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700059P

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27-hydroxycholesterol-d6

Avanti Research™ - A Croda Brand

Sinonimo/i:

25,26,26,26,27,27-hexadeuterocholest-5-ene-3β,27-diol; 27-hydroxycholest-5-en-3-ol(d6); 111011

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CHF 463.00

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About This Item

Formula empirica (notazione di Hill):
C27H40D6O2
Numero CAS:
1246302-95-3
Peso molecolare:
408.69
Codice UNSPSC:
41141804
NACRES:
NA.25

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Descrizione

25,26,26,26,27,27-hexadeuterocholest-5-ene-3β,27-diol

Saggio

>99% (TLC)

Stato

powder

Confezionamento

pkg of 1 × 1 mg (700059P-1mg)

Produttore/marchio commerciale

Avanti Research™ - A Croda Brand

Condizioni di spedizione

dry ice

Temperatura di conservazione

−20°C

Stringa SMILE

[H][C@@]12[C@]([C@](CC[C@H](O)C3)(C)C3=CC2)([H])CC[C@@]4(C)[C@@]1([H])CC[C@]4([H])[C@]([H])(C)CCC[C@@]([2H])(C([2H])([2H])[2H])C(O)([2H])[2H]

InChI

1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1/i1D3,17D2,18D
FYHRJWMENCALJY-UPBLXZCTSA-N

Descrizione generale

27-hydroxycholesterol (27-HC) is synthesized from cholesterol by the action of sterol 27-hydroxylase in the liver. It is an abundant oxysterol in the circulation ranging from 0.15 to 0.73 μM. 27-HC serves as a substrate for bile synthesis.[1] 27-hydroxycholesterol-d6 is a deuterated form of 27-hydroxycholesterol.

Applicazioni

27-hydroxycholesterol-d6 has been used:
  • as an internal standard in isotope dilution-mass spectrometry analysis of heart mitochondria samples[2]
  • as an internal standard in gas chromatography-mass spectrometry (GC–MS) for plasma sterol quantification[3]
  • as a deuterated internal standard for spiking plasma samples for liquid chromatography with tandem mass spectrometry (LC-MS-MS) analysis[4]

Azioni biochim/fisiol

27-hydroxycholesterol (27-HC) is a weak liver X receptor (LXR) agonist[5] and a selective estrogen receptor modulator (SERM).[6] Elevated levels of 27-HC is observed in hypercholesterolemia.[7] 27-HC is implicated in breast cancer tumor[8] and glioblastoma progression.[9] 27-HC may help in treating non-alcoholic steatohepatitis. Elevated levels of 27-HC is associated with atherosclerotic lesions.[1]

Confezionamento

5 mL Amber Glass Screw Cap Vial (700059P-1mg)

Note legali

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

No data available

Punto d’infiammabilità (°C)

No data available

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Certificati d'analisi (COA)

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24(S)-Hydroxycholesterol ≥98% (HPLC)

Sigma-Aldrich

SML1648

24(S)-Hydroxycholesterol

25-Hydroxycholesterol ≥98%

Sigma-Aldrich

H1015

25-Hydroxycholesterol

Sodium methoxide reagent grade, 95%, powder

Sigma-Aldrich

164992

Sodium methoxide

Di Li et al.
Obesity (Silver Spring, Md.), 26(4), 713-722 (2018-02-25)
Although 27-hydroxycholesterol (27-HC) has been reported as a potent regulator of lipid homeostasis, its role in hepatic lipogenesis remains obscure. The present study was designed to investigate the impact of 27-HC on sterol regulatory element-binding protein 1 (SREBP-1) and hepatic
Erik R Nelson et al.
Science (New York, N.Y.), 342(6162), 1094-1098 (2013-11-30)
Hypercholesterolemia is a risk factor for estrogen receptor (ER)-positive breast cancers and is associated with a decreased response of tumors to endocrine therapies. Here, we show that 27-hydroxycholesterol (27HC), a primary metabolite of cholesterol and an ER and liver X
Lu Liu et al.
Oncology letters, 18(4), 3623-3629 (2019-10-04)
Glioblastoma is the most frequent primary malignant brain tumor in adults. Oxysterols are oxidation products of cholesterol generated by enzymatic reactions. 27-hydroxycholesterol (27-HC), an oxysterol, is an abundant metabolite of cholesterol. 27-HC significantly accelerates mammary cancer growth, proliferation and progression
Irundika H K Dias et al.
Redox biology, 16, 139-145 (2018-03-04)
Oxysterols (OHC) are biologically active cholesterol metabolites circulating in plasma that may be formed enzymatically (e.g. 24S-OHC, 25-OHC and 27-OHC) or by autoxidative mechanisms (e.g. 7-ketocholesterol, 7β-OHC and 25-OHC). Oxysterols are more soluble than cholesterol and are reported to exert
Shaneabbas Raza et al.
Cancer cell international, 17, 52-52 (2017-05-16)
For every six men, one will be diagnosed with prostate cancer (PCa) in their lifetime. Estrogen receptors (ERs) are known to play a role in prostate carcinogenesis. However, it is unclear whether the estrogenic effects are mediated by estrogen receptor
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