Vomifoliol

Base Information

• Chemical Name: Vomifoliol
• CAS No.: 23526-45-6
• Molecular Formula: C13H20 O3
• Molecular Weight: 224.3
• UNII: P86438KC5J,B7QV234K84
• ChEMBL ID: CHEMBL463088
• DSSTox Substance ID: DTXSID601009964
• Metabolomics Workbench ID: 52508
• Nikkaji Number: J16.949H
• Wikidata: Q22911785
• Mol file: 23526-45-6.mol

Synonyms:vomifoliol

Chemical Property of Vomifoliol

Chemical Property:

• Vapor Pressure: 1.03E-06mmHg at 25°C
• Melting Point: 115 °C
• Boiling Point: 362.3°Cat760mmHg
• PKA: 12.72±0.60(Predicted)
• Flash Point: 187.1°C
• PSA: 57.53000
• Density: 1.13g/cm³
• LogP: 1.59980
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 224.14124450
• Heavy Atom Count: 16
• Complexity: 352

Purity/Quality:

99% ^*data from raw suppliers

Vomifoliol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)CC(C1(C=CC(C)O)O)(C)C
• Isomeric SMILES: CC1=CC(=O)CC([C@]1(/C=C/[C@@H](C)O)O)(C)C

Technology Process of Vomifoliol

There total 27 articles about Vomifoliol 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: 85.0%

vomifoliol acetate (84551-74-6) → blumenol A (23526-45-6)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 1.5h;

DOI:10.1248/cpb.53.541

Reference yield: 85.0%

(8R*)-4-((S*,E)-3-Acetoxybut-1-enyl)-4-hydroxy-3,5,5-trimethylcyclohex-2-enone → 6,9-dihydroxymegastigma-4,7-dien-3-one (23526-45-6,24427-77-8,50763-72-9,50763-73-0)

Guidance literature:

With sodium methylate; In methanol; chloroform; for 6h; Ambient temperature;

Reference yield: 51.7%

(+)-(S)-dehydrovomifoliol (39763-33-2) → blumenol A (23526-45-6) + (6S,7E,9S)-6,9-dihydroxy-4,7-megastigmadien-3-one (189351-15-3)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 0.5h;

DOI:10.1248/cpb.45.464

upstream raw materials:

(6S,9R)-roseoside

zizyvoside I

(+)-(S)-dehydrovomifoliol

vomifoliol acetate

Downstream raw materials:

3,5,5-Trimethylcyclohex-2-en-1-one

2,3,5-trimethylphenol

2,6,6-trimethyl-2-cyclohexene-1,4-dione

dihydro-oxoactinidol

Refernces

• 1、 Son, Min Jeoung,Jin, Changbae,Lee, Yong Sup,Lee, Jae Yeol,Kim, Hyoung Ja. "Characterization of caffeoylglucoside derivatives and hypouricemic activity of the ethyl acetate fraction from Aster glehni". . p. 503 - 512. Retrieved 2015.
• 2、 Mohamed, Khaled M.,Mohamed, Mahmoud H.,Ohtani, Kazuhiro,Kasai, Ryoji,Yamasaki, Kazuo. "Megastigmane glycosides from seeds of Trifolium alexandrinum". . p. 859 - 862. Retrieved 2007/10/03.