ChemicalBook > CAS DataBase List > (3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol

(3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol

Product Name
(3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol
CAS No.
1397692-46-4
Chemical Name
(3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol
Synonyms
Nat-20(S)-yne;Nat20(S)yne,Nat 20(S) yne;Nat-20(S)-yne Exclusive;SCMAJJQBADBBSM-CMJRPVKTSA-N;(3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol;26,27-Dinorcholest-5-en-24-yne-3,20-diol, (3β)-;(3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol, CAS 1397692-46-4
CBNumber
CB92694512
Molecular Formula
C25H38O2
Formula Weight
370.57
MOL File
1397692-46-4.mol
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(3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol Property

Boiling point:
510.0±25.0 °C(Predicted)
Density 
1.08±0.1 g/cm3(Predicted)
storage temp. 
Store at -20°C
solubility 
DMF: 14 mg/ml; DMSO: 0.5 mg/ml; Ethanol: 10 mg/ml
form 
A crystalline solid
pka
14.68±0.29(Predicted)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical
Product number
9001369
Product name
Nat-20(S)-yne
Purity
≥95%
Packaging
1mg
Price
$61
Updated
2024/03/01
Cayman Chemical
Product number
9001369
Product name
Nat-20(S)-yne
Purity
≥95%
Packaging
5mg
Price
$264
Updated
2024/03/01
Cayman Chemical
Product number
9001369
Product name
Nat-20(S)-yne
Purity
≥95%
Packaging
10mg
Price
$468
Updated
2024/03/01
Cayman Chemical
Product number
9001369
Product name
Nat-20(S)-yne
Purity
≥95%
Packaging
25mg
Price
$1019
Updated
2024/03/01
TRC
Product number
D480430
Product name
(3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol
Packaging
10mg
Price
$395
Updated
2021/12/16
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(3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol Chemical Properties,Usage,Production

Description

Smoothened (SMO) is a GPCR-like receptor which, with Patched, mediates hedgehog signaling to regulate gene expression through the Gli transcription factors. 20(S)-hydroxy Cholesterol (20(S)-OHC) is an oxysterol which binds SMO and activates hedgehog signaling (EC50 = 3 μM), and this activation is selective for the nat-20(S)-OHC enantiomer. Nat-20(S)-OHC synergizes with the SMO agonist SAG, suggesting an allosteric effect. Nat-20(S)-yne is a form of nat-20(S)-OHC with a terminal alkyne group, which can be used in linking reactions known as click chemistry. Click chemistry involves highly dependable and specific azide-alkyne bioconjugation reactions and can be used to capture or immobilize bioactive molecules. Thus, nat-20(S)-yne has been conjugated with magnetic beads to demonstrate that nat-20(S)-OHC directly binds SMO.

Uses

(3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol is a byproduct of cholesterol (C432501) oxidation and a potential agonists of the hedgehog signaling pathway.

References

[1] YOONJUNG KHO. A tagging-via-substrate technology for detection and proteomics of farnesylated proteins.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2004, 101 34: 12479-12484. DOI: 10.1073/pnas.0403413101
[2] JEAN-FRAN?OIS LUTZ  Zoya Z. Efficient construction of therapeutics, bioconjugates, biomaterials and bioactive surfaces using azide–alkyne “click” chemistry[J]. Advanced drug delivery reviews, 2008, 60 9: Pages 958-970. DOI: 10.1016/j.addr.2008.02.004
[3] SIGRID NACHTERGAELE. Oxysterols are allosteric activators of the oncoprotein Smoothened[J]. Nature chemical biology, 2012, 8 2: 211-220. DOI: 10.1038/nchembio.765

(3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol Preparation Products And Raw materials

Raw materials

Preparation Products

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(3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol Suppliers

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1397692-46-4, (3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diolRelated Search:


  • (3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol
  • SCMAJJQBADBBSM-CMJRPVKTSA-N
  • Nat-20(S)-yne
  • Nat-20(S)-yne Exclusive
  • 26,27-Dinorcholest-5-en-24-yne-3,20-diol, (3β)-
  • Nat20(S)yne,Nat 20(S) yne
  • (3β)-26,27-Dinorcholest-5-en-24-yne-3,20-diol, CAS 1397692-46-4
  • 1397692-46-4
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