2D Structure
3D Structure
| Properties | |
|---|---|
| PID | PID00069 |
| Mol. Weight | 120.151 g/mol |
| LogP | 1.78 |
| Water solubility | 0.0174 mol/L at 20 °C |
| Hydrogen Bond Donor | 0 |
| Hydrogen Bond Acceptor | 1 |
| Rotatable Bonds | 2 |
| XLogP3 | 1.8 |
| Identifiers | |
|---|---|
| Formula | C8H8O |
| PubChem CID | 998 |
| FEMA | 2874 |
| Flavor Profile | Berry, Geranium, Honey, Nut, Pungent |
| Smiles | O=CCc1ccccc1 |
| InChl Key | DTUQWGWMVIHBKE-UHFFFAOYSA-N |
| InChl | InChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2 |
| CAS Registry Number | 122-78-1 |
| IUPAC Systematic Name | 2-phenylacetaldehyde |
Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets
Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)
| English Name | Pinyin Name (Chinese Name) | Latin Name | Properties in TCM | merdians | View Graph |
|---|---|---|---|---|---|
| Ardisiae japonicae | Ai Di Cha(矮地茶) | Japanese Ardisia Herb | Mild,Pungent,Bitter | Spleen,Heart | View Graph |
| Artemisia argyi | Ai Ye(艾叶) | Argy Wormwood Leaf Equivalent plant: Artemisia mon | Warm,Pungent,Bitter | Lung,Spleen,Liver | View Graph |
| Styrax benzoin | An Xi Xiang(安息香) | Sumatra Snowbell Equivalent plant: Styrax tonkinen | Mild,Pungent,Bitter | Spleen,Heart | View Graph |
| Medicinal Indianmulberry | Ba Ji Tian(巴戟天) | Morindae Officinalis Radix | Warm, Pungent, Sweet | Lung, Bladder, Heart | View Graph |
| Rhizoma Typhonii | Bai Fu Zi(白附子) | rhizome of Giant Typhonium | Warm,Pungent,Sweet | Spleen,Liver,Heart | View Graph |
| Dahurian Angelica | Bai Zhi(白芷) | Angelicae Dahuricae Radix | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Barbed Skullcap | Ban Zhi Lian(半枝莲) | Scutellariae Barbatae Herba | Cold, Bitter, Pungent | Bladder, Spleen, Liver，Stomach | View Graph |
| Chinese Thorowax Equivalent plant: Bupleurum scorz | Chai Hu(柴胡) | Bupleuri Radix | Minor cold, Pungent, Bitter | Liver, Gallbladder, Lung | View Graph |
| Dichroa febrifuga | Chang Shan(常山) | Antifebrile Dichroa | Cold,Pungent,Bitter | Lung,Liver,Heart | View Graph |
| Centipeda minima | E Bu Shi Cao(鹅不食草) | Small Centipeda | Warm,Pungent | Spleen, Stomach, Kidney, Lung | View Graph |
| Chinese Nardostachys Equivalent plant: Nardostachy | Gan Song(甘松) | Nardostachyos Radix Et Rhizoma | Warm, Pungent, Sweet | Lung, Bladder, Heart | View Graph |
| Cassiabarktree Twig | Gui Zhi (桂枝) | Cinnamomi Ramulus | Warm, Pungent, Sweet | Lung, Bladder, Heart | View Graph |
| Safflower | Hong Hua (红花) | Carthami Flos | Warm,Pungent | Spleen, Stomach, Kidney, Lung | View Graph |
| bark of Officinal magnolia | Hou Pu(厚朴) | Magnoliae Officinalis Cortex | Warm, Pungent, Bitter | Spleen, Liver | View Graph |
| Brassica juncea | Jie Zi(芥子) | India Mustard Seed | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Bush Redpepper | La Jiao (辣椒) | Capsici Fructus | Hot, Pungent | Lung, Spleen, Stomach, Heart, Kidney | View Graph |
| Great Burdock Fruit | Niu Bang Zi(牛蒡子) | Arctii Fructus | Cold, Bitter, Pungent | Bladder, Spleen, Liver，Stomach | View Graph |
| Bugbane Equivalent plant: Cimicifuga dahurica, Ci | Sheng Ma(升麻) | Cimicifugae Rhizoma | Cold, Sweet, Pungent | Lung, Spleen, Large Intestine, Stomach | View Graph |
| Lepidium apetalum [Syn. Lepidium micranthum ] | Ting Li Zi(葶苈子) | Pepperweed Seed Equivalent plant: Descurainia sop | Extreme Cold,Pungent,Bitter | Lung,Bladder | View Graph |
| Curculigo orchioides | Xian Mao(仙茅) | Common Cruculigo | Hot,Pungent | Large Intestine, Stomach | View Graph |
| Paniculate Swallowwort | Xu Chang Qing(徐长卿) | Cynanchi Paniculati Radix Et Rhizoma | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Tokyo Violet | Zi Hua Di Ding (紫花地丁) | Peucedani Decursivi Radix | Cold, Pungent, Bitter | Liver, Heart, Lung | View Graph |
| Chuanxiong (Wallich Ligusticum) Equivalent plant | Chuan Xiong (川芎) | Ligusticum chuanxiong Hort | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers. Phenylacetaldehyde is responsible for the antibiotic activity of
maggot therapy.
phenylacetaldehyde are aromatic compounds found in a diverse range of fruit and other plant tissues.
Phenylacetaldehyde, a compound present in tomato fruit (14), is derived from phenylalanine by decarboxylation and oxidative removal of the amino group.
The gas phase isomerization of styrene oxide (STO) into phenylacetaldehyde (PhAD) in good yield and selectivity has been achieved using a steel tube
reactor as catalyst in an efficient and environmentally friendly process.
The aroma of pure substance can be described as honey-like, sweet, rose, green, grassy and is added to fragrances to impart hyacinth, narcissi, or rose
nuances.For similar reasons the compound can sometimes be found in flavored cigarettes and beverages.
Historically, before biotechnology approaches were developed, phenylacetaldehyde was also used to produce phenylalanine via the Strecker reaction as a step
in the production of aspartame sweetener.[1]
Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.
1. https://en.wikipedia.org/wiki/Phenylacetaldehyde
2. Kamimura, N., Goto, T., Takahashi, K., Kasai, D., Otsuka, Y., Nakamura, M., Masai, E A bacterial aromatic aldehyde dehydrogenase critical for the efficient catabolism of syringaldehyde[J]. Scientific Reports, 2017, 7: 44422.
3. Grosjean, Y., Rytz, R., Farine, J. P., Abuin, L., Cortot, J., Jefferis, G. S., Benton, R. An olfactory receptor for food-derived odours promotes male courtship in Drosophila[J]. Nature, 2011, 478(7368): 236.
4. Wightman F, Lighty D L. Identification of phenylacetic acid as a natural auxin in the shoots of higher plants[J]. Physiologia Plantarum, 1982, 55(1): 17-24.
5. Culler, L., Escudero, A., Cacho, J., Ferreira, V. Gas chromatography? olfactometry and chemical quantitative study of the aroma of six premium quality Spanish aged red wines[J]. Journal of Agricultural and Food Chemistry, 2004, 52(6): 1653-1660.
6. Tadmor, Y., Fridman, E., Gur, A., Larkov, O., Lastochkin, E., Ravid, U., Lewinsohn, E. Identification of malodorous, a wild species allele affecting tomato aroma that was selected against during domestication[J]. Journal of Agricultural and Food Chemistry, 2002, 50(7): 2005-2009.
7. Hayashi, S., Yagi, K., Ishikawa, T., Kawasaki, M., Asai, T., Picone, J., Ogawa, K. Emission of 2-phenylethanol from its -D-glucopyranoside and the biogenesis of these compounds from [2H8] L-phenylalanine in rose flowers[J]. Tetrahedron, 2004, 60(33): 7005-7013.
8. Hayashi, S., Yagi, K., Ishikawa, T., Kawasaki, M., Asai, T., Picone, J., Ogawa, K Emission of 2-phenylethanol from its -D-glucopyranoside and the biogenesis of these compounds from [2H8] L-phenylalanine in rose flowers[J]. Tetrahedron, 2004, 60(33): 7005-7013.
9. Pichersky E, Noel J P, Dudareva N. Biosynthesis of plant volatiles: nature's diversity and ingenuity[J]. Science, 2006, 311(5762): 808-811.
10. Cicconardi, F., Di Marino, D., Olimpieri, P. P., Arthofer, W., Schlick-Steiner, B. C., Steiner, F. M. Chemosensory adaptations of the mountain fly Drosophila nigrosparsa (Insecta: Diptera) through genomics and structural biologys lenses[J]. Scientific reports, 2017, 7: 43770.
11. Koh, E. I., Robinson, A. E., Bandara, N., Rogers, B. E., Henderson, J. P. Copper import in Escherichia coli by the yersiniabactin metallophore system[J]. Nature chemical biology, 2017, 13(9): 1016.
12. Widhalm, J. R., Gutensohn, M., Yoo, H., Adebesin, F., Qian, Y., Guo, L., Thimmapuram, J. Identification of a plastidial phenylalanine exporter that influences flux distribution through the phenylalanine biosynthetic network[J]. Nature communications, 2015, 6: 8142.
13. Widhalm J R, Gutensohn M, Yoo H, et al. Identification of a plastidial phenylalanine exporter that influences flux distribution through the phenylalanine biosynthetic network[J]. Nature communications, 2015, 6: 8142.
14. Spehr, M., Gisselmann, G., Poplawski, A., Riffell, J. A., Wetzel, C. H., Zimmer, R. K., Hatt, H. Identification of a testicular odorant receptor mediating human sperm chemotaxis[J]. Science, 2003, 299(5615): 2054-2058.
15. Kaminaga, Y., Schnepp, J., Peel, G., Kish, C. M., Ben-Nissan, G., Weiss, D., Porterfield, D. M. Plant phenylacetaldehyde synthase is a bifunctional homotetrameric enzyme that catalyzes phenylalanine decarboxylation and oxidation[J]. Journal of Biological Chemistry, 2006, 281(33): 23357-23366.
16. Payne, K. A., White, M. D., Fisher, K., Khara, B., Bailey, S. S., Parker, D., Barran, P. New cofactor supports , -unsaturated acid decarboxylation via 1, 3-dipolar cycloaddition[J]. Nature, 2015, 522(7557): 497.
17. Frost J R, Scully C C G, Yudin A K. Oxadiazole grafts in peptide macrocycles[J]. Nature Chemistry, 2016, 8(12): 1105-1111.
18. Goff S A, Klee H J. Plant volatile compounds: sensory cues for health and nutritional value?[J]. Science, 2006, 311(5762): 815-819.
19. Dong, G., Teo, P., Wickens, Z. K., Grubbs, R. H. Primary alcohols from terminal olefins: formal anti-Markovnikov hydration via triple relay catalysis[J]. Science, 2011, 333(6049): 1609-1612.
20. Terfassa, B., Nongwe, I., Ravat, V., Coville, N. J.. Selective gas phase isomerization of styrene oxide to phenylacetaldehyde in a steel tube reactor[J]. Reaction Kinetics, Mechanisms and Catalysis, 2017, 120(2): 543-554.
21. Folta K M, Klee H J. Sensory sacrifices when we mass-produce mass produce[J]. Horticulture research, 2016, 3: 16032.
22. Farhan, A., Gulati, J., Groe-Wilde, E., Vogel, H., Hansson, B. S., Knaden, M. The CCHamide 1 receptor modulates sensory perception and olfactory behavior in starved Drosophila[J]. Scientific reports, 2013, 3: 2765.
23. Mayuoni\Kirshinbaum L, Porat R. The flavor of pomegranate fruit: a review[J]. Journal of the Science of Food and Agriculture, 2014, 94(1): 21-27.
24. Harry J. Klee; Denise M. Tieman. The genetics of fruit flavour preferences.Nature Reviews Genetics. 2018,19(6):347.
25. Lin, Y., Qasim, M., Hussain, M., Akutse, K. S., Avery, P. B., Dash, C. K., Wang, L. The herbivore-induced plant volatiles methyl salicylate and menthol positively affect growth and pathogenicity of entomopathogenic fungi[J]. Scientific reports, 2017, 7: 40494.
26. Lin, Y., Hussain, M., Avery, P. B., Qasim, M., Fang, D., Wang, L. Volatiles from plants induced by multiple aphid attacks promote conidial performance of Lecanicillium lecanii[J]. PloS one, 2016, 11(3): e0151844.
27. Lin, Y., Qasim, M., Hussain, M., Akutse, K. S., Avery, P. B., Dash, C. K., Wang, L. The herbivore-induced plant volatiles methyl salicylate and menthol positively affect growth and pathogenicity of entomopathogenic fungi[J]. Scientific reports, 2017, 7: 40494.
28. Kaminaga, Y., Schnepp, J., Peel, G., Kish, C. M., Ben-Nissan, G., Weiss, D., Porterfield, D. M. Plant phenylacetaldehyde synthase is a bifunctional homotetrameric enzyme that catalyzes phenylalanine decarboxylation and oxidation[J]. Journal of Biological Chemistry, 2006, 281(33): 23357-23366.
29. Tieman, D. M., Loucas, H. M., Kim, J. Y., Clark, D. G., Klee, H. J. Tomato phenylacetaldehyde reductases catalyze the last step in the synthesis of the aroma volatile 2-phenylethanol[J]. Phytochemistry, 2007, 68(21): 2660-2669.
30. Cai, Jing, Pengjuan Zu, and Florian P. Schiestl. The molecular bases of floral scent evolution under artificial selection: insights from a transcriptome analysis in Brassica rapa. Scientific reports 6 (2016): 36966.
31. Wilmot, C. M., Hajdu, J., McPherson, M. J., Knowles, P. F., & Phillips, S. E. V. Visualization of dioxygen bound to copper during enzyme catalysis. Science 286.5445 (1999): 1724-1728.
32. Pavillard, E. R., and E. A. Wright. An antibiotic from maggots. Nature 180.4592 (1957): 916.