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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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450,00 €

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1 MG
450,00 €

About This Item

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

450,00 €

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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)

Lot/Batch Number

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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

Michihisa Umetani et al.
Cell metabolism, 20(1), 172-182 (2014-06-24)
Oxysterols are cholesterol metabolites that serve multiple functions in lipid metabolism, including as liver X receptor (LXR) ligands. 27-hydroxycholesterol (27HC) is an abundant oxysterol metabolized by CYP7B1. How 27HC impacts vascular health is unknown. We show that elevations in 27HC
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
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
Julien Musman et al.
Biochemical pharmacology, 142, 87-95 (2017-06-25)
A major cause of cell death during myocardial ischemia-reperfusion is mitochondrial dysfunction. We previously showed that the reperfusion of an ischemic myocardium was associated with an accumulation of cholesterol into mitochondria and a concomitant strong generation of auto-oxidized oxysterols. The
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