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50816-24-5

50816-24-5 Structure

50816-24-5 Structure
IdentificationBack Directory
[Name]

1α-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7aα-hexahydro-4aα-hydroxy-7α-methyl-5-oxocyclopenta[c]pyran-4-carboxylic acid methyl ester
[CAS]

50816-24-5
[Synonyms]

Hastatoside
1α-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7aα-hexahydro-4aα-hydroxy-7α-methyl-5-oxocyclopenta[c]pyran-4-carboxylic acid methyl ester
Cyclopenta[c]pyran-4-carboxylic acid, 1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-4a-hydroxy-7-methyl-5-oxo-, methyl ester, (1S,4aR,7S,7aR)-
[Molecular Formula]

C17H24O11
[MDL Number]

MFCD09752811
[MOL File]

50816-24-5.mol
[Molecular Weight]

404.366
Chemical PropertiesBack Directory
[Boiling point ]

653.5±55.0 °C(Predicted)
[density ]

1.58±0.1 g/cm3 (20 ºC 760 Torr)
[storage temp. ]

-20°C
[form ]

Solid
[pka]

10.20±0.70(Predicted)
[color ]

White to off-white
[Major Application]

food and beverages
[InChIKey]

PRZVXHGUJJPSME-INTLEKPZNA-N
[SMILES]

[C@]12(O)C(=O)C[C@H](C)[C@@]1([H])[C@@H](OC=C2C(OC)=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O |&1:0,5,7,9,18,20,23,25,27,r|
Safety DataBack Directory
[WGK Germany ]

WGK 3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Chemical Properties]

It is a white powder, soluble in organic solvents such as methanol, ethanol, and DMSO. It comes from the whole herb of Verbena officinalis L., a plant of the Verbenaceae family.
[Uses]

Hastatoside is an iridoid glucoside isolated found in Verbena officinalis and other herb plants.
[Definition]

ChEBI: Hastatoside is an iridoid monoterpenoid with formula C17H24O11 that is isolated from several plants including Verbena officinalis and exhibits a sleep-promoting effect. It has a role as a plant metabolite and a hepatoprotective agent. It is a beta-D-glucoside, an iridoid monoterpenoid, a cyclopentapyran, a monosaccharide derivative, a monoterpene glycoside, an alpha,beta-unsaturated carboxylic ester and a methyl ester.
[in vivo]

Hastatoside (0.32-0.64 mmol/kg; oral administration; for 9 hours; male rats of the Sprague-Dawley strain) treatment increases the total time of non-rapid eye movement sleep during a 9-h period, with a lag time of about 3-5 h after the administration at 20. 00 hours (lights-off time). Hastatoside also increases the delta activity during non-rapid eye movement sleep[1].

Animal Model:Male rats of the Sprague-Dawley strain (8 weeks old; 260-280 g)[1]
Dosage:0.32 mmol/kg, 0.48 mmol/kg, 0.64 mmol/kg
Administration:Oral administration; for 9 hours
Result:Increased the total time of non-rapid eye movement sleep during a 9-h period, with a lag time of about 3-5 h after the administration at 20. 00 hours (lights-off time). Also increased the delta activity during non-rapid eye movement sleep.
Spectrum DetailBack Directory
[Spectrum Detail]

1α-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7aα-hexahydro-4aα-hydroxy-7α-methyl-5-oxocyclopenta[c]pyran-4-carboxylic acid methyl ester(50816-24-5)1HNMR
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