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Merck
CN

T5200

曲帕拉醇

≥97% (HPLC), D24 reductase inhibitor, powder

别名:

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

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关于此项目

经验公式(希尔记法):
C27H32NO2Cl
化学文摘社编号:
分子量:
438.00
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
201-115-0
MDL number:
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产品名称

曲帕拉醇, ≥97% (HPLC), powder

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

SMILES string

CCN(CC)CCOc1ccc(cc1)C(O)(Cc2ccc(Cl)cc2)c3ccc(C)cc3

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

Quality Level

Gene Information

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

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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
F Echevarria et al.
The Journal of biological chemistry, 265(15), 8484-8489 (1990-05-25)
Zymosterol (5 alpha-cholesta-8(9),24-dien-3 beta-ol) comprised a negligible fraction of the mass of sterol in cultured human fibroblasts but was well labeled biosynthetically with radioactive acetate. Treatment of cells with triparanol, a potent inhibitor of sterol delta 24-reductase, led to a
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
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

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