Isovanillin

CAS# 621-59-0

Isovanillin

Catalog No. BCN2502----Order now to get a substantial discount!

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Isovanillin: 5mg $23 In Stock
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Quality Control of Isovanillin

Number of papers citing our products

Chemical structure

Isovanillin

3D structure

Chemical Properties of Isovanillin

Cas No. 621-59-0 SDF Download SDF
PubChem ID 12127 Appearance Powder
Formula C8H8O3 M.Wt 152.15
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 3-hydroxy-4-methoxybenzaldehyde
SMILES COC1=C(C=C(C=C1)C=O)O
Standard InChIKey JVTZFYYHCGSXJV-UHFFFAOYSA-N
Standard InChI InChI=1S/C8H8O3/c1-11-8-3-2-6(5-9)4-7(8)10/h2-5,10H,1H3
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 Isovanillin

The barks of Pinus yunnanensis

Biological Activity of Isovanillin

DescriptionIsovanillin is a reversible inhibitor of aldehyde oxidase. It is largely used as pharmaceutical intermediates and also applied in food and beverage industry, synthetic fragrances, chemical. Isovanillin is a selective inhibitor of aldehyde oxidase, is metabolized by aldehyde dehydrogenase into isovanillic acid ,and the LD50 (rat, ipr) is 1276 mg/kg.
Targets5-HT Receptor | AChR
In vivo

Antidiarrheal activities of isovanillin, iso-acetovanillon and Pycnocycla spinosa Decne ex.Boiss extract in mice.[Pubmed: 25657776]

Res Pharm Sci. 2014 Mar-Apr;9(2):83-9.

Isovanillin and iso-acetovanillon are two phenolic components isolated from a number of plants including Pycnocycla spinosa. P. spinosa extract has antispasmodic and antidiarrheal activities. However, no comparative study has been done on antidiarrheal action of Isovanillin and iso- acetovanillon, so far. The aim of this study was to investigate antidiarrheal action of Isovanillin and iso-acetovanillon and their effects on small intestinal transit, for comparison with propantheline.
METHODS AND RESULTS:
Male mice (25-30 g), fasted over night with free access to water, were treated with test compounds or control (p.o.). Thirty min later castor oil (0.5 ml) was given orally to the animals. In another groups of animals MgSO4 (0.5 ml of 10% solution) was given first and half an hour later the test drugs were administered. Onset and number of wet defecations were recorded for each animal over 3.5 h after treatment with diarrhoea inducing agents. In another groups, intestinal transit of charcoal meal was determined following administration of the compounds. Isovanillin (2 mg/kg & 5 mg/kg), iso-acetovanillon (2 mg/kg & 5 mg/kg) and P. spinosa extract (5 mg/kg) delayed onset of diarrhoea and significantly reduced wet defecation induced by castor oil and MgSO4. They all had antidiarrheal effect similar to propantheline (5 mg/kg). Isovanillin, iso-acetovanillon and P. spinosa extract compared to control groups, significantly reduced small intestinal transit of charcoal meal.
CONCLUSIONS:
This study shows that antidiarrheal effect of P. spinosa extract is at least partially due to presence of two active compounds Isovanillin and iso-acetovanillon.

Protocol of Isovanillin

Animal Research

Antispasmodic activity of isovanillin and isoacetovanillon in comparison with Pycnocycla spinosa Decne.exBoiss extract on rat ileum.[Pubmed: 25657788]

Res Pharm Sci. 2014 May-Jun;9(3):187-92.

Isovanillin and isoacetovanillon are two components found in P. spinosa Decne.exBoiss extract with no previously reported effect on ileum contractions.
METHODS AND RESULTS:
Spasmolytic effect of Isovanillin and isoacetovanillon were examined on response to electrical field stimulation (EFS), acetylcholine (ACh) and 5-HT in strips of rat ileum. Longitudinal ileum strips were set up in an organ bath containing oxygenated Tyrode's solution. All strips that was contracted in response to EFS, acetylcholine or 5-HT showed relaxation in the presence of Isovanillin (5-320 μg/ml), or isoacetovanillon (5-320 μg/ml). Isovanillin and isoacetovanillon inhibited the response to 5-HT with IC50 values of 356±50μM and 622±110μM respectively. They reduced the response to EFS without significantly affecting the acetylcholine response. P. spinosa extract (5-160 μg/ml) in a concentration dependent manner reduced the response to 5-HT, acetylcholine and EFS.
CONCLUSIONS:
This study demonstrated that Isovanillin and isoacetovanillon are relaxant of ileum contractions induced by 5-HT and EFS and they have contribution to the relaxant effect of P. spinosa extract but other components are responsible for the inhibition of acetylcholine by the extract.

Structure Identification
Org Biomol Chem. 2014 Apr 28;12(16):2552-8.

Isovanillin derived N-(un)substituted hydroxylamines possessing an ortho-allylic group: valuable precursors to bioactive N-heterocycles.[Pubmed: 24576957]


METHODS AND RESULTS:
The intramolecular 1,3-dipolar cycloaddition of Isovanillin derived N-aryl hydroxylamines possessing ortho-allylic dipolarophiles affords novel benzo analogues of tricyclic isoxazolidines that can be readily transformed into functionalized lactams, γ-aminoalcohols and oxazepines. The corresponding N-unsubstituted hydroxylamines give rise to tetrahydroisoquinolines.
CONCLUSIONS:
Anxiogenic properties of these compounds are tested in zebra fish.

Isovanillin Dilution Calculator

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Isovanillin Molarity Calculator

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Preparing Stock Solutions of Isovanillin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.5725 mL 32.8623 mL 65.7246 mL 131.4492 mL 164.3115 mL
5 mM 1.3145 mL 6.5725 mL 13.1449 mL 26.2898 mL 32.8623 mL
10 mM 0.6572 mL 3.2862 mL 6.5725 mL 13.1449 mL 16.4312 mL
50 mM 0.1314 mL 0.6572 mL 1.3145 mL 2.629 mL 3.2862 mL
100 mM 0.0657 mL 0.3286 mL 0.6572 mL 1.3145 mL 1.6431 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 Isovanillin

Isovanillin derived N-(un)substituted hydroxylamines possessing an ortho-allylic group: valuable precursors to bioactive N-heterocycles.[Pubmed:24576957]

Org Biomol Chem. 2014 Apr 28;12(16):2552-8.

The intramolecular 1,3-dipolar cycloaddition of Isovanillin derived N-aryl hydroxylamines possessing ortho-allylic dipolarophiles affords novel benzo analogues of tricyclic isoxazolidines that can be readily transformed into functionalized lactams, gamma-aminoalcohols and oxazepines. The corresponding N-unsubstituted hydroxylamines give rise to tetrahydroisoquinolines. Anxiogenic properties of these compounds are tested in zebra fish.

Antispasmodic activity of isovanillin and isoacetovanillon in comparison with Pycnocycla spinosa Decne.exBoiss extract on rat ileum.[Pubmed:25657788]

Res Pharm Sci. 2014 May-Jun;9(3):187-92.

Isovanillin and isoacetovanillon are two components found in P. spinosa Decne.exBoiss extract with no previously reported effect on ileum contractions. Spasmolytic effect of Isovanillin and isoacetovanillon were examined on response to electrical field stimulation (EFS), acetylcholine (ACh) and 5-HT in strips of rat ileum. Longitudinal ileum strips were set up in an organ bath containing oxygenated Tyrode's solution. All strips that was contracted in response to EFS, acetylcholine or 5-HT showed relaxation in the presence of Isovanillin (5-320 mug/ml), or isoacetovanillon (5-320 mug/ml). Isovanillin and isoacetovanillon inhibited the response to 5-HT with IC50 values of 356+/-50muM and 622+/-110muM respectively. They reduced the response to EFS without significantly affecting the acetylcholine response. P. spinosa extract (5-160 mug/ml) in a concentration dependent manner reduced the response to 5-HT, acetylcholine and EFS. This study demonstrated that Isovanillin and isoacetovanillon are relaxant of ileum contractions induced by 5-HT and EFS and they have contribution to the relaxant effect of P. spinosa extract but other components are responsible for the inhibition of acetylcholine by the extract.

Antidiarrheal activities of isovanillin, iso-acetovanillon and Pycnocycla spinosa Decne ex.Boiss extract in mice.[Pubmed:25657776]

Res Pharm Sci. 2014 Mar-Apr;9(2):83-9.

Isovanillin and iso-acetovanillon are two phenolic components isolated from a number of plants including Pycnocycla spinosa. P. spinosa extract has antispasmodic and antidiarrheal activities. However, no comparative study has been done on antidiarrheal action of Isovanillin and iso- acetovanillon, so far. The aim of this study was to investigate antidiarrheal action of Isovanillin and iso-acetovanillon and their effects on small intestinal transit, for comparison with propantheline. Male mice (25-30 g), fasted over night with free access to water, were treated with test compounds or control (p.o.). Thirty min later castor oil (0.5 ml) was given orally to the animals. In another groups of animals MgSO4 (0.5 ml of 10% solution) was given first and half an hour later the test drugs were administered. Onset and number of wet defecations were recorded for each animal over 3.5 h after treatment with diarrhoea inducing agents. In another groups, intestinal transit of charcoal meal was determined following administration of the compounds. Isovanillin (2 mg/kg & 5 mg/kg), iso-acetovanillon (2 mg/kg & 5 mg/kg) and P. spinosa extract (5 mg/kg) delayed onset of diarrhoea and significantly reduced wet defecation induced by castor oil and MgSO4. They all had antidiarrheal effect similar to propantheline (5 mg/kg). Isovanillin, iso-acetovanillon and P. spinosa extract compared to control groups, significantly reduced small intestinal transit of charcoal meal. This study shows that antidiarrheal effect of P. spinosa extract is at least partially due to presence of two active compounds Isovanillin and iso-acetovanillon.

Description

Isovanillin is an aldehyde oxidase inhibitor. Antispasmodic activities. Antidiarrheal activities.

Keywords:

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