Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for Erythritol (HMDB02994)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:24 -0600
Update Date 2013-02-08 17:12:13 -0700
HMDB ID HMDB02994
Secondary Accession Numbers None
Metabolite Identification
Common Name Erythritol
Description 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; 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 Link_out, Food and Chemical Toxicology (1998), 36(12), 1139-1174.).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1,2,3,4-Butanetetrol
  2. Antierythrite
  3. Butanetetrol
  4. C*Eridex
  5. Erythrit
  6. Erythrite
  7. Erythroglucin
  8. Erythrol
  9. i-Erythritol
  10. L-(-)-Threitol
  11. L-Erythritol
  12. L-Threitol
  13. Lichen sugar
  14. Meso-Erythritol
  15. Meso-Eythritol
  16. Mesoerythritol
  17. Paycite
  18. Phycite
  19. Phycitol
  20. Tetrahydroxybutane
Chemical Formula C4H10O4
Average Molecular Weight 122.1198
Monoisotopic Molecular Weight 122.057908808
IUPAC Name (2R,3S)-butane-1,2,3,4-tetrol
Traditional IUPAC Name meso-erythritol
CAS Registry Number 149-32-6
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 Key UNXHWFMMPAWVPI-ZXZARUISSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Sugar Alcohols
Sub Class N/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • a tetritol(Cyc)
  • tetritol(ChEBI)
Substituents
  • 1,2 Diol
  • Primary Alcohol
  • Secondary Alcohol
Direct Parent Sugar Alcohols
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 121.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 610 mg/mL at 22 °C Not Available
LogP -2.29 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 1160 g/L ALOGPS
LogP -2.03 ALOGPS
LogP -2.5 ChemAxon
LogS 0.98 ALOGPS
pKa (strongest acidic) 13.04 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 80.92 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 26.48 ChemAxon
Polarizability 11.69 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Epidermis
  • Prostate
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
4.10 +/- 1.64 uM Adult (>18 years old) Both Normal Measured in plasma
Blood Detected and Quantified
Article_icon
2.3 (0.0-5.0) uM Adolescent (13-18 years old) Both Normal Measured in plasma
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
37.0 (29.0-45.0) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
12 - 33 uM Adolescent (13-18 years old) Both Normal Not Available
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
60.0 +/- 23.0 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
149 +/- 30 umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
93 +/- 28 umol/mmol creatinine Children (1-13 year old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
51 +/- 18 umol/mmol creatinine Adult (>18 years old) Not Specified Normal Not Available
Urine Detected and Quantified
Article_icon
33.4 (6.8-64.0) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0 - 5.0 uM Adolescent (13-18 years old) Both Ribose-5-Phosphate Isomerase Deficiency Not Available
Associated Disorders and Diseases
Disease References
Ribose-5-phosphate isomerase deficiency
  • 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. Pubmed: 14988808 Link_out
    Associated OMIM IDs
    • 608611 Link_out (Ribose-5-phosphate isomerase deficiency)
    DrugBank ID DB04481 Link_out
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB000371
    KNApSAcK ID C00001161 Link_out
    Chemspider ID 192963 Link_out
    KEGG Compound ID C00503 Link_out
    BioCyc ID 2C-METH-D-ERYTHRITOL-CYCLODIPHOSPHATE Link_out
    BiGG ID Not Available
    Wikipedia Link Erythritol Link_out
    NuGOwiki Link HMDB02994 Link_out
    Metagene Link HMDB02994 Link_out
    METLIN ID 140 Link_out
    PubChem Compound 222285 Link_out
    PDB ID MRY Link_out
    ChEBI ID 17113 Link_out
    References
    Synthesis Reference New 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. Prandi D: Canalicular bile production in man. Eur J Clin Invest. 1975 Feb;5(1):1-6. Pubmed: 1122919 Link_out
    2. 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. Pubmed: 11275673 Link_out
    3. Hino H, Kobayasi T, Asboe-Hansen G: Desmosome formation in normal human epidermal cell culture. Acta Derm Venereol. 1982;62(3):185-91. Pubmed: 6179356 Link_out
    4. 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. Pubmed: 8933646 Link_out
    5. 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. Pubmed: 8039489 Link_out
    6. 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. Pubmed: 15914983 Link_out
    7. 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. Pubmed: 11283793 Link_out
    8. 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. Pubmed: 899714 Link_out
    9. 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. Pubmed: 320281 Link_out
    10. 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. Pubmed: 19212411 Link_out