ChemicalBook > CAS DataBase List > 20ALPHA-HYDROXYCHOLESTEROL

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: $187.15
Updated: 2025/07/31

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] An oxysterol signaling pathway mediated by the nuclear receptor LXR7alpha
[2] HOA TON KHA. Oxysterols Regulate Differentiation of Mesenchymal Stem Cells: Pro-Bone and Anti-Fat†[J]. Journal of Bone and Mineral Research, 2009, 19 5: 830-840. DOI:10.1359/jbmr.040115
[3] WOO-KYUN KIM. Osteogenic oxysterol, 20(S)-hydroxycholesterol, induces notch target gene expression in bone marrow stromal cells[J]. Journal of Bone and Mineral Research, 2010, 25 4: 782-795. DOI:10.1359/jbmr.091024
[4] JENNIFER R DWYER. Oxysterols are novel activators of the hedgehog signaling pathway in pluripotent mesenchymal cells.[J]. The Journal of Biological Chemistry, 2007, 282 12: 8959-8968. DOI:10.1074/jbc.m611741200
[5] DANIEL NEDELCU. Oxysterol binding to the extracellular domain of Smoothened in Hedgehog signaling[J]. Nature chemical biology, 2013, 9 9: 557-564. DOI:10.1038/nchembio.1290
[6] YU-SHIUAN CHENG. A proteome-wide map of 20(S)-hydroxycholesterol interactors in cell membranes[J]. Nature chemical biology, 2021, 17 12: 1271-1280. DOI:10.1038/s41589-021-00907-2

20ALPHA-HYDROXYCHOLESTEROL Preparation Products And Raw materials

Raw materials

Preparation Products

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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

20(S)-Hydroxycholesterol, 10 mM in DMSO

516-72-3

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