Rhein (molecule)

Chemical compound From Wikipedia, the free encyclopedia

Rhein, also known as cassic acid, is a substance in the anthraquinone group obtained from rhubarb.[2] Like all such substances, rhein is a cathartic, which is commonly found as a glycoside such as rhein-8-glucoside or glucorhein.[2] Rhein was first isolated in 1895.[3] It is found in rhubarb species like Rheum undulatum[4] and Rheum palmatum[5] as well as in Cassia reticulata.[6]

Quick facts Names, Identifiers ...
Rhein
Chemical structure of rhein
Chemical structure of rhein
Ball-and-stick model of rhein
Ball-and-stick model of rhein
Names
Preferred IUPAC name
4,5-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
Other names
Rhubarb Yellow
Monorhein
Cassic acid
Rheic acid
Chrysazin-3-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.839 Edit this at Wikidata
EC Number
  • 207-521-4
KEGG
MeSH Rhein
UNII
  • InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21) ☒N
    Key: FCDLCPWAQCPTKC-UHFFFAOYSA-N ☒N
  • InChI=1/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)
    Key: FCDLCPWAQCPTKC-UHFFFAOYAT
  • C1=CC2=C(C(=C1)O)C(=O)C3=C(C=C(C=C3C2=O)C(=O)O)O
Properties
C15H8O6
Molar mass 284.22 g/mol
Appearance Orange crystals[1]
Density 1.687 g/cm3
Melting point 350 to 352 °C (662 to 666 °F; 623 to 625 K)[1]
Boiling point 597.8 °C (1,108.0 °F; 870.9 K) at 760 mmHg
Insoluble in water
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
Flash point 329.4 °C (624.9 °F; 602.5 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Originally the rhubarb plant which contains rhein was used as a laxative. It was believed that rhein along with other anthraquinone glycosides imparted this activity.[2]

Rhein has been reevaluated as an antibacterial agent against Staphylococcus aureus in 2008.[7] Synergy or partial synergy has been demonstrated between rhein and the antibiotics oxacillin and ampicillin.[8]

Rhein has been shown to inhibit the fat mass and obesity-associated protein, an enzyme responsible for removing the methylation from N6-methyladenosine in nucleic acids.[9][10]

The pharmacokinetics of rhein have not been intensively studied in humans, but at least one study in healthy male volunteers found that rhein was better absorbed from oral administration of rhubarb than from a retention enema.[11] Rhein (at an oral dose of 50 mg twice per day) was shown to be safe when administered for five days to elderly patients with chronic congestive heart failure.[12]

See also

References

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