Dehydroergosterol

Base Information

• Chemical Name: Dehydroergosterol
• CAS No.: 516-85-8
• Molecular Formula: C28H42 O
• Molecular Weight: 394.641
• UNII: 123R6KJQ51
• DSSTox Substance ID: DTXSID601026574
• Nikkaji Number: J741.409I,J10.273C
• Wikidata: Q27133411
• Metabolomics Workbench ID: 34829
• Mol file: 516-85-8.mol

Synonyms:dehydroergosterol;delta(5,7,9(11)22)-ergostatetraen-3-ol;ergosta-5,7,9(11),22-tetraen-3 beta-ol

Chemical Property of Dehydroergosterol

Chemical Property:

• Vapor Pressure: 5.13E-13mmHg at 25°C
• Melting Point: 146°
• Refractive Index: 1.5100 (estimate)
• Boiling Point: 520.6°C at 760 mmHg
• PKA: 14.88±0.70(Predicted)
• Flash Point: 221°C
• PSA: 20.23000
• Density: 1.02g/cm³
• LogP: 7.25090
• Storage Temp.: −20°C
• Solubility.: Acetone (Slightly), Chloroform (Slightly)
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 394.323565959
• Heavy Atom Count: 29
• Complexity: 765

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dehydroergosterol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C)C=CC(C)C1CCC2C1(CC=C3C2=CC=C4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC=C3C2=CC=C4[C@@]3(CC[C@@H](C4)O)C)C
• Uses: Dehydroergosterol (DHE) is suitable for the transfer of DHE from a population of donor (LD) to acceptor (LA) liposomes. A fluorescent cholesterol analog useful as a probe in membrane research.

Technology Process of Dehydroergosterol

There total 16 articles about Dehydroergosterol 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: 55.0%

Ergosterol (57-87-4) → 9(11)-dehydroergosterol (516-85-8)

Guidance literature:

With mercury (II) acetate; acetic acid; In ethanol; chloroform; at 20 ℃; for 40h; Darkness;

DOI:10.1021/jacs.0c13426

Reference yield:

C38H50N2O4 (41238-09-9,56192-94-0) → ergosta-5,7,22-triene-3β-ol (57-87-4,128-27-8,474-69-1,474-70-4,6538-06-3,7056-23-7,57760-53-9,60018-27-1,70005-45-7,82863-18-1,122565-01-9) + ergosta-5,7,9(11),22-tetraen-3β-ol (516-85-8,26596-35-0,85798-12-5,98463-65-1)

Guidance literature:

With sodium hydroxide; sulfuric acid; Yield given. Multistep reaction; 1.) ethanol, reflux, 30 min; 2.) cooling with ice.;

Reference yield:

(3S,10S,13R,14R,17R)-7-Hydroperoxy-10,13-dimethyl-17-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-2,3,4,7,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol → 9(11)-dehydroergosterol (516-85-8)

Guidance literature:

With hydrogenchloride; In chloroform; for 0.0833333h;

DOI:10.1111/j.1751-1097.1994.tb05109.x

upstream raw materials:

ergosta-4,7,9⁽¹¹⁾,22t-tetraen-3-one

ergostatetraen-(5.7.9(11).22t)-yl-(3α)-acetate

aluminum isopropoxide

isopropyl alcohol

Downstream raw materials:

9,11-dehydroergosterol peroxide

3β-(toluene-4-sulfonyloxy)-ergosta-5,7,9(11),22t-tetraene

3.5-dinitro-benzoic acid-[ergostatetraen-(5.7.9(11).22t)-yl-(3β)-ester]

Ergosterol