1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one is a
natural product
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical s ...
, a
curcuminoid antioxidant
Antioxidants are Chemical compound, compounds that inhibit Redox, oxidation, a chemical reaction that can produce Radical (chemistry), free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants ...
found in
turmeric
Turmeric (), or ''Curcuma longa'' (), is a flowering plant in the ginger family Zingiberaceae. It is a perennial, rhizomatous, herbaceous plant native to the Indian subcontinent and Southeast Asia that requires temperatures between and high ...
(''Curcuma longa'') and
torch ginger (''Etlingera elatior'').
Structure and isolation
The
all-trans double bond isomer (1E,4E,6E)-1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one was first fully characterised when isolated from extracts of the rhizomes of turmeric (''Curcuma longa'') in 1993. It has subsequently been found in other species, including ''
etlingera elatior''.
A very large number of similar compounds are found in turmeric and ginger.
These have been extensively studied in their roles as antioxidants and for their potential
pharmacological
Pharmacology is the science of drugs and medications, including a substance's origin, composition, pharmacokinetics, pharmacodynamics, therapeutic use, and toxicology. More specifically, it is the study of the interactions that occur between ...
properties.
The (1Z) double bond isomer is poorly characterised in the literature and it and the compounds with unspecified
stereochemistry
Stereochemistry, a subdiscipline of chemistry, studies the spatial arrangement of atoms that form the structure of molecules and their manipulation. The study of stereochemistry focuses on the relationships between stereoisomers, which are defined ...
may in fact be the parent all-E molecule.
Properties
Mohamad et al. (2005) found that the curcuminoids 1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one,
demethoxycurcumin, and 16-hydroxylabda-8(17),11,13-trien-15,16-olide inhibit
lipid peroxidation more potently than does
alpha-tocopherol.
See also
*
Diarylheptanoid
References
Further reading
*
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{{DEFAULTSORT:Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one, 1,7-
Curcuminoids
Phenol antioxidants