Weight | 194.23 g/mol |
---|---|
Formula | C11H14O3 |
Hydrogen Acceptors | 3 |
Hydrogen Donors | 1 |
Aromatic Rings | 1 |
Rotatable Bonds | 4 |
Vanillylacetone (122-48-5)
zingerone · 4-(4-hydroxy-3-methoxyphenyl)butan-2-one · vanillyl acetone
Score:
#1279 in Biochemistry
,
#3146 in Biology
,
#3938 in Chemistry
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LabBot
- Antioxidant actions of thymol, carvacrol, 6-gingerol, zingerone and hydroxytyrosol (Food and Chemical Toxicology, 1994)
- A re-examination of gingerol, shogaol, and zingerone, the pungent principles of ginger (Zingiber officinale Roscoe) (Australian Journal of Chemistry, 1969)
- Similarities and differences in the currents activated by capsaicin, piperine, and zingerone in rat trigeminal ganglion cells (Journal of Neurophysiology, 1996)
- Zingerone [4-(4-hydroxy-3-methoxyphenyl)-2-butanone] Prevents 6-Hydroxydopamine-induced Dopamine Depression in Mouse Striatum and Increases Superoxide Scavenging Activity in Serum (Neurochemical Research, 2005)
- Modulation of age-related NF-B activation by dietary zingerone via MAPK pathway. (Experimental Gerontology, 2010)
- Zingerone as an Antioxidant against Peroxynitrite (Journal of Agricultural and Food Chemistry, 2005)
-
Including Acute Oral Tox, Skin Sensitization, Eye Irritation, Aquatic Tox, & more. - zingerone
- 4-(4-hydroxy-3-methoxyphenyl)butan-2-one
- vanillyl acetone
- 0 paradol
-
SMILESCC(=O)CCC1=CC(=C(C=C1)O)OC
-
InChIKeyOJYLAHXKWMRDGS-UHFFFAOYSA-N
- Pubchem - Vanillylacetone
- Wikipedia - zingerone
Zingerone, also called vanillylacetone, is thought by some to be a key component of the pungency of ginger, but imparts the "sweet" flavor of cooked ginger. Zingerone is a crystalline solid that is sparingly soluble in water and soluble in ether. When synthesized and tasted does not have any pungency, suggesting it is more likely that zingerone is a decomposition product of, rather than the direct source of, the pungency of ginger.
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Synthesis
Reactant
+
Methyl hydroperoxide
(Dakin oxidation)
Acetonitrile
+
Reactant
(Grignard carbonyl)
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