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T5200

Sigma-Aldrich

Triparanol

≥97% (HPLC), powder

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C27H32NO2Cl
Numero CAS:
78-41-1
Peso molecolare:
438.00
Numero CE:
201-115-0
Numero MDL:
MFCD00865748
Codice UNSPSC:
12352200
ID PubChem:
24724632
NACRES:
NA.77

Livello qualitativo

100

Saggio

≥97% (HPLC)

Forma fisica

powder

Colore

white to off-white

Punto di fusione

102.9-103.7 °C

Solubilità

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

Temperatura di conservazione

2-8°C

Stringa SMILE

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
SYHDSBBKRLVLFF-UHFFFAOYSA-N

Informazioni sul gene

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

Categorie correlate

Applicazioni

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.

Azioni biochim/fisiol

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

Nota sulla preparazione

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.

Pittogrammi

CorrosionExclamation mark
GHS05,GHS07

Avvertenze

Danger

Indicazioni di pericolo

H302,H318

Classi di pericolo

Acute Tox. 4 Oral - Eye Dam. 1

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

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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
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
A Ramu et al.
Cancer research, 44(10), 4392-4395 (1984-10-01)
The effects of the triparanol analogues chlorotrianisene, clomiphene, tamoxifen, 5-[p-(fluoren-9-ylidenemethyl)phenyl]-2-piperidineethanol (MDL 10393), MDL 8917v, nafoxidine, 2-[p-(6-methoxy-2-phenylinden-3-yl)phenoxy]triethylamine (U-11555A), 2-[p-(3,4-dihydro-6-methoxy-2-phenyl-1-naphthyl)phenoxy]triethylamine (U-10520A), and nitromifene, as well as triparanol itself, were studied in the P388 murine leukemia cell line and in a doxorubicin-resistant subline
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
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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