Tri-o-cresyl phosphate

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

MedKoo CAT#: 591660

CAS#: 78-30-8

Description: Tricresyl phosphate, abbreviated TCP, is an organophosphate compound that is used as a plasticizer and diverse other applications.

Chemical Structure

Tri-o-cresyl phosphate
CAS# 78-30-8

Theoretical Analysis

MedKoo Cat#: 591660
Name: Tri-o-cresyl phosphate
CAS#: 78-30-8
Chemical Formula: C7H7O4P2-
Exact Mass: 186.0093
Molecular Weight: 186.1
Elemental Analysis: C, 45.18; H, 3.79; O, 34.39; P, 16.64

Price and Availability

Size Price Availability Quantity
250.0mg USD 250.0 2 Weeks
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Synonym: Tri-o-cresyl phosphate; NSC 438; NSC-438; NSC438

IUPAC/Chemical Name: o-Tolyl phosphate


InChi Code: InChI=1S/C7H9O4P/c1-6-4-2-3-5-7(6)11-12(8,9)10/h2-5H,1H3,(H2,8,9,10)/p-2

SMILES Code: O=P([O-])([O-])OC1=CC=CC=C1C

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

Preparing Stock Solutions

The following data is based on the product molecular weight 186.1 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

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

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1: Xu HY, Wang P, Sun YJ, Xu MY, Zhu L, Wu YJ. Activation of Neuregulin 1/ErbB Signaling Is Involved in the Development of TOCP-Induced Delayed Neuropathy. Front Mol Neurosci. 2018 Apr 23;11:129. doi: 10.3389/fnmol.2018.00129. eCollection 2018. PubMed PMID: 29740279; PubMed Central PMCID: PMC5925568.

2: Xu HY, Wang P, Sun YJ, Jiang L, Xu MY, Wu YJ. Autophagy in Tri-o-cresyl Phosphate-Induced Delayed Neurotoxicity. J Neuropathol Exp Neurol. 2017 Jan 1;76(1):52-60. doi: 10.1093/jnen/nlw108. PubMed PMID: 28040792.

3: Petroianu GA. Neuropathic organophosphates: from Scrugham, Heim and Lorot to Jake leg paralysis. Pharmazie. 2016 Dec 1;71(12):738-744. doi: 10.1691/ph.2016.6080. PubMed PMID: 29442005.

4: Zhu L, Wang P, Sun YJ, Xu MY, Wu YJ. Disturbed phospholipid homeostasis in endoplasmic reticulum initiates tri-o-cresyl phosphate-induced delayed neurotoxicity. Sci Rep. 2016 Nov 24;6:37574. doi: 10.1038/srep37574. PubMed PMID: 27883027; PubMed Central PMCID: PMC5121615.

5: Lorke DE, Stegmeier-Petroianu A, Petroianu GA. Biologic activity of cyclic and caged phosphates: a review. J Appl Toxicol. 2017 Jan;37(1):13-22. doi: 10.1002/jat.3369. Epub 2016 Sep 9. Review. PubMed PMID: 27612208.

6: Liu X, Xu L, Shen J, Wang J, Ruan W, Yu M, Chen J. Involvement of oxidative stress in tri-ortho-cresyl phosphate-induced autophagy of mouse Leydig TM3 cells in vitro. Reprod Biol Endocrinol. 2016 Jun 7;14(1):30. doi: 10.1186/s12958-016-0165-x. PubMed PMID: 27267904; PubMed Central PMCID: PMC4897823.

7: Iwamura A, Watanabe K, Akai S, Nishinosono T, Tsuneyama K, Oda S, Kume T, Yokoi T. Zomepirac Acyl Glucuronide Is Responsible for Zomepirac-Induced Acute Kidney Injury in Mice. Drug Metab Dispos. 2016 Jul;44(7):888-96. doi: 10.1124/dmd.116.069575. Epub 2016 Apr 25. PubMed PMID: 27112166.

8: Schang G, Robaire B, Hales BF. Organophosphate Flame Retardants Act as Endocrine-Disrupting Chemicals in MA-10 Mouse Tumor Leydig Cells. Toxicol Sci. 2016 Apr;150(2):499-509. doi: 10.1093/toxsci/kfw012. Epub 2016 Jan 21. PubMed PMID: 26794138.

9: Xu LL, Long CY, Wang JL, Yu M, Chen JX. Involvement of oxidative stress in tri-ortho-cresyl phosphate-induced liver injury in male mice. Hum Exp Toxicol. 2016 Oct;35(10):1093-101. doi: 10.1177/0960327115621363. Epub 2016 Jan 12. PubMed PMID: 26757727.

10: Zhou SH, Ouyang XP, Tian SW, Yin WL, Hu B. Apelin-13 Prevents the Delayed Neuropathy Induced by Tri-ortho-cresyl Phosphate Through Regulation the Autophagy Flux in Hens. Neurochem Res. 2015 Nov;40(11):2374-82. doi: 10.1007/s11064-015-1725-8. Epub 2015 Oct 9. Retraction in: Neurochem Res. 2016 Nov;41(11):3160. PubMed PMID: 26453045.

11: Jarema KA, Hunter DL, Shaffer RM, Behl M, Padilla S. Acute and developmental behavioral effects of flame retardants and related chemicals in zebrafish. Neurotoxicol Teratol. 2015 Nov-Dec;52(Pt B):194-209. doi: 10.1016/ Epub 2015 Sep 5. PubMed PMID: 26348672; PubMed Central PMCID: PMC4768762.

12: Johnson D, Carter MD, Crow BS, Isenberg SL, Graham LA, Erol HA, Watson CM, Pantazides BG, van der Schans MJ, Langenberg JP, Noort D, Blake TA, Thomas JD, Johnson RC. Quantitation of ortho-cresyl phosphate adducts to butyrylcholinesterase in human serum by immunomagnetic-UHPLC-MS/MS. J Mass Spectrom. 2015 Apr;50(4):683-92. doi: 10.1002/jms.3576. PubMed PMID: 26149113; PubMed Central PMCID: PMC5713888.

13: Tong Y, Wang S, Wang Y, Wang F, Xie K, Song F. [Changes in the expression and phosphorylation state of autophagy-related protein ATG4 in nervous tissues of hens treated with tri-ortho-cresyl phosphate]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2015 Jan;33(1):7-10. Chinese. PubMed PMID: 25876965.

14: Reinen J, Nematollahi L, Fidder A, Vermeulen NP, Noort D, Commandeur JN. Characterization of human cytochrome P450s involved in the bioactivation of tri-ortho-cresyl phosphate (ToCP). Chem Res Toxicol. 2015 Apr 20;28(4):711-21. doi: 10.1021/tx500490v. Epub 2015 Mar 2. PubMed PMID: 25706813.

15: Liu ML, Wang JL, Wei J, Xu LL, Yu M, Liu XM, Ruan WL, Chen JX. Tri-ortho-cresyl phosphate induces autophagy of rat spermatogonial stem cells. Reproduction. 2015 Feb;149(2):163-70. doi: 10.1530/REP-14-0446. Epub 2014 Nov 10. PubMed PMID: 25385720.

16: Hausherr V, van Thriel C, Krug A, Leist M, Schöbel N. Impairment of glutamate signaling in mouse central nervous system neurons in vitro by tri-ortho-cresyl phosphate at noncytotoxic concentrations. Toxicol Sci. 2014 Nov;142(1):274-84. doi: 10.1093/toxsci/kfu174. Epub 2014 Sep 8. PubMed PMID: 25199799.

17: Long DX, Hu D, Wang P, Wu YJ. Induction of autophagy in human neuroblastoma SH-SY5Y cells by tri-ortho-cresyl phosphate. Mol Cell Biochem. 2014 Nov;396(1-2):33-40. doi: 10.1007/s11010-014-2139-7. Epub 2014 Jul 3. PubMed PMID: 24990248.

18: Schopfer LM, Masson P, Lamourette P, Simon S, Lockridge O. Detection of cresyl phosphate-modified butyrylcholinesterase in human plasma for chemical exposure associated with aerotoxic syndrome. Anal Biochem. 2014 Sep 15;461:17-26. doi: 10.1016/j.ab.2014.05.021. Epub 2014 Jun 2. PubMed PMID: 24892986; PubMed Central PMCID: PMC4119843.

19: Tacal O, Schopfer LM. Healthy F-16 pilots show no evidence of exposure to tri-ortho-cresyl phosphate through the on-board oxygen generating system. Chem Biol Interact. 2014 May 25;215:69-74. doi: 10.1016/j.cbi.2014.03.004. Epub 2014 Mar 22. PubMed PMID: 24661946.

20: Song F, Kou R, Zou C, Gao Y, Zeng T, Xie K. Involvement of autophagy in tri-ortho-cresyl phosphate- induced delayed neuropathy in hens. Neurochem Int. 2014 Jan;64:1-8. doi: 10.1016/j.neuint.2013.10.017. Epub 2013 Nov 9. PubMed PMID: 24220541.