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Chemical Structure| 109-80-8 Chemical Structure| 109-80-8

Structure of 1,3-Propanedithiol
CAS No.: 109-80-8

Chemical Structure| 109-80-8

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Product Citations

Product Citations

Hewawasam, Rukshika S. ; Blomberg, Rachel ; Serbedzija, Predrag ; Magin, Chelsea M. ;

Abstract: Tissue fibrosis remains a serious health condition with high morbidity and mortality rates. There is a critical need to engineer model systems that better recapitulate the spatial and temporal changes in the fibrotic extracellular microenvironment and enable study of the cellular and mol. alterations that occur during pathogenesis. Here, we present a process for chem. modifying human decellularized extracellular matrix (dECM) and incorporating it into a dynamically tunable hybrid-hydrogel system containing a poly(ethylene glycol)-α methacrylate (PEGαMA) backbone. Following modification and characterization, an off-stoichiometry thiol-ene Michael addition reaction resulted in hybrid-hydrogels with mech. properties that could be tuned to recapitulate many healthy tissue types. Next, photoinitiated, free-radical homopolymerization of excess α-methacrylates increased crosslinking d. and hybrid-hydrogel elastic modulus to mimic a fibrotic microenvironment. The incorporation of dECM into the PEGαMA hydrogel decreased the elastic modulus and, relative to fully synthetic hydrogels, increased the swelling ratio, the average mol. weight between crosslinks, and the mesh size of hybrid-hydrogel networks. These changes were proportional to the amount of dECM incorporated into the network. Dynamic stiffening increased the elastic modulus and decreased the swelling ratio, average mol. weight between crosslinks, and the mesh size of hybrid-hydrogels, as expected. Stiffening also activated human fibroblasts, as measured by increases in average cellular aspect ratio (1.59 ± 0.02 to 2.98 ± 0.20) and expression of α-smooth muscle actin (αSMA). Fibroblasts expressing αSMA increased from 25.8 to 49.1% upon dynamic stiffening, demonstrating that hybrid-hydrogels containing human dECM support investigation of dynamic mechanosensing. These results improve our understanding of the biomol. networks formed within hybrid-hydrogels: this fully human phototunable hybrid-hydrogel system will enable researchers to control and decouple the biochem. changes that occur during fibrotic pathogenesis from the resulting increases in stiffness to study the dynamic cell-matrix interactions that perpetuate fibrotic diseases.

Keywords: biomaterial ; hybrid-hydrogel ; fibrosis ; decellularized extracellular matrix ; fibroblast activation

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Product Details of [ 109-80-8 ]

CAS No. :109-80-8
Formula : C3H8S2
M.W : 108.23
SMILES Code : SCCCS
MDL No. :MFCD00004904
InChI Key :ZJLMKPKYJBQJNH-UHFFFAOYSA-N
Pubchem ID :8013

Safety of [ 109-80-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H301-H315-H319-H335
Precautionary Statements:P210-P240-P241-P242-P243-P261-P264-P270-P271-P280-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P312-P330-P363-P370+P378-P403+P233-P405-P501
Class:3(6.1)
UN#:1228
Packing Group:

Application In Synthesis of [ 109-80-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 109-80-8 ]

[ 109-80-8 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 109-80-8 ]
  • [ 37905-02-5 ]
  • [ 220343-93-1 ]
  • 2
  • [ 109-80-8 ]
  • [ 38430-55-6 ]
  • 4-(2-methyl-[1,3]dithian-2-yl)-benzoic acid ethyl ester [ No CAS ]
  • 3
  • [ 109-80-8 ]
  • [ 558-42-9 ]
  • 4,8-dithia-2,10-dimethylundecane-2,10-diol [ No CAS ]
  • 4
  • [ 109-80-8 ]
  • [ 6964-21-2 ]
  • S-3-mercaptopropyl-2-(thiophene-3-yl)ethanethioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 60℃; for 9h;Inert atmosphere; [Reaction 1] As shown in Reaction 1, 2-(thiophene-3-yl) acetic acid) (1 g, 7.03 mmol), propane-1,3-dithiol (0.753 g, 7.03 mmol), and 4-dimethylaminopyridine (4-DMAP) (2.014 g, 1.75 mmol) were dissolved in 80 ml of methylene chloride in a three-neck round bottom flask, after which stirring was performed at 60 C. in a nitrogen atmosphere. The stirred mixture solution was slowly added with N,N'-dicyclohexylcarbodiimide (DCC) (2.89 g, 14.06 mmol) dissolved in 20 ml of methylene chloride, and was then allowed to react for 9 hours. The reaction solution was washed using saturated aqueous Na2CO3, dried over MgSO4, and filtered. The remaining solvent was removed by rotary evaporation to obtain a yellowish solution. This solution was diluted with acetone, and cooled to 0 C., to obtain residual 1,3-dicyclohexylurea ("DCU") as a precipitate. This precipitate was removed by filtration through a paper filter, and addition of acetone and removal of the DCU precipitate were repeated until DCU precipitate was no longer evident in the solution. Finally, the remaining solvent was removed by rotary evaporation, and the crude purified using a silica column eluted with a solution of methylene chloride and methanol (60:1 v/v), thereby producing after collection of the fractions and removal of the solvent, S-3-mercaptopropyl-2-(thiophene-3-yl)ethanethioate ("MTE") (the monomer) as a pure yellow compound. The characteristic H1-NMR spectrum (in acetone-d6) of the product is shown in .
  • 5
  • [ 109-80-8 ]
  • [ 2632-14-6 ]
  • C23H28O2S2 [ No CAS ]
  • 6
  • [ 109-80-8 ]
  • [ 21906-31-0 ]
  • 2-(2-bromobenzyl)-2-methyl-1,3-dithiane [ No CAS ]
  • 7
  • [ 109-80-8 ]
  • [ 42019-78-3 ]
  • 4-(2-(4-chlorophenyl)-1,3-dithian-2-yl)phenol [ No CAS ]
  • 8
  • [ 109-80-8 ]
  • [ 3478-88-4 ]
  • 2,2-bis(2,4-dimethylphenyl)-1,3-dithiane [ No CAS ]
  • 9
  • [ 109-80-8 ]
  • [ 40359-32-8 ]
  • 2-(3-(allyloxy)phenyl)-1,3-dithiane [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With silica gel; toluene-4-sulfonic acid; In dichloromethane;Reflux; General procedure: To a round-bottom flask charged with magnetic stir bar was added 1,3-propanedithiane (1.1 equiv., 1.65 mmol), catalytic amount of SiO2 and PTSA, aldehyde/ketone (1 equiv, 1.5 mmol) and CH2Cl2 (15 mL). The reaction mixture was refluxed for 6-8 h.After which, the reaction mixture was cooled down to room temperature and excess 1,3-propanedithiane was quenched by adding saturated KOH solution (5 mL) and stirred for 30 min, and extracted with dichloromethane (3 20 mL). The extracts were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was further purified by column chromatography to afford the desired compound 1.
 

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