ChemicalBook > CAS DataBase List > DL-Dithiothreitol

DL-Dithiothreitol

Product Name
DL-Dithiothreitol
CAS No.
3483-12-3
Chemical Name
DL-Dithiothreitol
Synonyms
DTT;DITHIOTHREITOL;DL-1,4-DITHIOTHREITOL;1,4-DITHIOTHREITOL;1,4-DITHIO-DL-THREITOL;Sputolysin;Cleland's reagent;DTT-MBG;DITHIOTHRIETOL;cis-2,3-Dihydroxy-1,4-butanedithiol
CBNumber
CB6342919
Molecular Formula
C4H10O2S2
Formula Weight
154.25
MOL File
3483-12-3.mol
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DL-Dithiothreitol Property

Melting point:
41-44 °C(lit.)
Boiling point:
125 °C
alpha 
-0.2～+0.2°(20℃/D)(c=5,H2O)
Density 
1.04 g/mL at 20 °C
vapor density 
5.3 (vs air)
vapor pressure 
0.019-0.29Pa at 20-50℃
refractive index 
1.5200 (estimate)
Flash point:
>230 °F
storage temp. 
-20°C (or 4°C short term).
solubility 
H2O: 50 mg/mL, clear, colorless
form 
Powder
pka
pK1:8.9 (25°C)
color 
White
PH
4.0-6.0 (20-25℃, 0.1m in H2O)
Odor
Unpleasant Odor
PH Range
4 - 6 at 15,4 g/l at 25 °C
Water Solubility 
freely soluble
Sensitive 
Air Sensitive
λmax
λ: 260 nm Amax: 0.400
λ: 280 nm Amax: 0.100
Merck 
14,3376
BRN 
1719757
Stability:
Stability Stable, but heat sensitive. Incompatible with strong oxidizing agents. Keep frozen at -20 to -10 C.
InChIKey
VHJLVAABSRFDPM-UHFFFAOYSA-N
LogP
0.07 at 25℃ and pH5
CAS DataBase Reference
3483-12-3(CAS DataBase Reference)
NIST Chemistry Reference
2,3-Butanediol, 1,4-dimercapto-, (r*,r*)-(3483-12-3)
EPA Substance Registry System
1,4-Dithiothreitol (3483-12-3)
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Safety

Hazard Codes 
Xn
Risk Statements 
25-36/37/38-22-20/21/22
Safety Statements 
26-45-37/39-36
RIDADR 
UN 3335
WGK Germany 
3
RTECS 
EK1610000
F 
3-10-16-23
TSCA 
Yes
HS Code 
29309099
Hazardous Substances Data
3483-12-3(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H318Causes serious eye damage

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
DTT-RO
Product name
DTT
Purity
1,4-Dithiothreitol
Packaging
2g
Price
$89.3
Updated
2024/03/01
Sigma-Aldrich
Product number
DTT-RO
Product name
DTT
Purity
crystalline powder, =97% (Ellman′s reagent), Mr 154.3
Packaging
10G
Price
$251
Updated
2024/03/01
Sigma-Aldrich
Product number
DTT-RO
Product name
DTT
Purity
1,4-Dithiothreitol
Packaging
25g
Price
$547
Updated
2024/03/01
Sigma-Aldrich
Product number
646563
Product name
DL-Dithiothreitol solution
Purity
1?M in H2O
Packaging
10x0.5mL
Price
$107
Updated
2024/03/01
Sigma-Aldrich
Product number
233155
Product name
Cleland’s Reagent - CAS 3483-12-3 - Calbiochem
Packaging
5G
Price
$149
Updated
2024/03/01
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DL-Dithiothreitol Chemical Properties,Usage,Production

Chemical Properties

Dithiothreitol (DTT), also known as Cleland's reagent, is a small-molecule redox reagent . Its oxidized form is a disulfide-bonded 6-membered ring. DTT has an epimeric ('sister') compound, dithioerythritol (DTE).
DTT is a white crystalline powder. It is highly soluble in water (clear solution, OD<0.05 at 0.02M), but also in ethanol, chloroform, ether and ethyl acetate.
DTT is an unusually strong reducing agent, with a redox potential of -0.33 V at pH 7. The pKa of thiol groups is typically ~8.3.

The reduction of a typical disulfide bond proceeds by two sequential thiol-disulfide exchange reactions.

Uses

Dithiothreitol is a redox reagent commonly used as a reducing agent for thiolated DNA. Dithiothreitol is also used to reduce the disulfide bonds of proteins.

Uses

DL-dithiothreitol (DTT) is a sulfhydryl compound that acts both as a reagent reducing disulfide bonds and as a protein denaturant on staphylococcal biofilm (Wu et al. 2011). Thanks to these properties, DTT is routinely used in clinical microbiology to liquefy respiratory specimens, but it has also been proven effective to detach biofilm from orthopaedic prosthesis (Drago et al. 2012, 2013). Since it is crucial to discriminate implant-related infections from aseptic loosening in orthopaedics, and because of the difficulty to diagnose subclinical infections, a prompt diagnosis of indwelling device-related infection is important for successful treatments (Borens et al. 2013). A fast microbiological diagnosis and bacterial identification should be recommended in order to set up a specific antimicrobial therapy. According to this strategy, the bacterial detachment from biofilm on explants should be accelerated by supporting the pathogen viability.

Definition

ChEBI: 1,4-dithiothreitol is the threo-diastereomer of 1,4-dimercaptobutane-2,3-diol. It has a role as a reducing agent, a chelator and a human metabolite. It is a dithiol and a 1,4-dimercaptobutane-2,3-diol.

Application

Dithiothreitol (DTT) is a water-soluble reducing reagent used for various applications in biotechnology, biology and biochemistry :
reduces quantitatively disulfides, generating sulfhydryls (used typically at 1-10mM for protein SS reduction)
reduction of proteins before SDS-PAGE analysis, studies of protein structure and function (Kaji 1993)
keep sulfhydryl groups of biomolecules in the reduced state - protects biomolecules in various applications (enzymes or receptors, living cells under ionizing radiations)
prevents the fading of fluorescence such as FITC labeled conjugates (Picciolo 1984)

General Description

1,4-Dithiothreitol (DTT) is the threo isomer of 2,3-dihydroxy-1,4-dithiolbutane, and an isomer of 1,4-dithioerythritol. DTT is used in molecular biology to maintain sulfhydryl (-SH) groups in the reduced state and for quantitative reduction of disulfide (-S-S-) groups, as described by Cleland in his pioneering publication from the 1960's. Its usefulness as an reducing agent stems from its water solubility and reduced odor compared to previous thiol compounds.
DTT is oxidized to the cyclic disulfide, and thereby ensures the reduction of other disulfides in solution. The disulfide reduction is complete in minutes at pH 8. DTT is less pungent and less toxic than 2-mercaptoethanol. Typically, a 7-fold lower concentration of DTT (100 mM) is required compared to 2-mercaptoethanol (5% v/v, 700 mM).

Biochem/physiol Actions

DL-Dithiothreitol denatures proteins by reducing the disulphide bonds and reducing them to SH groups. It also prevents intramolecular and intermolecular disulfide bond formation between cysteine residues of proteins.

Toxicology

The thiol-containing compound Dithiothreitol (DTT) is toxic to cultured cells by inducing the generation of reactive oxygen species that ultimately cause cell death. DTT treatment triggers the transcription of the canonical apoptosis regulators grim, hid, and rpr at low amounts. The amplitude of this induction declines with elevating DTT amounts. Through Live microscopy, Wang et al. have observed apoptotic cells, especially in the gut of DTT-treated flies. In parallel, low DTT amounts also activate the expression of the cuticle barrier component gene snsl. This indicates that a physical defense response is launched upon DTT contact. This combined measure is seemingly successful in preventing fly death. The expression of several known detoxification genes, including cyp6a2, cyp6a8, cyp12d1, and GstD2, is also enhanced through DTT contact[1].

References

[1] Yiwen Wang . “Toxicity of Dithiothreitol (DTT) to Drosophila melanogaster.” Toxicology Reports 8 (2021): Pages 124-130.

Synthesis

The most widely used DL-Dithiothreitol (DTT) synthetic method is to be raw material with Soviet Union's moss sugar alcohol, use potassium permanganate oxidation earlier, obtains the sulfo-intermediate again under the thioacetic acid effect, and this sulfo-intermediate of hydrolysis obtains DTT at last.
Yu discloses a synthesizing method of DL-Dithiothreitol.1,4-butylene glycol is used as an initiating raw material and undergoes an addition reaction with bromine at first to obtain 2,3-dibromo-1,4-butylene glycol; hydrolyzation under the catalyzation of alkali is carried out to obtain dioxirane; addition reaction with thioacetic acid is carried out to obtain dithiothreitol diacetate; and finally hydrolyzation under the catalyzation of alkali is carried out to obtain the DL-Dithiothreitol.

storage

Store lyophilized at 4°C, desiccated. In lyophilized form, the chemical is stable for 12 months. Once in solution, store at -20°C and use within 3 months to prevent loss of potency. Aliquot to avoid multiple freeze/thaw cycles.
DTT solutions should be prepared fresh daily. If improperly stored (including room temperature and solution forms) its reducing ability may be reduced. Exposure to air should be minimized, even though DTT has a lower tendency to be oxidized directly by air than other reducing agents.
Recorded half-life of DTT solutions at various pH and temperatures (all are in M potassium phosphate buffer):
pH 6.5 @ 20°C= 40 hours
pH 7.5 @ 20°C = 10 hours
pH 8.5 @ 20°C = 1.4 hours
pH 8.5 @ 0°C = 11 hours
pH 8.5 @ 40°C = 0.2 hours
pH 8.5 @20°C (+0.1 mM Cu2+) = 0.6 hours
pH 8.5 @20°C (+0.1 mM EDTA) = 4 hours

DL-Dithiothreitol Preparation Products And Raw materials

Raw materials

Ethanol Acetic anhydride (E)-1,4-Dibromobut-2-ene Diethyl ether Hydrochloric acid Potassium permanganate Acetic acid Methanol Sodium hydroxide Potassium thioacetate Sulfuric acid

Preparation Products

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View Lastest Price from DL-Dithiothreitol manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
DL-1,4-Dithiothreitol 3483-12-3
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-21
WUHAN FORTUNA CHEMICAL CO., LTD
Product
DL-Dithiothreitol 3483-12-3
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
200kg/month
Release date
2021-06-10
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
DL-Dithiothreitol 3483-12-3
Price
US $100.00-75.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000Ton
Release date
2024-08-12

3483-12-3, DL-DithiothreitolRelated Search:

2,3-Butanediol Sodium thiosulfate Panthenol Mercaptoacetic acid DL-Dithiothreitol Sorbitol Succimer 2-Ethylhexyl mercaptoacetate Thioacetamide Maltitol 1,4-Butanediol 2,2'-Thiodiethanol 2-Mercaptoethanol L-(+)-THREOSE L-THREITOL 1,4-BUTANEDITHIOL L-DITHIOTHREITOL DL-1,4-DITHIOTHREITOL (D10)

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