Phenylacetaldehyde
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Basic Info
| Common Name | Phenylacetaldehyde(F05522) |
| 2D Structure | |
| Description | Phenylacetaldehyde is one important oxidation-related aldehyde. Exposure to styrene gives phenylacetaldehyde as a secondary metabolite. Styrene has been implicated as reproductive toxicant, neurotoxicant, or carcinogen in vivo or in vitro. Phenylacetaldehyde could be formed by diverse thermal reactions during the cooking process together with C8 compounds is identified as a major aroma- active compound in cooked pine mushroom. Phenylacetaldehyde is readily oxidized to phenylacetic acid. Therefore will eventually be hydrolyzed and oxidized to yield phenylacetic acid that will be excreted primarily in the urine in conjugated form. (A7898, A7899, A7900). Phenylacetaldehyde is an aromatic compound found in buckwheat, chocolate and many other foods and flowers. It is also responsible for the antibiotic activity of maggot therapy and it is also a compound that is added to cigarettes to improve their aroma. |
| FRCD ID | F05522 |
| CAS Number | 122-78-1 |
| PubChem CID | 998 |
| Formula | C8H8O |
| IUPAC Name | 2-phenylacetaldehyde |
| InChI Key | DTUQWGWMVIHBKE-UHFFFAOYSA-N |
| InChI | InChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2 |
| Canonical SMILES | C1=CC=C(C=C1)CC=O |
| Isomeric SMILES | C1=CC=C(C=C1)CC=O |
| Wikipedia | Phenylacetaldehyde |
| Synonyms |
2-phenylacetaldehyde
phenylacetaldehyde
Benzeneacetaldehyde
122-78-1
Hyacinthin
alpha-Tolualdehyde
Phenylethanal
2-Phenylethanal
Phenylacetic aldehyde
alpha-Toluic aldehyde
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Phenylacetaldehydes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenylacetaldehydes |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Phenylacetaldehyde - Alpha-hydrogen aldehyde - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aldehyde - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenylacetaldehydes. These are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 120.151 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 2 |
| Complexity | 82.6 |
| Monoisotopic Mass | 120.058 |
| Exact Mass | 120.058 |
| XLogP | 1.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 9 |
| 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+ | 0.9826 |
| Human Intestinal Absorption | HIA+ | 0.9909 |
| Caco-2 Permeability | Caco2+ | 0.9175 |
| P-glycoprotein Substrate | Non-substrate | 0.8161 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9608 |
| Non-inhibitor | 0.9868 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8610 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5919 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8249 |
| CYP450 2D6 Substrate | Non-substrate | 0.9402 |
| CYP450 3A4 Substrate | Non-substrate | 0.8189 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5562 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9404 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9502 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8683 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9593 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7643 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8888 |
| Non-inhibitor | 0.9741 | |
| AMES Toxicity | Non AMES toxic | 0.9139 |
| Carcinogens | Non-carcinogens | 0.5626 |
| Fish Toxicity | High FHMT | 0.7072 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9964 |
| Honey Bee Toxicity | High HBT | 0.7060 |
| Biodegradation | Ready biodegradable | 0.6159 |
| Acute Oral Toxicity | III | 0.9328 |
| Carcinogenicity (Three-class) | Non-required | 0.7290 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.3239 | LogS |
| Caco-2 Permeability | 1.9770 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8351 | LD50, mol/kg |
| Fish Toxicity | 0.3860 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.1622 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Strecker Aldehyde Formation in Wine: New Insights into the Role of Gallic Acid,Glucose, and Metals in Phenylacetaldehyde Formation. | J Agric Food Chem | 2018 Mar 14 | 28238260 |
| Role of α-Dicarbonyl Compounds in the Inhibition Effect of Reducing Sugars on theFormation of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. | J Agric Food Chem | 2017 Nov 22 | 29083168 |
| Engineering Eschericha coli for Enhanced Tyrosol Production. | J Agric Food Chem | 2017 Jun 14 | 28530096 |
| Comparative study on fermentation performance in the genome shuffled Candidaversatilis and wild-type salt tolerant yeast strain. | J Sci Food Agric | 2017 Jan | 27012958 |
| Application of chitooligosaccharides as antioxidants in beer to improve theflavour stability by protecting against beer staling during storage. | Biotechnol Lett | 2017 Feb | 27812822 |
| Effect of sugarcane molasses extract on the formation of2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in a model system. | Food Chem | 2016 Apr 15 | 26617035 |
| Identification and characterization of the aroma-impact components of Thai fishsauce. | J Agric Food Chem | 2015 Mar 18 | 25730550 |
| Functional characterization of SlscADH1, a fruit-ripening-associated short-chain alcohol dehydrogenase of tomato. | J Plant Physiol | 2012 Oct 15 | 22818888 |
| Engineering of a tyrosol-producing pathway, utilizing simple sugar and thecentral metabolic tyrosine, in Escherichia coli. | J Agric Food Chem | 2012 Feb 1 | 22225426 |
| Effect of oxygen on volatile and sensory characteristics of Cabernet Sauvignonduring secondary shelf life. | J Agric Food Chem | 2011 Nov 9 | 21954937 |
| Food volatile compounds facilitating HII mesophase formation: solubilization and stability. | J Agric Food Chem | 2011 May 25 | 21495722 |
| Essential oil of Terminalia chebula fruits as a repellent for the indian honeybee Apis florea. | Chem Biodivers | 2010 May | 20491085 |
| Recruits of the stingless bee Scaptotrigona pectoralis learn food odors from the nest atmosphere. | Naturwissenschaften | 2010 May | 20358172 |
| Comparison of tomatillo and tomato volatile compounds in the headspace byselected ion flow tube mass spectrometry (SIFT-MS). | J Food Sci | 2010 Apr | 20492278 |
| Influence of lipids in the generation of phenylacetaldehyde in wort-related modelsystems. | J Agric Food Chem | 2008 May 14 | 18386901 |
| Impact of forced-aging process on madeira wine flavor. | J Agric Food Chem | 2008 Dec 24 | 19053377 |
| Insect odour perception: recognition of odour components by flower foragingmoths. | Proc Biol Sci | 2006 Aug 22 | 16846910 |
| Kinetics of oxidative degradation of white wines and how they are affected byselected technological parameters. | J Agric Food Chem | 2002 Oct 9 | 12358460 |
| Formation of aroma-active strecker-aldehydes by a direct oxidative degradation ofAmadori compounds. | J Agric Food Chem | 2000 Sep | 10995354 |
| Quantitative model studies on the formation of aroma-active aldehydes and acidsby strecker-type reactions. | J Agric Food Chem | 2000 Feb | 10691653 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 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 ]