Erythritol (CHEM017867)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:42:20 UTC
Update Date2016-11-09 01:15:41 UTC
Accession NumberCHEM017867
Identification
Common NameErythritol
ClassSmall Molecule
DescriptionThe meso-diastereomer of butane-1,2,3,4-tetrol.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical 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 Mass122.120 g/mol
Monoisotopic Mass122.058 g/mol
CAS Registry Number149-32-6
IUPAC Name(2R,3S)-butane-1,2,3,4-tetrol
Traditional Nameerythritol
SMILESOC[C@H](O)[C@H](O)CO
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0gba-0930000000-dc2d1a78c7a0457d1e5eSpectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0gb9-0950000000-0284cb64008968df5b85Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gba-0960000000-e3c06af410ada4c51c35Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-0930000000-dc2d1a78c7a0457d1e5eSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-0950000000-0284cb64008968df5b85Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9000000000-83a8654b82fe1d2a6b5eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0ab9-7249000000-2b2a68afd8e4a9b09f96Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05tr-9500000000-c66e9c2cdca98e1a3073Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-8c8289ff9dce6ace80fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-9a74ea83fa64739762c7Spectrum
LC-MS/MSLC-MS/MS Spectrum - NA , negativesplash10-00di-0977660000-980b1600279271fd2359Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-0a4i-9000000000-4fe19533227dfec09d04Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-00di-0900000000-0cbbbbc44cf97b2ea7f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-00di-0900000000-948580de674ae2465726Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-00di-1900000000-03dd3eb75814753c7dd8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-00di-2900000000-e0bdb19395892dbf87feSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-00di-3900000000-6d0568d8fc874a1395a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-00di-5900000000-b8fd7722fd366e306d83Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-00di-9700000000-986ad1d639ba9b797f68Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-00di-9300000000-9d2ec013afa970d97ce1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-00di-9100000000-7bc378bdb49e237807d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-00di-9000000000-cba6793c794a22d5688eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-00di-9000000000-7d0b3257438b54283d7aSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-0udi-3900000000-e73f20eee360d9f91e3dSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-05fr-9000000000-556e5bf5855545978335Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-001i-9000000000-063b6d0b520fb710203cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2900000000-b21b0229b3cca7a445e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-9500000000-793c9703aa07422f1014Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pd-9000000000-c17f1bba91d64dbd9f41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-7900000000-12421f1c391587323fb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9400000000-45979a06d5c9cf0240d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-e4d3d8da279144816016Spectrum
MSMass Spectrum (Electron Ionization)splash10-01ox-9000000000-3ac2b797c104b943b1d7Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04481
HMDB IDHMDB0002994
FooDB IDFDB000371
Phenol Explorer IDNot Available
KNApSAcK IDC00001161
BiGG IDNot Available
BioCyc IDERYTHRITOL
METLIN ID140
PDB IDMRY
Wikipedia LinkErythritol
Chemspider ID192963
ChEBI ID17113
PubChem Compound ID222285
Kegg Compound IDC00503
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12639570
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=163226
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16901854
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17336832
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=17979222
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=18369603
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19632091
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23421980
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23574577
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23890177
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24643482
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=25108762
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=9862657
15. New Synthesis of Natural and of Racemic Erythrite. Pariselle, H. Compt. rend. (1910), 150 1343-6.
16. New Synthesis of Natural and of Racemic Erythrite. Pariselle, H. Compt. rend. (1910), 150 1343-6.
17. Prandi D: Canalicular bile production in man. Eur J Clin Invest. 1975 Feb;5(1):1-6.
18. Makinen KK, Isotupa KP, Kivilompolo T, Makinen PL, Toivanen J, Soderling E: Comparison of erythritol and xylitol saliva stimulants in the control of dental plaque and mutans streptococci. Caries Res. 2001 Mar-Apr;35(2):129-35.
19. Hino H, Kobayasi T, Asboe-Hansen G: Desmosome formation in normal human epidermal cell culture. Acta Derm Venereol. 1982;62(3):185-91.
20. Bornet FR, Blayo A, Dauchy F, Slama G: Gastrointestinal response and plasma and urine determinations in human subjects given erythritol. Regul Toxicol Pharmacol. 1996 Oct;24(2 Pt 2):S296-302.
21. Noda K, Nakayama K, Oku T: Serum glucose and insulin levels and erythritol balance after oral administration of erythritol in healthy subjects. Eur J Clin Nutr. 1994 Apr;48(4):286-92.
22. Makinen KK, Saag M, Isotupa KP, Olak J, Nommela R, Soderling E, Makinen PL: Similarity of the effects of erythritol and xylitol on some risk factors of dental caries. Caries Res. 2005 May-Jun;39(3):207-15.
23. Verhoeven NM, Huck JH, Roos B, Struys EA, Salomons GS, Douwes AC, van der Knaap MS, Jakobs C: Transaldolase deficiency: liver cirrhosis associated with a new inborn error in the pentose phosphate pathway. Am J Hum Genet. 2001 May;68(5):1086-92. Epub 2001 Mar 27.
24. Servo C, Palo J, Pitkanen E: Gas chromatographic separation and mass spectrometric identification of polyols in human cerebrospinal fluid and plasma. Acta Neurol Scand. 1977 Aug;56(2):104-10.
25. Utili R, Abernathy CO, Zimmerman HJ: Studies on the effects of C. coli endotoxin on canalicular bile formation in the isolated perfused rat liver. J Lab Clin Med. 1977 Mar;89(3):471-82.
26. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
27. 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.
28. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.