Vanillylidenacetone

Vanillylidenacetone Property

Melting point:

125-130 °C

Boiling point:

268.19°C (rough estimate)

Density 

1.1503 (rough estimate)

refractive index 

1.4600 (estimate)

FEMA 

3738 | VANILLYLIDENE ACETONE

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 20 mg/ml).

form 

solid

pka

9.94±0.31(Predicted)

color 

Pale yellow

Odor

at 100.00 %. sweet powdery vanilla creamy balsam

Odor Type

vanilla

JECFA Number

732

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.

LogP

1.40

CAS DataBase Reference

1080-12-2(CAS DataBase Reference)

EPA Substance Registry System

3-Buten-2-one, 4-(4-hydroxy-3-methoxyphenyl)- (1080-12-2)

Safety

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

RTECS 

EM9960000

F 

10-23

HS Code 

29145090

Toxicity

LD50 intraperitoneal in mouse: 610mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Vanillylidenacetone Chemical Properties,Usage,Production

Description

Dehydrozingerone (1080-12-2) is a structural half analog of curcumin (Cat.# 10-1243) and is isolated from ginger rhizomes. Dehydrozingerone displays antioxidant, antibacterial and antifungal properties.1 It has also been shown to possess various antitumor effects2,3 and inhibit growth factor/peroxide-stimulated vascular smooth muscle function4.

Chemical Properties

Vanillylidene acetone has a very sweet, warm and tenacious odor.

Physical properties

Yellowish, needlelike crystals. Slightly soluble in water, soluble in alcohol and oils.

Uses

Vanillylidenacetone is one of ferulic acid derivatives. Studies have shown that vanillyl acetone has a certain inhibitory effect on Amaranthus, barnyardgrass, matang, dogwood and rape, among which the best inhibitory effect is on rape and Amaranthus.

Definition

ChEBI: Dehydrozingerone is a hydroxycinnamic acid.

Taste threshold values

Taste characteristics at 200 ppm: balsamic vanilla, with sweet aromatic spicy nuances.

Synthesis

General method: 20% (w/v) aqueous NaOH solution was slowly added to an ethanol solution of vanillin (6a1-d1,6e,6f) and acetone (10-25 eq., excess) at 0-5 °C. The reaction mixture was stirred at room temperature and the progress of the reaction was monitored by thin layer chromatography (TLC). When the vanillin was completely consumed, the excess acetone was evaporated under reduced pressure; subsequently, cold water was added and the resulting mixture was acidified with 3M HCl solution to pH < 7. The precipitated solid product was collected by filtration, washed with cold water and dried under vacuum. The crude product can be purified by column chromatography or recrystallized from a suitable solvent system to afford the target compound 4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one (7a1-d1,7e and 7f).

References

[1] ISMAIL RAHATH KUBRA. Structure-function activity of dehydrozingerone and its derivatives as antioxidant and antimicrobial compounds[J]. Journal of Food Science and Technology, 2011, 51 2: 245-255. DOI:10.1007/s13197-011-0488-8
[2] NORIKO MOTOHASHI . Inhibitory effects of dehydrozingerone and related compounds on 12-O-tetradecanoylphorbol-13-acetate induced Epstein–Barr virus early antigen activation[J]. Cancer letters, 1998, 134 1: Pages 37-42. DOI:10.1016/s0304-3835(98)00239-0
[3] SHINGO YOGOSAWA. Dehydrozingerone, a Structural Analogue of Curcumin, Induces Cell-Cycle Arrest at the G2/M Phase and Accumulates Intracellular ROS in HT-29 Human Colon Cancer Cells[J]. Journal of Natural Products , 2012, 75 12: 2088-2093. DOI:10.1021/np300465f
[4] YIZHEN LIU. Inhibitory effect of dehydrozingerone on vascular smooth muscle cell function.[J]. Journal of Cardiovascular Pharmacology, 2008, 52 5: 422-429. DOI:10.1097/fjc.0b013e31818aed93