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T5200

Sigma-Aldrich

Triparanol

≥97% (HPLC), powder

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C27H32NO2Cl
Número CAS:
78-41-1
Peso molecular:
438.00
Número CE:
201-115-0
Número MDL:
MFCD00865748
Código UNSPSC:
12352200
ID de substância PubChem:
24724632
NACRES:
NA.77

Nível de qualidade

100

Ensaio

≥97% (HPLC)

Formulário

powder

cor

white to off-white

pf

102.9-103.7 °C

solubilidade

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

temperatura de armazenamento

2-8°C

cadeia de caracteres 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

chave InChI

SYHDSBBKRLVLFF-UHFFFAOYSA-N

Informações sobre genes

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

Aplicação

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.

Ações bioquímicas/fisiológicas

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

Nota de preparo

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.

Pictogramas

CorrosionExclamation mark
GHS05,GHS07

Palavra indicadora

Danger

Frases de perigo

H302,H318

Classificações de perigo

Acute Tox. 4 Oral - Eye Dam. 1

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
090M4626V
090M4626
074K4610

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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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