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20ALPHA-HYDROXYCHOLESTEROL

Product Name
20ALPHA-HYDROXYCHOLESTEROL
CAS No.
516-72-3
Chemical Name
20ALPHA-HYDROXYCHOLESTEROL
Synonyms
C05500;20-hydroxycholesterol;20A-HYDROXYCHOLESTEROL;20α-Hydroxy Cholesterol;Cholesterol Impurity 32;5-Cholestene-3B,20a-diol;5-cholestene-3β,20α-diol;Cholest-5-ene-3,20a-diol;Cholest-5-ene-3β,20-diol;20[S]-HYDROXYCHOLESTEROL
CBNumber
CB2372501
Molecular Formula
C27H46O2
Formula Weight
402.65
MOL File
516-72-3.mol
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20ALPHA-HYDROXYCHOLESTEROL Property

Melting point:
136-137°C
Boiling point:
512.3±23.0 °C(Predicted)
Density 
1.03±0.1 g/cm3(Predicted)
storage temp. 
Inert atmosphere,2-8°C
solubility 
Soluble in DMSO or in Ethanol.
form 
Solid
pka
15.04±0.70(Predicted)
color 
White
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
H6378
Product name
20α-Hydroxycholesterol
Purity
analytical standard
Packaging
5mg
Price
$115.8
Updated
2024/03/01
Cayman Chemical
Product number
20103
Product name
20(S)-hydroxy Cholesterol
Purity
≥98%
Packaging
1mg
Price
$50
Updated
2024/03/01
Cayman Chemical
Product number
20103
Product name
20(S)-hydroxy Cholesterol
Purity
≥98%
Packaging
5mg
Price
$111
Updated
2024/03/01
Cayman Chemical
Product number
20103
Product name
20(S)-hydroxy Cholesterol
Purity
≥98%
Packaging
10mg
Price
$195
Updated
2024/03/01
Tocris
Product number
4474
Product name
20(S)-Hydroxycholesterol
Purity
≥95%(HPLC)
Packaging
10
Price
$184
Updated
2021/12/16
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20ALPHA-HYDROXYCHOLESTEROL Chemical Properties,Usage,Production

Description

20(S)-hydroxy Cholesterol is an allosteric agonist of the smoothened (Smo) receptor that activates the hedgehog (Hh) signaling pathway with an EC50 value of approxiately 3 μM in a gene transcription reporter assay using NIH3T3 cells. 20(S)-hydroxy Cholesterol is necessary for normal Hh signaling. It induces Smo accumulation in primary cilia, an early event in signaling, and binds to the extracellular, cysteine-rich domain of Smo. 20(S)-hydroxy Cholesterol also stimulates osteogenic differentiation of pluripotent bone marrow stromal cells, a process mediated via Hh and Notch signaling.

Chemical Properties

White Solid

Uses

A metabolite of Cholesterol. Cholesterol oxidation product having cytotoxicity effects

Uses

A metabolite of Cholesterol (C432501). Cholesterol oxidation product having cytotoxicity effects.

Definition

ChEBI: An oxysterol that is cholesterol substituted by a hydroxy group at position 20.

storage

Store at -20°C

References

1) Janowski?et al. (1996),?An oxysterol signaling pathway mediated by the nuclear receptor LXR7alpha; Nature,?383?728 2) Kha?et al. (2004),?Oxysterols regulate differentiation of mesenchymal stem cells: Pro-bone and Anti-fat: J. Bone Min. Res.,?19?830 3) Kim?et al. (2010),?Osteogenic oxysterol, 20(S)-hydroxycholesterol, induces notch target gene expression in bone marrow stromal cells; J. Bone Miner. Res.,?25?7823 4) Dwyer?et al. (2007),?Oxysterols are novel activators of the hedgehog signaling pathway in pluripotent mesenchymal cells; J. Biol. Chem.,?282?8959 5) Nedelcu?et al. (2013);?Oxysterol binding to the extracellular domain of Smoothened in Hedgehog signaling; Nat. Chem. Biol.,?9?557 6) Cheng?et al. (2021);?A proteome-wide map of 20(S)-hydroxycholesterol interactors in cell membranes; Nat. Chem. Biol.,?17?1271

20ALPHA-HYDROXYCHOLESTEROL Preparation Products And Raw materials

Raw materials

Preparation Products

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20ALPHA-HYDROXYCHOLESTEROL Suppliers

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516-72-3, 20ALPHA-HYDROXYCHOLESTEROLRelated Search:

2,3-DIMETHYL-2-HEXANOL octadecene 4-CYCLOHEXYLCYCLOHEXANOL 5-ETHYL-3-NONANOL 3-DECANOL 5-METHYL-5-NONANOL 2-BUTYL-1-OCTANOL (S)-(+)-4-METHYL-2-PENTANOL 6-TRIDECANOL CIS-4-NONENE 20ALPHA-HYDROXYCHOLESTEROL 4-METHYL-5-OCTANOL 3-DODECANOL TRANS-9-DODECEN-1-OL (S)-(+)-2-NONANOL 4-METHYL-4-PENTEN-2-OL 3-METHYL-4-OCTANOL dodec-11-enol

  • 20alpha-Hydroxycholesterol (not deuterated)
  • 5-Cholestene-3B,20a-diol
  • Cholest-5-ene-3,20-diol, (3.beta.)-
  • 5-cholestene-3β,20α-diol
  • (3S,8S,9S,10R,13S,14S,17S)-17-[(2R)-2-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
  • 20α-Hydroxycholesterol (not deuterated)
  • (20S)-Cholest-5-ene-3,20-diol
  • (3S,8S,9S,10R,13S,14S,17S)-17-((S)-2-hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
  • 20(S)-hydroxyCholesterol (20α-Hydroxycholesterol)
  • (3)-Cholest-5-ene-3,20-diol
  • 20S-Cholest-5-ene-3,20-diol
  • Cholest-5-ene-3,20a-diol
  • (20S)-20-Hydroxycholesterol
  • Cholest-5-ene-3β,20-diol
  • C05500
  • 20A-HYDROXYCHOLESTEROL
  • 20ALPHA-HYDROXYCHOLESTEROL
  • 20[S]-HYDROXYCHOLESTEROL
  • 3BETA,20ALPHA-DIHYDROXY-5-CHOLESTENE
  • 5-CHOLESTENE-3B,20ALPHA-DIOL
  • 5-CHOLESTENE-3BETA,20ALPHA-DIOL
  • 5-CHOLESTEN-3-BETA, 20-ALPHA-DIOL
  • 20-hydroxycholesterol
  • Cholest-5-ene-3,20-diol, (3β)-
  • 20α-Hydroxy Cholesterol
  • Cholesterol Impurity 32
  • (8S,9S,10R,13S,14S,17S)-17-((R)-2-Hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
  • 5-CHOLESTEN-3β, 20α-DIOL
  • 20(S)-Hydroxycholesterol, Smoothened activator
  • 516-72-3
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