Showing Compound Card for Erythritol (CDB006160)

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Record Information
Version1.0
Created at2020-03-18 23:22:05 UTC
Updated at2020-12-07 19:06:56 UTC
CannabisDB IDCDB006160
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameErythritol
DescriptionErythritol, also known as erythrite or phycite, 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 of the reducing sugar) has been reduced to a primary or secondary hydroxyl group. Erythritol is an extremely weak basic (essentially neutral) compound (based on its pKa). Erythritol occurs widely in nature and has been found to occur naturally in several foods including wine, sake, beer, watermelon, pear, grape, and soy sauce. Erythritol is 60–70% as sweet as sucrose (table sugar), yet it is almost noncaloric and does not affect blood sugar or cause tooth decay (PMID:20186409 , PMID1468100 ). 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 is related to their molecular size; 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 has also 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 ). Altered levels of erythritol have been found to be associated with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(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
Chemical FormulaC4H10O4
Average Molecular Weight122.12
Monoisotopic Molecular Weight122.0579
IUPAC Name(2R,3S)-butane-1,2,3,4-tetrol
Traditional Nameerythritol
CAS Registry Number149-32-6
SMILES
OC[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4+
InChI KeyUNXHWFMMPAWVPI-ZXZARUISSA-N
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.
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point121.5 °CNot Available
Boiling Point329 - 331 °CWikipedia
Water Solubility610 mg/mL at 22 °CNot Available
logP-2.29HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-01ox-9000000000-3ac2b797c104b943b1d72018-05-25View Spectrum
GC-MSErythritol, non-derivatized, GC-MS Spectrumsplash10-0gba-0930000000-dc2d1a78c7a0457d1e5eSpectrum
GC-MSErythritol, 4 TMS, GC-MS Spectrumsplash10-0gb9-0950000000-0284cb64008968df5b85Spectrum
GC-MSErythritol, non-derivatized, GC-MS Spectrumsplash10-0gba-0960000000-e3c06af410ada4c51c35Spectrum
GC-MSErythritol, non-derivatized, GC-MS Spectrumsplash10-0gba-0930000000-dc2d1a78c7a0457d1e5eSpectrum
GC-MSErythritol, non-derivatized, GC-MS Spectrumsplash10-0gb9-0950000000-0284cb64008968df5b85Spectrum
Predicted GC-MSErythritol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-9000000000-83a8654b82fe1d2a6b5eSpectrum
Predicted GC-MSErythritol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-7249000000-2b2a68afd8e4a9b09f96Spectrum
Predicted GC-MSErythritol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSErythritol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05tr-9500000000-c66e9c2cdca98e1a30732012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-8c8289ff9dce6ace80fb2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-9a74ea83fa64739762c72012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - NA , negativesplash10-00di-0977660000-980b1600279271fd23592020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-0a4i-9000000000-4fe19533227dfec09d042020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-00di-0900000000-0cbbbbc44cf97b2ea7f92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-00di-0900000000-948580de674ae24657262020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-00di-1900000000-03dd3eb75814753c7dd82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-00di-2900000000-e0bdb19395892dbf87fe2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-00di-3900000000-6d0568d8fc874a1395a12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-00di-5900000000-b8fd7722fd366e306d832020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-00di-9700000000-986ad1d639ba9b797f682020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-00di-9300000000-9d2ec013afa970d97ce12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-00di-9100000000-7bc378bdb49e237807d32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-00di-9000000000-cba6793c794a22d5688e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-00di-9000000000-7d0b3257438b54283d7a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-0udi-3900000000-e73f20eee360d9f91e3d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-05fr-9000000000-556e5bf58555459783352020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-001i-9000000000-063b6d0b520fb710203c2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-b21b0229b3cca7a445e12017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-9500000000-793c9703aa07422f10142017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pd-9000000000-c17f1bba91d64dbd9f412017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-7900000000-12421f1c391587323fb62017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9400000000-45979a06d5c9cf0240d82017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-e4d3d8da2791448160162017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Ribose-5-phosphate isomeraseRPIA2p11.2P49247 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002994
DrugBank IDDB04481
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000371
KNApSAcK IDC00001161
Chemspider ID192963
KEGG Compound IDC00503
BioCyc IDERYTHRITOL
BiGG IDNot Available
Wikipedia LinkErythritol
METLIN ID140
PubChem Compound222285
PDB IDMRY
ChEBI ID17113
References
General References
  1. Moon HJ, Jeya M, Kim IW, Lee JK: Biotechnological production of erythritol and its applications. Appl Microbiol Biotechnol. 2010 Apr;86(4):1017-25. doi: 10.1007/s00253-010-2496-4. Epub 2010 Feb 26. [PubMed:20186409 ]
  2. Kawanabe J, Hirasawa M, Takeuchi T, Oda T, Ikeda T: Noncariogenicity of erythritol as a substrate. Caries Res. 1992;26(5):358-62. doi: 10.1159/000261468. [PubMed:1468100 ]
  3. Munro IC, Berndt WO, Borzelleca JF, Flamm G, Lynch BS, Kennepohl E, Bar EA, Modderman J: Erythritol: an interpretive summary of biochemical, metabolic, toxicological and clinical data. Food Chem Toxicol. 1998 Dec;36(12):1139-74. doi: 10.1016/s0278-6915(98)00091-x. [PubMed:9862657 ]

Enzymes

Enzyme Details
1. Ribose-5-phosphate isomerase
General function:
Involved in ribose-5-phosphate isomerase activity
Specific function:
Not Available
Gene Name:
RPIA
Uniprot ID:
P49247
Molecular weight:
33268.72