ベンゾイン、安息香、アンソッコウ
WordNet
- gum resin used especially in treating skin irritation (同)gum_benzoin, benjamin, gum_benjamin, asa dulcis
- used in some classifications for the American spicebush and certain other plants often included in the genus Lindera (同)genus Benzoin
PrepTutorEJDIC
- 安息香(香水・化粧品に用いられる)
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/04/14 19:17:02」(JST)
[Wiki en表示]
Benzoin |
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IUPAC name
2-hydroxy-1,2-di(phenyl)ethanone
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Other names
2-hydroxy-2-phenylacetophenone, 2-hydroxy-1,2-diphenylethanone, desyl alcohol, bitter almond oil camphor
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Identifiers |
CAS number |
119-53-9 Y |
PubChem |
8400 |
ChemSpider |
8093 Y |
UNII |
L7J6A1NE81 Y |
KEGG |
C01408 Y |
ChEBI |
CHEBI:17682 Y |
ChEMBL |
CHEMBL190677 Y |
Jmol-3D images |
Image 1
Image 2 |
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O=C(c1ccccc1)C(O)c2ccccc2
c1ccc(cc1)C(C(=O)c2ccccc2)O
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InChI=1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H Y
Key: ISAOCJYIOMOJEB-UHFFFAOYSA-N Y
InChI=1/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H
Key: ISAOCJYIOMOJEB-UHFFFAOYAO
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Properties |
Molecular formula |
C14H12O2 |
Molar mass |
212.24 g mol−1 |
Appearance |
off-white crystals |
Density |
1.31 g/cm3 |
Melting point |
132–137 °C
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Boiling point |
344 °C
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Solubility in water |
Slightly Soluble |
Solubility in Chlorine |
Soluble |
Hazards |
NFPA 704 |
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Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
Infobox references |
Not to be confused with Benzoin resin.
Benzoin (pron.: /ˈbɛnzoʊ.ɨn/ or /-ɔɪn/) is an organic compound with the formula PhCH(OH)C(O)Ph. It is a hydroxy ketone attached to two phenyl groups. It appears as off-white crystals, with a light camphor-like odor. Benzoin is synthesized from benzaldehyde in the benzoin condensation. It is chiral and it exists as a pair of enantiomers: (R)-benzoin and (S)-benzoin.
Benzoin is not a constituent of benzoin resin obtained from the benzoin tree (Styrax) or tincture of benzoin. The main component in these natural products is benzoic acid.
Contents
- 1 History
- 2 Uses
- 3 References
- 4 External links
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History
Benzoin was first reported in 1832 by Justus von Liebig and Friedrich Woehler during their research on oil of bitter almond, which is benzaldehyde with traces of hydrocyanic acid.[1] The catalytic synthesis by the benzoin condensation was improved by Nikolay Zinin during his time with Liebig.[2][3]
Uses
The main uses of benzoin are as a precursor to benzil, which is a photoinitiator.[4] The conversion proceeds by organic oxidation using copper(II),[5] nitric acid, or oxone. In one study, this reaction is carried out with atmospheric oxygen and basic alumina in dichloromethane.[6]
References
- ^ Wöhler, Liebig; Liebig (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Pharmacie 3 (3): 249–282. doi:10.1002/jlac.18320030302.
- ^ N. Zinin (1839). "Beiträge zur Kenntniss einiger Verbindungen aus der Benzoylreihe". Annalen der Pharmacie 31 (3): 329–332. doi:10.1002/jlac.18390310312.
- ^ N. Zinin (1840). "Ueber einige Zersetzungsprodukte des Bittermandelöls". Annalen der Pharmacie 34 (2): 186–192. doi:10.1002/jlac.18400340205.
- ^ Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, 2002 by Wiley-VCH, Wienheim. doi:10.1002/14356007.a15_077
- ^ Clarke, H. T.; Dreger.E. E. (1941), "Benzil", Org. Synth. ; Coll. Vol. 1: 87
- ^ Konstantinos Skobridis, Vassiliki Theodorou, Edwin Weber (2006). "A very simple and chemoselective air oxidation of benzoins to benzils using alumina". Arkivoc. 06-1798JP: 102–106.
External links
- Benzoin synthesis, Organic Syntheses, Coll. Vol. 1, p.94 (1941); Vol. 1, p.33 (1921)
UpToDate Contents
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English Journal
- Synthesis, structure and theoretical investigation into a homoleptic tris(dithiolene) tungsten.
- Arifin K1, Minggu LJ1, Daud WR2, Yamin BM3, Daik R3, Kassim MB4.Author information 1Fuel Cell Institute, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia.2Fuel Cell Institute, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia; Department of Chemical and Process Engineering, Faculty of Engineering and Built Environment, University of Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia.3School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia.4Fuel Cell Institute, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia; School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia. Electronic address: mbkassim@ukm.my.AbstractA new homoleptic dithiolene tungsten complex, tris-{1,2-bis(3,5-dimethoxyphenyl)-1,2-ethylenodithiolene-S,S'}tungsten, was successfully synthesized via a reaction of the thiophosphate ester and sodium tungstate. The thiophosphate ester was prepared from 3,5-dimethoxybenzaldehyde via benzoin condensation to produce the intermediate 1,2-bis-(3,5-dimethoxyphenyl)-2-hydroxy-ethanone compound, followed by a reaction of the intermediate with phosphorus pentasulfide. FTIR, UV-Vis spectroscopy, (1)H NMR and (13)C NMR and elemental analysis confirmed the product as tris{1,2-bis-(3,5-dimethoxyphenyl)-1,2-ethylenodithiolene-S,S'}tungsten with the molecular formula of C54H54O12S6W. Crystals of the product adopted a monoclinic system with space group of P2(1)/n, where a=12.756(2)Å, b=21.560(3)Å, c=24.980(4)Å and β=103.998(3)°. Three thioester ligands were attached to the tungsten as bidentate chelates to form a distorted octahedral geometry. Density functional theory calculations were performed to investigate the molecular properties in a generalized-gradient approximation framework system using Perdew-Burke-Ernzerhof functions and a double numeric plus polarization basis set. The HOMO was concentrated on the phenyl ligands, while the LUMO was found along the W(S2C2)3 rings. The theoretical optical properties showed a slight blue shift in several low dielectric solvents. The solvatochromism effect was insignificant for high polar solvents.
- Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2014 Feb 24;120:208-15. doi: 10.1016/j.saa.2013.09.069. Epub 2013 Oct 16.
- A new homoleptic dithiolene tungsten complex, tris-{1,2-bis(3,5-dimethoxyphenyl)-1,2-ethylenodithiolene-S,S'}tungsten, was successfully synthesized via a reaction of the thiophosphate ester and sodium tungstate. The thiophosphate ester was prepared from 3,5-dimethoxybenzaldehyde via benzoin condensa
- PMID 24184623
- Catalytic Scope of the Thiamine-Dependent Multifunctional Enzyme Cyclohexane-1,2-dione Hydrolase.
- Loschonsky S, Waltzer S, Fraas S, Wacker T, Andrade SL, Kroneck PM, Müller M.Author information Institut für Pharmazeutische Wissenschaften, Albert-Ludwigs-Universität Freiburg, Albertstrasse 25, 79104 Freiburg (Germany).AbstractThe thiamine diphosphate (ThDP)-dependent enzyme cyclohexane-1,2-dione hydrolase (CDH) was expressed in Escherichia coli and purified by affinity chromatography (Ni-NTA). Recombinant CDH showed the same CC bond-cleavage and CC bond-formation activities as the native enzyme. Furthermore, we have shown that CDH catalyzes the asymmetric cross-benzoin reaction of aromatic aldehydes and (decarboxylated) pyruvate (up to quantitative conversion, 92-99 % ee). CDH accepts also hydroxybenzaldehydes and nitrobenzaldehydes; these previously have not (or only in rare cases) been known as substrates of other ThDP-dependent enzymes. On a semipreparative scale, sterically demanding 4-(tert-butyl)benzaldehyde and 2-naphthaldehyde were transformed into the corresponding 2-hydroxy ketone products in high yields. Additionally, certain benzaldehydes with electron withdrawing substituents were identified as potential inhibitors of the ligase activity of CDH.
- Chembiochem : a European journal of chemical biology.Chembiochem.2014 Jan 16. doi: 10.1002/cbic.201300673. [Epub ahead of print]
- The thiamine diphosphate (ThDP)-dependent enzyme cyclohexane-1,2-dione hydrolase (CDH) was expressed in Escherichia coli and purified by affinity chromatography (Ni-NTA). Recombinant CDH showed the same CC bond-cleavage and CC bond-formation activities as the native enzyme. Furthermore, we hav
- PMID 24436243
- 1-azadienes as regio- and chemoselective dienophiles in aminocatalytic asymmetric diels-alder reaction.
- Ma C, Gu J, Teng B, Zhou QQ, Li R, Chen YC.Author information Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu, Sichuan 610041, China, and College of Pharmacy, Third Military Medical University , Shapingba, Chongqing 400038, China.AbstractElectron-deficient 1-aza-1,3-butadienes containing a 1,2-benzoisothiazole-1,1-dioxide or 1,2,3-benzoxathiazine-2,2-dioxide motif act as regio- and chemoselective dienophiles in normal-electron-demand Diels-Alder reactions with HOMO-raised trienamines, rather than typical 4π-participation in inverse-electron-demand versions. The enantioenriched cycloadducts could be efficiently converted to spiro or fused frameworks with high structural and stereogenic complexity by a sequential aza-benzoin reaction or other transformations.
- Organic letters.Org Lett.2013 Dec 20;15(24):6206-9. doi: 10.1021/ol4030474. Epub 2013 Nov 11.
- Electron-deficient 1-aza-1,3-butadienes containing a 1,2-benzoisothiazole-1,1-dioxide or 1,2,3-benzoxathiazine-2,2-dioxide motif act as regio- and chemoselective dienophiles in normal-electron-demand Diels-Alder reactions with HOMO-raised trienamines, rather than typical 4π-participation in inverse
- PMID 24215629
Japanese Journal
- N-Heterocyclic Carbene-Catalyzed Benzoin Strategy for Divergent Synthesis of Cyclitol Derivatives from Alditols
- Development of Photobase Generator with Benzoin Derivatives and Its Application to Photosensitive Materials
- Photosensitivity Characteristics of UV Curable Organic-Inorganic Hybrids Sensitized with Benzoin Derivatives as Photobase Generators
- Journal of Photopolymer Science and Technology 27(2), 223-225, 2014
- NAID 130004678343
Related Links
- ベンゾイン(benzoin)は、芳香族に分類される有機化合物のひとつ。示性式は C6H5C( =O)CH(OH)C6H5、IUPAC命名法では2-ヒドロキシ-1,2-ジフェニルエタノン (2-hydroxy -1,2-diphenylethanone) と表される。ベンゾイン縮合の反応生成物として知られる。
- Benzoin (pron.: /ˈbɛnzoʊ.ɨn/ or /-ɔɪn/) is an organic compound with the formula PhCH(OH)C(O)Ph. It is a hydroxy ketone attached to two phenyl groups. It appears as off-white crystals, with a light camphor-like odor. Benzoin is synthesized ...
Related Pictures
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[★]
- 英
- benzoin
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- アンソッコウチンキ、安息香チンキ
- 関
- ベンゾイン、安息香
[★]
- 英
- benzoin, gum benzoin, gum benjamin
- 関
- ベンゾイン、アンソッコウ
[★]
- 英
- benzoin
- 関
- 安息香、アンソッコウ