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T5200

Sigma-Aldrich

Triparanol

≥97% (HPLC), 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
EC Number:
201-115-0
MDL number:
MFCD00865748
UNSPSC Code:
12352200
PubChem Substance ID:
24724632
NACRES:
NA.77

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

Triparanol is known to repress Hedgehog signaling in cancer cells and can also inhibit tumor growth3.
Desmosterol Delta24 (D24) reductase inhibitor.

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

Signal Word

Danger

Hazard Statements

H302,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jana Sánchez-Wandelmer et al.
Biochimica et biophysica acta, 1788(9), 1731-1739 (2009-05-13)
Lipid rafts are plasma membrane microdomains that are highly enriched with cholesterol and sphingolipids and in which various receptors and other proteins involved in signal transduction reside. In the present work, we analyzed the effect of cholesterol biosynthesis inhibition on
Pushpendra Singh et al.
PloS one, 8(3), e58833-e58833 (2013-04-05)
The cell cycle is a ubiquitous, multi-step process that is essential for growth and proliferation of cells. The role of membrane lipids in cell cycle regulation is not explored well, although a large number of cytoplasmic and nuclear regulators have
Tri Dung Tiet et al.
The American journal of pathology, 168(1), 321-330 (2006-01-10)
Chondrosarcoma is a malignant cartilage tumor that may arise from benign precursor lesions, such as enchondromas. Some cases of multiple enchondromas are caused by a mutation that results in constitutive activation of Hedgehog-mediated signaling. We found that chondrosarcomas expressed high
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 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
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