Coixol

CAS# 532-91-2

Coixol

Catalog No. BCN5703----Order now to get a substantial discount!

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Chemical structure

Coixol

3D structure

Chemical Properties of Coixol

Cas No. 532-91-2 SDF Download SDF
PubChem ID 10772 Appearance Powder
Formula C8H7NO3 M.Wt 165.1
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms 6-Methoxy-2-benzoxazolinone; 6-MBOA
Solubility DMSO : ≥ 30 mg/mL (181.65 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 6-methoxy-3H-1,3-benzoxazol-2-one
SMILES COC1=CC2=C(C=C1)NC(=O)O2
Standard InChIKey MKMCJLMBVKHUMS-UHFFFAOYSA-N
Standard InChI InChI=1S/C8H7NO3/c1-11-5-2-3-6-7(4-5)12-8(10)9-6/h2-4H,1H3,(H,9,10)
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 Coixol

The seed of Coix lacryma-jobi L. var. meyuan (Romen.) Stapf

Biological Activity of Coixol

DescriptionCoixol acts as a central muscle relaxant with an anti-convulsant effect; it can regulate gene expression, production and secretion of mucin, by directly acting on airway epithelial cells. Coixol interacts with the pituitary to stimulate reproduction in voles, it also has the ability to interact with FSH to stimulate follicular development and increase ovulation.
TargetsEGFR | TNF-α
In vitro

Suppressive effects of coixol, glyceryl trilinoleate and natural products derived from Coix Lachryma-Jobi var. ma-yuen on gene expression, production and secretion of airway MUC5AC mucin.[Pubmed: 24733673]

Arch Pharm Res. 2015 May;38(5):620-7.

In this study, we investigated whether natural products including Coixol derived from Coix Lachryma-Jobi var. ma-yuen affect MUC5AC mucin gene expression, production and secretion from airway epithelial cells.
METHODS AND RESULTS:
Confluent NCI-H292 cells were pretreated with oleic acid, linoleic acid, glyceryl trilinoleate, beta-stigmasterol or Coixol for 30 min and then stimulated with PMA (phorbol 12-myristate 13-acetate), EGF (epidermal growth factor) or TNF-α (tumor necrosis factor-α) for 24 h. The MUC5AC mucin gene expression, mucin protein production and secretion were measured by RT-PCR and ELISA. The results were as follows: (1) Oleic acid, linoleic acid, glyceryl trilinoleate, beta-stigmasterol and Coixol inhibited the expression of MUC5AC mucin gene induced by PMA from NCI-H292 cells; (2) Oleic acid, linoleic acid, glyceryl trilinoleate, beta-stigmasterol and Coixol also inhibited the production of MUC5AC mucin protein induced by the same inducers from NCI-H292 cells; (3) Coixol inhibited the expression of MUC5AC mucin gene and production of MUC5AC mucin protein, induced by EGF or TNF-α from NCI-H292 cells; (4) Coixol decreased PMA-induced MUC5AC mucin secretion from NCI-H292 cells.
CONCLUSIONS:
This result suggests that Coixol, the characteristic component among the examined five natural products derived from C. Lachryma-Jobi var. ma-yuen, can regulate gene expression, production and secretion of mucin, by directly acting on airway epithelial cells.

Behavioral and EEG effects of coixol (6-methoxybenzoxazolone), one of the components in Coix Lachryma-Jobi L. var. ma-yuen Stapf.[Pubmed: 7052357]

Nihon Yakurigaku Zasshi. 1981 Mar;77(3):245-59.

Coixol (6-methoxybenzoxazolone) contained in Coix Lachryma-Jobi L. var. ma-yuen Stapf was compared with chlorzoxazone with respect to behavioral and EEG effects in mice and rats.
METHODS AND RESULTS:
Coixol 50-100 mg/kg, i.p. decreased locomotor activities of both species and produced hypothermia in rats. These effects of Coixol were the same in potency as chlorzoxazone given in the same dose. Coixol was approximately twice as potent as chlorzoxazone in potentiating thiopental-induced sleep. This compound attenuated the writhing syndrome induced by 1% acetic acid and increased the threshold to jumping response induced by foot shock, to the same degree as seen with chlorzoxazone. Coixol was equipotent to chlorzoxazone in preventing convulsions induced by maximal electro-shock, while it was about 1.5 times more potent than chlorzoxazone in suppressing pentylenetetrazol-induced convulsion. Coixol 20-100 mg/kg inhibited the lever pressing response of hypothalamic self-stimulation in rats. In rats with chronically implanted electrodes, Coixol 50-100 mg/kg induced drowsy patterns on the spontaneous EEG. The EEG arousal response to the external auditory stimulation was inhibited by the same doses of Coixol, whereas it failed to suppress the arousal response to the midbrain reticular stimulation.
CONCLUSIONS:
These results indicate that Coixol has pharmacological properties qualitatively similar to chlorzoxazone and acts as a central muscle relaxant with an anti-convulsant effect.

In vivo

The plant metabolite 6-methoxybenzoxazolinone interacts with follicle-stimulating hormone to enhance ovarian growth.[Pubmed: 3140906]

Biol Reprod. 1988 Sep;39(2):465-71.

6-Methoxybenzoxazolinone (6-MBOA) is a novel plant metabolite that enhances reproductive status in vertebrate consumers while it inhibits insect, fungal, and bacterial infestation of the plant. Ovaries of prepubertal rats show a dose response to increasing amounts of 6-MBOA.administered in Silastic capsule implants.
METHODS AND RESULTS:
Ovaries increased in size in response to capsules with 0.5-3.0 cm exposed surface area of 6-MBOA, whereas larger capsules (6 cm 6-MBOA) had no effect. Removal of the pituitary in both prepubertal and mature rats eliminated the stimulatory influence of 6-MBOA. In hypophysectomized animals treated with diethylstibestrol implants, 6-MBOA did not affect ovarian weight and no animals ovulated. Administration of follicle-stimulating hormone (FSH) increased ovarian weight and stimulated production of ova, and FSH combined with 6-MBOA resulted in larger ovaries that released more ova. 6-MBOA also enhanced ovarian growth in intact prepubertal animals treated with pregnant mare's serum gonadotropin.
CONCLUSIONS:
These results show that 6-MBOA has the ability to interact with FSH to stimulate follicular development and increase ovulation. Non-steroidal plant compounds may have a significant impact on the reproductive patterns of wild animal populations.

Protocol of Coixol

Animal Research

Effects of melatonin and 6-methoxybenzoxazolinone on photoperiodic control of testis size in adult male golden hamsters.[Pubmed: 3210136]

The plant metabolite, 6-methoxybenzoxazolinone, stimulates an increase in secretion of follicle-stimulating hormone and size of reproductive organs in Microtus pinetorum.[Pubmed: 3135852]

Biol Reprod. 1988 May;38(4):817-20.

The plant metabolite, 6-methoxybenzoxazolinone (6-MBOA), occurring in leaf tissue of rapidly growing monocots, cues reproduction in some mammals.
METHODS AND RESULTS:
In the pine vole, Microtus pinetorum, peripubertal females respond to this nonestrogenic compound with a 40% increase in serum levels of follicle-stimulating hormone (FSH). In addition, 6-MBOA significantly increases the weight of the ovary and uterus in both peripubertal and mature voles.
CONCLUSIONS:
This study is the first to offer evidence that 6-MBOA interacts with the pituitary to stimulate reproduction in voles.

J Pineal Res. 1988;5(4):351-65.

Consumption of young plants containing 6-methoxybenzoxazolinone (6-MBOA) appears to play an important role in the initiation of reproduction each spring in wild populations of the montane vole. Following its identification, 6-MBOA has been found to stimulate the reproductive system in a number of rodent species, but the mechanism of action remains unknown. The chemical structure of 6-MBOA is similar to melatonin, which, in addition to its well-known antigonadal effects, can exert a progonadal influence under certain experimental conditions. To determine if 6-MBOA might act as a melatonin agonist, four experiments were conducted to compare the effect of these two compounds on testis size in the golden hamster, a rodent whose responses to melatonin are well characterized.
METHODS AND RESULTS:
1) Hamsters exposed to 14 h light per day (14L:10D) received a daily injection of melatonin (25.0 micrograms) or 6-MBOA (17.8 micrograms). 2) Hamsters exposed to 6L:18D received Silastic capsules (50 or 200 mm) containing melatonin or 6-MBOA. 3) Hamsters exposed to 6L:18D received chow containing melatonin (21.1 or 42.2 micrograms/gm chow) or 6-MBOA (15.0 or 30.0 micrograms/gm). 4) Hamsters exposed to 6L:18D received drinking water containing melatonin (15.5 micrograms/ml) or 6-MBOA (11.0 micrograms/ml). Testis widths were determined at 2--3 week intervals, and after 66-73 days testes were removed and weighed. Melatonin significantly influenced testis size in each experiment, but treatment with 6-MBOA had no effect in any of these experimental paradigms, indicating that 6-MBOA does not act as a melatonin agonist in the hamster.
CONCLUSIONS:
However, these results indicate that the consumption of melatonin (and presumably melatonin agonists) could serve as an environmental stimulus for reproductive activity.

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Preparing Stock Solutions of Coixol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.0569 mL 30.2847 mL 60.5694 mL 121.1387 mL 151.4234 mL
5 mM 1.2114 mL 6.0569 mL 12.1139 mL 24.2277 mL 30.2847 mL
10 mM 0.6057 mL 3.0285 mL 6.0569 mL 12.1139 mL 15.1423 mL
50 mM 0.1211 mL 0.6057 mL 1.2114 mL 2.4228 mL 3.0285 mL
100 mM 0.0606 mL 0.3028 mL 0.6057 mL 1.2114 mL 1.5142 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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Background on Coixol

Coixol is a natural product extracted from Coix Lachryma-Jobi var. ma-yuen. IC50 value: Target: In vitro: Confluent NCI-H292 cells were pretreated with oleic acid, linoleic acid, glyceryl trilinoleate, beta-stigmasterol or coixol for 30 min and then stimulated with PMA (phorbol 12-myristate 13-acetate), EGF (epidermal growth factor) or TNF-α (tumor necrosis factor-α) for 24 h. Coixol inhibited the expression of MUC5AC mucin gene and production of MUC5AC mucin protein, induced by EGF or TNF-α from NCI-H292 cells; Coixol decreased PMA-induced MUC5AC mucin secretion from NCI-H292 cells [1]. βTC-6 cells were incubated in 2 mM and 20 mM glucose in the presence of coixol (200 μM) for 60 min at 37°C in Krebs-Ringer Bicarbonate buffer. Decreased insulin staining was observed by coixol at 20 mM glucose (bottom) suggest that coixol stimulated insulin secretion at high glucose concentration [2]. In vivo:

References:
[1]. Lee HJ, et al. Suppressive effects of coixol, glyceryl trilinoleate and natural products derived from Coix Lachryma-Jobi var. ma-yuen on gene expression, production and secretion of airway MUC5AC mucin. Arch Pharm Res. 2015;38(5):620-7. [2]. Rahman M Hafizur, et al. Coixol Exerts an Exclusive Glucose-dependent Insulinotropic Effect in βTC-6 Cells. Hafizur et al., J Cytol Histol 2015, 6:3

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References on Coixol

The plant metabolite 6-methoxybenzoxazolinone interacts with follicle-stimulating hormone to enhance ovarian growth.[Pubmed:3140906]

Biol Reprod. 1988 Sep;39(2):465-71.

6-Methoxybenzoxazolinone (6-MBOA) is a novel plant metabolite that enhances reproductive status in vertebrate consumers while it inhibits insect, fungal, and bacterial infestation of the plant. Ovaries of prepubertal rats show a dose response to increasing amounts of 6-MBOA.administered in Silastic capsule implants. Ovaries increased in size in response to capsules with 0.5-3.0 cm exposed surface area of 6-MBOA, whereas larger capsules (6 cm 6-MBOA) had no effect. Removal of the pituitary in both prepubertal and mature rats eliminated the stimulatory influence of 6-MBOA. In hypophysectomized animals treated with diethylstibestrol implants, 6-MBOA did not affect ovarian weight and no animals ovulated. Administration of follicle-stimulating hormone (FSH) increased ovarian weight and stimulated production of ova, and FSH combined with 6-MBOA resulted in larger ovaries that released more ova. 6-MBOA also enhanced ovarian growth in intact prepubertal animals treated with pregnant mare's serum gonadotropin. These results show that 6-MBOA has the ability to interact with FSH to stimulate follicular development and increase ovulation. Non-steroidal plant compounds may have a significant impact on the reproductive patterns of wild animal populations.

The plant metabolite, 6-methoxybenzoxazolinone, stimulates an increase in secretion of follicle-stimulating hormone and size of reproductive organs in Microtus pinetorum.[Pubmed:3135852]

Biol Reprod. 1988 May;38(4):817-20.

The plant metabolite, 6-methoxybenzoxazolinone (6-MBOA), occurring in leaf tissue of rapidly growing monocots, cues reproduction in some mammals. In the pine vole, Microtus pinetorum, peripubertal females respond to this nonestrogenic compound with a 40% increase in serum levels of follicle-stimulating hormone (FSH). In addition, 6-MBOA significantly increases the weight of the ovary and uterus in both peripubertal and mature voles. This study is the first to offer evidence that 6-MBOA interacts with the pituitary to stimulate reproduction in voles.

[Behavioral and EEG effects of coixol (6-methoxybenzoxazolone), one of the components in Coix Lachryma-Jobi L. var. ma-yuen Stapf].[Pubmed:7052357]

Nihon Yakurigaku Zasshi. 1981 Mar;77(3):245-59.

Coixol (6-methoxybenzoxazolone) contained in Coix Lachryma-Jobi L. var. ma-yuen Stapf was compared with chlorzoxazone with respect to behavioral and EEG effects in mice and rats. Coixol 50-100 mg/kg, i.p. decreased locomotor activities of both species and produced hypothermia in rats. These effects of Coixol were the same in potency as chlorzoxazone given in the same dose. Coixol was approximately twice as potent as chlorzoxazone in potentiating thiopental-induced sleep. This compound attenuated the writhing syndrome induced by 1% acetic acid and increased the threshold to jumping response induced by foot shock, to the same degree as seen with chlorzoxazone. Coixol was equipotent to chlorzoxazone in preventing convulsions induced by maximal electro-shock, while it was about 1.5 times more potent than chlorzoxazone in suppressing pentylenetetrazol-induced convulsion. Coixol 20-100 mg/kg inhibited the lever pressing response of hypothalamic self-stimulation in rats. In rats with chronically implanted electrodes, Coixol 50-100 mg/kg induced drowsy patterns on the spontaneous EEG. The EEG arousal response to the external auditory stimulation was inhibited by the same doses of Coixol, whereas it failed to suppress the arousal response to the midbrain reticular stimulation. These results indicate that Coixol has pharmacological properties qualitatively similar to chlorzoxazone and acts as a central muscle relaxant with an anti-convulsant effect.

Suppressive effects of coixol, glyceryl trilinoleate and natural products derived from Coix Lachryma-Jobi var. ma-yuen on gene expression, production and secretion of airway MUC5AC mucin.[Pubmed:24733673]

Arch Pharm Res. 2015;38(5):620-7.

In this study, we investigated whether natural products including Coixol derived from Coix Lachryma-Jobi var. ma-yuen affect MUC5AC mucin gene expression, production and secretion from airway epithelial cells. Confluent NCI-H292 cells were pretreated with oleic acid, linoleic acid, glyceryl trilinoleate, beta-stigmasterol or Coixol for 30 min and then stimulated with PMA (phorbol 12-myristate 13-acetate), EGF (epidermal growth factor) or TNF-alpha (tumor necrosis factor-alpha) for 24 h. The MUC5AC mucin gene expression, mucin protein production and secretion were measured by RT-PCR and ELISA. The results were as follows: (1) Oleic acid, linoleic acid, glyceryl trilinoleate, beta-stigmasterol and Coixol inhibited the expression of MUC5AC mucin gene induced by PMA from NCI-H292 cells; (2) Oleic acid, linoleic acid, glyceryl trilinoleate, beta-stigmasterol and Coixol also inhibited the production of MUC5AC mucin protein induced by the same inducers from NCI-H292 cells; (3) Coixol inhibited the expression of MUC5AC mucin gene and production of MUC5AC mucin protein, induced by EGF or TNF-alpha from NCI-H292 cells; (4) Coixol decreased PMA-induced MUC5AC mucin secretion from NCI-H292 cells. This result suggests that Coixol, the characteristic component among the examined five natural products derived from C. Lachryma-Jobi var. ma-yuen, can regulate gene expression, production and secretion of mucin, by directly acting on airway epithelial cells.

Effects of melatonin and 6-methoxybenzoxazolinone on photoperiodic control of testis size in adult male golden hamsters.[Pubmed:3210136]

J Pineal Res. 1988;5(4):351-65.

Consumption of young plants containing 6-methoxybenzoxazolinone (6-MBOA) appears to play an important role in the initiation of reproduction each spring in wild populations of the montane vole. Following its identification, 6-MBOA has been found to stimulate the reproductive system in a number of rodent species, but the mechanism of action remains unknown. The chemical structure of 6-MBOA is similar to melatonin, which, in addition to its well-known antigonadal effects, can exert a progonadal influence under certain experimental conditions. To determine if 6-MBOA might act as a melatonin agonist, four experiments were conducted to compare the effect of these two compounds on testis size in the golden hamster, a rodent whose responses to melatonin are well characterized. 1) Hamsters exposed to 14 h light per day (14L:10D) received a daily injection of melatonin (25.0 micrograms) or 6-MBOA (17.8 micrograms). 2) Hamsters exposed to 6L:18D received Silastic capsules (50 or 200 mm) containing melatonin or 6-MBOA. 3) Hamsters exposed to 6L:18D received chow containing melatonin (21.1 or 42.2 micrograms/gm chow) or 6-MBOA (15.0 or 30.0 micrograms/gm). 4) Hamsters exposed to 6L:18D received drinking water containing melatonin (15.5 micrograms/ml) or 6-MBOA (11.0 micrograms/ml). Testis widths were determined at 2--3 week intervals, and after 66-73 days testes were removed and weighed. Melatonin significantly influenced testis size in each experiment, but treatment with 6-MBOA had no effect in any of these experimental paradigms, indicating that 6-MBOA does not act as a melatonin agonist in the hamster. However, these results indicate that the consumption of melatonin (and presumably melatonin agonists) could serve as an environmental stimulus for reproductive activity.

Description

Coixol is a natural product extracted from Coix Lachryma-Jobi var.

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