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T5200

Triparanol

Name: Triparanol
Brand: SIGMA

≥97% (HPLC), D24 reductase inhibitor, powder

Synonym(s):

1-(4-(2-Diethylaminoethoxy)phenyl)-1-p-tolyl-2-(4-chlorophenyl)ethanol

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About This Item

Empirical Formula (Hill Notation):

C₂₇H₃₂NO₂Cl

CAS Number:

78-41-1

Molecular Weight:

438.00

NACRES:

NA.77

PubChem Substance ID:

24724632

UNSPSC Code:

12352200

EC Number:

201-115-0

MDL number:

MFCD00865748

Assay:

≥97% (HPLC)

Form:

powder

Quality level:

100

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Product Name

Triparanol, ≥97% (HPLC), powder

Quality Level

100

assay

≥97% (HPLC)

form

powder

color

white to off-white

mp

102.9-103.7 °C

solubility

DMSO: 20 mg/mL, H₂O: insoluble, alcohol: soluble, olive oil: slightly soluble

storage temp.

2-8°C

SMILES string

CCN(CC)CCOc1ccc(cc1)C(O)(Cc2ccc(Cl)cc2)c3ccc(C)cc3

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

InChI key

SYHDSBBKRLVLFF-UHFFFAOYSA-N

Gene Information

human ... DHCR24(1718), EBP(10682)

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

Triparanol has been used to inhibit cholesterol biosynthesis in lipid rafts¹. Triparanol has also been used as a 3β-hydroxysterol-Δ24-reductase inhibitor to study its effect on delayed-rectifier potassium current (I_ks) channels².

Biochem/physiol Actions

Desmosterol Delta24 (D24) reductase inhibitor.

Triparanol is known to repress Hedgehog signaling in cancer cells and can also inhibit tumor growth³.

Preparation Note

Triparanol is soluble in DMSO at 20 mg/ml and is also soluble in alcohol. It is slightly soluble in olive oil and is insoluble in water.

pictograms

GHS05,GHS07

signalword

Danger

hcodes

H302,H318

pcodes

P280 - P301 + P312 + P330 - P305 + P351 + P338 + P310

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Polyterpenoids as cholesterol and tetrahymanol surrogates in the ciliate Tetrahymena pyriformis.

D Raederstorff et al.

Biochimica et biophysica acta, 960(2), 190-199 (1988-05-22)

The tetracyclic sterol precursors, cyclolaudenol, cycloartenol and lanosterol, inhibit efficiently the tetrahymanol biosynthesis in the ciliate Tetrahymena pyriformis, as reported earlier for cholesterol and other sterols. The prokaryotic bacteriohopanetetrols have little effect, and diplopterol, another hopanoid, as well as the

Relationships between dietary cholesterol, cholesterol absorption, cholesterol synthesis, and plasma cholesterol in rhesus monkeys.

A K Bhattacharyya et al.

Atherosclerosis, 67(1), 33-39 (1987-09-01)

The relationships between the cholesterol content of the diet, plasma cholesterol concentration, cholesterol absorption, and cholesterol synthesis (measured indirectly by desmosterol suppression technique) are explored in groups of high- and low-responding rhesus monkeys fed diets containing 0.02, 0.15 and 0.75

Regulation of 3-hydroxy-3-methylglutaryl-coenzyme A reductase in human hepatoma cell line Hep G2. Effects of inhibitors of cholesterol synthesis on enzyme activity.

A Boogaard et al.

The Biochemical journal, 241(2), 345-351 (1987-01-15)

Incubating Hep G2 cells for 18 h with triparanol, buthiobate and low concentrations (less than 0.5 microM) of U18666A, inhibitors of desmosterol delta 24-reductase, of lanosterol 14 alpha-demethylase and of squalene-2,3-epoxide cyclase (EC 5.4.99.7) respectively, resulted in a decrease of

High affinity of sigma 1-binding sites for sterol isomerization inhibitors: evidence for a pharmacological relationship with the yeast sterol C8-C7 isomerase.

F F Moebius et al.

British journal of pharmacology, 121(1), 1-6 (1997-05-01)

1. The sigma-drug binding site of guinea-pig liver is carried by a protein which shares significant amino acid sequence similarities with the yeast sterol C8-C7 isomerase (ERG2 protein). Pharmacologically-but not structurally-the sigma 1-site is also related to the emopamil binding

Newborn response to cationic amphiphilic drugs.

S Kacew et al.

Federation proceedings, 44(7), 2323-2327 (1985-04-01)

Administration of various cationic amphiphilic drugs in utero results in induction of a phospholipid storage disorder in many tissues, particularly in lungs. In addition to the phospholipidosis in utero, drug exposure results in toxicity to the offspring; newborn rats die

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Global Trade Item Number

SKU	GTIN
T5200-25MG	04061833058787
T5200-5MG	04061833058794

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