1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one

Natural product found in turmeric and ginger 1,7-bis (4-hydroxyphenyl)-1,4,6-heptatrien-3-one.svg (1E,4E,6E)-1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one (1E,4E,6E) (1Z,4E,6E) (Unspecified stereochemistry) 8622469 30777515 28688976 10447050 470466-05-8 149732-52-5 Human Metabolome Database: Showing metabocard for (all-E)-1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one (HMDB0040889) http://www.hmdb.ca/metabolites/HMDB0040889 www.hmdb.ca 65502 correct EMBL 469419 c1cc(ccc1C=CC=CC(=O)C=Cc2ccc(cc2)O)O 1S/C19H16O3/c20-17(10-7-16-8-13-19(22)14-9-16)4-2-1-3-15-5-11-18(21)12-6-15/h1-14,21-22H/b3-1+,4-2+,10-7+ PALMCMYYFAHUGA-BPTNNVFMSA-N PALMCMYYFAHUGA-ZRFKDBLFSA-N PALMCMYYFAHUGA-UHFFFAOYSA-N 22605941 Antitumour-Promoting and Cytotoxic Constituents of Etlingera Elatior. The Malaysian Journal of Medical Sciences 12 1 6–12 2005 Habsah M. Ali A.M. Lajis N.H. Sukari M.A. Yap Y.H. Kikuzaki H. Nakatani N. 3349407 19 16 3 Yellow powder 168-170 1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one is a natural product, a curcuminoid antioxidant found in turmeric (Curcuma longa) and torch ginger (Etlingera elatior). 10.1021/np010039x Park S. Y. Kim D. S. Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: A drug discovery effort against Alzheimer's disease Journal of Natural Products 65 9 1227–1231 2002 12350137 2002JNAtP..65.1227P Mohamad H. Lajis N. H. Abas F. Ali A. M. Sukari M. A. Kikuzaki H. Nakatani N. 10.1021/np040098l Antioxidative Constituents of Etlingera elatior Journal of Natural Products 68 2 285–288 2005 15730265 2005JNAtP..68..285M 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 1993.10.1016/0031-9422(93)85548-6 Two curcuminoid pigments from Curcuma domestica 1993 Nakayama Reiko Tamura Yoshiyuki Yamanaka Hiroyuki Kikuzaki Hiroe Nakatani Nobuji Phytochemistry 33 2 501–502 1993PChem..33..501N It has subsequently been found in other species, including etlingera elatior. A very large number of similar compounds are found in turmeric10.1080/10408398.2016.1176554 Chemical constituents and biological research on plants in the genus Curcuma 2017 Sun Wen Wang Sheng Zhao Wenwen Wu Chuanhong Guo Shuhui Gao Hongwei Tao Hongxun Lu Jinjian Wang Yitao Chen Xiuping Critical Reviews in Food Science and Nutrition 57 7 1451–1523 27229295 20902215 and ginger.10.1039/C6RA27830B free An overview of chemical constituents from Alpinia species in the last six decades 2017 Ma Xiao-Ni Xie Chun-Lan Miao Zi Yang Quan Yang Xian-Wen RSC Advances 7 23 14114–14144 2017RSCAd...714114M These have been extensively studied in their roles as antioxidants and for their potential pharmacological properties. The (1Z) double bond isomer is poorly characterised in the literature and it and the compounds with unspecified stereochemistry 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 10.1016/B978-0-12-811518-3.00010-7 Turmeric: A Review of Its Chemical Composition, Quality Control, Bioactivity, and Pharmaceutical Application Natural and Artificial Flavoring Agents and Food Dyes 2018 Meng Fan-Cheng Zhou Yan-Qing Ren Dai Wang Ruibing Wang Chunming Lin Li-Gen Zhang Xiao-Qi Ye Wen-Cai Zhang Qing-Wen 299–350 9780128115183 10.1016/B978-0-08-102071-5.00005-2 Turmeric: Isolation and synthesis of important biological molecules Synthesis of Medicinal Agents from Plants 2018 Agarwal Shweta Mishra Ritu Gupta Anil Kumar Gupta Atul 105–125 9780081020715 Category:Curcuminoids Category:Phenol antioxidants