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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.

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.

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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