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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:
Assay:
≥97% (HPLC)
Form:
powder
Quality level:
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产品名称

曲帕拉醇, ≥97% (HPLC), powder

Quality Level

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

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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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
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
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



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