Hastatoside

CAS# 50816-24-5

Hastatoside

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Chemical structure

Hastatoside

3D structure

Chemical Properties of Hastatoside

Cas No. 50816-24-5 SDF Download SDF
PubChem ID 92043450 Appearance Light yellow powder
Formula C17H24O11 M.Wt 404.37
Type of Compound Iridoids Storage Desiccate at -20°C
Solubility Soluble in methan
Chemical Name 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
SMILES CC1CC(=O)C2(C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O
Standard InChIKey PRZVXHGUJJPSME-CZMSZWGTSA-N
Standard InChI InChI=1S/C17H24O11/c1-6-3-9(19)17(24)7(14(23)25-2)5-26-15(10(6)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h5-6,8,10-13,15-16,18,20-22,24H,3-4H2,1-2H3/t6-,8+,10-,11+,12-,13+,15-,16-,17+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Hastatoside

The herbs of Verbena officinalis L.

Biological Activity of Hastatoside

DescriptionHastatoside and verbenalin are major sleep-promoting components of V. officinalis. Hastatoside has anti-inflammatory activity.
TargetsImmunology & Inflammation related
In vivo

Antiinflammatory activity and chemical composition of extracts of Verbena officinalis.[Pubmed: 10960904]

Phytother Res. 2000 Sep;14(6):463-5.


METHODS AND RESULTS:
In an attempt to locate the biologically active fraction(s) of the plant Verbena officinalis Linn. (Verbenaceae), a preliminary screening of successive petroleum ether, chloroform and methanol extracts of aerial parts for antiinflammatory activity using carrageenan paw oedema model was carried out. All three extracts were found to exhibit antiinflammatory activity with the chloroform extract being the most active. Chemical investigations of petroleum ether and chloroform extracts led to the isolation of beta-sitosterol, ursolic acid, oleanolic acid, 3-epiursolic acid, 3-epioleanolic acid, and minor triterpenoids of derivatives of ursolic acid and oleanolic acids.
CONCLUSIONS:
Chromatographic purification of the methanol extract yielded two iridoid glucosides, verbenalin and Hastatoside, a phenylpropanoid glycoside, verbascoside and beta-sitosterol-D-glucoside.

Hastatoside and verbenalin are sleep‐promoting components in Verbena officinalis[Reference: WebLink]

Sleep & Biological Rhythms, 2009, 7(3):211–217.

Herbal tea made from Verbena officinalis (V. officinalis) has traditionally been used for the treatment of insomnia and other nervous conditions.
METHODS AND RESULTS:
In this study, we examined the sleep-promoting activity of Hastatoside, verbenalin, and verbascoside, which are the major iridoids (Hastatoside and verbenalin) and polyphenol (verbascoside) components responsible for the pharmacological activity of V. officinalis, by electroencephalographic analysis of rats after oral administration of the compounds. Hastatoside (0.64 mmol/kg of body weight) and verbenalin (1.28 mmol/kg of body weight) increased the total time of non-rapid eye movement sleep during a 9-h period from 23.00 to 08.00 hours by 81% and 42%, respectively, with a lag time of about 3–5 h after the administration at 20.00 hours (lights-off time). Both compounds also increased the delta activity during non-rapid eye movement sleep. However, verbascoside had no effect on the amount of sleep.
CONCLUSIONS:
Therefore, Hastatoside and verbenalin are major sleep-promoting components of V. officinalis.

Hastatoside Dilution Calculator

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Hastatoside Molarity Calculator

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Preparing Stock Solutions of Hastatoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.473 mL 12.3649 mL 24.7298 mL 49.4597 mL 61.8246 mL
5 mM 0.4946 mL 2.473 mL 4.946 mL 9.8919 mL 12.3649 mL
10 mM 0.2473 mL 1.2365 mL 2.473 mL 4.946 mL 6.1825 mL
50 mM 0.0495 mL 0.2473 mL 0.4946 mL 0.9892 mL 1.2365 mL
100 mM 0.0247 mL 0.1236 mL 0.2473 mL 0.4946 mL 0.6182 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Hastatoside

Antiinflammatory activity and chemical composition of extracts of Verbena officinalis.[Pubmed:10960904]

Phytother Res. 2000 Sep;14(6):463-5.

In an attempt to locate the biologically active fraction(s) of the plant Verbena officinalis Linn. (Verbenaceae), a preliminary screening of successive petroleum ether, chloroform and methanol extracts of aerial parts for antiinflammatory activity using carrageenan paw oedema model was carried out. All three extracts were found to exhibit antiinflammatory activity with the chloroform extract being the most active. Chemical investigations of petroleum ether and chloroform extracts led to the isolation of beta-sitosterol, ursolic acid, oleanolic acid, 3-epiursolic acid, 3-epioleanolic acid, and minor triterpenoids of derivatives of ursolic acid and oleanolic acids. Chromatographic purification of the methanol extract yielded two iridoid glucosides, verbenalin and Hastatoside, a phenylpropanoid glycoside, verbascoside and beta-sitosterol-D-glucoside.

HPLC-DAD-ESI-MS analysis of the constituents of aqueous preparations of verbena and lemon verbena and evaluation of the antioxidant activity.[Pubmed:18155378]

J Pharm Biomed Anal. 2008 Feb 13;46(3):463-70.

Verbena and lemon verbena aqueous preparations were investigated for their content of constituents, especially polyphenols by HPLC/DAD/ESI/MS analysis because they are used worldwide as herbal teas. The main class of compounds of these plants were phenylpropanoids (from 16 to 120 mg/g of dried extract), being verbascoside the most abundant in all the preparations up to 97% of the total phenylpropanoids. Also iridoids, Hastatoside and verbenalin together with flavonoids, mono- and di-glucuronidic derivatives of luteolin and apigenin were found. These simple preparations, especially that obtained from infusion of lemon verbena, could be lyophilized to obtain a powder having interesting technological properties to be used as ingredients of cosmetics, food supplements and herbal medicinal products do to the many biological properties of verbascoside. In addition, the antioxidant property of the lemon verbena infusion was evaluated by the DPPH test using Trolox as the reference compound.

Iridoid Glucosides from Penstemon nitidus.[Pubmed:17226148]

Planta Med. 1991 Apr;57(2):184-6.

From the leaves of PENSTEMON NITIDUS Dougl. (smooth blue beardtongue) besides the known iridoid glucosides cornin (syn. verbenalin), Hastatoside and beta-dihydroHastatoside the new compound 10-hydroxycornin has been isolated. The structures of all compounds were established by spectroscopic means (FD-MS, (1)H-, (13)C-, 2D-NMR, and NOE). This is the first report of cornin and analogous 6-keto iridoids in scrophulariaceous plants. Up to now iridoid glucosides like these have only been found in plants belonging to the Cornaceae and its allies and to the Lamiaceae-Verbenaceae complex.

Two new iridoids from Verbena officinalis L.[Pubmed:25045888]

Molecules. 2014 Jul 18;19(7):10473-9.

Two new iridoids, 3-(5-(methoxycarbonyl)-2-oxo-2H-pyran-3-yl)butanoic acid, named verbeofflin I (1), and 7-hydroxydehydroHastatoside (2), were isolated from the aerial part of Verbena officinalis L, along with three known iridoids, verbenalin (3), 3,4-dihydroverbenalin (4), Hastatoside (5) by means of various column chromatography steps. The structures of these compounds were elucidated through analysis of their spectroscopic data obtained using 1D and 2D NMR and MS techniques. Verbeofflin I (1) is the new class of secoiridoid in the family Verbenaceae.

Description

Hastatoside is an iridoid glycoside that is isolated from Verbena officinalis and has a role in promoting sleep.

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