フェニルエチルアルコール
WordNet
- any of a series of volatile hydroxyl compounds that are made from hydrocarbons by distillation
- a liquor or brew containing alcohol as the active agent; "alcohol (or drink) ruined him" (同)alcoholic drink, alcoholic_beverage, intoxicant, inebriant
PrepTutorEJDIC
- 『アルコール』,酒精 / 『アルコール飲料』,酒
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/12/22 18:15:39」(JST)
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Phenethyl alcohol[1]
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| Names |
| IUPAC name
2-Phenylethanol
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Other names
Phenethyl alcohol
Benzyl carbinol
β-Hydroxyethylbenzene
Benzenethanol |
| Identifiers |
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CAS Number
|
60-12-8 Y |
| ChEBI |
CHEBI:49000 Y |
| ChEMBL |
ChEMBL448500 Y |
| ChemSpider |
5830 Y |
| DrugBank |
DB02192 Y |
| Jmol interactive 3D |
Image |
| PubChem |
6054 |
| UNII |
ML9LGA7468 Y |
InChI
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InChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2 Y
Key: WRMNZCZEMHIOCP-UHFFFAOYSA-N Y
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InChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
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InChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
Key: WRMNZCZEMHIOCP-UHFFFAOYSA-N
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| Properties |
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Chemical formula
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C8H10O |
| Molar mass |
122.16 g/mol |
| Odor |
Soft, like roses |
| Density |
1.017 g/cm3 |
| Melting point |
−27 °C (−17 °F; 246 K) |
| Boiling point |
219 to 221 °C (426 to 430 °F; 492 to 494 K) |
| Hazards |
| Safety data sheet |
JT Baker MSDS |
| NFPA 704 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Y verify (what is YN ?) |
| Infobox references |
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Phenethyl alcohol, or 2-phenylethanol, is the organic compound that consists of a phenethyl group (C6H5CH2CH2) group attached to OH. It is a colourless liquid that is slightly soluble in water (2 mL/100 mL H2O), but miscible with most organic solvents. It occurs widely in nature, being found in a variety of essential oils. It has a pleasant floral odor.
Contents
- 1 Synthesis
- 2 Occurrence and uses
- 3 See also
- 4 References
Synthesis
Phenethyl alcohol is prepared commercially via two routes. Most common is the Friedel-Crafts reaction between benzene and ethylene oxide in the presence of aluminium trichloride.
- C6H6 + CH2CH2O + AlCl3 → C6H5CH2CH2OAlCl2 + HCl
The reaction affords the aluminium alkoxide that is subsequently hydrolyzed to the desired product. The main side product is diphenylethane, which can be avoided by use of excess benzene. Hydrogenation of styrene oxide also affords phenethyl alcohol.[2]
Laboratory methods
Phenethyl alcohol can also be prepared by the reaction between phenylmagnesium bromide and ethylene oxide:
- C6H5MgBr + CH2CH2O → C6H5CH2CH2OMgBr
- C6H5CH2CH2OMgBr + H+ → C6H5CH2CH2OH
Phenethyl alcohol can also be produced by biotransformation from L-phenylalanine using immobilized yeast Saccharomyces cerevisiae.[3]
Occurrence and uses
Phenethyl alcohol is found in extract of rose, carnation, hyacinth, Aleppo pine, orange blossom, ylang-ylang, geranium, neroli, and champaca. It is also an autoantibiotic produced by the fungus Candida albicans[4]
It is therefore a common ingredient in flavors and perfumery, particularly when the odor of rose is desired.[2] It is used as an additive in cigarettes. It is also used as a preservative in soaps due to its stability in basic conditions. It is of interest due to its antimicrobial properties.
See also
- Congener
- Wine chemistry
- Phenethylamine
References
- ^ Merck Index (11th ed.). p. 7185.
- ^ a b Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, Dorothea; Surburg, Horst (2003). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_141. ISBN 978-3-527-30673-2.
- ^ Eshkol, N.; M. Sendovski M. Bahalul T. Katz-Ezov Y. Kashi & A. Fishman (2009). "Production of 2-phenylethanol from L-phenylalanine by a stress tolerant Saccharomyces cerevisiae strain" (PDF). Journal of Applied Microbiology 2 (106): 534–542. doi:10.1111/j.1365-2672.2008.04023.x. PMID 19200319. Retrieved 29 April 2013.
- ^ Lingappa, BT; Prasad, M; Lingappa, Y; Hunt, DF; Biemann, K (1969). "Phenethyl alcohol and tryptophol: Autoantibiotics produced by the fungus Candida albicans". Science 163 (3863): 192–4. doi:10.1126/science.163.3863.192. PMID 5762768.
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Alcohols
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Straight-chain
primary
alcohols (1°) |
- Methanol (C
1)
- Ethanol (C
2)
- 1-Propanol (C
3)
- n-Butanol (C
4)
- 1-Pentanol (C
5)
- 1-Hexanol (C
6)
- 1-Heptanol (C
7)
- 1-Octanol (C
8)
- 1-Nonanol (C
9)
- 1-Decanol (C
10)
- Undecanol (C
11)
- Dodecanol (C
12)
- Tridecan-1-ol (C
13)
- 1-Tetradecanol (C
14)
- Pentadecan-1-ol (C
15)
- Cetyl alcohol (C
16)
- Heptadecan-1-ol (C
17)
- Stearyl alcohol (C
18)
- Nonadecan-1-ol (C
19)
- Arachidyl alcohol (C
20)
- Heneicosan-1-ol (C
21)
- Docosanol (C
22)
- Tricosan-1-ol (C
23)
- 1-Tetracosanol (C
24)
- Pentacosan-1-ol (C
25)
- 1-Hexacosanol (C
26)
- 1-Heptacosanol (C
27)
- 1-Octacosanol (C
28)
- 1-Nonacosanol (C
29)
- Triacontanol (C
30)
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Other primary
alcohols |
- Isobutanol (C
4)
- Isoamyl alcohol (C
5)
- 2-Methyl-1-butanol (C
5)
- Phenethyl alcohol (C
8)
- Tryptophol (C
10)
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Secondary
alcohols (2°) |
- Isopropanol (C
3)
- 2-Butanol (C
4)
- 2-Pentanol (C
5)
- 2-Hexanol (C
6)
- 2-Heptanol (C
7)
- Cyclohexanol (C
6)
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Tertiary
alcohols (3°) |
- tert-Butyl alcohol (C
4)
- tert-Amyl alcohol (C
5)
- 2-Methyl-2-pentanol (C
6)
- 2-Methylhexan-2-ol (C
7)
- 2-Methylheptan-2-ol (C
8)
- 3-Methyl-3-pentanol (C
6)
- 3-Methyloctan-3-ol (C
9)
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UpToDate Contents
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English Journal
- Ability of human oral microbiota to produce wine odorant aglycones from odourless grape glycosidic aroma precursors.
- Muñoz-González C1, Cueva C1, Ángeles Pozo-Bayón M1, Victoria Moreno-Arribas M2.
- Food chemistry.Food Chem.2015 Nov 15;187:112-9. doi: 10.1016/j.foodchem.2015.04.068. Epub 2015 Apr 22.
- Grape aroma precursors are odourless glycosides that represent a natural reservoir of potential active odorant molecules in wines. Since the first step of wine consumption starts in the oral cavity, the processing of these compounds in the mouth could be an important factor in influencing aroma perc
- PMID 25977005
- Evaluation of the performance of Torulaspora delbrueckii, Williopsis saturnus, and Kluyveromyces lactis in lychee wine fermentation.
- Chen D1, Yap ZY1, Liu SQ2.
- International journal of food microbiology.Int J Food Microbiol.2015 Aug 3;206:45-50. doi: 10.1016/j.ijfoodmicro.2015.04.020. Epub 2015 Apr 18.
- This study evaluated the effects of three non-Saccharomyces yeasts, namely Torulaspora delbrueckii PRELUDE, Williopsis saturnus NCYC22, and Kluyveromyces lactis KL71 on lychee juice fermentation. The fermentation performance of these non-Saccharomyces yeasts was significantly different. T. delbrueck
- PMID 25955287
- The smelling of Hedione results in sex-differentiated human brain activity.
- Wallrabenstein I1, Gerber J2, Rasche S3, Croy I4, Kurtenbach S5, Hummel T6, Hatt H7.
- NeuroImage.Neuroimage.2015 Jun;113:365-73. doi: 10.1016/j.neuroimage.2015.03.029. Epub 2015 Mar 19.
- A large family of vomeronasal receptors recognizes pheromone cues in many animals including most amphibia, reptiles, rhodents, and other mammals. Humans possess five vomeronasal-type 1 receptor genes (VN1R1-VN1R5), which code for proteins that are functional in recombinant expression systems. We use
- PMID 25797832
Japanese Journal
- 3P-078 酵母Kluyveromyces marxianus 2-フェニルエタノール産生向上株にみられた代謝変動(代謝工学,一般講演)
- Chemical Compositions and Aroma Evaluation of Volatile Oil from the Industrial Cultivation Medium of <i>Enter</i><i>ococcus faecalis </i>
- Chemical Compositions and Aroma Evaluation of Volatile Oil from the Industrial Cultivation Medium of <i>Enter</i><i>ococcus faecalis</i>
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