Eckol

Names
Preferred IUPAC name

4-(3,5-Dihydroxyphenoxy)oxanthrene-1,3,6,8-tetrol

Other names

1-(3,5-Dihydroxyphenoxy)-2,4,7,9-tetrahydroxydibenzo-1,4-dioxin

Identifiers

CAS Number

* 88798-74-7 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:65819 N

ChEMBL |

* ChEMBL471187 N

ChemSpider |

* 128740 N

PubChem CID

* 145937

UNII |

* 4A5E8354UB Y

InChI

* InChI=1S/C18H12O9/c19-7-1-8(20)3-10(2-7)25-16-12(23)6-13(24)17-18(16)27-15-11(22)4-9(21)5-14(15)26-17/h1-6,19-24H N

Key: PCZZRBGISTUIOA-UHFFFAOYSA-N N

* InChI=1/C18H12O9/c19-7-1-8(20)3-10(2-7)25-16-12(23)6-13(24)17-18(16)27-15-11(22)4-9(21)5-14(15)26-17/h1-6,19-24H

Key: PCZZRBGISTUIOA-UHFFFAOYAJ

SMILES

* C1=C(C=C(C=C1O)OC2=C(C=C(C3=C2OC4=C(C=C(C=C4O3)O)O)O)O)O

Properties

Chemical formula

| C18H12O9
Molar mass | 372.285 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Eckol is a phlorotannin isolated from brown algae in the family Lessoniaceae such as species in the genus Ecklonia[1] such as E. cava[2] or E. kurome[3] or in the genus Eisenia such as Eisenia bicyclis.[4]

The molecule possesses a dibenzo-p-dioxin skeleton and a phloroglucinol component. The molecule can also be viewed as a phloroglucinol trimer.[5]

It exhibits an antiplasmin inhibitory effect[3] and a radioprotective effect in a mouse model.[1][6] It also exhibits an in vitro cytoprotective effect against oxidative stress in Chinese hamster lung fibroblasts.[2] It also shows antithrombotic and profibrinolytic activities.[4]

## References

1. ↑ 1.0 1.1 Moon, Changjong; Kim, Sung-Ho; Kim, Jong-Choon; Hyun, Jin Won; Lee, Nam Ho; Park, Jae Woo; Shin, Taekyun (2008). "Protective effect of phlorotannin components phloroglucinol and eckol on radiation-induced intestinal injury in mice". Phytotherapy Research 22 (2): 238–42. doi:10.1002/ptr.2298. PMID 17886227.
2. ↑ 2.0 2.1 Kang, Kyoung Ah; Lee, Kyoung Hwa; Chae, Sungwook; Zhang, Rui; Jung, Myung Sun; Lee, Youngki; Kim, So Young; Kim, Hee Sun et al. (2005). "Eckol isolated from Ecklonia cava attenuates oxidative stress induced cell damage in lung fibroblast cells". FEBS Letters 579 (28): 6295–304. doi:10.1016/j.febslet.2005.10.008. PMID 16253238.
3. ↑ 3.0 3.1 Fukuyama, Y; Kodama, M; Miura, I; Kinzyo, Z; Kido, M; Mori, H; Nakayama, Y; Takahashi, M (1989). "Structure of an anti-plasmin inhibitor, eckol, isolated from the brown alga Ecklonia kurome Okamura and inhibitory activities of its derivatives on plasma plasmin inhibitors". Chemical & Pharmaceutical Bulletin 37 (2): 349–53. doi:10.1248/cpb.37.349. PMID 2525966.
4. ↑ 4.0 4.1 Kim, Tae Hoon; Ku, Sae-Kwang; Bae, Jong-Sup (2012). "Antithrombotic and profibrinolytic activities of eckol and dieckol". Journal of Cellular Biochemistry 113 (9): 2877–83. doi:10.1002/jcb.24163. PMID 22511271.
5. ↑ Shibata, Toshiyuki; Fujimoto, Ken; Nagayama, Kohki; Yamaguchi, Kuniko; Nakamura, Takashi (2002). "Inhibitory activity of brown algal phlorotannins against hyaluronidase". International Journal of Food Science and Technology 37 (6): 703. doi:10.1046/j.1365-2621.2002.00603.x.
6. ↑ Nakayama, Yasuo; Takahashi, Masayuki; Fukuyama, Yoshiyasu; Kinzyo, Zyunei (1989). "Anti-plasmin inhibitor. Part IV. An anti-plasmin inhibitor, eckol, isolated from the brown alga Ecklonia kurome OKAMURA". Agricultural and Biological Chemistry 53 (11): 3025. doi:10.1271/bbb1961.53.3025.

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Eckol. Read more

|

Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Eckol&oldid=176082"
*[CID]: Compound ID