(3beta)-Ergosta-5,7,22-trien-3-ol

Base Information

• Chemical Name: (3beta)-Ergosta-5,7,22-trien-3-ol
• CAS No.: 57-87-4
• Molecular Formula: C28H44O
• Molecular Weight: 396.657
• Hs Code.: 29334900
• ChEMBL ID: CHEMBL222608
• Wikidata: Q63392683
• Mol file: 57-87-4.mol

Synonyms:NSC-62791;(22E)-Ergosta-5,7,22-trien-3-ol #;(3.beta.)-Ergosta-5,7,22- trien-3-ol;Ergosta-5,7,22-trien-3-ol, (3.beta.,22E)-;CHEMBL222608;SCHEMBL21927817;DNVPQKQSNYMLRS-NBEWGGKZSA-N;Q63392683

Chemical Property of (3beta)-Ergosta-5,7,22-trien-3-ol

Chemical Property:

• Appearance/Colour: white to yellow crystalline powder
• Vapor Pressure: 3.7E-12mmHg at 25°C
• Melting Point: 156-158 °C(lit.)
• Refractive Index: -112.5 ° (C=1, THF)
• Boiling Point: 501.5 °C at 760 mmHg
• PKA: 14.91±0.70(Predicted)
• Flash Point: 216.3 °C
• PSA: 20.23000
• Density: 1 g/cm³
• LogP: 7.33080
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Acetone (Slightly, Heated), Chloroform (Slightly), Ethyl Acetate (Slightly, Heat
• Water Solubility.: PRACTICALLY INSOLUBLE
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 396.339216023
• Heavy Atom Count: 29
• Complexity: 712

Purity/Quality:

97% ^*data from raw suppliers

Ergosterol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+,T,Xn
• Statements: 28-48/20/22-40-38-25-67-36/38-22-20-63
• Safety Statements: 28-36/37-45-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C)C=CC(C)C1CCC2C1(CCC3C2=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[C@H]3C2=CC=C4[C@@]3(CC[C@@H](C4)O)C)C
• Description: Ergosterol is a membrane component and with few exceptions is restricted to eumycotic fungi (101). As a constituent of intact membranes, its abundance should reflect the amount of living fungal biomass in an environment. This membrane component has been related to biomass by a number of investigators and the values range from 1.9 to 11.5 mg ergosterol g?1 mycelium (102). These conversion factors yield very high values for fungal biomass, and seem unrealistic (102) when compared with independent measures of bacterial biomass. It is likely that the ergosterol assay detects nonliving hyphae and these measures may overestimate viable fungal biomass. Similarly, chitin is a dominant cell wall component in most fungi and has been proposed as a unique marker for total fungal biomass.
• Uses: Most important of the provitamins D. Usually obtained from yeast which synthesizes it from simple sugars such as glucose. Vitamin (antirachitic). Ergosterol may be used to study the function of anti-fungal drugs such as Amphotericin B and its analogues and to study the ergosterol biosynthesis pathway within various fungi. It acts as a useful indicator of living fungal biomass. Ergosterol is a steroid alcohol that when irradiated with ultraviolet light yields calciferol (vitamin d2). irradiated ergosterol is added to milk for vitamin d fortification.

Technology Process of (3beta)-Ergosta-5,7,22-trien-3-ol

There total 45 articles about (3beta)-Ergosta-5,7,22-trien-3-ol 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: 76.0%

C42H61N3O6S*C6H15N → Ergosterol (57-87-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 16h; Heating;

DOI:10.1021/jo00164a005

Reference yield: 70.0%

3β-acetoxy-5α,8α-(4-phenyl-1,2,4-triazolidine-3,5-dione-1,2-diyl)ergosta-6,22-diene (28421-56-9) → Ergosterol (57-87-4) + 1-Isobutyl-4-phenyl-[1,2,4]triazolidin-3-one

Guidance literature:

With diisobutylaluminium hydride; In hexane; toluene; at 0 ℃; for 0.166667h;

Reference yield: 51.0%

3β-hydroxy-3',5'-dioxo-4'-phenyl-5,8<1',2'>-1',2',4'-triazolidino-5α,8α-ergosta-6,22-diene (10123-90-7) → Ergosterol (57-87-4) + 1-Isobutyl-4-phenyl-[1,2,4]triazolidin-3-one

Guidance literature:

With diisobutylaluminium hydride; In hexane; toluene; at 0 ℃; for 0.166667h;

upstream raw materials:

diethyl ether

previtamin D₂

(22E,24R)-ergosta-4,7,22-triene-3-one

lanosterol

Downstream raw materials:

succinic acid monoergosteryl ester

benzoic acid-(3β.5-dihydroxy-5α-ergostadien-(7.22t)-yl-(6α)-ester)

Calciferol

lumisterol

Refernces

• 1、 Windaus,Buchholz. "-". . . Retrieved 1939.
• 2、 -. "MOLECULARLY IMPRINTED POLYMERS". . . Retrieved 2012/03/12.
• 3、 Kondo, Fumihiro,Miyashita, Misako,Konno, Katsuhiro,Takayama, Hiroaki. "Facile retro-cycloaddition of adducts derived from steroidal 5,7-diene and 4-phenyl-1,2,4-triazoline-3,5-dione by diisobutylaluminium hydride". . p. 2679 - 2680. Retrieved 2007/10/02.