| Identification | More | [Name]
4-(4-HYDROXY-3-METHOXYPHENYL)-3-BUTEN-2-ONE | [CAS]
1080-12-2 | [Synonyms]
4-(4-HYDROXY-3-METHOXYPHENYL)-3-BUTEN-2-ONE
4-(4-HYDROXY-3-METHOXYPHENYL)-3-BUTENE-2-ONE
4-(4-HYDROXY-3-METHOXYPHENYL)BUT-3-EN-2-ONE
DEHYDROZINGERONE
FEMA 3738
VANILLYLIDENACETONE
VANILLYLIDENEACETONE
VANILLYLIDINE ACETONE
4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-on
dehydro(o)-paradol
feruloylmethane
methyl-3-methoxy-4-hydroxystyrylketone
mhsk
vanillalacetone
Vanillideneacetone
3-Buten-2-one, 4-(4-hydroxy-3-methoxyphenyl)-
4-(3-Methoxy-4-hydroxyphenyl)-3-butene-2-one
Dehydrogingerone
Ferulic methyl ketone | [EINECS(EC#)]
214-096-9 | [Molecular Formula]
C11H12O3 | [MDL Number]
MFCD00012210 | [Molecular Weight]
192.21 | [MOL File]
1080-12-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
125-130 °C | [Boiling point ]
268.19°C (rough estimate) | [density ]
1.1503 (rough estimate) | [FEMA ]
3738 | [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). | [form ]
solid | [pka]
9.94±0.31(Predicted) | [color ]
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. | [InChI]
1S/C11H12O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h3-7,13H,1-2H3/b4-3+ | [InChIKey]
AFWKBSMFXWNGRE-ONEGZZNKSA-N | [SMILES]
COc1cc(\C=C\C(C)=O)ccc1O | [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 Data | Back Directory | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
EM9960000
| [F ]
10-23 | [TSCA ]
TSCA listed | [HS Code ]
29145090 | [Storage Class]
11 - Combustible Solids | [Toxicity]
LD50 intraperitoneal in mouse: 610mg/kg |
| Hazard Information | Back Directory | [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]
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) 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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