Zingerone

Base Information

• Chemical Name: Zingerone
• CAS No.: 122-48-5
• Molecular Formula: C11H14O3
• Molecular Weight: 194.23
• Hs Code.: 29333999
• European Community (EC) Number: 204-548-3
• NSC Number: 15335
• UNII: 4MMW850892
• DSSTox Substance ID: DTXSID8047420
• Nikkaji Number: J5.356B
• Wikipedia: Zingerone
• Wikidata: Q1064625
• RXCUI: 2199325
• Metabolomics Workbench ID: 45631
• ChEMBL ID: CHEMBL25894
• Mol file: 122-48-5.mol

Synonyms:0 paradol;4-(4-hydroxy-3-methoxyphenyl)butan-2-one;vanillyl acetone;vanillylacetone;zingerone

Chemical Property of Zingerone

Chemical Property:

• Appearance/Colour: Clear slightly yellow liquid.
• Vapor Pressure: 0.000143mmHg at 25°C
• Melting Point: 40-41 °C(lit.)
• Refractive Index: n20/D 1.541(lit.)
• Boiling Point: 323 °C at 760 mmHg
• PKA: 10.03±0.20(Predicted)
• Flash Point: 123.7 °C
• PSA: 46.53000
• Density: 1.111 g/cm³
• LogP: 1.92240
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 194.094294304
• Heavy Atom Count: 14
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

Zingerone ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Food Additives
• Canonical SMILES: CC(=O)CCC1=CC(=C(C=C1)O)OC
• Uses: Vanillylacetone is a phenolic compound that naturally occurs in cranberry and ginger. Studies shows that Vanillylacetone exhibits variable cytotoxic, cytoprotective and antioxidant activity against liver and human tumor cells. Vanillylacetone is also used in herbal medicine for various purposes. Vanillylacetone is a phenolic compound that naturally occurs in cranberry and ginger. Studies shows that Vanillylacetone exhibits variable cytotoxic, cytoprotective and antioxidant activity against li ver and human tumor cells. Vanillylacetone is also used in herbal medicine for various purposes. In fragrances, flavors and cosmetics; in artificial spice oils.

Technology Process of Zingerone

There total 33 articles about Zingerone 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: 70.0%

4-((tert-butyldiphenylsilyl)oxy)-3-methoxybenzyl 3-oxobutanoate → 4-(4-hydroxy-3-methoxyphenyl)-2-butanone (122-48-5)

Guidance literature:

With tetrabutyl ammonium fluoride; zinc(II) chloride; In tetrahydrofuran; toluene; at 20 ℃; for 0.75h;

DOI:10.1039/c6cc03835b

Reference yield: 37.0%

Dehydrozingerone (1080-12-2) → 4-(4-hydroxy-3-methoxyphenyl)-2-butanone (122-48-5) + 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)butane (39728-80-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; at 20 ℃; for 24h;

DOI:10.1055/s-0029-1218389

Reference yield: 36.6%

methyl vinyl ketone (78-94-4,25038-87-3) + 2-methoxy-phenol (90-05-1) → 4-(4-hydroxy-3-methoxyphenyl)-2-butanone (122-48-5)

Guidance literature:

With amberlyst-15; In toluene; at 20 - 40 ℃;

upstream raw materials:

(E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one

Dehydrozingerone

(E)-ethyl 2-(4-hydroxy-3-methoxybenzylidene)-3-oxo-butanoate

4-(3-methoxy-4-trimethylsilyloxyphenyl)butan-2-one

Downstream raw materials:

4-(3-methoxy-4-trimethylsilyloxyphenyl)butan-2-one

5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)tetradecan-3-one

5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one

4-(3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)butan-2-one

Refernces

• 1、 Bandarenko, Mikhail,Kovalenko, Vitaly. "Synthesis of raspberry and ginger ketones by nickel boride-catalyzed hydrogenation of 4-arylbut-3-en-2-ones". . p. 885 - 888. Retrieved 2014.
• 2、 -. "GINGEROL DERIVATIVE HAVING INHIBITORY ACTIVITY AGAINST BIOFILM FORMATION AND PHARMACEUTICAL COMPOSITION COMPRISING SAME AS EFFECTIVE INGREDIENT FOR PREVENTING OR TREATING BIOFILM-CAUSED INFECTION SYMPTOM". . . Retrieved 2020/09/22.
• 3、 Nam, SangJin,Ham, So-Young,Kwon, Hongmok,Kim, Han-Shin,Moon, Suhyun,Lee, Jeong-Hoon,Lim, Taehyeong,Son, Sang-Hyun,Park, Hee-Deung,Byun, Youngjoo. "Discovery and Characterization of Pure RhlR Antagonists against Pseudomonas aeruginosa Infections". . p. 8388 - 8407. Retrieved 2020/09/21.