Vanillylidenacetone

Synonym(s):4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one

CAS NO.：1080-12-2
Empirical Formula: C11H12O3
Molecular Weight: 192.21
MDL number: MFCD00012210
EINECS: 214-096-9
SAFETY DATA SHEET (SDS)
Update Date: 2024-10-28 16:48:35

What is Vanillylidenacetone?

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.

The Uses of Vanillylidenacetone

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.

What are the applications of Application

Vanillylidenacetone is n intermediate shown to inhibit cell growth

Definition

ChEBI: Dehydrozingerone is a hydroxycinnamic acid.

Taste threshold values

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

References

1) Kubra et al. (2014), Structure-function activity of dehydrozingerone and its derivatives as antioxidant and antimicrobial compounds; J. Food Sci. Technol., 51 245 2) Motohashi et al. (1998), Inhibitory effects of dehydrozingerone and related compounds on 12-O-tetradecanoylphorbol-13-acetate induced Epstein-Barr virus early antigen activation; Cancer Lett., 134 37 3) Yogosawa et al. (2012), Dehydrozingerone, a structural analog of curcumin, induces cell-cycle arrest at the G2/M phase and accumulates intracellular ROS in HT-29 human colon cancer cells; J. Nat. Prod., 75 2088 4) Liu et al. (2008), Inhibitory effect of dehydrozingerone on vascular smooth muscle cell function; J. Cardiovasc. Pharmacol., 52 422

Properties of Vanillylidenacetone

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
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.
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 information for Vanillylidenacetone

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.