1α-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7aα-hexahydro-4aα-hydroxy-7α-methyl-5-oxocyclopenta[c]pyran-4-carboxylic acid methyl ester
1α-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7aα-hexahydro-4aα-hydroxy-7α-methyl-5-oxocyclopenta[c]pyran-4-carboxylic acid methyl ester Basic information
- Product 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
- Synonyms:
-
- 1α-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7aα-hexahydro-4aα-hydroxy-7α-methyl-5-oxocyclopenta[c]pyran-4-carboxylic acid methyl ester
- Hastatoside
- 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)-
- methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,6,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
- Hastatoside-RM
- Hastatoside, 10 mM in DMSO
- Methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
- CAS:
- 50816-24-5
- MF:
- C17H24O11
- MW:
- 404.37
- Mol File:
- 50816-24-5.mol
1α-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7aα-hexahydro-4aα-hydroxy-7α-methyl-5-oxocyclopenta[c]pyran-4-carboxylic acid methyl ester Chemical Properties
- 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
- 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|
1α-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7aα-hexahydro-4aα-hydroxy-7α-methyl-5-oxocyclopenta[c]pyran-4-carboxylic acid methyl ester Usage And Synthesis
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. |
1α-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7aα-hexahydro-4aα-hydroxy-7α-methyl-5-oxocyclopenta[c]pyran-4-carboxylic acid methyl esterSupplier
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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)Related Product Information
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