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.[5] It has subsequently been found in other species, including etlingera elatior.[2] A very large number of similar compounds are found in turmeric[6] and ginger.[7] 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.
Propertiesedit
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.[4]
^"Human Metabolome Database: Showing metabocard for (all-E)-1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one (HMDB0040889)". www.hmdb.ca.
^ abHabsah, M.; Ali, A.M.; Lajis, N.H.; Sukari, M.A.; Yap, Y.H.; Kikuzaki, H.; Nakatani, N. (2005). "Antitumour-Promoting and Cytotoxic Constituents of Etlingera Elatior". The Malaysian Journal of Medical Sciences. 12 (1): 6–12. PMC3349407. PMID 22605941.
^Park, S. Y.; Kim, D. S. (2002). "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. doi:10.1021/np010039x. PMID 12350137.
^ abMohamad, H.; Lajis, N. H.; Abas, F.; Ali, A. M.; Sukari, M. A.; Kikuzaki, H.; Nakatani, N. (2005). "Antioxidative Constituents of Etlingera elatior". Journal of Natural Products. 68 (2): 285–288. doi:10.1021/np040098l. PMID 15730265.
^Sun, Wen; Wang, Sheng; Zhao, Wenwen; Wu, Chuanhong; Guo, Shuhui; Gao, Hongwei; Tao, Hongxun; Lu, Jinjian; Wang, Yitao; Chen, Xiuping (2017). "Chemical constituents and biological research on plants in the genus Curcuma". Critical Reviews in Food Science and Nutrition. 57 (7): 1451–1523. doi:10.1080/10408398.2016.1176554. PMID 27229295. S2CID 20902215.
^Ma, Xiao-Ni; Xie, Chun-Lan; Miao, Zi; Yang, Quan; Yang, Xian-Wen (2017). "An overview of chemical constituents from Alpinia species in the last six decades". RSC Advances. 7 (23): 14114–14144. Bibcode:2017RSCAd...714114M. doi:10.1039/C6RA27830B.
Further readingedit
Meng, Fan-Cheng; Zhou, Yan-Qing; Ren, Dai; Wang, Ruibing; Wang, Chunming; Lin, Li-Gen; Zhang, Xiao-Qi; Ye, Wen-Cai; Zhang, Qing-Wen (2018). "Turmeric: A Review of Its Chemical Composition, Quality Control, Bioactivity, and Pharmaceutical Application". Natural and Artificial Flavoring Agents and Food Dyes. pp. 299–350. doi:10.1016/B978-0-12-811518-3.00010-7. ISBN9780128115183.
Agarwal, Shweta; Mishra, Ritu; Gupta, Anil Kumar; Gupta, Atul (2018). "Turmeric: Isolation and synthesis of important biological molecules". Synthesis of Medicinal Agents from Plants. pp. 105–125. doi:10.1016/B978-0-08-102071-5.00005-2. ISBN9780081020715.
May 07, 2024
hydroxyphenyl, heptatrien, natural, product, curcuminoid, antioxidant, found, turmeric, curcuma, longa, torch, ginger, etlingera, elatior, names, preferred, iupac, name, identifiers, number, 470466, 149732, model, jsmol, interactive, image, chebi, chebi, 65502. 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 3 4 1 7 Bis 4 hydroxyphenyl 1 4 6 heptatrien 3 one Names Preferred IUPAC name 1E 4E 6E 1 7 Bis 4 hydroxyphenyl 1 4 6 heptatrien 3 one Identifiers CAS Number 1E 4E 6E 470466 05 8 1 1Z 4E 6E 149732 52 5 3D model JSmol 1E 4E 6E Interactive image ChEBI 1E 4E 6E CHEBI 65502 ChEMBL 1E 4E 6E ChEMBL469419 Y EMBL ChemSpider 1E 4E 6E 8622469 1Z 4E 6E 30777515 Unspecified stereochemistry 28688976 PubChem CID 1E 4E 6E 10447050 InChI 1E 4E 6E InChI 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 Key PALMCMYYFAHUGA BPTNNVFMSA N 1Z 4E 6E Key PALMCMYYFAHUGA ZRFKDBLFSA N Unspecified stereochemistry Key PALMCMYYFAHUGA UHFFFAOYSA N SMILES 1E 4E 6E c1cc ccc1C CC CC O C Cc2ccc cc2 O O Properties 2 Chemical formula C 19H 16O 3 Molar mass 292 334 g mol 1 Appearance Yellow powder Melting point 168 170 C 334 338 F 441 443 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Structure and isolation 2 Properties 3 See also 4 References 5 Further readingStructure and isolation editThe 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 5 It has subsequently been found in other species including etlingera elatior 2 A very large number of similar compounds are found in turmeric 6 and ginger 7 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 editMohamad 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 4 See also editDiarylheptanoidReferences edit Human Metabolome Database Showing metabocard for all E 1 7 bis 4 hydroxyphenyl 1 4 6 heptatrien 3 one HMDB0040889 www hmdb ca a b Habsah M Ali A M Lajis N H Sukari M A Yap Y H Kikuzaki H Nakatani N 2005 Antitumour Promoting and Cytotoxic Constituents of Etlingera Elatior The Malaysian Journal of Medical Sciences 12 1 6 12 PMC 3349407 PMID 22605941 Park S Y Kim D S 2002 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 doi 10 1021 np010039x PMID 12350137 a b Mohamad H Lajis N H Abas F Ali A M Sukari M A Kikuzaki H Nakatani N 2005 Antioxidative Constituents of Etlingera elatior Journal of Natural Products 68 2 285 288 doi 10 1021 np040098l PMID 15730265 Nakayama Reiko Tamura Yoshiyuki Yamanaka Hiroyuki Kikuzaki Hiroe Nakatani Nobuji 1993 Two curcuminoid pigments from Curcuma domestica Phytochemistry 33 2 501 502 doi 10 1016 0031 9422 93 85548 6 Sun Wen Wang Sheng Zhao Wenwen Wu Chuanhong Guo Shuhui Gao Hongwei Tao Hongxun Lu Jinjian Wang Yitao Chen Xiuping 2017 Chemical constituents and biological research on plants in the genus Curcuma Critical Reviews in Food Science and Nutrition 57 7 1451 1523 doi 10 1080 10408398 2016 1176554 PMID 27229295 S2CID 20902215 Ma Xiao Ni Xie Chun Lan Miao Zi Yang Quan Yang Xian Wen 2017 An overview of chemical constituents from Alpinia species in the last six decades RSC Advances 7 23 14114 14144 Bibcode 2017RSCAd 714114M doi 10 1039 C6RA27830B Further reading editMeng Fan Cheng Zhou Yan Qing Ren Dai Wang Ruibing Wang Chunming Lin Li Gen Zhang Xiao Qi Ye Wen Cai Zhang Qing Wen 2018 Turmeric A Review of Its Chemical Composition Quality Control Bioactivity and Pharmaceutical Application Natural and Artificial Flavoring Agents and Food Dyes pp 299 350 doi 10 1016 B978 0 12 811518 3 00010 7 ISBN 9780128115183 Agarwal Shweta Mishra Ritu Gupta Anil Kumar Gupta Atul 2018 Turmeric Isolation and synthesis of important biological molecules Synthesis of Medicinal Agents from Plants pp 105 125 doi 10 1016 B978 0 08 102071 5 00005 2 ISBN 9780081020715 Retrieved from https en wikipedia org w index php title 1 7 Bis 4 hydroxyphenyl 1 4 6 heptatrien 3 one amp oldid 1198301084, wikipedia, wiki, book, books, library,
