Anemonin

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Anemonin
Skeletal formula of anemonin
Ball-and-stick model of the anemonin molecule
Names
IUPAC names
trans-4,7-Dioxadispiro[4.0.46.25]dodeca-1,9-diene-3,8-dione
trans-1,7-Dioxadispiro[4.0.4.2]dodeca-3,9-diene-2,8-dione[1]
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C10H8O4/c11-7-1-3-9(13-7)5-6-10(9)4-2-8(12)14-10/h1-4H,5-6H2 checkY
    Key: JLUQTCXCAFSSLD-UHFFFAOYSA-N checkY
  • C1CC2(C13C=CC(=O)O3)C=CC(=O)O2
Properties
C10H8O4
Molar mass 192.170 g·mol−1
Appearance Colourless, odourless solid
Density 1.45g/cm3
Melting point 158[1] °C (316 °F; 431 K)
Boiling point 535.7 °C (996.3 °F; 808.9 K) @ 760mmHg
low
Solubility in chloroform very soluble[1]
Hazards
Flash point 300.7 °C (573.3 °F; 573.8 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 150 mg·kg−1 (mouse, i. p.)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Anemonin is a compound found in plants of the buttercup family (Ranunculaceae). It is the dimerization product of the toxin protoanemonin[2] and is easily hydrolysed to a dicarboxylic acid.[3]

4,7-Dioxo-2-decenedioic acid, the hydrolysis product of anemonin

The name of the substance comes from the plant genus Anemone, from which it was first identified.[4]

Potential uses[]

Antispasmodic and analgetic properties have been described.[5]

The compound appears to inhibit pigmentation synthesis, and has therefore been suggested as a potential candidate for cosmetic use.[6]

References[]

  1. ^ a b c William M. Haynes (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton: CRC Press. p. 3-26. ISBN 978-1-4987-5429-3.
  2. ^ List, PH; Hörhammer, L, eds. (1979). Hagers Handbuch der pharmazeutischen Praxis (in German) (4 ed.). Springer Verlag. ISBN 3-540-07738-3.
  3. ^ "Aktuelles aus der Natur" (PDF) (in German). TU Graz. 2 April 2009. p. 4. Retrieved 27 November 2010.[permanent dead link]
  4. ^ Chemie der organischen Verbindungen, Carl Löwig (in German)
  5. ^ Anemonin, Wissenschaft online (in German)
  6. ^ Huang, Yen-Hua; Lee, Tzong-Huei; Chan, Kuei-Jung; Hsu, Feng-Lin; Wu, Yu-Chih; Lee, Mei-Hsien (February 2008). "Anemonin is a natural bioactive compound that can regulate tyrosinase-related proteins and mRNA in human melanocytes". Journal of Dermatological Science. 49 (2): 115–123. doi:10.1016/j.jdermsci.2007.07.008. PMID 17766092.
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