Thiodipropionic acid
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MedKoo CAT#: 658611

CAS#: 111-17-1

Description: Thiodipropionic acid is an organic disulfide used as a ligand for the synthesis of cadminum and zinc coordination polymers that have luminescent properties.


Chemical Structure

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Thiodipropionic acid
CAS# 111-17-1

Theoretical Analysis

MedKoo Cat#: 658611
Name: Thiodipropionic acid
CAS#: 111-17-1
Chemical Formula: C6H10O4S
Exact Mass: 178.03
Molecular Weight: 178.200
Elemental Analysis: C, 40.44; H, 5.66; O, 35.91; S, 17.99

Price and Availability

Size Price Availability Quantity
100g USD 205
500g USD 320
3kg USD 630
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Synonym: Thiodipropionic acid; TDPA; Thiahydracrylic acid; Thiodihydracrylic acid;

IUPAC/Chemical Name: 3,3'-Thiodi(propionic acid)

InChi Key: ODJQKYXPKWQWNK-UHFFFAOYSA-N

InChi Code: InChI=1S/C6H10O4S/c7-5(8)1-3-11-4-2-6(9)10/h1-4H2,(H,7,8)(H,9,10)

SMILES Code: O=C(O)CCSCCC(O)=O

Appearance: Solid powder

Purity: >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).

Solubility: Soluble in DMSO

Shelf Life: >3 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).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 178.20 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Doberstein C, Grote J, Wübbeler JH, Steinbüchel A. Polythioester synthesis in Ralstonia eutropha H16: novel insights into 3,3'-thiodipropionic acid and 3,3'-dithiodipropionic acid catabolism. J Biotechnol. 2014 Aug 20;184:187-98. doi: 10.1016/j.jbiotec.2014.05.022. Epub 2014 Jun 3. PubMed PMID: 24953213.

2: Wübbeler JH, Hiessl S, Meinert C, Poehlein A, Schuldes J, Daniel R, Steinbüchel A. The genome of Variovorax paradoxus strain TBEA6 provides new understandings for the catabolism of 3,3'-thiodipropionic acid and hence the production of polythioesters. J Biotechnol. 2015 Sep 10;209:85-95. doi: 10.1016/j.jbiotec.2015.06.390. Epub 2015 Jun 11. PubMed PMID: 26073999.

3: Wübbeler JH, Bruland N, Wozniczka M, Steinbüchel A. Biodegradation of the xenobiotic organic disulphide 4,4'-dithiodibutyric acid by Rhodococcus erythropolis strain MI2 and comparison with the microbial utilization of 3,3'-dithiodipropionic acid and 3,3'-thiodipropionic acid. Microbiology. 2010 Apr;156(Pt 4):1221-33. doi: 10.1099/mic.0.036178-0. Epub 2009 Dec 3. PubMed PMID: 19959574.

4: Diamante C, Fiume MZ, Bergfeld WF, Belsito DV, Hill RA, Klaassen CD, Liebler DC, Marks JG Jr, Shank RC, Slaga TJ, Snyder PW, Alan Andersen F. Final safety assessment of thiodipropionic acid and its dialkyl esters as used in cosmetics. Int J Toxicol. 2010 Jul;29(4 Suppl):137S-50S. doi: 10.1177/1091581810373150. PubMed PMID: 20634504.

5: Khairy H, Wübbeler JH, Steinbüchel A. The NADH:flavin oxidoreductase Nox from Rhodococcus erythropolis MI2 is the key enzyme of 4,4'-dithiodibutyric acid degradation. Lett Appl Microbiol. 2016 Dec;63(6):434-441. doi: 10.1111/lam.12662. Epub 2016 Nov 3. PubMed PMID: 27564089.

6: Bruland N, Wübbeler JH, Steinbüchel A. 3-mercaptopropionate dioxygenase, a cysteine dioxygenase homologue, catalyzes the initial step of 3-mercaptopropionate catabolism in the 3,3-thiodipropionic acid-degrading bacterium variovorax paradoxus. J Biol Chem. 2009 Jan 2;284(1):660-72. doi: 10.1074/jbc.M806762200. Epub 2008 Nov 10. PubMed PMID: 19001372.

7: Kamei Y, Nagai A, Nishida H, Kimura H, Endo T. Biosynthesis and biodegradability of copolythioesters from 3,3'-thiodipropionic acid and plant oils by Cupriviadus necator. Macromol Biosci. 2007 Mar 8;7(3):364-72. PubMed PMID: 17370275.

8: Fehling E, Klein E, Vosmann K, Bergander K, Weber N. Linear copolymeric poly(thia-alkanedioates) by lipase-catalyzed esterification and transesterification of 3,3'-thiodipropionic acid and its dimethyl ester with alpha,omega-alkanediols. Biotechnol Bioeng. 2008 Apr 1;99(5):1074-84. PubMed PMID: 17969136.

9: McDonald LC, Hackney CR, Ray B. Enhanced recovery of injured Escherichia coli by compounds that degrade hydrogen peroxide or block its formation. Appl Environ Microbiol. 1983 Feb;45(2):360-5. PubMed PMID: 6338823; PubMed Central PMCID: PMC242293.

10: Schürmann M, Deters A, Wübbeler JH, Steinbüchel A. A novel 3-sulfinopropionyl coenzyme A (3SP-CoA) desulfinase from Advenella mimigardefordensis strain DPN7T acting as a key enzyme during catabolism of 3,3'-dithiodipropionic acid is a member of the acyl-CoA dehydrogenase superfamily. J Bacteriol. 2013 Apr;195(7):1538-51. doi: 10.1128/JB.02105-12. Epub 2013 Jan 25. PubMed PMID: 23354747; PubMed Central PMCID: PMC3624521.

11: Rawat PC, Gupta CM. Behaviour of the thiodipropionic complex of In(III) and U(VI) at the DME in aqueous and aqueous methanolic solutions. Talanta. 1972 May;19(5):706-7. PubMed PMID: 18961104.

12: Wenning L, Stöveken N, Wübbeler JH, Steinbüchel A. Substrate and Cofactor Range Differences of Two Cysteine Dioxygenases from Ralstonia eutropha H16. Appl Environ Microbiol. 2015 Nov 20;82(3):910-21. doi: 10.1128/AEM.02568-15. Print 2016 Feb 1. PubMed PMID: 26590284; PubMed Central PMCID: PMC4725276.

13: Chandra S, Gautam S, Kumar A, Madan M. Coordination mode of pentadentate ligand derivative of 5-amino-1,3,4-thiadiazole-2-thiol with nickel(II) and copper(II) metal ions: synthesis, spectroscopic characterization, molecular modeling and fungicidal study. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Feb 5;136 Pt B:672-81. doi: 10.1016/j.saa.2014.09.081. Epub 2014 Oct 6. PubMed PMID: 25448967.

14: Peplinski K, Ehrenreich A, Döring C, Bömeke M, Steinbüchel A. Investigations on the microbial catabolism of the organic sulfur compounds TDP and DTDP in Ralstonia eutropha H16 employing DNA microarrays. Appl Microbiol Biotechnol. 2010 Nov;88(5):1145-59. doi: 10.1007/s00253-010-2915-6. Epub 2010 Oct 6. PubMed PMID: 20924576; PubMed Central PMCID: PMC3128720.

15: Xu M, Qian J, Suo A, Wang H, Yong X, Liu X, Liu R. Reduction/pH dual-sensitive PEGylated hyaluronan nanoparticles for targeted doxorubicin delivery. Carbohydr Polym. 2013 Oct 15;98(1):181-8. doi: 10.1016/j.carbpol.2013.05.077. Epub 2013 Jun 5. PubMed PMID: 23987334.

16: Lütke-Eversloh T, Steinbüchel A. Novel precursor substrates for polythioesters (PTE) and limits of PTE biosynthesis in Ralstonia eutropha. FEMS Microbiol Lett. 2003 Apr 25;221(2):191-6. PubMed PMID: 12725926.

17: Lütke-Eversloh T, Bergander K, Luftmann H, Steinbüchel A. Identification of a new class of biopolymer: bacterial synthesis of a sulfur-containing polymer with thioester linkages. Microbiology. 2001 Jan;147(Pt 1):11-9. PubMed PMID: 11160796.

18: Schürmann M, Hirsch B, Wübbeler JH, Stöveken N, Steinbüchel A. Succinyl-CoA:3-sulfinopropionate CoA-transferase from Variovorax paradoxus strain TBEA6, a novel member of the class III coenzyme A (CoA)-transferase family. J Bacteriol. 2013 Aug;195(16):3761-73. doi: 10.1128/JB.00456-13. Epub 2013 Jun 14. PubMed PMID: 23772073; PubMed Central PMCID: PMC3754582.

19: Hirose M, Masuda A, Fukushima S, Ito N. Effects of subsequent antioxidant treatment on 7,12-dimethylbenz[a]anthracene-initiated carcinogenesis of the mammary gland, ear duct and forestomach in Sprague-Dawley rats. Carcinogenesis. 1988 Jan;9(1):101-4. PubMed PMID: 3121204.

20: Guo H, Kim JC. Reduction-Sensitive Poly(ethylenimine) Nanogel Bearing Dithiodipropionic Acid. Chem Pharm Bull (Tokyo). 2017;65(8):718-725. doi: 10.1248/cpb.c17-00029. PubMed PMID: 28768925.