AFCDB: Erythritol (FDB000371)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:32 UTC

Update date

2019-11-26 02:54:41 UTC

Primary ID

FDB000371

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Erythritol

Description

Bulk sweetener with good taste props. Not metabolised, excreted unchanged in urine. Less sweet than sucrose. Use not yet permitted in most countries (1997). GRAS status for use as a sweetener, thickener, stabiliser, humectant, etc. in food Erythritol ((2R,3S)-butane-1,2,3,4-tetraol) is a natural sugar alcohol (a type of sugar substitute) which has been approved for use in the United States and throughout much of the world. It occurs naturally in fruits and fermented foods. At industrial level, it is produced from glucose by fermentation with a yeast, Moniliella pollinis. It is 60?70% as sweet as table sugar yet it is almost non-caloric, does not affect blood sugar, does not cause tooth decay, and is absorbed by the body, therefore unlikely to cause gastric side effects unlike other sugar alcohols. Under U.S. Food and Drug Administration (FDA) labeling requirements, it has a caloric value of 0.2 calories per gram (95% less than sugar and other carbohydrates), though nutritional labelling varies from country to country?some countries like Japan label it as zero-calorie, while European Union regulations currently label it and all other sugar alcohols at 2.4 kcal/g.; Erythritol occurs widely in nature and has been found to occur naturally in several foods including wine, sake, beer, water melon, pear, grape and soy sauce. Evidence indicates that erythritol also exists endogenously in the tissues and body fluids of humans and animals. Erythritol is absorbed from the proximal intestine by passive diffusion in a manner similar to that of many low molecular weight organic molecules which do not have associated active transport systems, the rate of absorption being related to their molecular size; In the body, erythritol is absorbed into the bloodstream in the small intestine, and then for the most part excreted unchanged in the urine. Because erythritol is normally absorbed before it enters the large intestine, it does not normally cause laxative effects as are often experienced after over-consumption of other sugar alcohols (such as xylitol and maltitol) and most people will consume erythritol with no side effects. This is a unique characteristic, as other sugar alcohols are not absorbed directly by the body in this manner, and consequently are more prone to causing gastric distress.; erythritol, a 4-carbon molecule, passes through the intestinal membranes at a faster rate than larger molecules such as mannitol or glucose. In diabetics, erythritol also has been shown to be rapidly absorbed and excreted unchanged in the urine. Following absorption, ingested erythritol is rapidly distributed throughout the body and has been reported to occur in hepatocytes, pancreatic cells, and vascular smooth muscle cells. Erythritol also has been reported to cross the human placenta and to pass slowly from the plasma into the brain and cerebrospinal fluid. (PMID: 9862657, Food and Chemical Toxicology (1998), 36(12), 1139-1174.). Erythritol is found in caraway and garden tomato.

CAS Number

149-32-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1160 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.5	ChemAxon
logS	0.98	ALOGPS
pKa (Strongest Acidic)	13.04	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.48 m³·mol⁻¹	ChemAxon
Polarizability	11.62 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C4H10O4

IUPAC name

butane-1,2,3,4-tetrol

InChI Identifier

InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2

InChI Key

UNXHWFMMPAWVPI-UHFFFAOYSA-N

Isomeric SMILES

OCC(O)C(O)CO

Average Molecular Weight

122.1198

Monoisotopic Molecular Weight

122.057908808

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
Secondary alcohol
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tetritol (CHEBI:48299 )
a tetritol (ERYTHRITOL )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 39.34%; H 8.25%; O 52.41%	DFC
Melting Point	Mp 121.5°	DFC
Boiling Point	Bp200 294-296°	DFC
Experimental Water Solubility	610 mg/mL at 22 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-2.29	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-01ox-9000000000-3ac2b797c104b943b1d7	2015-03-01	View Spectrum
GC-MS	Erythritol, 4 TMS, GC-MS Spectrum	splash10-0gb9-0971000000-8e67d051d85e34209185	Spectrum
Predicted GC-MS	Erythritol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03di-9000000000-8f6f577c436c69d84442	Spectrum
Predicted GC-MS	Erythritol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-7249000000-2b2a68afd8e4a9b09f96	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-6900000000-993b4f8840593bb01df4	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-074i-9600000000-120187de75cfe655f4d8	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btc-9000000000-4da3c6e09ab3a9c35f25	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1900000000-42e92109aadc752f861b	2017-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03k9-9500000000-b3d2ffc98a4ae371becb	2017-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01pd-9000000000-6d1841dbd6795c6e454a	2017-09-21	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, D₂O, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17113

Phenol-Explorer ID

Not Available

DrugBank ID

DB04481

HMDB ID

HMDB02994

CRC / DFC (Dictionary of Food Compounds) ID

BBF48-I:BBF48-I

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00001161

HET ID

MRY

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1257251

SuperScent ID

Not Available

Wikipedia ID

Erythritol

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
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	CHEBI

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	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.

Erythritol (FDB000371)

Structure for FDB000371 (Erythritol)