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'''Anemonin''' is a compound found in plants of the [[buttercup family]] (Ranunculaceae). It is the [[Dimer (chemistry)|dimerization]] product of the [[toxin]] [[protoanemonin]]<ref name="Hager" /> and is easily [[hydrolyse]]d to a [[dicarboxylic acid]].<ref name="TUGraz" />
'''Anemonin''' is a compound found in plants of the [[buttercup family]] (Ranunculaceae). It is the [[Dimer (chemistry)|dimerization]] product of the [[toxin]] [[protoanemonin]]<ref name="Hager" /> and is easily [[hydrolyse]]d to a [[dicarboxylic acid]].<ref name="TUGraz" />
[[File:Anemoninsäure.svg|thumb|left|The hydrolysis product of anemonin]]{{clear-left}}


The name of the substance comes from the plant genus ''[[Anemone]]'', from which it was first identified.<ref name="ChemOrgVerb" /> [[Antispasmodic]] and [[analgetic]] properties have been described.<ref name="w-online" />
The name of the substance comes from the plant genus ''[[Anemone]]'', from which it was first identified.<ref name="ChemOrgVerb" /> [[File:Anemoninsäure.svg|thumb|The hydrolysis product of anemonin|alt=]]
== Potential Uses ==
[[Antispasmodic]] and [[analgetic]] properties have been described.<ref name="w-online" />

The compound appears to inhibit pigmentation synthesis, and has therefore been suggested as a potential candidate for cosmetic use.<ref>{{Cite web|url=https://www.sciencedirect.com/science/article/pii/S0923181107002575|title=ScienceDirect|website=www.sciencedirect.com|access-date=2019-04-03}}</ref>


== References ==
== References ==

Revision as of 18:17, 3 April 2019

Anemonin
Skeletal formula of anemonin
Ball-and-stick model of the anemonin molecule
Names
IUPAC name
trans-4,7-Dioxadispiro[4.0.46.25]dodeca-1,9-diene-3,8-dione
Identifiers
3D model (JSmol)
ChemSpider
  • 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 °C (316 °F; 431 K)
Boiling point 535.7 °C (996.3 °F; 808.9 K) @ 760mmHg
low
Solubility in chloroform soluble
Hazards
Flash point 300.7 °C (573.3 °F; 573.8 K)
Lethal dose or concentration (LD, LC):
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).
checkY verify (what is checkY☒N ?)

Anemonin is a compound found in plants of the buttercup family (Ranunculaceae). It is the dimerization product of the toxin protoanemonin[1] and is easily hydrolysed to a dicarboxylic acid.[2]

The name of the substance comes from the plant genus Anemone, from which it was first identified.[3]

The hydrolysis product of anemonin

Potential Uses

Antispasmodic and analgetic properties have been described.[4]

The compound appears to inhibit pigmentation synthesis, and has therefore been suggested as a potential candidate for cosmetic use.[5]

References

  1. ^ List, PH; Hörhammer, L, eds. (1979). Hagers Handbuch der pharmazeutischen Praxis (in German) (4 ed.). Springer Verlag. ISBN 3-540-07738-3.
  2. ^ "Aktuelles aus der Natur" (PDF) (in German). TU Graz. 2 April 2009. p. 4. Retrieved 27 November 2010.[permanent dead link]
  3. ^ Chemie der organischen Verbindungen, Carl Löwig Template:De icon
  4. ^ Anemonin, Wissenschaft online Template:De icon
  5. ^ "ScienceDirect". www.sciencedirect.com. Retrieved 2019-04-03.