Taleranol

Base Information

• Chemical Name: Taleranol
• CAS No.: 42422-68-4
• Molecular Formula: C18H26O5
• Molecular Weight: 322.401
• European Community (EC) Number: 636-982-8
• UNII: HUN219N434
• DSSTox Substance ID: DTXSID3022532
• Nikkaji Number: J16.878E
• Wikipedia: Taleranol
• Wikidata: Q27116399
• NCI Thesaurus Code: C74260
• Pharos Ligand ID: B2UB36DVNKLY
• Metabolomics Workbench ID: 138884
• ChEMBL ID: CHEMBL491510
• Mol file: 42422-68-4.mol

Synonyms:beta-zearalanol;estrogen P 1560;estrogen P-1560;taleranol

Chemical Property of Taleranol

Chemical Property:

• Vapor Pressure: 4.16E-14mmHg at 25°C
• Melting Point: 134-137oC
• Boiling Point: 576°Cat760mmHg
• Flash Point: 207.9°C
• PSA: 86.99000
• Density: 1.153g/cm³
• LogP: 3.29080
• Storage Temp.: −20°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 322.17802393
• Heavy Atom Count: 23
• Complexity: 372

Purity/Quality:

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

β-Zearalanol ~98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 4844761
• Hazard Codes: T,Xn,F
• Statements: 60-36/37/38-36-20/21/22-11
• Safety Statements: 53-36/37/39-45-36/37-16

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCCC(CCCCCC2=C(C(=CC(=C2)O)O)C(=O)O1)O
• Isomeric SMILES: C[C@H]1CCC[C@H](CCCCCC2=C(C(=CC(=C2)O)O)C(=O)O1)O
• Uses: β-Zearalanol is a minor analogue of the zearalenone family of resorcinyl macrocyclic lactones, produced by several species of Fusarium. Like the other zearalenones, β-zearalanol exhibits estrogenic activity in animals. β-Zearalanol was investigated as a growth promotant for animals but did not advance to commercialisation. Animal growth promotant. Anabolic. Controlled substance.

Technology Process of Taleranol

There total 6 articles about Taleranol 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: 97.0%

beta-zearalenol (71030-11-0,40790-12-3) → taleranol (42422-68-4)

Guidance literature:

With 5 mol% Pd/C; hydrogen; In ethanol; at 20 ℃;

DOI:10.1016/j.bmcl.2016.06.007

Reference yield: 50.0%

zearalenone (17924-92-4,7645-23-0) → taleranol (42422-68-4)

Guidance literature:

With dipotassium hydrogenphosphate; sodium chloride; In N,N-dimethyl-formamide; glucose, yeast extract, neopeptone, Aspergillus niger X-170;

DOI:10.1021/jo00238a008

Reference yield:

(3S,7R)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one (325142-22-1) → taleranol (42422-68-4) + zeranol (26538-44-3)

Guidance literature:

With water; at 40 ℃; for 96h; Yield given. Yields of byproduct given; lipases from pseudomonas species; other lipases;

DOI:10.1016/S0040-4020(01)88241-7

upstream raw materials:

zearalenone

(3S,7R)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one

Acetic acid (S)-2,4-dihydroxy-7-methyl-5-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-5H-6-oxa-benzocyclotetradecen-11-yl ester

vinyl acetate

Refernces

• 1、 Hellwig, Veronika,Mayer-Bartschmid, Anke,Müller, Hartwig,Greif, Gisela,Kleymann, Gerald,Zitzmann, Werner,Tichy, Hans-Volker,Stadler, Marc. "Pochonins A-F, new antiviral and antiparasitic resorcylic acid lactones from Pochonia chlamydosporia var. catenulata". . p. 829 - 837. Retrieved 2007/10/03.
• 2、 Gelo, Mirjana,Sunjic, Vitomir. "Enzymatic kinetic separation of stereoisomeric macrocyclic lactone derivatives, 7α,β-O-acyl trans-zearalenols and 7α,β-O-acyl zearanols". . p. 6511 - 6520. Retrieved 2007/10/02.