Record Information
Version1.0
Creation date2010-04-08 22:04:32 UTC
Update date2018-01-23 18:43:42 UTC
Primary IDFDB000371
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameErythritol
DescriptionBulk 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 Number149-32-6
Structure
Thumb
Synonyms
SynonymSource
(2R,3S)-Butane-1,2,3,4-tetrolChEBI
ErythritChEBI
ErythriteChEBI
Erythro-tetritolChEBI
ErythrolChEBI
L-ErythritolChEBI
MESO-erythritolChEBI
MesoerythritolChEBI
PhyciteChEBI
PhycitolChEBI
1,2,3,4-ButanetetrolHMDB
AntierythriteHMDB
ButanetetrolHMDB
C*EridexHMDB
ErythroglucinHMDB
I-erythritolHMDB
L-(-)-ThreitolHMDB
L-ThreitolHMDB
Lichen sugarHMDB
Meso-eythritolHMDB
PayciteHMDB
TetrahydroxybutaneHMDB
1,2,3,4-TetrahydroxybutaneHMDB
(2S,3S)-butane-1,2,3,4-tetrolbiospider
(R*,S*)-1,2,3,4-Butanetetrol, 9CI, 8CIdb_source
1,2,3, 4-Tetrahydroxybutanebiospider
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
2(R),3(S)-1,2,3,4-Butanetetrolbiospider
butane-1,2,3,4-tetrolbiospider
C*eridexbiospider
D-erythritolbiospider
D-treitolbiospider
DL-1,2,3,4-Butanetetrolbiospider
DL-threitolbiospider
Erythritol, meso-biospider
erythro-TetritolChEBI
Erythrol (van)biospider
L-(-)-threitolbiospider
L-erythritolbiospider
L-threitolbiospider
Meso-erythritolbiospider
Predicted Properties
PropertyValueSource
Water Solubility1160 g/LALOGPS
logP-2ALOGPS
logP-2.5ChemAxon
logS0.98ALOGPS
pKa (Strongest Acidic)13.04ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.48 m³·mol⁻¹ChemAxon
Polarizability11.62 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H10O4
IUPAC name(2R,3S)-butane-1,2,3,4-tetrol
InChI IdentifierInChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2
InChI KeyUNXHWFMMPAWVPI-UHFFFAOYSA-N
Isomeric SMILESOCC(O)C(O)CO
Average Molecular Weight122.1198
Monoisotopic Molecular Weight122.057908808
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 39.34%; H 8.25%; O 52.41%DFC
Melting PointMp 121.5°DFC
Boiling PointBp200 294-296°DFC
Experimental Water Solubility610 mg/mL at 22 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-2.29HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0gba-0930000000-dc2d1a78c7a0457d1e5eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0gb9-0950000000-0284cb64008968df5b85View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gba-0960000000-e3c06af410ada4c51c35View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-0930000000-dc2d1a78c7a0457d1e5eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-0950000000-0284cb64008968df5b85View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9000000000-83a8654b82fe1d2a6b5eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0ab9-7249000000-2b2a68afd8e4a9b09f96View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05tr-9500000000-c66e9c2cdca98e1a3073View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-8c8289ff9dce6ace80fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-9a74ea83fa64739762c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-b21b0229b3cca7a445e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-9500000000-793c9703aa07422f1014View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pd-9000000000-c17f1bba91d64dbd9f41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-7900000000-12421f1c391587323fb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9400000000-45979a06d5c9cf0240d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-e4d3d8da279144816016View in MoNA
MSMass Spectrum (Electron Ionization)splash10-01ox-9000000000-3ac2b797c104b943b1d7View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID192963
ChEMBL IDCHEMBL349605
KEGG Compound IDC00503
Pubchem Compound ID222285
Pubchem Substance IDNot Available
ChEBI ID17113
Phenol-Explorer IDNot Available
DrugBank IDDB04481
HMDB IDHMDB02994
CRC / DFC (Dictionary of Food Compounds) IDBBF48-I:BBF48-I
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00001161
HET IDMRY
Flavornet IDNot Available
GoodScent IDrw1257251
SuperScent IDNot Available
Wikipedia IDErythritol
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
antioxidant22586 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  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.