Xanthoxylin CAS NO.90-24-4

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90-24-4
Xanthoxylin
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ProName: Xanthoxylin
CasNo: 90-24-4
Molecular Formula: C10H12O4
Appearance: detailed see specifications
Application: analysis,activity test,Botanical Refer...
DeliveryTime: 1-3 working days after confirming
PackAge: According to the clients requirement.
Port: China main port
ProductionCapacity: /
Purity: HPLC≥98%
Storage: Store at 2~8°C
Transportation: by air or by ocean shipping
LimitNum: 0
Plant of Origin: Chinese herbal medicine
Testing Method: NMR/MS/HPLC
Product Ecification: 1mg-1kg
Heavy Metal: <10ppm
Voluntary Standards: Company standard

Superiority

Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，Traditional Chinese Medicine), Natural Active Pharmaceutical Ingredients worldwide. From small quantities for R&D or reference standard, to large quantities for customizing or manufacturing, Biopurify emphasizes on consistent and reliable services for his customers.
With excellent quality products and good service, we have clients from more than dozens countries and regions, and we pride ourselves in providing our customers with a total satisfaction experiences.
We are doing our best to be your reliable partner for high quality Phytochemicals and Reference Standards from china.

Our main services:
A. Supply active ingredients and reference standards ofTraditional Chinese Medicine, from mgs to kgs scale.
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR, CM and PD services from lab scale, pilot scale to commercial scale(GMP is also available)
E.Traditional Chinese Medicine compounds library

1.Provide traditional Chinese medicine reference materials and natural active ingredients;
2.More than 2200 compounds are available for selection, continuously building high-quality natural product libraries for drug research and development;
3.Provide various screening libraries and more inhibitor products;
4.Provide separation and structural determination of natural products;
5.Laboratory scale pilot to commercial scale collaborative research and process development services.More than 180 experiences in phytochemistry (still increasing)
Each product has passed very strict testing (NMR/MS/HPLC)
Agents from many countries

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.

Details

Chemical Properties of Xanthoxylin

Cas No.	90-24-4
PubChem ID	66654	Appearance	Powder
Formula	C₁₀H₁₂O₄	M.Wt	196.2
Type of Compound	Phenols	Storage	Desiccate at -20°C
Solubility	Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name	1-(2-hydroxy-4,6-dimethoxyphenyl)ethanone
SMILES	CC(=O)C1=C(C=C(C=C1OC)OC)O
Standard InChIKey	FBUBVLUPUDBFME-UHFFFAOYSA-N
Standard InChI	InChI=1S/C10H12O4/c1-6(11)10-8(12)4-7(13-2)5-9(10)14-3/h4-5,12H,1-3H3
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 Xanthoxylin

The roots of Zanthoxylum simulans

Biological Activity of Xanthoxylin

Description	Xanthoxyline has antispasmodic, fungistatic, antinociceptive and antioedematogenic activities. Xanthoxylin has inhibitory effect on blood platelet aggregation; it induces melanogenesis mainly via cAMP-mediated PKA activation, other signaling pathways may also play a role in xanthoxylin-induced melanogenesis.
Targets	PKA \| cAMP \| PKC \| Antifection
In vitro	Effect of xanthoxylin on melanin content and melanogenic protein expression in B16F10 melanoma[Reference: WebLink] Asian Biomed., 2012, 6(3):413-22. Reduced production of melanin and decreased or absence of melanocytes leads to various hypopigmentation disorders. Melanin synthesis is regulated by melanogenic proteins such as tyrosinase, tyrosinase-related protein 1 (TRP-1) and tyrosinase-related protein 2 (TRP -2), as well as their transcription factors. This study elucidated the effects of Xanthoxylin on melanin content, dendriticity, melanogenic protein expression and its signal transduction pathways in mouse B16F10 melanoma cells (B16F10 cells). METHODS AND RESULTS: Melanin production of B16F10 cells was measured by using a melanin content assay. The effect of Xanthoxylin on the dendriticity of B16F10 cells was determined by a melanocyte dendricity assay. RT-PCR was used to investigate the effects of Xanthoxylin on the melanogenic protein expression. We found that Xanthoxylin increased melanin production, number of dendrites, tyrosinase, and microphthalmia-associated transcription factor (MITF) expression in cultured B16F10 cells. In addition, PKA and PKC inhibitor decreased melanin production, tyrosinase, and MITF expression in Xanthoxylin-treated cells. However, Xanthoxylin did not inhibit TRP-1 and TRP-2 expression. CONCLUSIONS: These results indicated that Xanthoxylin induces melanogenesis mainly via cAMP-mediated PKA activation. Other signaling pathways may also play a role in Xanthoxylin-induced melanogenesis. Antispasmodic activity of xanthoxyline derivatives: structure-activity relationships.[Pubmed: 7629739] J Pharm Sci. 1995 Apr;84(4):473-5. METHODS AND RESULTS: The antispasmodic activity of several Xanthoxyline derivatives against acetylcholine-induced contraction of the guinea pig ileum was evaluated in vitro. The acetophenones with two methoxyl groups, mainly in the 3,4 positions, exhibited potent antispasmodic activity. Modification of the hydroxyl group in Xanthoxyline by the introduction of benzoyl, acetyl, or tosyl groups produced inactive compounds, whereas the introduction of benzyl or p-methoxybenzyl groups furnished compounds that were four- to eight-fold more potent than Xanthoxyline. In marked contrast, the introduction of a methyl group gave a compound that caused contractant activity. Modification of the carbonyl group of Xanthoxyline lead to inactive compounds, whereas the condensation of Xanthoxyline with benzaldehydes gave chalkones that were about fivefold more potent than Xanthoxyline. The introduction of benzyl and styrene groups, on the basis of the similarity with papaverine, improves the antispasmodic action of the Xanthoxyline derivates. CONCLUSIONS: Our results suggest that the methoxyl and carbonyl groups are critical structural points for the antispasmodic activity of Xanthoxyline derivatives. The hydroxyl group improves antispasmodic activity, but is not fundamental to its manifestation. In vitro antifungal evaluation and studies on the mode of action of xanthoxyline derivatives.[Pubmed: 10635452] Arzneimittelforschung. 1999 Dec;49(12):1039-43. METHODS AND RESULTS: This study describes the fungistatic effect of Xanthoxyline (CAS 90-24-4) and its derivatives against a panel of yeasts, filamentous fungi and dermatophytes, by using the agar dilution method. Results indicated that simple structural modifications led to more potent derivatives, especially in relation with dermatophytes. The most active compound tested (10), which is a benzenesulphonyl derivative, was 12-fold more potent than Xanthoxyline itself against Trichophyton rubrum. CONCLUSIONS: The evaluation of the mode of action with the whole cell Neurospora crassa assay, suggested that some selected compounds may be acting by the inhibition of fungal cell-wall polymers synthesis or assembly.
In vivo	Inhibitory Effect of Xanthoxylin on Blood Platelet Aggregation in Rabbits.[Reference: WebLink] Traditional Chinese Drug Research & Clinical Pharmacology,2000, 11(6):352-3. Turbidimetry was used to examine the inhibitory effect of Xanthoxyin on adenosine diphosphate (ADP)-, arachidic acid (AA )- and thrombin-induced platelet aggregation in rabbits. METHODS AND RESULTS: In-vitro experiment showed that Xanthoxyin 0.037,0.l85,0.924,9.240,92.40μmol. L -1 , can significantly inhibit ADP-, AA- and thrombin-induced platelet aggregation. The inhibition rates were 22.4%-70.l%,l5.3%-68.2% and 25.8%-74.6% respectively. In-vivo experiment showed that Xanthoxylin (ig. 5 mg/kg) cand also inhibited ADP-, AA-and throbin-induced platelet aggregations. The inhibition rates were 2l.0%,35.7%,50.9% and 32.7% in ADP-induced group,23.2%,46.3%,52.4% and 4l.6% in AA-induced group, and 26.7%, 44.5%,6l.6% and 54.2% in thrombin-induced group respectively l5,30, 60 and 90 minutes after ig. Xanthoxylin.

Protocol of Xanthoxylin

Structure Identification

Zhong Yao Cai. 2014 Apr;37(4):608-10.

Chemical constituents of n-BuOH extract from Phyllanthus matsumurae.[Pubmed: 25345134]

To study the chemical constituents of n-BuOH extract from Phyllanthus matsumurae.
METHODS AND RESULTS:
Column chromatography was used for the isolation and purification. Spectroscopic methods including H-NMR, 13C-NMR and MS were used for the identification of structures. Six compounds were isolated from the n-BuOH extract of 75% alcohol extract of the whole plant and identified as ellagic acid (1), phyllanthuspermin B (2), phyllanthuspermin C (3), Xanthoxylin (4), hesperetin-7-O-[6-O-(alpha-L-rhamnopy ranosyl)] -beta-D-glucopyranoside (5) and 4-O-methylgallic acid (6).
CONCLUSIONS:
Compounds 2 - 6 are obtained from this plant for the first time.

Eur. J. Med. Chem., 1996, 31(10):833-9.

Synthesis of xanthoxyline derivatives with antinociceptive and antioedematogenic activities.[Reference: WebLink]

Synthesis of Xanthoxyline Derivatives with Antinociceptive and Antioedematogenic Activities.

Preparing Stock Solutions of Xanthoxylin

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	5.0968 mL	25.4842 mL	50.9684 mL	101.9368 mL	127.421 mL
5 mM	1.0194 mL	5.0968 mL	10.1937 mL	20.3874 mL	25.4842 mL
10 mM	0.5097 mL	2.5484 mL	5.0968 mL	10.1937 mL	12.7421 mL
50 mM	0.1019 mL	0.5097 mL	1.0194 mL	2.0387 mL	2.5484 mL
100 mM	0.051 mL	0.2548 mL	0.5097 mL	1.0194 mL	1.2742 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.

References on Xanthoxylin

[Chemical constituents of n-BuOH extract from Phyllanthus matsumurae].[Pubmed:25345134]

Zhong Yao Cai. 2014 Apr;37(4):608-10.

OBJECTIVE: To study the chemical constituents of n-BuOH extract from Phyllanthus matsumurae. METHODS: Column chromatography was used for the isolation and purification. Spectroscopic methods including H-NMR, 13C-NMR and MS were used for the identification of structures. RESULTS: Six compounds were isolated from the n-BuOH extract of 75% alcohol extract of the whole plant and identified as ellagic acid (1), phyllanthuspermin B (2), phyllanthuspermin C (3), Xanthoxylin (4), hesperetin-7-O-[6-O-(alpha-L-rhamnopy ranosyl)] -beta-D-glucopyranoside (5) and 4-O-methylgallic acid (6). CONCLUSION: Compounds 2 - 6 are obtained from this plant for the first time.

In vitro antifungal evaluation and studies on the mode of action of xanthoxyline derivatives.[Pubmed:10635452]

Arzneimittelforschung. 1999 Dec;49(12):1039-43.

This study describes the fungistatic effect of Xanthoxyline (CAS 90-24-4) and its derivatives against a panel of yeasts, filamentous fungi and dermatophytes, by using the agar dilution method. Results indicated that simple structural modifications led to more potent derivatives, especially in relation with dermatophytes. The most active compound tested (10), which is a benzenesulphonyl derivative, was 12-fold more potent than Xanthoxyline itself against Trichophyton rubrum. The evaluation of the mode of action with the whole cell Neurospora crassa assay, suggested that some selected compounds may be acting by the inhibition of fungal cell-wall polymers synthesis or assembly.

Antispasmodic activity of xanthoxyline derivatives: structure-activity relationships.[Pubmed:7629739]

J Pharm Sci. 1995 Apr;84(4):473-5.

The antispasmodic activity of several Xanthoxyline derivatives against acetylcholine-induced contraction of the guinea pig ileum was evaluated in vitro. The acetophenones with two methoxyl groups, mainly in the 3,4 positions, exhibited potent antispasmodic activity. Modification of the hydroxyl group in Xanthoxyline by the introduction of benzoyl, acetyl, or tosyl groups produced inactive compounds, whereas the introduction of benzyl or p-methoxybenzyl groups furnished compounds that were four- to eight-fold more potent than Xanthoxyline. In marked contrast, the introduction of a methyl group gave a compound that caused contractant activity. Modification of the carbonyl group of Xanthoxyline lead to inactive compounds, whereas the condensation of Xanthoxyline with benzaldehydes gave chalkones that were about fivefold more potent than Xanthoxyline. The introduction of benzyl and styrene groups, on the basis of the similarity with papaverine, improves the antispasmodic action of the Xanthoxyline derivates. Our results suggest that the methoxyl and carbonyl groups are critical structural points for the antispasmodic activity of Xanthoxyline derivatives. The hydroxyl group improves antispasmodic activity, but is not fundamental to its manifestation.

Description

Xanthoxylin (Xanthoxyline) is isolated from Zanthoxylum simulans. Xanthoxylin (Xanthoxyline) has antifungal and antispasmodic activities.

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