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T5200

Triparanol

≥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)

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 (Iks) 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

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H302,H318

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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Certificates of Analysis (COA)

Lot/Batch Number
0000164587
0000164588
090M4626V
0000164588
0000164587

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Related Content

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
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
D E Rhoads et al.
Biochimica et biophysica acta, 795(1), 20-29 (1984-08-15)
Paramecium requires oleic acid for growth and can grow in media containing no other fatty acids. In the present study, we have shown that this ciliate utilized oleate mainly as a carbon and energy source, even though this fatty acid
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