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Vanillylidenacetone

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Vanillylidenacetone Basic information

Product Name:
Vanillylidenacetone
Synonyms:
  • VANILLYLIDENACETONE
  • VANILLYLIDENEACETONE
  • VANILLYLIDINE ACETONE
  • FEMA 3738
  • DEHYDROZINGERONE
  • 4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-on
  • dehydro(o)-paradol
  • feruloylmethane
CAS:
1080-12-2
MF:
C11H12O3
MW:
192.21
EINECS:
214-096-9
Product Categories:
  • Aromatic Ketones (substituted)
Mol File:
1080-12-2.mol
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Vanillylidenacetone 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.
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)
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Safety Information

Risk Statements 
36/37/38
Safety Statements 
26-36/37/39
WGK Germany 
3
RTECS 
EM9960000
10-23
HS Code 
29145090
Toxicity
LD50 intraperitoneal in mouse: 610mg/kg

MSDS

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Vanillylidenacetone 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.

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.

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

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