB Link	KEGG Link
Fructose and Mannose Degradation	SMP00064	map00051
Galactose Metabolism	SMP00043	map00052

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramel	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not 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).

D-Glucitol (FDB011676)

Structure for FDB011676 (D-Glucitol)