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 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)
Safety Information
- Risk Statements
- 36/37/38
- Safety Statements
- 26-36/37/39
- WGK Germany
- 3
- RTECS
- EM9960000
- F
- 10-23
- HS Code
- 29145090
- Toxicity
- LD50 intraperitoneal in mouse: 610mg/kg
MSDS
- Language:English Provider:SigmaAldrich
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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Vanillylidenacetone(1080-12-2)Related Product Information
- Ethyl 4-hydroxy-3-methoxybenzoate
- Coumalic acid
- 2-(2-OXO-2H-CHROMEN-3-YL)ACETIC ACID
- 3,7-DIHYDROXY-3',4',5'-TRIMETHOXYFLAVONE
- QUERCETIN-3,7,3',4'-TETRAMETHYL ETHER
- 3',4',5',6,7,8-HEXAMETHOXY-5-HYDROXYFLAVONE
- Vanillylidenacetone
- Isorhamnetin
- 3,7,3',4'-TETRAMETHYLGOSSYPETIN
- 3,4-DIMETHOXYBENZYLIDENEACETONE
- 5,7-DIHYDROXY-3',4',5'-TRIMETHOXYFLAVONE
- CHRYSOERIOL
- Curcumin
- 3,4-(METHYLENEDIOXY)BENZYLIDENEACETONE
- SYRINGETIN
- HOMOBUTEIN
- 3'-BENZYLOXY-4',5,6,7-TETRAMETHOXYFLAVONE
- 3'-BENZYLOXY-5,7-DIHYDROXY-3,4'-DIMETHOXYFLAVONE