Vanillyl alcohol

CAS# 498-00-0

Vanillyl alcohol

Catalog No. BCN3832----Order now to get a substantial discount!

Product Name & Size Price Stock
Vanillyl alcohol: 5mg $12 In Stock
Vanillyl alcohol: 10mg Please Inquire In Stock
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Quality Control of Vanillyl alcohol

Number of papers citing our products

Chemical structure

Vanillyl alcohol

3D structure

Chemical Properties of Vanillyl alcohol

Cas No. 498-00-0 SDF Download SDF
PubChem ID 62348 Appearance Powder
Formula C8H10O3 M.Wt 154.17
Type of Compound Miscellaneous Storage Desiccate at -20°C
Solubility DMSO : 125 mg/mL (810.85 mM; Need ultrasonic)
Chemical Name 4-(hydroxymethyl)-2-methoxyphenol
SMILES COC1=C(C=CC(=C1)CO)O
Standard InChIKey ZENOXNGFMSCLLL-UHFFFAOYSA-N
Standard InChI InChI=1S/C8H10O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,9-10H,5H2,1H3
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 Vanillyl alcohol

The herbs of Gastrodia elata Bl.

Biological Activity of Vanillyl alcohol

DescriptionVanillyl alcohol possesses anti-angiogenic, anticonvulsive, anti-inflammatory, anti-oxidant, neuroprotective, and anti-nociceptive activities. Vanillyl alcohol can effectively inhibit the cytotoxicity and improved cell viability in 1-methyl-4-phenylpyridinium (MPP+)-induced MN9D dopaminergic cells, it also can attenuate the elevation of reactive oxygen species (ROS) levels, decrease in the Bax/Bcl-2 ratio and poly (ADP-ribose) polymerase proteolysis.
TargetsROS | PARP | Bcl-2/Bax
In vitro

Specificity of maltase to maltose in three different directions of reaction: hydrolytic, vanillyl alcohol glucoside and vanillyl alcohol isomaltoside synthesis.[Pubmed: 22927369]

Biotechnol Prog. 2012 Nov-Dec;28(6):1450-6.

Vanillyl alcohol glucoside is very attractive molecule due to its very powerful physiological activity.
METHODS AND RESULTS:
In this article, a detailed kinetic study of transglucosylation of Vanillyl alcohol was performed. It was demonstrated that this reaction is very efficient (selectivity factor is 149) and occurred by a ping-pong mechanism with inhibition by glucose acceptor. At low concentration of Vanillyl alcohol one additional transglucosylation product was detected. Its structure was determined to be α-isomaltoside of Vanillyl alcohol, indicating that Vanillyl alcohol glucoside is a product of the first transglucosylation reaction and a substrate for second, so the whole reaction mechanism was proposed.
CONCLUSIONS:
It was demonstrated that the rate of isomaltoside synthesis is two orders of magnitude smaller than glucoside synthesis, and that maltase has interestingly high K(m) value to maltose when Vanillyl alcohol glucoside is second transglucosylation substrate.

Ultrasonographic Imaging and Anti-inflammatory Therapy of Muscle and Tendon Injuries Using Polymer Nanoparticles.[Pubmed: 28744328 ]

Theranostics. 2017 Jun 24;7(9):2463-2476.

Ultrasonography is a reliable diagnostic modality for muscle and tendon injuries, but it has been challenging to find right diagnosis of minor musculoskeletal injuries by conventional ultrasonographic imaging.
METHODS AND RESULTS:
A large amount of hydrogen peroxide (H2O2) are known to be generated during tissue damages such as mechanical injury and therefore H2O2 holds great potential as a diagnostic and therapeutic marker for mechanical injuries in the musculoskeletal system. We previously developed poly(Vanillyl alcohol-co-oxalate) (PVAX), which rapidly scavenges H2O2 and exerts antioxidant and anti-inflammatory activity in H2O2-associated diseases. Based on the notion that PVAX nanoparticles generate CO2 bubbles through H2O2-triggered hydrolysis, we postulated that PVAX nanoparticles could serve as ultrasonographic contrast agents and therapeutic agents for musculoskeletal injuries associated with overproduction of H2O2. In the agarose gel phantom study, PVAX nanoparticles continuously generated CO2 bubbles to enhance ultrasonographic echogenicity significantly. Contusion injury significantly elevated the level of H2O2 in skeletal muscles and Achilles tendons. Upon intramuscular injection, PVAX nanoparticles significantly elevated the ultrasound contrast and suppressed inflammation and apoptosis in the contusion injury of musculoskeletal systems.
CONCLUSIONS:
We anticipate that PVAX nanoparticles hold great translational potential as theranostic agents for musculoskeletal injuries.

Protocol of Vanillyl alcohol

Cell Research

Neuroprotective effects of vanillyl alcohol in Gastrodia elata Blume through suppression of oxidative stress and anti-apoptotic activity in toxin-induced dopaminergic MN9D cells.[Pubmed: 21705974 ]

Molecules, 2011, 16(7):5349-61.

Gastrodia elata Blume (GE) has long been used in oriental countries as a traditional herbal medicine to relieve symptoms associated with neurological ailments such as vertigo, general paralysis and epilepsy.
METHODS AND RESULTS:
In this study, we have investigated the effects of GE extracts and its major bioactive components on 1-methyl-4-phenylpyridinium (MPP+)-treated MN9D dopaminergic cells, a classic in vitro model for Parkinson's disease (PD). We found that Vanillyl alcohol effectively inhibited the cytotoxicity and improved cell viability in MPP+-induced MN9D dopaminergic cells. The underlying mechanisms of Vanillyl alcohol action were also studied. Vanillyl alcohol attenuated the elevation of reactive oxygen species (ROS) levels, decreased in the Bax/Bcl-2 ratio and poly (ADP-ribose) polymerase proteolysis.
CONCLUSIONS:
These results indicate that Vanillyl alcohol protected dopaminergic MN9D cells against MPP+-induced apoptosis by relieving oxidative stress and modulating the apoptotic process and is therefore a potential candidate for treatment of neurodegenerative diseases such as Parkinson's disease.

Vanillyl alcohol Dilution Calculator

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Vanillyl alcohol Molarity Calculator

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Preparing Stock Solutions of Vanillyl alcohol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.4863 mL 32.4317 mL 64.8635 mL 129.7269 mL 162.1587 mL
5 mM 1.2973 mL 6.4863 mL 12.9727 mL 25.9454 mL 32.4317 mL
10 mM 0.6486 mL 3.2432 mL 6.4863 mL 12.9727 mL 16.2159 mL
50 mM 0.1297 mL 0.6486 mL 1.2973 mL 2.5945 mL 3.2432 mL
100 mM 0.0649 mL 0.3243 mL 0.6486 mL 1.2973 mL 1.6216 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 Vanillyl alcohol

Neuroprotective effects of vanillyl alcohol in Gastrodia elata Blume through suppression of oxidative stress and anti-apoptotic activity in toxin-induced dopaminergic MN9D cells.[Pubmed:21705974]

Molecules. 2011 Jun 24;16(7):5349-61.

Gastrodia elata Blume (GE) has long been used in oriental countries as a traditional herbal medicine to relieve symptoms associated with neurological ailments such as vertigo, general paralysis and epilepsy. In this study, we have investigated the effects of GE extracts and its major bioactive components on 1-methyl-4-phenylpyridinium (MPP+)-treated MN9D dopaminergic cells, a classic in vitro model for Parkinson's disease (PD). We found that Vanillyl alcohol effectively inhibited the cytotoxicity and improved cell viability in MPP+-induced MN9D dopaminergic cells. The underlying mechanisms of Vanillyl alcohol action were also studied. Vanillyl alcohol attenuated the elevation of reactive oxygen species (ROS) levels, decreased in the Bax/Bcl-2 ratio and poly (ADP-ribose) polymerase proteolysis. These results indicate that Vanillyl alcohol protected dopaminergic MN9D cells against MPP+-induced apoptosis by relieving oxidative stress and modulating the apoptotic process and is therefore a potential candidate for treatment of neurodegenerative diseases such as Parkinson's disease.

Specificity of maltase to maltose in three different directions of reaction: hydrolytic, vanillyl alcohol glucoside and vanillyl alcohol isomaltoside synthesis.[Pubmed:22927369]

Biotechnol Prog. 2012 Nov-Dec;28(6):1450-6.

Vanillyl alcohol glucoside is very attractive molecule due to its very powerful physiological activity. In this article, a detailed kinetic study of transglucosylation of Vanillyl alcohol was performed. It was demonstrated that this reaction is very efficient (selectivity factor is 149) and occurred by a ping-pong mechanism with inhibition by glucose acceptor. At low concentration of Vanillyl alcohol one additional transglucosylation product was detected. Its structure was determined to be alpha-isomaltoside of Vanillyl alcohol, indicating that Vanillyl alcohol glucoside is a product of the first transglucosylation reaction and a substrate for second, so the whole reaction mechanism was proposed. It was demonstrated that the rate of isomaltoside synthesis is two orders of magnitude smaller than glucoside synthesis, and that maltase has interestingly high K(m) value to maltose when Vanillyl alcohol glucoside is second transglucosylation substrate.

Description

Vanillyl alcohol (p-(Hydroxymethyl)guaiacol), derived from vanillin, is a phenolic alcohol and is used as a flavoring agent in foods and beverages.

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