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

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  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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