Damascenone

Base Information

• Chemical Name: Damascenone
• CAS No.: 23726-93-4
• Deprecated CAS: 36649-63-5
• Molecular Formula: C13H18 O
• Molecular Weight: 190.285
• European Community (EC) Number: 245-844-2,245-833-2
• UNII: U66V25TBO0
• DSSTox Substance ID: DTXSID90885242
• Nikkaji Number: J16.558A,J60.974I
• Wikipedia: Damascenone
• Wikidata: Q416126
• Metabolomics Workbench ID: 29023
• ChEMBL ID: CHEMBL3733030
• Mol file: 23726-93-4.mol

Synonyms:damascenone

Chemical Property of Damascenone

Chemical Property:

• Vapor Pressure: 0.00503mmHg at 25°C
• Melting Point: 116-118oC
• Boiling Point: 275.6°C at 760 mmHg
• Flash Point: 111°C
• PSA: 17.07000
• Density: 0.926g/cm³
• LogP: 3.43420
• Water Solubility.: 188mg/L at 20℃
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 190.135765193
• Heavy Atom Count: 14
• Complexity: 327

Purity/Quality:

99.9% ^*data from raw suppliers

1-(2,6,6-Trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC(=O)C1=C(C=CCC1(C)C)C
• Isomeric SMILES: C/C=C/C(=O)C1=C(C=CCC1(C)C)C
• Uses: A terpenic ketone; odorant in fruits, vegetables, honey, wine and beer

Technology Process of Damascenone

There total 85 articles about Damascenone 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: 100.0%

(E)-1-(2,6,6-Trimethylcyclohexa-1,3-dienyl)but-2-en-1-ol (78182-05-5) → Damascenon (23726-93-4)

Guidance literature:

With manganese(IV) oxide; In Petroleum ether; for 1h;

Reference yield: 81.0%

→ Damascenon (23726-93-4) + 2,6,6-trimethylcyclohex-2-en-1-one (20013-73-4)

Guidance literature:

Reference yield: 74.0%

C20H24O3 → Damascenon (23726-93-4)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 50 ℃; for 12h; Inert atmosphere; Glovebox;

DOI:10.1016/j.tet.2017.04.002

upstream raw materials:

allyl phenyl ether

2,6,6-trimethyl-1,3-cyclohexadiene-1-carboxylic acid ethyl ester

1-(2,6,6-Trimethyl-cyclohexa-2,4-dienyl)-but-3-en-1-one

2,6,6-trimethyl-cyclohexa-1,3-dien-1-yl methyl ketone

Downstream raw materials:

(E)-1-(2,3,6-Trimethyl-phenyl)-but-2-en-1-one

2,6,6-trimethyl-1-(but-2-enoyl)-cyclohexa-1,3-dien-5-one

3-(2-hydroxy-ethylsulfanyl)-1-(2,6,6-trimethyl-cyclohexa-1,3-dienyl)-butan-1-one

1-(2,6,6-Trimethyl-cyclohexa-1,3-dienyl)-butan-1-ol

Refernces

• 1、 Ren, Tian-Lu,Xu, Bao-Hua,Mahmood, Sajid,Sun, Ming-Xue,Zhang, Suo-Jiang. "Cobalt-catalyzed oxidative esterification of allylic/benzylic C(sp3)–H bonds". supporting information. p. 2943 - 2948. Retrieved 2017/04/26.
• 2、 Campagnole,Delmond, Bernard. "New straightforward synthesis of β-damascenone and β-damascone derivatives from β-ionone via retro-α-ionol". . p. 1077 - 1090. Retrieved 2008/02/01.