Verbenalin

Verbenalin is a chemical compound, classified as an iridoid glucoside, that is found in Verbena officinalis.[1] It is one of the sleep-promoting (soporific) components in Verbena officinalis.[2]

Verbenalin
Names
IUPAC name
Methyl (1S,4aS,7S,7aR)-1-(β-D-glucopyranosyloxy)-7-methyl-5-oxo-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Systematic IUPAC name
Methyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Other names
Verbenalol β-D-glucopyranoside; Verbenalol glucoside; Cornin
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C17H24O10/c1-6-3-8(19)11-7(15(23)24-2)5-25-16(10(6)11)27-17-14(22)13(21)12(20)9(4-18)26-17/h5-6,9-14,16-18,20-22H,3-4H2,1-2H3/t6-,9+,10+,11-,12+,13-,14+,16-,17-/m0/s1 checkY
    Key: HLXRWTJXGMHOFN-XJSNKYLASA-N checkY
  • InChI=1S/C17H24O10/c1-6-3-8(19)11-7(15(23)24-2)5-25-16(10(6)11)27-17-14(22)13(21)12(20)9(4-18)26-17/h5-6,9-14,16-18,20-22H,3-4H2,1-2H3/t6-,9+,10+,11-,12+,13-,14+,16-,17-/m0/s1
    Key: HLXRWTJXGMHOFN-XJSNKYLASA-N
  • C[C@H]1CC(=O)[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
Properties
C17H24O10
Molar mass 388.369 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Deepak, M.; Handa, S. S. (2000). "Antiinflammatory activity and chemical composition of extracts of Verbena officinalis". Phytotherapy Research. 14 (6): 463–465. doi:10.1002/1099-1573(200009)14:6<463::AID-PTR611>3.0.CO;2-G. PMID 10960904. S2CID 24506417.
  2. Makino, Y.; Kondo, S.; Nishimura, Y.; Tsukamoto, Y.; Huang, Z. L.; Urade, Y. (2009). "Hastatoside and verbenalin are sleep-promoting components in Verbena officinalis". Sleep and Biological Rhythms. 7 (3): 211–217. doi:10.1111/j.1479-8425.2009.00405.x. S2CID 74435229.
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