Vanillylidenacetone
- Product Name
- Vanillylidenacetone
- CAS No.
- 1080-12-2
- Chemical Name
- Vanillylidenacetone
- Synonyms
- mhsk;FEMA 3738;feruloylmethane;vanillalacetone;DEHYDROZINGERONE;Dehydrogingerone;dehydro(o)-paradol;Vanillideneacetone;VANILLYLIDENACETONE;VANILLYLIDENEACETONE
- CBNumber
- CB2126546
- Molecular Formula
- C11H12O3
- Formula Weight
- 192.21
- MOL File
- 1080-12-2.mol
Vanillylidenacetone Property
- 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
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 07551
- Product name
- Vanillylidenacetone
- Purity
- ≥98.5%
- Packaging
- 5G-F
- Price
- $102
- Updated
- 2023/06/20
- Product number
- 07551
- Product name
- Vanillylidenacetone
- Purity
- ≥98.5%
- Packaging
- 5G
- Price
- $102
- Updated
- 2023/01/07
- Product number
- 90609
- Product name
- Vanillylidenacetone
- Purity
- analytical standard
- Packaging
- 100mg
- Price
- $69.5
- Updated
- 2022/05/15
- Product number
- H533360
- Product name
- 4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one
- Packaging
- 10g
- Price
- $60
- Updated
- 2021/12/16
- Product number
- H533360
- Product name
- 4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one
- Packaging
- 5g
- Price
- $45
- Updated
- 2021/12/16
Vanillylidenacetone Chemical Properties,Usage,Production
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.
Synthesis
121-33-5
67-64-1
1080-12-2
General method: 20% (w/v) aqueous NaOH solution was slowly added to an ethanol solution of vanillin (6a1-d1,6e,6f) and acetone (10-25 eq., excess) at 0-5 °C. The reaction mixture was stirred at room temperature and the progress of the reaction was monitored by thin layer chromatography (TLC). When the vanillin was completely consumed, the excess acetone was evaporated under reduced pressure; subsequently, cold water was added and the resulting mixture was acidified with 3M HCl solution to pH < 7. The precipitated solid product was collected by filtration, washed with cold water and dried under vacuum. The crude product can be purified by column chromatography or recrystallized from a suitable solvent system to afford the target compound 4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one (7a1-d1,7e and 7f).
References
[1] ISMAIL RAHATH KUBRA. Structure-function activity of dehydrozingerone and its derivatives as antioxidant and antimicrobial compounds[J]. Journal of Food Science and Technology, 2011, 51 2: 245-255. DOI:10.1007/s13197-011-0488-8
[2] NORIKO MOTOHASHI . Inhibitory effects of dehydrozingerone and related compounds on 12-O-tetradecanoylphorbol-13-acetate induced Epstein–Barr virus early antigen activation[J]. Cancer letters, 1998, 134 1: Pages 37-42. DOI:10.1016/s0304-3835(98)00239-0
[3] SHINGO YOGOSAWA. Dehydrozingerone, a Structural Analogue of Curcumin, Induces Cell-Cycle Arrest at the G2/M Phase and Accumulates Intracellular ROS in HT-29 Human Colon Cancer Cells[J]. Journal of Natural Products , 2012, 75 12: 2088-2093. DOI:10.1021/np300465f
[4] YIZHEN LIU. Inhibitory effect of dehydrozingerone on vascular smooth muscle cell function.[J]. Journal of Cardiovascular Pharmacology, 2008, 52 5: 422-429. DOI:10.1097/fjc.0b013e31818aed93
Vanillylidenacetone Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Vanillylidenacetone manufacturers
- Product
- 4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one 1080-12-2
- Price
- US $3.00-9.00/KG
- Min. Order
- 0.1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2025-06-21
- Product
- Vanillylidenacetone 1080-12-2
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 2000
- Release date
- 2025-06-05
- Product
- Dehydrozingerone 1080-12-2
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 0.99
- Supply Ability
- 1000kg
- Release date
- 2025-04-28