MedKoo Cat#: 592615 | Name: Triparanol
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Description:

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

Triparanol is an antilipemic agent with high ophthalmic toxicity. According to Merck Index, 11th ed, the compound was withdrawn from the market in 1962 because of its association with the formation of irreversible cataracts.

Chemical Structure

Triparanol
Triparanol
CAS# 78-41-1

Theoretical Analysis

MedKoo Cat#: 592615

Name: Triparanol

CAS#: 78-41-1

Chemical Formula: C27H32ClNO2

Exact Mass: 437.2122

Molecular Weight: 438.01

Elemental Analysis: C, 74.04; H, 7.36; Cl, 8.09; N, 3.20; O, 7.31

Price and Availability

Size Price Availability Quantity
5mg USD 370.00
25mg USD 900.00
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Related CAS #
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Synonym
Triparanol; NSC 65345; NSC-65345; NSC65345
IUPAC/Chemical Name
2-p-Chlorophenyl-1-(p-(2-diethylaminoethoxy)phenyl)-1-p-tolylethanol
InChi Key
SYHDSBBKRLVLFF-UHFFFAOYSA-N
InChi Code
InChI=1S/C27H32ClNO2/c1-4-29(5-2)18-19-31-26-16-12-24(13-17-26)27(30,23-10-6-21(3)7-11-23)20-22-8-14-25(28)15-9-22/h6-17,30H,4-5,18-20H2,1-3H3
SMILES Code
CC1=CC=C(C(C2=CC=C(OCCN(CC)CC)C=C2)(O)CC3=CC=C(Cl)C=C3)C=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
>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

Preparing Stock Solutions

The following data is based on the product molecular weight 438.01 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
1: Officioso A, Manna C, Alzoubi K, Lang F. Triggering of Erythrocyte Death by Triparanol. Toxins (Basel). 2015 Aug 24;7(8):3359-71. doi: 10.3390/toxins7083359. PubMed PMID: 26305256; PubMed Central PMCID: PMC4549755. 2: Bi X, Han X, Zhang F, He M, Zhang Y, Zhi XY, Zhao H. Triparanol suppresses human tumor growth in vitro and in vivo. Biochem Biophys Res Commun. 2012 Aug 31;425(3):613-8. doi: 10.1016/j.bbrc.2012.07.136. Epub 2012 Aug 1. Erratum in: Biochem Biophys Res Commun. 2012 Nov 2;427(4):808. PubMed PMID: 22877755. 3: Ramu A, Glaubiger D, Fuks Z. Reversal of acquired resistance to doxorubicin in P388 murine leukemia cells by tamoxifen and other triparanol analogues. Cancer Res. 1984 Oct;44(10):4392-5. PubMed PMID: 6467200. 4: Mizuno GR, Chapman CJ, Chipault JR, Pfeiffer DR. Lipid composition and (Na+ + K+)-ATPase activity in rat lens during triparanol-induced cataract formation. Biochim Biophys Acta. 1981 Jun 9;644(1):1-12. PubMed PMID: 6266459. 5: Popják G, Meenan A, Parish EJ, Nes WD. Inhibition of cholesterol synthesis and cell growth by 24(R,S),25-iminolanosterol and triparanol in cultured rat hepatoma cells. J Biol Chem. 1989 Apr 15;264(11):6230-8. PubMed PMID: 2703486. 6: Singh P, Saxena R, Srinivas G, Pande G, Chattopadhyay A. Cholesterol biosynthesis and homeostasis in regulation of the cell cycle. PLoS One. 2013;8(3):e58833. doi: 10.1371/journal.pone.0058833. Epub 2013 Mar 15. PubMed PMID: 23554937; PubMed Central PMCID: PMC3598952. 7: Rhoads DE, Kaneshiro ES. Fatty acid metabolism in Paramecium. Oleic acid metabolism and inhibition of polyunsaturated fatty acid synthesis by triparanol. Biochim Biophys Acta. 1984 Aug 15;795(1):20-9. PubMed PMID: 6466696. 8: KRAFT RO. Triparanol in the treatment of disseminated mammary carcinoma. Cancer Chemother Rep. 1962 Dec;25:113-5. PubMed PMID: 14035390. 9: FUMAGALLI R, GROSSI-PAOLETTI E, PAOLETTI P. [EFFECT OF TRIPARANOL ON DESMOSTEROL CONTENT OF SOME EXPERIMENTAL CEREBRAL TUMORS]. Arch Ital Patol Clin Tumori. 1964 Jul-Dec;152:317-25. Italian. PubMed PMID: 14265677. 10: Rubright WC, Keller O, Hruban Z. Ultrastructural changes produced by triparanol in Morris 5123 and Novikoff hepatomas. Cancer Res. 1967 Jan;27(1):165-71. PubMed PMID: 4289796. 11: Ghanbari-Azarnier R, Sato S, Wei Q, Al-Jazrawe M, Alman BA. Targeting stem cell behavior in desmoid tumors (aggressive fibromatosis) by inhibiting hedgehog signaling. Neoplasia. 2013 Jul;15(7):712-9. PubMed PMID: 23814483; PubMed Central PMCID: PMC3689234. 12: SCANU A, HAWK WA, PAGE IH. Lethal effect in dogs of prolonged triparanol oral administration. Arch Pathol. 1962 Jun;73:445-50. PubMed PMID: 14497794. 13: Fumagalli R, Grossipaoletti E, Paoletti P. [Modification of sterol composition of experimental cerebral tumors by means of treatment with triparanol]. Minerva Neurochir. 1965;9(1):67-9. Italian. PubMed PMID: 5856707. 14: Weiss J, Ransohoff J, Kayden H. Evaluation of patients undergoing therapy for gliomas by examination of CSF sterols after triparanol treatment. Trans Am Neurol Assoc. 1971;96:324-6. PubMed PMID: 5159123. 15: Raederstorff D, Rohmer M. Polyterpenoids as cholesterol and tetrahymanol surrogates in the ciliate Tetrahymena pyriformis. Biochim Biophys Acta. 1988 May 22;960(2):190-9. PubMed PMID: 3130105. 16: Fumagalli R, Grossi-Paoletti E, Paoletti P, Paoletti R. Lipids in brain tumours. II. Effect of triparanol and 20,25-diazacholesterol on sterol composition in experimental and human brain tumours. J Neurochem. 1966 Oct;13(10):1005-10. PubMed PMID: 5954183. 17: Wang CY, Wei Q, Han I, Sato S, Ghanbari-Azarnier R, Whetstone H, Poon R, Hu J, Zheng F, Zhang P, Wang W, Wunder JS, Alman BA. Hedgehog and Notch signaling regulate self-renewal of undifferentiated pleomorphic sarcomas. Cancer Res. 2012 Feb 15;72(4):1013-22. doi: 10.1158/0008-5472.CAN-11-2531. Epub 2012 Jan 9. PubMed PMID: 22232736. 18: Sánchez-Wandelmer J, Dávalos A, Herrera E, Giera M, Cano S, de la Peña G, Lasunción MA, Busto R. Inhibition of cholesterol biosynthesis disrupts lipid raft/caveolae and affects insulin receptor activation in 3T3-L1 preadipocytes. Biochim Biophys Acta. 2009 Sep;1788(9):1731-9. doi: 10.1016/j.bbamem.2009.05.002. Epub 2009 May 9. PubMed PMID: 19433058. 19: Sandhu JS, Fraser DR. Effect of dietary cereals on intestinal permeability in experimental enteropathy in rats. Gut. 1983 Sep;24(9):825-30. PubMed PMID: 6411526; PubMed Central PMCID: PMC1420099. 20: Moebius FF, Reiter RJ, Hanner M, Glossmann H. High affinity of sigma 1-binding sites for sterol isomerization inhibitors: evidence for a pharmacological relationship with the yeast sterol C8-C7 isomerase. Br J Pharmacol. 1997 May;121(1):1-6. PubMed PMID: 9146879; PubMed Central PMCID: PMC1564641.