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D-Threitol

Cat No.:V31263 Purity: ≥98%
D-threitol works as an antifreeze for Alaskan beetles.
D-Threitol
D-Threitol Chemical Structure CAS No.: 2418-52-2
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price
100mg
Other Sizes

Other Forms of D-Threitol:

  • L-Threitol (L-1,2,3,4-Butanetetrol)
  • (-)-1,4-Di-O-tosyl-2,3-O-isopropylidene-L-threitol
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Top Publications Citing lnvivochem Products
Product Description
D-threitol works as an antifreeze for Alaskan beetles.
Biological Activity I Assay Protocols (From Reference)
ln Vivo
- In the freeze-tolerant beetle Upis ceramboides , D-Threitol is selectively accumulated as a major cryoprotectant. Its concentration increases significantly in response to low temperatures: from undetectable levels at 22°C (room temperature) to approximately 250 mM in beetles acclimated to -5°C, and further to ~300 mM in those exposed to -10°C. This accumulation correlates with enhanced freeze tolerance, preventing intracellular ice formation and protecting cellular structures during freezing [1]
Enzyme Assay
- Assay for aldose reductase (AR) activity: Tissue homogenates were prepared from beetle tissues and centrifuged to obtain supernatants. The reaction mixture contained the supernatant, NADPH, and D-erythrose (substrate). The activity was measured by monitoring the decrease in NADPH absorbance at 340 nm over time. The rate of NADPH oxidation was used to calculate AR activity, which is involved in the conversion of D-erythrose to D-Threitol [1]
- Assay for polyol dehydrogenase (PDH) activity: Tissue extracts were mixed with reaction buffer containing NAD+ and D-Threitol (substrate). PDH activity was determined by measuring the increase in NADH absorbance at 340 nm, reflecting the oxidation of D-Threitol to D-erythrose. The reaction rate was normalized to protein concentration in the extracts [1]
- Assay for glucose-6-phosphate dehydrogenase (G6PDH) activity: The enzyme activity was assessed using tissue supernatants, with glucose-6-phosphate as substrate and NADP+ as cofactor. The formation of NADPH was monitored spectrophotometrically at 340 nm, and activity was calculated based on the molar extinction coefficient of NADPH [1]
Animal Protocol
- Sample collection and acclimation: Upis ceramboides beetles were collected from natural habitats in Alaska. They were divided into groups and acclimated to different temperatures: 22°C (control), -5°C, and -10°C. Acclimation was conducted in environmental chambers with a 12:12 light-dark cycle for 7 days. Beetles had access to water but no food during acclimation [1]
- Tissue preparation and cryoprotectant extraction: After acclimation, beetles were sacrificed by freezing at -80°C. Whole-body homogenates were prepared in ice-cold buffer, and centrifuged to remove debris. The supernatant was used for cryoprotectant extraction via ethanol precipitation. The extract was dried under vacuum and reconstituted in water for subsequent analysis [1]
- Temperature exposure experiment: Additional beetle groups were exposed to acute freezing (-15°C for 24 hours) and subzero acclimation (-5°C for 14 days). Tissue samples were collected at different time points (0, 6, 12, 24 hours) during exposure to assess dynamic changes in D-Threitol concentration [1]
References

[1]. Cryoprotectant biosynthesis and the selective accumulation of threitol in the freeze-tolerant Alaskan beetle, Upis ceramboides. J Biol Chem. 2009 Jun 19;284(25):16822-31.

Additional Infomation
D-Threitol is the D-enantiomer of threitol and plays a metabolic role in the human body. It is the enantiomer of L-threitol. D-Threitol has been reported to be found in Cnidium monnieri, Potamogeton crispus, and other organisms with relevant data. D-Threitol is a polyol cryoprotectant synthesized de novo from Aster tataricus for use in dealing with sub-zero temperatures. Its biosynthesis involves the conversion of glucose to D-erythritol via the pentose phosphate pathway, followed by reduction to D-threitol by aldose reductase [1] - The selective accumulation of D-threitol is a key adaptation strategy for the beetle to withstand freezing, as it can lower the freezing point of the cell sap and stabilize the cell membrane and proteins, protecting them from freezing damage [1] - Unlike other cryoprotectants (such as glycerol and sorbitol), D-threitol is the main polyol in Upis ceramboides, accounting for more than 80% of the total cryoprotectant content at temperatures below zero [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C4H10O4
Molecular Weight
122.1198
Exact Mass
122.058
CAS #
2418-52-2
Related CAS #
L-Threitol;2319-57-5
PubChem CID
169019
Appearance
Off-white to light yellow solid powder
Density
1.43g/cm3
Boiling Point
330ºC at 760mmHg
Melting Point
88-90ºC(lit.)
Flash Point
208.7ºC
LogP
-2.3
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Heavy Atom Count
8
Complexity
48
Defined Atom Stereocenter Count
2
SMILES
C([C@H]([C@@H](CO)O)O)O
InChi Key
UNXHWFMMPAWVPI-QWWZWVQMSA-N
InChi Code
InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m1/s1
Chemical Name
(2R,3R)-butane-1,2,3,4-tetrol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~250 mg/mL (~2047.17 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (17.03 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (17.03 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (17.03 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 8.1887 mL 40.9433 mL 81.8867 mL
5 mM 1.6377 mL 8.1887 mL 16.3773 mL
10 mM 0.8189 mL 4.0943 mL 8.1887 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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