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700059P

Avanti

27-hydroxycholesterol-d6

Avanti Research™ - A Croda Brand

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C27H40D6O2
Número de CAS:
1246302-95-3
Peso molecular:
408.69
Código UNSPSC:
41141804
NACRES:
NA.25
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descripción

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

Ensayo

>99% (TLC)

Formulario

powder

envase

pkg of 1 × 1 mg (700059P-1mg)

fabricante / nombre comercial

Avanti Research™ - A Croda Brand

Condiciones de envío

dry ice

temp. de almacenamiento

−20°C

cadena SMILES

[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

Clave InChI

FYHRJWMENCALJY-UPBLXZCTSA-N

Descripción general

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.

Aplicación

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]

Acciones bioquímicas o fisiológicas

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]

Envase

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

Información legal

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

No data available

Punto de inflamabilidad (°C)

No data available

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Certificados de análisis (COA)

Lot/Batch Number

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7-ketocholesterol-d7 Avanti Research™ - A Croda Brand

Avanti

700046P

7-ketocholesterol-d7

24(S)-Hydroxycholesterol ≥98% (HPLC)

Sigma-Aldrich

SML1648

24(S)-Hydroxycholesterol

25-Hydroxycholesterol ≥98%

Sigma-Aldrich

H1015

25-Hydroxycholesterol

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
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
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
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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