Vanillylidenacetone

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
Vanillylidenacetone Structure
Vanillylidenacetone Chemical Properties
Melting point 125-130 °C
Boiling point 268.19°C (rough estimate)
density 1.1503 (rough estimate)
FEMA 3738 | VANILLYLIDENE ACETONE
refractive index 1.4600 (estimate)
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).
pka9.94±0.31(Predicted)
form solid
color Pale yellow
Odorat 100.00 %. sweet powdery vanilla creamy balsam
Odor Typevanilla
JECFA Number732
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.
LogP1.40
CAS DataBase Reference1080-12-2(CAS DataBase Reference)
EPA Substance Registry System3-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
10-23
HS Code 29145090
ToxicityLD50 intraperitoneal in mouse: 610mg/kg
MSDS Information
ProviderLanguage
SigmaAldrich English
Vanillylidenacetone Usage And Synthesis
DescriptionDehydrozingerone (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 PropertiesVanillylidene acetone has a very sweet, warm and tenacious odor.
UsesVanillylidenacetone 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.
DefinitionChEBI: Dehydrozingerone is a hydroxycinnamic acid.
Taste threshold valuesTaste characteristics at 200 ppm: balsamic vanilla, with sweet aromatic spicy nuances.
References1) 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
Vanillylidenacetone Preparation Products And Raw materials
Preparation Products6-Shogaol
3,7-DIHYDROXY-3',4',5'-TRIMETHOXYFLAVONE HOMOBUTEIN Isorhamnetin 3,7,3',4'-TETRAMETHYLGOSSYPETIN Vanillylidenacetone 3,4-(METHYLENEDIOXY)BENZYLIDENEACETONE SYRINGETIN Curcumin 5,7-DIHYDROXY-3',4',5'-TRIMETHOXYFLAVONE CHRYSOERIOL 3'-BENZYLOXY-5,7-DIHYDROXY-3,4'-DIMETHOXYFLAVONE 3,7-DIHYDROXY-3',4'-DIMETHOXYFLAVONE 3,4-DIMETHOXYBENZYLIDENEACETONE GERALDOL 3',4'-DIMETHOXY-BETA-NAPHTHOFLAVONE SINENSETIN QUERCETIN-3,7,3',4'-TETRAMETHYL ETHER 3',4',5',6,7,8-HEXAMETHOXY-5-HYDROXYFLAVONE

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