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Record Information
Version3.6
Creation Date2006-05-22 15:12:24 UTC
Update Date2016-02-11 01:05:57 UTC
HMDB IDHMDB02994
Secondary Accession NumbersNone
Metabolite Identification
Common NameErythritol
DescriptionErythritol 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; 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.).
Structure
Thumb
Synonyms
ValueSource
(2R,3S)-Butane-1,2,3,4-tetrolChEBI
ErythritChEBI
ErythriteChEBI
erythro-TetritolChEBI
ErythrolChEBI
meso-ERYTHRITOLChEBI
MesoerythritolChEBI
PhyciteChEBI
PhycitolChEBI
1,2,3,4-ButanetetrolHMDB
AntierythriteHMDB
ButanetetrolHMDB
C*EridexHMDB
ErythroglucinHMDB
I-erythritolHMDB
L-(-)-ThreitolHMDB
L-ErythritolHMDB
L-ThreitolHMDB
Lichen sugarHMDB
meso-EythritolHMDB
PayciteHMDB
TetrahydroxybutaneHMDB
Chemical FormulaC4H10O4
Average Molecular Weight122.1198
Monoisotopic Molecular Weight122.057908808
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 KeyInChIKey=UNXHWFMMPAWVPI-ZXZARUISSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar alcohols
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point121.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility610 mg/mL at 22 °CNot Available
LogP-2.29HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1160.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.48 m3·mol-1ChemAxon
Polarizability11.62 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0gba-0930000000-dc2d1a78c7a0457d1e5eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0gb9-0950000000-0284cb64008968df5b85View 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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Epidermis
  • Prostate
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.10 +/- 1.64 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified2.3 (0.0-5.0) uMAdolescent (13-18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified37.0 (29.0-45.0) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified12 - 33 uMAdolescent (13-18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified60.0 +/- 23.0 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified149 +/- 30 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified93 +/- 28 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified51 +/- 18 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified33.4 (6.8-64.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0 - 5.0 uMAdolescent (13-18 years old)BothRibose-5-Phosphate Isomerase Deficiency details
Associated Disorders and Diseases
Disease References
Ribose-5-phosphate isomerase deficiency
  1. Huck JH, Verhoeven NM, Struys EA, Salomons GS, Jakobs C, van der Knaap MS: Ribose-5-phosphate isomerase deficiency: new inborn error in the pentose phosphate pathway associated with a slowly progressive leukoencephalopathy. Am J Hum Genet. 2004 Apr;74(4):745-51. Epub 2004 Feb 25. [14988808 ]
Associated OMIM IDs
  • 608611 (Ribose-5-phosphate isomerase deficiency)
DrugBank IDDB04481
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000371
KNApSAcK IDC00001161
Chemspider ID192963
KEGG Compound IDC00503
BioCyc ID2C-METH-D-ERYTHRITOL-CYCLODIPHOSPHATE
BiGG IDNot Available
Wikipedia LinkErythritol
NuGOwiki LinkHMDB02994
Metagene LinkHMDB02994
METLIN ID140
PubChem Compound222285
PDB IDMRY
ChEBI ID17113
References
Synthesis ReferenceNew Synthesis of Natural and of Racemic Erythrite. Pariselle, H. Compt. rend. (1910), 150 1343-6.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [11283793 ]
  2. 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. [19212411 ]
  3. Prandi D: Canalicular bile production in man. Eur J Clin Invest. 1975 Feb;5(1):1-6. [1122919 ]
  4. 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. [11275673 ]
  5. Hino H, Kobayasi T, Asboe-Hansen G: Desmosome formation in normal human epidermal cell culture. Acta Derm Venereol. 1982;62(3):185-91. [6179356 ]
  6. 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. [8933646 ]
  7. 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. [8039489 ]
  8. 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. [15914983 ]
  9. 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. [899714 ]
  10. 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. [320281 ]
  11. 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. [9862657 ]