(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

Pharmaceuticals, Intermediates & Fine Chemicals, Steroids