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Rhein (molecule)

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Rhein
Chemical structure 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 100.006.839Edit 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
GHSlabelling:
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 theirstandard state(at 25 °C [77 °F], 100 kPa).

Rhein,also known ascassic acid,is a substance in theanthraquinonegroup obtained fromrhubarb.[2]Like all such substances, rhein is acathartic,which is commonly found as aglycosidesuch as rhein-8-glucoside or glucorhein.[2]Rhein was first isolated in 1895.[3]It is found inrhubarbspecies likeRheum undulatum[4]andRheum palmatum[5]as well as inCassia reticulata.[6]

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 againstStaphylococcus aureusin 2008.[7]Synergy or partial synergy has been demonstrated between rhein and the antibioticsoxacillinandampicillin.[8]

Rhein has been shown to inhibit thefat mass and obesity-associated protein,an enzyme responsible for removing themethylationfromN6-methyladenosinein nucleic acids.[9][10]

Thepharmacokineticsof 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[edit]

References[edit]

  1. ^abCassic acid on www.naturestandard.comArchived2011-07-14 at theWayback Machine
  2. ^abcPharmacognosy of Rhubarb | Chemical Constituents
  3. ^Hesse O (1895). "The Chemistry of rhubarb (EN)".Pharmaceutical Journal and Transactions.1:325.
  4. ^Lee JH, Kim JM, Kim CS (2003). "Pharmacokinetic analysis of rhein inRheum undulatumL. ".J Ethnopharmacol.84(1): 5–9.doi:10.1016/S0378-8741(02)00222-2.PMID12499069.
  5. ^Hoerhammer L, Wagner H, Koehler I (1959). "Neue Untersuchungen über die Inhaltsstoffe vonRheum palmatumL. 1. Mitteilung: Zur Analytik des Rheins "[New investigations on the components ofRheum palmatumL. Part 1: On the analysis of rhein].Archiv der Pharmazie(in German).292(64): 591–601.doi:10.1002/ardp.19592921105.PMID14402302.S2CID94169376.
  6. ^Anchel M (1949)."Identification of the antibiotic substance fromCassia reticulataas 4,5-Dihydroxyanthraquinone-2-carboxylic acid "(PDF).J Biol Chem.177(1): 169–177.doi:10.1016/S0021-9258(18)57072-1.PMID18123056.
  7. ^Yu L, Xiang H, Fan J, et al. (2008). "Global transcriptional response ofStaphylococcus aureusto rhein, a natural plant product ".J Biotechnol.135(3): 304–308.doi:10.1016/j.jbiotec.2008.04.010.PMID18514345.
  8. ^Joung DK, Joung H, Yang DW, et al. (2012)."Synergistic effect of rhein in combination with ampicillin or oxacillin against methicillin-resistantStaphylococcus aureus".Exp Ther Med.3(4): 608–612.doi:10.3892/etm.2012.459.PMC3438619.PMID22969937.
  9. ^Yu, Jun; Chen, Mengxian; Huang, Haijiao; Zhu, Junda; Song, Huixue; Zhu, Jian; Park, Jaewon; Ji, Sheng-Jian (2017-11-23)."Dynamic m6A modification regulates local translation of mRNA in axons ".Nucleic Acids Research.46(3): 1412–1423.doi:10.1093/nar/gkx1182.ISSN0305-1048.PMC5815124.PMID29186567.
  10. ^Jia, Guifang; Fu, Ye; Zhao, Xu; Dai, Qing; Zheng, Guanqun; Yang, Ying; Yi, Chengqi; Lindahl, Tomas; Pan, Tao (2011-10-16)."N6-Methyladenosine in nuclear RNA is a major substrate of the obesity-associated FTO ".Nature Chemical Biology.7(12): 885–887.doi:10.1038/nchembio.687.ISSN1552-4450.PMC3218240.PMID22002720.
  11. ^Zhu W, Wang XM, Zhang L, Li XY, Wang BX (2005). "Pharmacokinetic of rhein in healthy male volunteers following oral and retention enema administration of rhubarb extract: a single dose study".Am J Chin Med.33(6): 839–850.doi:10.1142/S0192415X05003508.PMID16355440.
  12. ^La Villa G, Marra F, Laffi G, et al. (1989). "Effects of rhein on renal arachidonic acid metabolism and renal function in patients with congestive heart failure".Eur J Clin Pharmacol.37(1): 1–5.doi:10.1007/bf00609415.PMID2512175.S2CID6338421.
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