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