Verbenalin

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
CAS Number	548-37-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	66163 ;
PubChem CID	73467;
UNII	71B68181Z6 ;
CompTox Dashboard (EPA)	DTXSID50970143 ;
	InChI 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 ; 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;
	SMILES 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
Chemical formula	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

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]

References

^ 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.
^ 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.

[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.

[1]

[2]

v t e Glycosides
Bond	O-glycosidic bond N-glycosidic bond S-glycosidic bond C-glycosidic bond
Geometry	α-Glycoside β-Glycoside 1,4-Glycoside 1,6-Glycoside
Glycone	Fructoside Galactoside Glucoside Glucuronide Rhamnoside Riboside
Aglycone	Alcoholic glycoside Cardiac glycoside Bufadienolide Cardenolide Cyanogenic glycoside Glycosylamine Phenolic glycoside Anthraquinone glycoside Coumarin glycoside Flavonoid glycoside Saponin Steviol glycoside Thioglycoside

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
CAS Number	548-37-8^Y
3D model (JSmol)	Interactive image
ChemSpider	66163^Y
PubChem CID	73467
UNII	71B68181Z6^Y
CompTox Dashboard (EPA)	DTXSID50970143
InChI 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^Y Key: HLXRWTJXGMHOFN-XJSNKYLASA-N^Y 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
SMILES 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
Chemical formula	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

Verbenalin

References

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