Damascenone

Base Information

• Chemical Name: Damascenone
• CAS No.: 23696-85-7
• Molecular Formula: C13H18O
• Molecular Weight: 190.285
• Hs Code.: 33021090
• DSSTox Substance ID: DTXSID6041397
• Wikidata: Q72461358
• Mol file: 23696-85-7.mol

Synonyms:1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one;1-(2,6,6-Trimethyl-1,3-cyclohexadienyl)-2-buten-1-one;1-Crotonoyl-2,6,6-trimethyl-1,3-cyclohexadiene;2,6,6-Trimethyl-1-(2-butenoyl)-1,3-cyclohexadiene;2,6,6-Trimethyl-1-crotonyl-1,3-cyclohexadiene;

Chemical Property of Damascenone

Chemical Property:

• Appearance/Colour: COLORLESS LIQUID
• Vapor Pressure: 0.00503mmHg at 25°C
• Refractive Index: 1.350-1.380
• Boiling Point: 275.6 °C at 760 mmHg
• Flash Point: 111 °C
• PSA: 17.07000
• Density: 0.926 g/cm³
• LogP: 3.43420
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• 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:

Damascenone natural, 1.1-1.4?wt. % (190 proof ethanol), FG ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F,Xi
• Statements: 11-43
• Safety Statements: 7-16-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC=CC(=O)C1=C(C=CCC1(C)C)C
• Uses: Damascenone is a fragrance ingredient that can be used in shampoos, fine fragrances, decorative cosmetics, toilet soaps as well as non-cosmetic products like household cleaners and detergents.

Technology Process of Damascenone

There total 11 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: 88.6%

1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one (35044-68-9) → 1-(2,6,6-trimethyl-1,3-cyclohexadiene-1-yl)-2-butene-1-one (23696-85-7)

Guidance literature:

With N-Bromosuccinimide; sodium sulfate; dibenzoyl peroxide; In benzene; at 50 ℃; for 3h; Inert atmosphere;

Reference yield:

(E)-2-(2-butenyl)-1,3,3-trimethyl-1-cyclohexene (53941-13-2) → 1-(2,6,6-trimethyl-1,3-cyclohexadiene-1-yl)-2-butene-1-one (23696-85-7)

Guidance literature:

With pyridine; chromium(VI) oxide; In dichloromethane; at 20 - 30 ℃; for 1h; Reagent/catalyst; Temperature; Solvent;

Reference yield:

3-hydroxy-β-damascone → 1-(2,6,6-trimethyl-1,3-cyclohexadiene-1-yl)-2-butene-1-one (23696-85-7)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 12h; Inert atmosphere; Reflux;

upstream raw materials:

1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one

4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

(E)-2-(2-butenyl)-1,3,3-trimethyl-1-cyclohexene

2,6,6-trimethylcyclohex-2-en-1-ylidene ketene

Refernces

• 1、 -. "A β- malaysian ketene method for the preparation of perfume". Paragraph 0049-0050. . Retrieved 2017/03/14.