ChemicalBook Product Catalog Flavors and fragrances Synthetic fragrances Ketones spices Aromatic ketone Vanillylidenacetone

Vanillylidenacetone

Product NameVanillylidenacetone
CAS1080-12-2
MFC11H12O3
MW192.21
EINECS214-096-9
MOL File1080-12-2.mol

Chemical Properties

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.
InChI	1S/C11H12O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h3-7,13H,1-2H3/b4-3+
InChIKey	AFWKBSMFXWNGRE-ONEGZZNKSA-N
SMILES	COc1cc(\C=C\C(C)=O)ccc1O
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 Information

Risk Statements	36/37/38
Safety Statements	26-36/37/39
WGK Germany	3
RTECS	EM9960000
F	10-23
TSCA	TSCA listed
HS Code	29145090
Storage Class	11 - Combustible Solids
Toxicity	LD50 intraperitoneal in mouse: 610mg/kg

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

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

121-33-5

67-64-1

1080-12-2

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

Vanillylidenacetone

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

Vanillylidenacetone Supplier

Vanillylidenacetone manufacturers

Related Product Information