FComEx: Erythritol (PC000689)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:58 UTC

Update date

2017-01-19 02:36:33 UTC

FoodComEx ID

PC000689

FoodDB Record

FDB000371

Chemical Information

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
(2R,3S)-Butane-1,2,3,4-tetrol	ChEBI
(2S,3S)-butane-1,2,3,4-tetrol	biospider
(R,S)-1,2,3,4-Butanetetrol, 9CI, 8CI	db_source
1,2,3, 4-Tetrahydroxybutane	biospider
1,2,3,4-Butanetetrol	biospider
1,2,3,4-Butanetetrol, (2R,3S)-rel-	biospider
1,2,3,4-Butanetetrol, (R,S)-	biospider
1,2,3,4-Butanetetrol, (theta,S)-	biospider
1,2,3,4-Butanetetrol, [S-(R,R)]-	biospider
1,2,3,4-Tetrahydroxybutane	biospider
2(R),3(S)-1,2,3,4-Butanetetrol	biospider
Antierythrite	biospider
butane-1,2,3,4-tetrol	biospider
Butanetetrol	biospider
C*eridex	biospider
D-erythritol	biospider
D-treitol	biospider
DL-1,2,3,4-Butanetetrol	biospider
DL-threitol	biospider
Erythrit	biospider
Erythrite	biospider
Erythritol, meso-	biospider
erythro-Tetritol	ChEBI
Erythroglucin	db_source
Erythrol	biospider
Erythrol (van)	biospider
I-erythritol	biospider
L-(-)-threitol	biospider
L-erythritol	biospider
L-threitol	biospider
Lichen sugar	biospider
Meso-erythritol	biospider
Meso-eythritol	biospider
Mesoerythritol	db_source
Paycite	biospider
Phycite	biospider
Phycitol	db_source
Tetrahydroxybutane	biospider

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

Chemical Taxonomy

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 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-2.29	HANSCH,C ET AL. (1995)
Experimental Water Solubility	610 mg/mL at 22 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 121.5°	DFC

Foods of Origin