2,2'-Dipyridyl disulfide

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 581011

CAS#: 2127-03-9

Description: 2,2'-Dipyridyl disulfide, also known as OPSS, is a useful reagent for determination of sulfhydryl groups, preparation of amino acid active esters and the thio esters of phosphoric acid. It acts as a peptide coupling reagent and as an oxidizing agent. It is also used for the activation of glycosides.

Price and Availability


USD 210

USD 400

USD 1210

2,2'-Dipyridyl disulfide, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

Chemical Structure


Theoretical Analysis

MedKoo Cat#: 581011
Name: 2,2'-Dipyridyl disulfide
CAS#: 2127-03-9
Chemical Formula: C10H8N2S2
Exact Mass: 220.0129
Molecular Weight: 220.3
Elemental Analysis: C, 54.52; H, 3.66; N, 12.72; S, 29.10

Synonym: 2,2'-Dipyridyl disulfide; Orthopyridyl disulfide; Aldrithiol 2; OPSS.

IUPAC/Chemical Name: 2,2"-Dithiodipyridine


InChi Code: InChI=1S/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H


Technical Data

Solid powder

>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:


1: Watanabe D, Kanzaki K, Kuratani M, Matsunaga S, Yanaka N, Wada M. Contribution
of impaired myofibril and ryanodine receptor function to prolonged low-frequency force depression after in situ stimulation in rat skeletal muscle. J Muscle Res
Cell Motil. 2015 Jun;36(3):275-86. doi: 10.1007/s10974-015-9409-1. Epub 2015 Feb 20. PubMed PMID: 25697123.

2: Miller E, Spadaccia M, Sabado R, Chertova E, Bess J, Trubey CM, Holman RM,
Salazar A, Lifson J, Bhardwaj N. Autologous aldrithiol-2-inactivated HIV-1
combined with polyinosinic-polycytidylic acid-poly-L-lysine
carboxymethylcellulose as a vaccine platform for therapeutic dendritic cell
immunotherapy. Vaccine. 2015 Jan 3;33(2):388-95. doi:
10.1016/j.vaccine.2014.10.054. Epub 2014 Nov 15. PubMed PMID: 25444812; PubMed
Central PMCID: PMC4272884.

3: Kanishchev OS, Dolbier WR Jr. Synthesis and characterization of
2-pyridylsulfur pentafluorides. Angew Chem Int Ed Engl. 2015 Jan 2;54(1):280-4.
doi: 10.1002/anie.201409990. Epub 2014 Nov 6. PubMed PMID: 25376393.

4: Basak D, Kumar R, Ghosh S. Telechelic Poly(disulfide)s and Related Block
Copolymer. Macromol Rapid Commun. 2014 Aug;35(15):1340-4. doi:
10.1002/marc.201400237. Epub 2014 May 20. PubMed PMID: 24840860.

5: Clausen A, McClanahan T, Ji SG, Weiss JH. Mechanisms of rapid reactive oxygen species generation in response to cytosolic Ca2+ or Zn2+ loads in cortical
neurons. PLoS One. 2013 Dec 10;8(12):e83347. doi: 10.1371/journal.pone.0083347.
eCollection 2013. PubMed PMID: 24340096; PubMed Central PMCID: PMC3858366.

6: Lee YM, Wang YT, Duh Y, Yuan HS, Lim C. Identification of labile Zn sites in
drug-target proteins. J Am Chem Soc. 2013 Sep 25;135(38):14028-31. doi:
10.1021/ja406300c. Epub 2013 Sep 11. PubMed PMID: 24010488.

7: McCord MC, Aizenman E. Convergent Ca2+ and Zn2+ signaling regulates apoptotic Kv2.1 K+ currents. Proc Natl Acad Sci U S A. 2013 Aug 20;110(34):13988-93. doi:
10.1073/pnas.1306238110. Epub 2013 Aug 5. PubMed PMID: 23918396; PubMed Central
PMCID: PMC3752224.

8: Gökce H, Bahçeli S. FT-IR, micro-Raman and UV-vis spectroscopic and quantum
chemical investigations of free 2,2'-dithiodipyridine and its metal (Co, Cu and
Zn) halide complexes. Spectrochim Acta A Mol Biomol Spectrosc. 2013
Oct;114:61-73. doi: 10.1016/j.saa.2013.04.112. Epub 2013 May 9. PubMed PMID:

9: Fateixa S, Pinheiro PC, Nogueira HI, Trindade T. Composite blends of gold
nanorods and poly(t-butylacrylate) beads as new substrates for SERS. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Sep;113:100-6. doi: 10.1016/j.saa.2013.04.070. Epub 2013 May 3. PubMed PMID: 23714187.

10: Nagao R, Tsutsui H, Mochizuki T, Takayama T, Kuwabara T, Min JZ, Inoue K,
Todoroki K, Toyo'oka T. Novel chiral derivatization reagents possessing a
pyridylthiourea structure for enantiospecific determination of amines and
carboxylic acids in high-throughput liquid chromatography and
electrospray-ionization mass spectrometry for chiral metabolomics identification.
J Chromatogr A. 2013 Jun 28;1296:111-8. doi: 10.1016/j.chroma.2013.03.019. Epub
2013 Mar 26. PubMed PMID: 23582770.

11: Tsutsui H, Mochizuki T, Maeda T, Noge I, Kitagawa Y, Min JZ, Todoroki K,
Inoue K, Toyo'oka T. Simultaneous determination of DL-lactic acid and
DL-3-hydroxybutyric acid enantiomers in saliva of diabetes mellitus patients by
high-throughput LC-ESI-MS/MS. Anal Bioanal Chem. 2012 Oct;404(6-7):1925-34. doi: 10.1007/s00216-012-6320-0. Epub 2012 Aug 16. PubMed PMID: 22895741.

12: Ismaylova SR, Matsulevich ZV, Borisova GN, Borisov AV, Khrustalev VN.
Dichloridobis(pyridine-2-thiol-ato-κ²N,S)tin(IV): a new polymorph. Acta
Crystallogr Sect E Struct Rep Online. 2012 Jul 1;68(Pt 7):m875-6. doi:
10.1107/S1600536812024026. Epub 2012 Jun 13. PubMed PMID: 22807723; PubMed
Central PMCID: PMC3393155.

13: Cotella D, Hernandez-Enriquez B, Wu X, Li R, Pan Z, Leveille J, Link CD, Oddo
S, Sesti F. Toxic role of K+ channel oxidation in mammalian brain. J Neurosci.
2012 Mar 21;32(12):4133-44. doi: 10.1523/JNEUROSCI.6153-11.2012. Erratum in: J
Neurosci. 2012 Jul 4;32(27):9449. PubMed PMID: 22442077.

14: Mollica JP, Dutka TL, Merry TL, Lamboley CR, McConell GK, McKenna MJ, Murphy RM, Lamb GD. S-glutathionylation of troponin I (fast) increases contractile
apparatus Ca2+ sensitivity in fast-twitch muscle fibres of rats and humans. J
Physiol. 2012 Mar 15;590(6):1443-63. doi: 10.1113/jphysiol.2011.224535. Epub 2012
Jan 16. PubMed PMID: 22250211; PubMed Central PMCID: PMC3382333.

15: Gibon J, Richaud P, Bouron A. Hyperforin changes the zinc-storage capacities of brain cells. Neuropharmacology. 2011 Dec;61(8):1321-6. doi:
10.1016/j.neuropharm.2011.08.002. Epub 2011 Aug 12. PubMed PMID: 21854792.

16: Dallas ML, Boyle JP, Milligan CJ, Sayer R, Kerrigan TL, McKinstry C, Lu P,
Mankouri J, Harris M, Scragg JL, Pearson HA, Peers C. Carbon monoxide protects
against oxidant-induced apoptosis via inhibition of Kv2.1. FASEB J. 2011
May;25(5):1519-30. doi: 10.1096/fj.10-173450. Epub 2011 Jan 19. PubMed PMID:

17: Lewis DJ, Glover PB, Solomons MC, Pikramenou Z. Purely heterometallic
lanthanide(III) macrocycles through controlled assembly of disulfide bonds for
dual color emission. J Am Chem Soc. 2011 Feb 2;133(4):1033-43. doi:
10.1021/ja109157g. Epub 2010 Dec 23. PubMed PMID: 21182290.

18: Dutka TL, Mollica JP, Posterino GS, Lamb GD. Modulation of contractile
apparatus Ca2+ sensitivity and disruption of excitation-contraction coupling by
S-nitrosoglutathione in rat muscle fibres. J Physiol. 2011 May 1;589(Pt
9):2181-96. doi: 10.1113/jphysiol.2010.200451. Epub 2010 Nov 29. PubMed PMID:
21115647; PubMed Central PMCID: PMC3098697.

19: Mochida K, Amano H, Onduka T, Kakuno A, Fujii K. Toxicity and metabolism of
copper pyrithione and its degradation product, 2,2'-dipyridyldisulfide in a
marine polychaete. Chemosphere. 2011 Jan;82(3):390-7. doi:
10.1016/j.chemosphere.2010.09.074. Epub 2010 Oct 20. PubMed PMID: 20965543.

20: Che KF, Sabado RL, Shankar EM, Tjomsland V, Messmer D, Bhardwaj N, Lifson JD,
Larsson M. HIV-1 impairs in vitro priming of naïve T cells and gives rise to
contact-dependent suppressor T cells. Eur J Immunol. 2010 Aug;40(8):2248-58. doi:
10.1002/eji.201040377. PubMed PMID: 20455275; PubMed Central PMCID: PMC3258541.