TCDD | CAS#1746-01-6 | dibenzo-p-dioxin

MedKoo Cat#: 561613 | Name: TCDD

Description:

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

TCDD is a polychlorinated dibenzo-p-dioxin that acts via the aryl hydrocarbon (AH) receptor. This receptor is a transcription factor which is involved in expression of genes. At sufficiently high doses TCDD has caused cancer in all animals tested.

Chemical Structure

TCDD

CAS#1746-01-6

Theoretical Analysis

MedKoo Cat#: 561613

Name: TCDD

CAS#: 1746-01-6

Chemical Formula: C12H4Cl4O2

Exact Mass: 319.8965

Molecular Weight: 321.96

Elemental Analysis: C, 44.77; H, 1.25; Cl, 44.04; O, 9.94

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

TCDD; Dioxin; Tetradioxin; Tetrachlorodibenzodioxin; Dioxine;

IUPAC/Chemical Name

2,3,7,8-Tetrachlorodibenzo-p-dioxin

InChi Key

HGUFODBRKLSHSI-UHFFFAOYSA-N

InChi Code

InChI=1S/C12H4Cl4O2/c13-5-1-9-10(2-6(5)14)18-12-4-8(16)7(15)3-11(12)17-9/h1-4H

SMILES Code

ClC1=C(Cl)C=C2C(OC3=CC(Cl)=C(Cl)C=C3O2)=C1

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

>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).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 321.96 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.

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

1: Deierlein AL, Rock S, Park S. Persistent Endocrine-Disrupting Chemicals and Fatty Liver Disease. Curr Environ Health Rep. 2017 Dec;4(4):439-449. doi: 10.1007/s40572-017-0166-8. Review. PubMed PMID: 28980219. 2: Docea AO, Vassilopoulou L, Fragou D, Arsene AL, Fenga C, Kovatsi L, Petrakis D, Rakitskii VN, Nosyrev AE, Izotov BN, Golokhvast KS, Zakharenko AM, Vakis A, Tsitsimpikou C, Drakoulis N. CYP polymorphisms and pathological conditions related to chronic exposure to organochlorine pesticides. Toxicol Rep. 2017 May 26;4:335-341. doi: 10.1016/j.toxrep.2017.05.007. eCollection 2017. Review. PubMed PMID: 28959657; PubMed Central PMCID: PMC5615117. 3: Swedish Council on Health Technology Assessment. Occupational Health and Safety -- Chemical Exposure: A Systematic Review and Assessment of the Social, Medical and Ethical Aspects [Internet]. Stockholm: Swedish Council on Health Technology Assessment (SBU); 2017 Mar 28. Available from http://www.ncbi.nlm.nih.gov/books/NBK448041/ PubMed PMID: 28876751. 4: Mossanen M, Kibel AS, Goldman RH. Exploring exposure to Agent Orange and increased mortality due to bladder cancer. Urol Oncol. 2017 Nov;35(11):627-632. doi: 10.1016/j.urolonc.2017.07.030. Epub 2017 Aug 18. Review. PubMed PMID: 28826703. 5: Yao M, Hu T, Wang Y, Du Y, Hu C, Wu R. Polychlorinated biphenyls and its potential role in endometriosis. Environ Pollut. 2017 Oct;229:837-845. doi: 10.1016/j.envpol.2017.06.088. Epub 2017 Jul 31. Review. PubMed PMID: 28774553. 6: Malisch R, Denison MS, Fiedler H, Fürst P, Hoogenboom RLAP, Schaechtele A, Schrenk D, van den Berg M. Do PCDD/PCDF standard solutions used in dioxin analysis pose a risk as potentially acutely toxic to lab personnel? Chemosphere. 2017 Oct;185:489-498. doi: 10.1016/j.chemosphere.2017.07.021. Epub 2017 Jul 5. Review. PubMed PMID: 28715759. 7: Formosa R, Vassallo J. The Complex Biology of the Aryl Hydrocarbon Receptor and Its Role in the Pituitary Gland. Horm Cancer. 2017 Aug;8(4):197-210. doi: 10.1007/s12672-017-0300-y. Epub 2017 Jun 20. Review. PubMed PMID: 28634910. 8: Kolluri SK, Jin UH, Safe S. Role of the aryl hydrocarbon receptor in carcinogenesis and potential as an anti-cancer drug target. Arch Toxicol. 2017 Jul;91(7):2497-2513. doi: 10.1007/s00204-017-1981-2. Epub 2017 May 15. Review. Erratum in: Arch Toxicol. 2017 Sep;91(9):3209. PubMed PMID: 28508231. 9: Shiizaki K, Kawanishi M, Yagi T. Modulation of benzo[a]pyrene-DNA adduct formation by CYP1 inducer and inhibitor. Genes Environ. 2017 Apr 10;39:14. doi: 10.1186/s41021-017-0076-x. eCollection 2017. Review. PubMed PMID: 28405246; PubMed Central PMCID: PMC5385587. 10: Bock KW. 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD)-mediated deregulation of myeloid and sebaceous gland stem/progenitor cell homeostasis. Arch Toxicol. 2017 Jun;91(6):2295-2301. doi: 10.1007/s00204-017-1965-2. Epub 2017 Apr 6. Review. PubMed PMID: 28386637. 11: Bambino K, Chu J. Zebrafish in Toxicology and Environmental Health. Curr Top Dev Biol. 2017;124:331-367. doi: 10.1016/bs.ctdb.2016.10.007. Epub 2016 Dec 21. Review. PubMed PMID: 28335863. 12: Pilsner JR, Parker M, Sergeyev O, Suvorov A. Spermatogenesis disruption by dioxins: Epigenetic reprograming and windows of susceptibility. Reprod Toxicol. 2017 Apr;69:221-229. doi: 10.1016/j.reprotox.2017.03.002. Epub 2017 Mar 7. Review. PubMed PMID: 28286111. 13: Kawajiri K, Fujii-Kuriyama Y. The aryl hydrocarbon receptor: a multifunctional chemical sensor for host defense and homeostatic maintenance. Exp Anim. 2017 May 3;66(2):75-89. doi: 10.1538/expanim.16-0092. Epub 2016 Dec 15. Review. PubMed PMID: 27980293; PubMed Central PMCID: PMC5411294. 14: Fiorito F, Santamaria R, Irace C, De Martino L, Iovane G. 2,3,7,8-tetrachlorodibenzo-p-dioxin and the viral infection. Environ Res. 2017 Feb;153:27-34. doi: 10.1016/j.envres.2016.11.004. Epub 2016 Nov 22. Review. PubMed PMID: 27883971. 15: Lopez-Echartea E, Macek T, Demnerova K, Uhlik O. Bacterial Biotransformation of Pentachlorophenol and Micropollutants Formed during Its Production Process. Int J Environ Res Public Health. 2016 Nov 17;13(11). pii: E1146. Review. PubMed PMID: 27869691; PubMed Central PMCID: PMC5129356. 16: Fracchiolla NS, Annaloro C, Guidotti F, Fattizzo B, Cortelezzi A. 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) role in hematopoiesis and in hematologic diseases: A critical review. Toxicology. 2016 Dec 30;374:60-68. doi: 10.1016/j.tox.2016.10.007. Epub 2016 Oct 17. Review. PubMed PMID: 27765685. 17: Iyer R, Aggarwal J, Iken B. A review of the Texas, USA San Jacinto Superfund site and the deposition of polychlorinated dibenzo-p-dioxins and dibenzofurans in the San Jacinto River and Houston Ship Channel. Environ Sci Pollut Res Int. 2016 Dec;23(23):23321-23338. Epub 2016 Sep 24. Review. PubMed PMID: 27662860. 18: van den Berg M, Kypke K, Kotz A, Tritscher A, Lee SY, Magulova K, Fiedler H, Malisch R. WHO/UNEP global surveys of PCDDs, PCDFs, PCBs and DDTs in human milk and benefit-risk evaluation of breastfeeding. Arch Toxicol. 2017 Jan;91(1):83-96. doi: 10.1007/s00204-016-1802-z. Epub 2016 Jul 20. Review. PubMed PMID: 27438348; PubMed Central PMCID: PMC5225187. 19: Hankinson O. The role of AHR-inducible cytochrome P450s in metabolism of polyunsaturated fatty acids. Drug Metab Rev. 2016 Aug;48(3):342-50. doi: 10.1080/03602532.2016.1197240. Epub 2016 Jun 30. Review. PubMed PMID: 27358009; PubMed Central PMCID: PMC5026385. 20: Bock KW. From dioxin toxicity to putative physiologic functions of the human Ah receptor in homeostasis of stem/progenitor cells. Biochem Pharmacol. 2017 Jan 1;123:1-7. doi: 10.1016/j.bcp.2016.06.015. Epub 2016 Jun 25. Review. PubMed PMID: 27349986.