Emodin

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Emodin
Skeletal formula
Ball-and-stick model
Names
IUPAC name
1,3,8-trihydroxy-6-methylanthracene-9,10-dione[clarification needed]
Other names
6-methyl-1,3,8-trihydroxyanthraquinone
Identifiers
518-82-1 YesY
ChEBI CHEBI:42223 YesY
ChEMBL ChEMBL289277 YesY
ChemSpider 3107 YesY
DrugBank DB07715 YesY
Jmol 3D model Interactive image
KEGG C10343 YesY
PubChem 3220
UNII KA46RNI6HN YesY
  • InChI=1S/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3 YesY
    Key: RHMXXJGYXNZAPX-UHFFFAOYSA-N YesY
  • InChI=1/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3
    Key: RHMXXJGYXNZAPX-UHFFFAOYAD
  • O=C2c1cc(cc(O)c1C(=O)c3c2cc(O)cc3O)C
Properties
C15H10O5
Molar mass 270.24 g·mol−1
Appearance orange solid[1]
Density 1.583±0.06 g/cm3
Melting point 256 to 257 °C (493 to 495 °F; 529 to 530 K)
Boiling point 586.9 ± 39.0 °C [2]
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Emodin (from Rheum emodi, a Himalayan rhubarb) is a purgative resin, 6-methyl-1,3,8-trihydroxyanthraquinone, from rhubarb, buckthorn and Japanese knotweed (Fallopia japonica syn. Polygonum cuspidatum).[3] It is also produced by many species of fungi, including members of the genera Aspergillus, Pyrenochaeta, and Pestalotiopsis, inter alia. Synonyms for emodin include emodol, frangula emodin, rheum emodin, 3-methyl-1,6,8-trihydroxyanthraquinone, Schuttgelb, and Persian Berry Lake.[4]

Pharmacology

Lua error in package.lua at line 80: module 'strict' not found. Emodin is being studied as a potential agent that could reduce the impact of type 2 diabetes. It is a potent selective inhibitor of the enzyme 11β-HSD1.[5] In studies in obese mice, emodin limits the effect of glucocorticoids and may therefore ameliorate diabetes and insulin resistance.[6]

Pharmacological studies have demonstrated that emodin when isolated from rhubarb exhibits anti-cancer effects on several human cancers, including human pancreatic cancer.[7][8][9] Emodin in rhubarb extracts may also have neuroprotective properties against glutamate toxicity.[10]

Aloe-emodin (1,3,8-trihydroxyanthraquinone) is a variety of emodin found in Socotrine, Barbados, and Zanzibar aloes, but not in Natal aloes.[citation needed]

Emodin is also shown to block cytomegalovirus infections as well as herpes simplex. Research is currently being performed in this area.

List of species that produce emodin

Compendial status

References

  1. ↑ Herbal Extract Online. http://herbalextractonline.com/Herbal-Extract/Emodin.html (accessed 9 November 2014).
  2. ↑ Scifinder (accessed 9 November 2014). Emodin (518-82-1) Experimental Properties.
  3. ↑ Dorland's Medical Dictionary (1938)
  4. ↑ PubChem. http://pubchem.ncbi.nlm.nih.gov/compound/emodin (accessed Sept 17, 2014)
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Novel diabetes hope comes from Chinese herbs, esciencenews.com, 17 August 2010
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Dr. Duke's Phytochemical and Ethnobotanical Databases
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ http://www.ars-grin.gov/cgi-bin/duke/highchem.pl[dead link]
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  19. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  20. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  21. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  22. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  23. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  24. ↑ http://www.mdpi.net/molecules/papers/80800614.pdf
  25. ↑ 25.0 25.1 Lua error in package.lua at line 80: module 'strict' not found.
  26. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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