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

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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • (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
  • (1E,4E,6E): c1cc(ccc1C=CC=CC(=O)C=Cc2ccc(cc2)O)O
Properties[2]
C19H16O3
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).

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]

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.[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

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]

See also

References

  1. ^ "Human Metabolome Database: Showing metabocard for (all-E)-1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one (HMDB0040889)". www.hmdb.ca.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  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.
  7. ^ 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

  • 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. 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.
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