Dehydrovomifoliol

Base Information

• Chemical Name: Dehydrovomifoliol
• CAS No.: 15764-81-5
• Molecular Formula: C13H18 O3
• Molecular Weight: 222.284
• Hs Code.: 2914400090
• UNII: 3J9E6P8K84
• Nikkaji Number: J14.882B,J2.747.725I
• Wikidata: Q27106358
• Metabolomics Workbench ID: 28235
• ChEMBL ID: CHEMBL461278
• Mol file: 15764-81-5.mol

Synonyms:dehydrovomifoliol

Chemical Property of Dehydrovomifoliol

Chemical Property:

• Vapor Pressure: 6.84E-07mmHg at 25°C
• Boiling Point: 367.4°Cat760mmHg
• Flash Point: 190.2°C
• PSA: 54.37000
• Density: 1.125g/cm³
• LogP: 1.80800
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 222.125594432
• Heavy Atom Count: 16
• Complexity: 388

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Dehydrovomifoliol

There total 6 articles about Dehydrovomifoliol 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: 52.0%

(E)-4-(6',7',7'-Trimethyl-2',3'-dioxabicyclo<2.2.2>oct-5'-en-1'-yl)-3-buten-2-on (14482-66-7) → dehydrovomifoliol (15764-81-5) + (3E,8Z)-6,6-dimethyl-3,8-undecadiene-2,5,10-trione (80114-21-2) + (E,1'RS,2'SR,3'SR,4'SR)-4-(1',2';3',4'-diepoxy-2',6',6'-trimethylcyclohexyl)-3-buten-2-one

Guidance literature:

In toluene; at 130 ℃; for 24h;

DOI:10.1002/hlca.19810640606

Reference yield:

alpha-ionone (127-41-3) → dehydrovomifoliol (15764-81-5) + 2,6,6-trimethyl-2-cyclohexene-1,4-dione (1125-21-9) + 3,5,5-trimethyl-4-[(E)-3-oxo-1-butenyl]-2-cyclohexen-1-one (79734-43-3)

Guidance literature:

With t-butyl chromate; In tert-butyl alcohol; benzene; at 60 ℃;

Reference yield:

alpha-ionone (127-41-3,6901-97-9,14398-36-8,24190-29-2,30685-95-1,31798-12-6,52340-45-1,67529-94-6,67529-95-7) → dehydrovomifoliol (15764-81-5)

Guidance literature:

With t-butyl chromate; In tert-butyl alcohol;

DOI:10.1016/S0040-4039(97)00172-X

upstream raw materials:

(E)-4-(6',7',7'-Trimethyl-2',3'-dioxabicyclo<2.2.2>oct-5'-en-1'-yl)-3-buten-2-on

alpha-ionone

(±)-2-trans,4-trans-abscisic acid

alpha-ionone

Downstream raw materials:

6,9-dihydroxymegastigma-4,7-dien-3-one

(2E,4E)-2-Fluoro-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-enyl)-3-methyl-penta-2,4-dienoic acid ethyl ester

(2E,4E)-2-Fluoro-5-((R)-1-hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-enyl)-3-methyl-penta-2,4-dienoic acid ethyl ester

(2E,4E)-2-Fluoro-5-((S)-1-hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-enyl)-3-methyl-penta-2,4-dienoic acid ethyl ester

Refernces

• 1、 Kim, Bum Tae,Min, Yong Ki,Asami, Tadao,Park, No Kyun,Kwon, Oh Young,Cho, Kwang Yun,Yoshida, Shigeo. "Synthesis of 2-fluoroabscisic acid: A potential photo-stable abscisic acid". . p. 1797 - 1800. Retrieved 2007/10/03.
• 2、 Hasegawa, Shin,Poling, Stephen M.,Maier, V. P.,Bennett, Raymond D.. "METABOLISM OF ABSCISIC ACID: BACTERIAL CONVERSION TO DEHYDROVOMIFOLIOL AND VOMIFOLIOL DEHYDROGENASE ACTIVITY". . p. 2769 - 2772. Retrieved 2007/10/02.