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D3511

Sigma-Aldrich

trans-4,5-Dihydroxy-1,2-dithiane

greener alternative

≥99%

Synonym(s):

trans-1,2-Dithiane-4,5-diol, Oxidized DTT

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About This Item

Empirical Formula (Hill Notation):
C4H8O2S2
CAS Number:
14193-38-5
Molecular Weight:
152.24
EC Number:
238-047-6
MDL number:
MFCD00006661
UNSPSC Code:
12352100
PubChem Substance ID:
57654093
NACRES:
NA.22

Assay

≥99%

form

powder

greener alternative product score

old score: 9
new score: 6
Find out more about DOZN™ Scoring

greener alternative product characteristics

Atom Economy
Less Hazardous Chemical Syntheses
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

130-132 °C (lit.)

greener alternative category

Re-engineered,

storage temp.

2-8°C

SMILES string

O[C@@H]1CSSC[C@H]1O

InChI

1S/C4H8O2S2/c5-3-1-7-8-2-4(3)6/h3-6H,1-2H2/t3-,4-/m1/s1

InChI key

YPGMOWHXEQDBBV-QWWZWVQMSA-N

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General description

trans-4,5-Dihydroxy-1,2-dithiane (oxidized dtt) is an intramolecular disulfide form of dithiothreitol. It is a strong reducing agent with an ability to elicit a molecular stress response by activating the stress-responsive genes.
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Atom Economy”, “Less Hazardous Chemical Syntheses” and “Use of Renewable Feedstock”. Click here to view its DOZN scorecard.

Linkage

Oxidized form of dithiothreitol (DTT).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jing Li et al.
PloS one, 12(2), e0172504-e0172504 (2017-02-23)
Starch breakdown in leaves at night is tightly matched to the duration of the dark period, but the mechanism by which this regulation is achieved is unknown. In Arabidopsis chloroplasts, β-amylase BAM3 hydrolyses transitory starch, producing maltose and residual maltotriose.
Reduction of trans-4, 5-Dihydroxy-1, 2-dithiane by Cellular Oxidoreductases Activates gadd153/chop and grp78 Transcription and Induces Cellular Tolerance in Kidney Epithelial Cells.
Halleck MM
The Journal of Biological Chemistry, 272(35), 21760-21766 (1997)
Francesca Sparla et al.
Plant physiology, 141(3), 840-850 (2006-05-16)
Nine genes of Arabidopsis (Arabidopsis thaliana) encode for beta-amylase isozymes. Six members of the family are predicted to be extrachloroplastic isozymes and three contain predicted plastid transit peptides. Among the latter, chloroplast-targeted beta-amylase (At4g17090) and thioredoxin-regulated beta-amylase (TR-BAMY; At3g23920; this
Hélène Launay et al.
Journal of molecular biology, 430(8), 1218-1234 (2018-03-05)
Among intrinsically disordered proteins, conditionally disordered proteins undergo dramatic structural disorder rearrangements upon environmental changes and/or post-translational modifications that directly modulate their function. Quantifying the dynamics of these fluctuating proteins is extremely challenging but paramount to understanding the regulation of
Modulating the endoplasmic reticulum stress response with trans-4, 5-dihydroxy-1, 2-dithiane prevents chemically induced renal injury in vivo.
Asmellash S
Toxicological Sciences, 88(2), 576-584 (2005)
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