Vanillin
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
Common Name | Vanillin(F05551) |
2D Structure | |
Description | Vanillin is the primary component of the extract of the vanilla bean. Synthetic vanillin, instead of natural vanilla extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. It is used by the food industry as well as ethylvanillin.Artificial vanilla flavoring is a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, there has long been interest in the synthetic preparation of its predominant component. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. (Wiki). |
FRCD ID | F05551 |
CAS Number | 121-33-5 |
PubChem CID | 1183 |
Formula | C8H8O3 |
IUPAC Name | 4-hydroxy-3-methoxybenzaldehyde |
InChI Key | MWOOGOJBHIARFG-UHFFFAOYSA-N |
InChI | InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3 |
Canonical SMILES | COC1=C(C=CC(=C1)C=O)O |
Isomeric SMILES | COC1=C(C=CC(=C1)C=O)O |
Wikipedia | Vanillin |
Synonyms | 4-Hydroxy-3-methoxybenzaldehyde vanillin 121-33-5 Vanillaldehyde Vanillic aldehyde Vanilla p-Vanillin 2-Methoxy-4-formylphenol Vanilline Lioxin |
Classifies | Predicted: Veterinary Drug |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Benzenoids |
Class | Phenols |
Subclass | Methoxyphenols |
Intermediate Tree Nodes | Not available |
Direct Parent | Methoxyphenols |
Alternative Parents | |
Molecular Framework | Aromatic homomonocyclic compounds |
Substituents | Methoxyphenol - Hydroxybenzaldehyde - Anisole - Benzaldehyde - Benzoyl - Phenoxy compound - Phenol ether - Methoxybenzene - Alkyl aryl ether - Aryl-aldehyde - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Ether - Organooxygen compound - Aldehyde - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Aromatic homomonocyclic compound |
Description | This compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 152.149 |
Hydrogen Bond Donor Count | 1 |
Hydrogen Bond Acceptor Count | 3 |
Rotatable Bond Count | 2 |
Complexity | 135 |
Monoisotopic Mass | 152.047 |
Exact Mass | 152.047 |
XLogP | 1.2 |
Formal Charge | 0 |
Heavy Atom Count | 11 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.7465 |
Human Intestinal Absorption | HIA+ | 0.9954 |
Caco-2 Permeability | Caco2+ | 0.9065 |
P-glycoprotein Substrate | Non-substrate | 0.6592 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.8476 |
Non-inhibitor | 0.8664 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8820 |
Distribution | ||
Subcellular localization | Mitochondria | 0.9328 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7444 |
CYP450 2D6 Substrate | Non-substrate | 0.8552 |
CYP450 3A4 Substrate | Non-substrate | 0.6548 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.7125 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9643 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9662 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.7401 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9561 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8592 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9664 |
Non-inhibitor | 0.9442 | |
AMES Toxicity | Non AMES toxic | 0.9311 |
Carcinogens | Non-carcinogens | 0.8759 |
Fish Toxicity | High FHMT | 0.7007 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9242 |
Honey Bee Toxicity | High HBT | 0.7610 |
Biodegradation | Ready biodegradable | 0.7561 |
Acute Oral Toxicity | III | 0.8545 |
Carcinogenicity (Three-class) | Non-required | 0.5099 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -1.3461 | LogS |
Caco-2 Permeability | 1.3620 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.9642 | LD50, mol/kg |
Fish Toxicity | 1.7984 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.1291 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Expression of Gre2p improves tolerance of engineered xylose-fermenting Saccharomyces cerevisiae to glycolaldehyde under xylose metabolism. | Appl Microbiol Biotechnol | 2018 Sep | 30027490 |
Toasted vine-shoot chips as enological additive. | Food Chem | 2018 Oct 15 | 29784334 |
Evaluation of e-liquid toxicity using an open-source high-throughput screening assay. | PLoS Biol | 2018 Mar | 29584716 |
Changes in the Key Odorants and Aroma Profiles of Hamlin and Valencia OrangeJuices Not from Concentrate (NFC) during Chilled Storage. | J Agric Food Chem | 2018 Jul 18 | 29889522 |
Olfactory toxicity in rats following manganese chloride nasal instillation: Apilot study. | Neurotoxicology | 2018 Jan | 28917718 |
Vanillin biotechnology: the perspectives and future. | J Sci Food Agric | 2018 Aug 9 | 30094833 |
A colorimetric assay for vanillin detection by determination of the luminescence of o-toluidine condensates. | PLoS One | 2018 Apr 20 | 29677193 |
Vertical Leaching of Allelochemicals Affecting Their Bioactivity and theMicrobial Community of Soil. | J Agric Food Chem | 2017 Sep 13 | 28800227 |
Groove Binding of Vanillin and Ethyl Vanillin to Calf Thymus DNA. | J Fluoresc | 2017 Sep | 28547116 |
Effects of organic acids and essential oils blend on growth, gut microbiota,immune response and disease resistance of Pacific white shrimp (Litopenaeusvannamei) against Vibrio parahaemolyticus. | Fish Shellfish Immunol | 2017 Nov | 28882791 |
Homodimers of Vanillin and Apocynin Decrease the Metastatic Potential of HumanCancer Cells by Inhibiting the FAK/PI3K/Akt Signaling Pathway. | J Agric Food Chem | 2017 Mar 22 | 28248106 |
Simple synthesis of cobalt sulfide nanorods for efficient electrocatalyticoxidation of vanillin in food samples. | J Colloid Interface Sci | 2017 Mar 15 | 27951514 |
Low-dose acute vanillin is beneficial against harmaline-induced tremors in rats. | Neurol Res | 2017 Mar | 28095756 |
Facile Synthesis of Novel Vanillin Derivatives Incorporating aBis(2-hydroxyethyl)dithhioacetal Moiety as Antiviral Agents. | J Agric Food Chem | 2017 Jun 14 | 28545296 |
Porous calcium carbonate as a carrier material to increase the dissolution rateof poorly soluble flavouring compounds. | Food Funct | 2017 Apr 19 | 28295108 |
Impact of preharvest and postharvest alginate treatments enriched with vanillinon postharvest decay, biochemical properties, quality and sensory attributes oftable grapes. | Food Chem | 2017 Apr 15 | 27979175 |
Aldehyde Oxidase 4 Plays a Critical Role in Delaying Silique Senescence by Catalyzing Aldehyde Detoxification. | Plant Physiol | 2017 Apr | 28188272 |
Conditions Optimizing and Application of Laccase-mediator System (LMS) for theLaccase-catalyzed Pesticide Degradation. | Sci Rep | 2016 Oct 24 | 27775052 |
Airway epithelial cell exposure to distinct e-cigarette liquid flavorings revealstoxicity thresholds and activation of CFTR by the chocolate flavoring2,5-dimethypyrazine. | Respir Res | 2016 May 17 | 27184162 |
Assessment of Angelica sinensis (Oliv.) Diels as a repellent for personalprotection against mosquitoes under laboratory and field conditions in northernThailand. | Parasit Vectors | 2016 Jun 29 | 27357395 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Can degrade fibronectin, laminin, gelatins of type I, III, IV, and V; collagens III, IV, X, and IX, and cartilage proteoglycans. Activates procollagenase.
- Gene Name:
- MMP3
- Uniprot ID:
- P08254
- Molecular Weight:
- 53976.84 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]