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T5200

Sigma-Aldrich

Triparanol

≥97% (HPLC), powder

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C27H32NO2Cl
Numéro CAS:
78-41-1
Poids moléculaire :
438.00
Numéro CE :
201-115-0
Numéro MDL:
MFCD00865748
Code UNSPSC :
12352200
ID de substance PubChem :
24724632
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥97% (HPLC)

Forme

powder

Couleur

white to off-white

Pf

102.9-103.7 °C

Solubilité

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

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

SYHDSBBKRLVLFF-UHFFFAOYSA-N

Informations sur le gène

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.

Actions biochimiques/physiologiques

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

Notes préparatoires

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.

Pictogrammes

CorrosionExclamation mark
GHS05,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302,H318

Classification des risques

Acute Tox. 4 Oral - Eye Dam. 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
C Roux et al.
The American journal of clinical nutrition, 71(5 Suppl), 1270S-1279S (2000-05-09)
We showed previously that 3 distal inhibitors of cholesterol synthesis are highly teratogenic in rats. AY 9944 and BM 15766 inhibit 7-dehydrocholesterol reductase, which catalyzes the last step of cholesterol synthesis, and triparanol inhibits Delta(24)-dehydrocholesterol reductase, which catalyzes the last
W E Ribelin
Fundamental and applied toxicology : official journal of the Society of Toxicology, 4(1), 105-119 (1984-02-01)
The susceptibility of the endocrine tissues to compound-induced lesions may be ranked in the following decreasing order of frequency: adrenal, testis, thyroid, ovary, pancreas, pituitary, and parathyroid. The first two are by far the most frequently affected. Pathologists unaccustomed to
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
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
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