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.
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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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