(25S)-Δ7-Dafachronic Acid

Base Information

• Chemical Name: (25S)-Δ7-Dafachronic Acid
• CAS No.: 949004-12-0
• Molecular Formula: C₂₇H₄₂O₃
• Molecular Weight: 414.629
• Mol file: 949004-12-0.mol

Synonyms:(25S)-Δ7-Dafachronic Acid

Chemical Property of (25S)-Δ7-Dafachronic Acid

Chemical Property:

• PSA: 54.37000
• LogP: 6.66160

Purity/Quality:

99% ^*data from raw suppliers

(25S)-Δ7-Dafachronic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: During unfavorable environmental conditions, C. elegans larvae undergo arrest and form dauer larvae that can attach to other animals as a parasitic strategy for survival. DAF-12 is an orphan nuclear hormone receptor that regulates dauer larva diapause, reproductive development, fat metabolism, and life cycle/longevity in C. elegans. DAF-12 is required for entry into dauer when it is not bound to ligand by acting as a transcriptional repressor of target genes that favor reproductive development. (25S)-Δ7-Dafachronic acid is a sterol-derived hormone that acts as a ligand of DAF-12 with an EC50 value of 23 nM. At 50 nM, (25S)-Δ7-Dafachronic acid inhibits the dauer-promoting activity of DAF-12, blocking the formation of infective larvae in several parasitic nematodes in favor of reproductive maturation to adults. Thus, selective ligand modulators of DAF-12 are a potential therapeutic approach to stop larvae progression during parasitic infection.

Technology Process of (25S)-Δ7-Dafachronic Acid

There total 49 articles about (25S)-Δ7-Dafachronic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

C28H44O3 (950602-13-8) → (25S)-3-keto-5α-cholest-7-en-26-oic acid (949004-12-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 6h;

DOI:10.1021/ja074306i

Reference yield: 91.0%

C27H40O3 → (25S)-3-keto-5α-cholest-7-en-26-oic acid (949004-12-0)

Guidance literature:

With ((-)-(1S)-[1,1'-binaphthalene]-2,2'-diylbis[diphenylphosphine-κP])chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium(1+) chloride; hydrogen; In methanol; water; at 55 ℃; for 22h; diastereoselective reaction; Sealed tube;

DOI:10.1021/ol5006642

Reference yield: 89.0%

(25S)-26-hydroxy-5α-cholest-7-en-3β-ol (1097641-36-5) → (25S)-3-keto-5α-cholest-7-en-26-oic acid (949004-12-0)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In acetone; at 0 ℃; for 1.5h;

DOI:10.1039/b815064h

upstream raw materials:

C₂₈H₄₄O₃

C₂₉H₄₈O₃

methyl 3β-acetoxy-25(S)-methyl-24-bishomochol-5-en-26-oate

methyl 3β-acetoxy-7-keto-25(S)-methyl-24-bishomochol-5-en-26-oate

Refernces

• 1、 Judkins, Joshua C.,Mahanti, Parag,Hoffman, Jacob B.,Yim, Isaiah,Antebi, Adam,Schroeder, Frank C.. "A photocleavable masked nuclear-receptor ligand enables temporal control of C.elegans development". . p. 2110 - 2113. Retrieved 2014/03/21.
• 2、 Gioiello, Antimo,Sabbatini, Paola,Rosatelli, Emiliano,MacChiarulo, Antonio,Pellicciari, Roberto. "Divergent and stereoselective synthesis of dafachronic acids". . p. 1924 - 1929. Retrieved 2011/04/17.