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Details

Stereochemistry ABSOLUTE
Molecular Formula C4H10O4
Molecular Weight 122.1198
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THREITOL

SMILES

OC[C@@H](O)[C@H](O)CO

InChI

InChIKey=UNXHWFMMPAWVPI-QWWZWVQMSA-N
InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m1/s1

HIDE SMILES / InChI

Molecular Formula C4H10O4
Molecular Weight 122.1198
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Threitol is a four carbon sugar primarily used in the chemical synthesis of other compounds. It is a diastereomer of erythritol an FDA approved low-calorie sweetener. Threitol can be found in meaningful concentrations in the edible fungus Armillaria mellea and is used by some organisms as an antifreeze agent, such as the Alaskan beetle. Threitol is a very weak inhibitor of Carbonic anhydrase. Threitol is the main end product of D-xylose metabolism in humans and deficiency is associated with inborn errors of metabolism.

CNS Activity

Curator's Comment: alternative metabolism

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P00918
Gene ID: 760.0
Gene Symbol: CA2
Target Organism: Homo sapiens (Human)
Target ID: Q16790
Gene ID: 768.0
Gene Symbol: CA9
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Dithiothreitol causes HIV-1 integrase dimer dissociation while agents interacting with the integrase dimer interface promote dimer formation.
2011-03-15
The complex genetic architecture of the metabolome.
2010-11-04
Urinary metabonomics study in a rat model in response to protein-energy malnutrition by using gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry.
2010-11
Differential phenotyping of Brucella species using a newly developed semi-automated metabolic system.
2010-10-23
Practical enantiospecific synthesis of an orthogonally protected 1,4-trans-1,5-cis- 4,5-diamino-2-cyclopenten-1-ol derivative.
2010-09-03
Comparative studies of the dynamics in viscous liquids by means of dielectric spectroscopy and field cycling NMR.
2010-08-05
Identifying new lignin bioengineering targets: 1. Monolignol-substitute impacts on lignin formation and cell wall fermentability.
2010-06-17
Aspergillusol A, an alpha-glucosidase inhibitor from the marine-derived fungus Aspergillus aculeatus.
2009-11
Cryoprotectant biosynthesis and the selective accumulation of threitol in the freeze-tolerant Alaskan beetle, Upis ceramboides.
2009-06-19
Universal critical-like scaling of dynamic properties in symmetry-selected glass formers.
2008-11-14
Exudation of alcohol and aldehyde sugars from roots of defoliated Lolium perenne L. grown under sterile conditions.
2008-11
Analysis of the metabolic footprint and tissue metabolome of placental villous explants cultured at different oxygen tensions reveals novel redox biomarkers.
2008-08
Spatial and seasonal trends in biogenic secondary organic aerosol tracers and water-soluble organic carbon in the southeastern United States.
2008-07-15
CH2-units on (poly-)ethylene glycol radially dehydrate cytoplasm of resting skinned skeletal muscle.
2008-06
Cutting edge: nonglycosidic CD1d lipid ligands activate human and murine invariant NKT cells.
2008-05-15
Amino alcohol-based degradable poly(ester amide) elastomers.
2008-05
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX.
2008-03-15
CH2-units on (poly-)ethylene glycol radially dehydrate cytoplasm of resting skinned skeletal muscle.
2008-01
Reductively aminated D-xylose-albumin conjugate as the immunogen for generation of IgG and IgE antibodies specific to D-xylitol, a haptenic allergen.
2007-11-06
Sugar-alcohol complexes of palladium(II): on the variable rigidity of open-chain carbohydrate ligands.
2007-08-03
Multiple component system of sugars and polyols in the overwintering spruce bark beetle, Ips typographus.
2007-06
Seasonal variation of 2-methyltetrols in ambient air samples.
2006-11-15
Generation of an antibody specific to erythritol, a non-immunogenic food additive.
2006-09
Determination of the enthalpy of solute-solvent interaction from the enthalpy of solution: aqueous solutions of erythritol and L-threitol.
2006-05-11
Mimicking the atmospheric OH-radical-mediated photooxidation of isoprene: formation of cloud-condensation nuclei polyols monitored by electrospray ionization mass spectrometry.
2006
Investigation of the binding geometry of a peripheral membrane protein.
2005-12-13
Enthalpy of sublimation in the study of the solid state of organic compounds. Application to erythritol and threitol.
2005-09-29
Conformational study of erythritol and threitol in the gas state by density functional theory calculations.
2005-02-07
Glyco- and peptidomimetics from three-component Joullié-Ugi coupling show selective antiviral activity.
2005-01-19
Synthesis of l-lyxo-phytosphingosine and its 1-phosphonate analogue using a threitol acetal synthon.
2004-08-06
Effect of large hydrostatic pressure on the dielectric loss spectrum of type- a glass formers.
2004-05
Fragmentation study of diastereoisomeric 2-methyltetrols, oxidation products of isoprene, as their trimethylsilyl ethers, using gas chromatography/ion trap mass spectrometry.
2004
Amplification of dynamic chiral crown ether complexes during cyclic acetal formation.
2003-09-15
Enantioselective synthesis of 15-epi-haterumalide NA methyl ester and revised structure of haterumalide NA.
2003-03-20
From strong to fragile glass formers: secondary relaxation in polyalcohols.
2002-03-04
Synthesis of erythro and threo furanoid glycals from 1- and 2-phenylselenenyl-carbohydrate derivatives.
2001-11-08
Reductive fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of alditols with potential utility as chiral synthons.
2001-10-19

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Apr 02 18:23:35 GMT 2025
Edited
by admin
on Wed Apr 02 18:23:35 GMT 2025
Record UNII
6DN82XBT5M
Record Status Validated (UNII)
Record Version
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Name Type Language
D-THREITOL
Preferred Name English
THREITOL
INCI  
INCI  
Official Name English
THREITOL, D-
Common Name English
1,2,3,4-BUTANETETROL, (2R,3R)-
Systematic Name English
1,2,3,4-BUTANETETROL, (R-(R*,R*))-
Common Name English
Classification Tree Code System Code
LOINC 48153-1
Created by admin on Wed Apr 02 18:23:35 GMT 2025 , Edited by admin on Wed Apr 02 18:23:35 GMT 2025
Code System Code Type Description
PUBCHEM
169019
Created by admin on Wed Apr 02 18:23:35 GMT 2025 , Edited by admin on Wed Apr 02 18:23:35 GMT 2025
PRIMARY
MESH
C003460
Created by admin on Wed Apr 02 18:23:35 GMT 2025 , Edited by admin on Wed Apr 02 18:23:35 GMT 2025
PRIMARY
EPA CompTox
DTXSID801336604
Created by admin on Wed Apr 02 18:23:35 GMT 2025 , Edited by admin on Wed Apr 02 18:23:35 GMT 2025
PRIMARY
WIKIPEDIA
THREITOL
Created by admin on Wed Apr 02 18:23:35 GMT 2025 , Edited by admin on Wed Apr 02 18:23:35 GMT 2025
PRIMARY
CHEBI
48300
Created by admin on Wed Apr 02 18:23:35 GMT 2025 , Edited by admin on Wed Apr 02 18:23:35 GMT 2025
PRIMARY
FDA UNII
6DN82XBT5M
Created by admin on Wed Apr 02 18:23:35 GMT 2025 , Edited by admin on Wed Apr 02 18:23:35 GMT 2025
PRIMARY
CAS
2418-52-2
Created by admin on Wed Apr 02 18:23:35 GMT 2025 , Edited by admin on Wed Apr 02 18:23:35 GMT 2025
PRIMARY