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WordNet

the univalent hydrocarbon radical C2H5 derived from ethane by the removal of one hydrogen atom (同)ethyl_group, ethyl radical
a crystalline compound found in vanilla beans and some balsam resins; used in perfumes and flavorings

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/01/05 23:04:19」(JST)

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Ethylvanillin is the organic compound with the formula (C₂H₅O)(HO)C₆H₃CHO. This colorless solid consists of a benzene ring with hydroxyl, ethoxy, and formyl groups on the 4, 3, and 1 positions, respectively.

Preparation

Ethylvanillin is a synthetic molecule, not found in nature. It is prepared via several steps from catechol, beginning with ethylation to give "guethol" (1). This ether condenses with glyoxylic acid to give the corresponding mandelic acid derivative (2), which via oxidation (3) and decarboxylation gives ethylvanillin (4).^[1]

Application

As a flavorant, ethylvanillin is about three times as potent as vanillin and is used in the production of chocolate.^[1]

The molecule revolutionized both the design and aesthetics of olfactory art; artist Aimé Guerlain used it in "Jicky" (1889), one of the earliest uses of the synthetic molecules that freed scent artists from the limits of natural materials.^[2]

References

^ ^a ^b Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim: 2002. Published online: 15 January 2003; doi:10.1002/14356007.a11_141.
^ "Vanillin:Molecule of the Month". Bristol University.

UpToDate Contents

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English Journal

Mild deoxygenation of aromatic ketones and aldehydes over Pd/C using polymethylhydrosiloxane as the reducing agent.

Volkov A1, Gustafson KP, Tai CW, Verho O, Bäckvall JE, Adolfsson H.
Angewandte Chemie (International ed. in English).Angew Chem Int Ed Engl.2015 Apr 20;54(17):5122-6. doi: 10.1002/anie.201411059. Epub 2015 Feb 26.
Herein, a practical and mild method for the deoxygenation of a wide range of benzylic aldehydes and ketones is described, which utilizes heterogeneous Pd/C as the catalyst together with the green hydride source, polymethylhydrosiloxane. The developed catalytic protocol is scalable and robust, as exe
PMID 25728614

Flavour chemicals in electronic cigarette fluids.

Tierney PA1, Karpinski CD2, Brown JE1, Luo W2, Pankow JF3.
Tobacco control.Tob Control.2015 Apr 15. pii: tobaccocontrol-2014-052175. doi: 10.1136/tobaccocontrol-2014-052175. [Epub ahead of print]
BACKGROUND: Most e-cigarette liquids contain flavour chemicals. Flavour chemicals certified as safe for ingestion by the Flavor Extracts Manufacturers Association may not be safe for use in e-cigarettes. This study identified and measured flavour chemicals in 30 e-cigarette fluids.METHODS: Two brand
PMID 25877377

Medicinal plants from the genus Acalypha (Euphorbiaceae)--a review of their ethnopharmacology and phytochemistry.

Seebaluck R1, Gurib-Fakim A2, Mahomoodally F3.
Journal of ethnopharmacology.J Ethnopharmacol.2015 Jan 15;159:137-57. doi: 10.1016/j.jep.2014.10.040. Epub 2014 Oct 30.
ETHNOPHARMACOLOGICAL RELEVANCE: Acalypha is the fourth largest genus of the Euphorbiaceae family with approximately 450-570 species. Several Acalypha species are used as medicinal plants in Africa and in the Mascarene Islands. Almost every part of the plant including the leaves, stem and roots are u
PMID 25446604

Japanese Journal

食品添加物ブドウ果皮抽出物の含有成分のクロマトグラフィーによる評価

日本食品化学学会誌 22(2), 108-114, 2015-08-26
NAID 110009987550

温室メロンの特徴的な香気成分と追熟段階による変化

静岡県農林技術研究所研究報告 (6), 57-64, 2013-03
NAID 120005580645

前頭葉の酸素ヘモグロビン濃度変化に及ぼす匂い刺激の効果:―光トポグラフィー装置を用いての検討―

昭和学士会雑誌 73(3), 216-223, 2013
NAID 130004627306

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「ethyl」

Ethylvanillin
	Other names 3-ethoxy-4-hydroxybenzaldehyde, bourbonal
Identifiers
CAS number	121-32-4
PubChem	8467
ChemSpider	8154
UNII	YC9ST449YJ
KEGG	D01086
ChEBI	CHEBI:48408
ChEMBL	CHEMBL508676
Jmol-3D images	Image 1
	SMILES O=Cc1cc(OCC)c(O)cc1 ;
	InChI InChI=1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3 ; Key: CBOQJANXLMLOSS-UHFFFAOYSA-N InChI=1/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3; Key: CBOQJANXLMLOSS-UHFFFAOYAD ;
Properties
Molecular formula	C9H10O3
Molar mass	166.17 g mol−1
Appearance	colourless powder
Density	1.186 g/mL
Melting point	76 °C (169 °F; 349 K)
Boiling point	295.1 °C (563.2 °F; 568.2 K)
Solubility in water	slightly soluble in water
Hazards
Main hazards	Harmful, Irritant
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

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関: Et

[Ullmann-1] Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim: 2002. Published online: 15 January 2003; doi:10.1002/14356007.a11_141.

[2] "Vanillin:Molecule of the Month". Bristol University.

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案内

ethyl vanillin