安息香酸ベンジル
WordNet
- any salt or ester of benzoic acid
- the univalent radical derived from toluene (同)benzyl_group, benzyl radical
PrepTutorEJDIC
- 安息香酸の塩またはエステル
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/25 23:39:17」(JST)
[Wiki en表示]
Benzyl benzoate
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| Names |
| Other names
Ascabin, Ascabiol, Ascarbin, Benzylate, Scabanca, Tenutex, Vanzoate, Venzoate, Benzoic acid phenylmethyl ester, Benzy alcohol benzoic ester
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| Identifiers |
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CAS Number
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120-51-4 Y |
| Abbreviations |
BnBzO |
| ChEBI |
CHEBI:41237 Y |
| ChEMBL |
ChEMBL1239 Y |
| ChemSpider |
13856959 Y |
| DrugBank |
DB02775 Y |
| Jmol 3D model |
Interactive image |
| KEGG |
D01138 Y |
| PubChem |
2345 |
| UNII |
N863NB338G Y |
InChI
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InChI=1S/C14H12O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1-10H,11H2 Y
Key: SESFRYSPDFLNCH-UHFFFAOYSA-N Y
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InChI=1/C14H12O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1-10H,11H2
Key: SESFRYSPDFLNCH-UHFFFAOYAD
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| Properties |
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Chemical formula
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C14H12O2 |
| Molar mass |
212.25 g·mol−1 |
| Appearance |
Colorless liquid |
| Odor |
faint aromatic |
| Density |
1.118 g/cm3 |
| Melting point |
18 °C (64 °F; 291 K) |
| Boiling point |
323 °C (613 °F; 596 K) |
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Solubility in water
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insoluble |
| Solubility |
miscible in alcohol, chloroform, ether, oils
soluble in acetone, benzene
insoluble in glycerol |
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Refractive index (nD)
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1.5681 (21 °C) |
| Pharmacology |
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ATC code
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P03AX01 (WHO) QP53AX11 (WHO) |
| Hazards |
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EU classification (DSD)
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Harmful (Xn) |
| NFPA 704 |
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| Flash point |
158 °C (316 °F) (closed cup) |
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Autoignition
temperature
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481 °C (898 °F; 754 K) |
| Lethal dose or concentration (LD, LC): |
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LD50 (median dose)
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1700 mg/kg (rat, oral) |
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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Benzyl benzoate is an organic compound with the formula C6H5CH2O2CC6H5. It is the ester of benzyl alcohol and benzoic acid. It forms either a viscous liquid or solid flakes and has a weak, sweet-balsamic odor. It occurs in a number of blossoms (e. g. tuberose, hyacinth) and is a component of Balsam of Peru and Tolu balsam.[1][2]
It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[3]
Contents
- 1 Uses
- 2 Side effects
- 3 Production
- 4 References
Uses
Benzyl benzoate is used as an acaricide, scabicide, and pediculicide in veterinary hospitals. It is also a repellent for chiggers, ticks, and mosquitoes.[4] It is an effective and inexpensive topical treatment for human scabies.[5] It has vasodilating and spasmolytic effects and is present in many asthma and whooping cough drugs.[6]
Benzyl benzoate is also used as a dye carrier, solvent for cellulose derivatives, plasticizer, and fixative in the perfume industry.[1]
Side effects
Benzyl benzoate has low acute toxicity in laboratory animals. It is rapidly hydrolyzed to benzoic acid and benzyl alcohol, which are subsequently metabolized to benzoic acid. The conjugates of benzoic acid are rapidly eliminated in urine. When given in large doses to laboratory animals, benzyl benzoate can cause hyperexcitation, loss of coordination, ataxia, convulsions, and respiratory paralysis.[4]
Benzyl benzoate is irritant to the skin.[5]
Production
Benzyl benzoate is produced industrially by the reaction of sodium benzoate with benzyl alcohol in the presence of a base, or by transesterification of methylbenzoate and benzyl alcohol.[6] It is a byproduct of benzoic acid synthesis by toluene oxidation.[1] It can also be synthesized by the Tishchenko reaction, using benzaldehyde with sodium benzylate and aluminium benzylate as catalysts:[7]
- 2 PhCHO → PhCH2O2CPh
References
- ^ a b c Takao Maki; et al. (2007), "Benzoic Acid and Derivatives", Ullman's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 6
- ^ Karl-Georg Fahlbusch; et al. (2007), "Flavors and Fragrances", Ullman's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 59
- ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ^ a b Jamaluddin Shaikh (2005), "Benzyl Benzoate", in Philip Wexler, Encyclopedia of Toxicology 1 (2nd ed.), Elsevier, pp. 264–265
- ^ a b D.A. Burns (2010), "Diseases Caused by Arthropods and Other Noxious Animals", in Tony Burns; et al., Rook's Textbook of Dermatology 2 (8th ed.), Wiley-Blackwell, p. 38.41
- ^ a b Friedrich Brühne, Elaine Wright (2007), "Benzyl Alcohol", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 7
- ^ Friedrich Brühne, Elaine Wright (2007), "Benzaldehyde", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 3
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Ectoparasiticides / arthropod (P03A)
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| Insecticide/pediculicide |
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Chlorine-containing products
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Chloride channel
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Organophosphate
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| Acaricide/miticide/scabicide |
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Pyrethrines
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- Permethrin#
- Pyrethrum
- Phenothrin
- Bioallethrin
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Chloride channel
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Sulfur-containing products
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- Disulfiram
- Dixanthogen
- Mesulfen
- Thiram
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Chlorine-containing products
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Benzoate
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Organophosphate
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Other/ungrouped
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- Dimethicone
- Quassia
- toluidine (Crotamiton)
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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UpToDate Contents
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English Journal
- The utility of three-dimensional optical projection tomography in nerve injection injury imaging.
- Cvetko E1, Čapek M2, Damjanovska M3, Reina MA4, Eržen I1, Stopar-Pintarič T3.
- Anaesthesia.Anaesthesia.2015 Aug;70(8):939-47. doi: 10.1111/anae.13066. Epub 2015 Mar 31.
- The examination of nerve microarchitecture has hitherto been limited solely to two-dimensional imaging techniques. The objective of this study was to evaluate the ability of optical projection tomography to discern the nerve microarchitecture and injection injury in three dimensions. Five piglets we
- PMID 25827062
- Development of new tissue conditioner using acetyl tributyl citrate and novel hyperbranched polyester to improve viscoelastic stability.
- Yang TC1, Cheng KC2, Huang CC3, Lee BS4.
- Dental materials : official publication of the Academy of Dental Materials.Dent Mater.2015 Jun;31(6):695-701. doi: 10.1016/j.dental.2015.03.012. Epub 2015 Apr 14.
- OBJECTIVE: The objective was to develop a new tissue conditioner using acetyl tributyl citrate (ATBC), tributyl citrate (TBC), and a novel hyperbranched polyester (TAH) with long-term stable viscoelasticity.METHODS: Plasticizers, i.e., ATBC, TBC, TAH (number-average molecular weight, 1306 g/mol; wei
- PMID 25888003
- C12-15 alkyl benzoate: a new cosmetic allergen?
- Werbrouck J1, Lambrecht C, Goossens A.
- Contact dermatitis.Contact Dermatitis.2015 May 5. doi: 10.1111/cod.12419. [Epub ahead of print]
- PMID 25943945
Japanese Journal
- Elicitor(s) in Sogatella furcifera (Horváth) Causing the Japanese Rice Plant (Oryza sativa L.) to Induce the Ovicidal Substance, Benzyl Benzoate
- YANG Jeong-Oh,NAKAYAMA Naoya,TODA Kyohei,TEBAYASHI Shinichi,KIM Chul-Sa
- Bioscience, Biotechnology, and Biochemistry, 2013
- … We elucidate the mechanism for inducing the production of ovicidal benzyl benzoate by Japonica rice varieties to kill eggs of the whitebacked planthopper, Sogatella furcifera (Horváth), lying in the rice plant. … Even when subjected to physical damage by a needle or damage with water, the rice plant produced no benzyl benzoate. …
- NAID 130003361103
- Benzylation of hydroxy groups with tertiary amine as a base
- Gathirwa Jeremiah W.,Maki Toshihide
- Tetrahedron 68(1), 370-375, 2012-01-07
- … A mixture of an alcohol and a benzyl halide afforded the corresponding benzyl ether in good to excellent yields in the presence of diisopropylethylamine. … The reaction showed high tolerance to many functional groups including benzoate, even at a reaction temperature of 150 °C. …
- NAID 80022289425
- 阿部 裕,山口 未来,六鹿 元雄 [他],平原 嘉親,河村 葉子
- 食品衛生学雑誌 53(1), 19-27, 2012
- わが国で流通するポリ塩化ビニル(PVC)製玩具101検体の可塑剤使用実態を調査した．指定玩具からは，いずれのフタル酸エステルも検出されず使用は認められなかったが，指定玩具以外の半数以上からフタル酸ビス（2-エチルヘキシル），フタル酸ジイソノニル，フタル酸ジイソブチル，フタル酸ジブチル，フタル酸ジイソデシル，フタル酸ベンジルブチルが検出された．また，フタル酸エステルの代替可塑剤として2,2,4-トリ …
- NAID 130002109400
Related Links
- Benzyl Benzoate Manufacturers Suppliers Exporters, Exports to USA UAE Europe South Africa Brazil Chile Argentina Dubai ... Anmol Chemicals is a several decades old manufacturing company. It is the pioneer manufacturers of ...
- benzyl [ben´zil] the hydrocarbon radical, C 7 H 7 or C 6 H 5 CH 2-, found in benzyl alcohol and various other compounds. benzyl benzoate one of the active substances in peruvian and tolu balsams, and produced synthetically; applied ...
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ベンジル
- 関
- benzil、benzylic
