(2R,3S)-butane-1,2,3,4-tetrol

• ChemBase ID: 4057
• Molecular Formular: C4H10O4
• Molecular Mass: 122.1198
• Monoisotopic Mass: 122.0579088
• SMILES: OC[C@H](O)[C@H](O)CO
• Canonical SMILES: OC[C@H]([C@H](CO)O)O
• InChI: InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4+
• InChIKey: UNXHWFMMPAWVPI-ZXZARUISSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-butane-1,2,3,4-tetrol
• IUPAC Traditional name: erythritol; meso-erythritol
• Synonyms: Erythritol; 1,2,3,4-Butanetetrol; meso-1,2,3,4-Tetrahydroxybutane; i-Erythritol; meso-Erythritol; Meso-Erythritol; Erythritol

Database IDs

• CAS Number: 10030-58-7; 149-32-6
• EC Number: 205-737-3
• MDL Number: MFCD00004710
• Beilstein Number: 1719753
• PubChem SID: 24894646; 160967491; 46507139
• PubChem CID: 222285
• CHEBI ID: 17113
• CHEMBL: 349605
• Chemspider ID: 192963
• DrugBank ID: DB04481
• KEGG ID: D08915
• Unique Ingredient Identifier: RA96B954X6
• Wikipedia Title: Erythritol

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.044993
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -2.469349
• LogD (pH = 7.4): -2.4693499
• Log P: -2.469349
• Molar Refractivity: 26.4786 cm^3
• Polarizability: 10.746415 Å^3
• Polar Surface Area: 80.92 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.03
• LOG S: 0.98
• Solubility (Water): 1.16e+03 g/l

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear to almost clear, colorless
• Apperance: Oil
• Melting Point: 118-120 °C(lit.); 118-121 °C; 121°C
• Boiling Point: 329 - 331°C; 329-331 °C(lit.)
• Density: 1.45 g/cm3
• Sweetness: 0.7 × sucrose

Safety Information

• RTECS: KF2000000
• German water hazard class: 3
• NFPA704:
  

  1

  1

  0
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥99%; ≥99.0% (HPLC)
• Linear Formula: HOCH2[CH(OH)]2CH2OH

DETAILS

DrugBank - DB04481

• Drug Groups: experimental
• Description: A four-carbon sugar that is found in algae, fungi, and lichens. It is twice as sweet as sucrose and can be used as a coronary vasodilator. [PubChem]

Sigma Aldrich - E7500

Biochem/physiol Actions
Allelic variation of the Tas1r3 gene affects behavioral taste responses to this sugar alcohol, suggesting that it is a T1R3 receptor ligand.1
Packaging
25, 100 g in poly bottle
Application
Meso-Erythritol is a precursor to the important tanning agent L-erythrulose which can be commercially generated by Gluconobacter oxydans DSM 7145. Meso-Erythritol, an aliphatic poly-alcohol, is used in the chemical analysis of the reativity of various radicals and radical anions.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E7500.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 45670

Biochem/physiol Actions
Allelic variation of the Tas1r3 gene affects behavioral taste responses to this sugar alcohol, suggesting that it is a T1R3 receptor ligand.1