Ethylvanillin

Last updated
Ethylvanillin
Ethylvanillin.svg
Ethylvanillin 3D ball.png
Ethylvanilin.jpg
Names
Preferred IUPAC name
3-Ethoxy-4-hydroxybenzaldehyde
Other names
Bourbonal
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.059 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3 Yes check.svgY
    Key: CBOQJANXLMLOSS-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3
    Key: CBOQJANXLMLOSS-UHFFFAOYAD
  • O=Cc1cc(OCC)c(O)cc1
Properties
C9H10O3
Molar mass 166.176 g·mol−1
AppearanceColourless 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)
Slightly soluble in water
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Harmful, irritant
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H319, H402
P264, P273, P280, P305+P351+P338, P337+P313, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 145 °C (293 °F; 418.15K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. It is a homologue of vanillin, differing on the 3 position.

Contents

Preparation

Ethylvanillin is prepared from catechol, beginning with ethylation to give guaethol (1). This ether condenses with glyoxylic acid to give the corresponding mandelic acid derivative (2), which by oxidation (3) and decarboxylation, gives ethylvanillin (4). [1]

Synthesis Ethylvanillin.svg

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 Jacques Guerlain added a large quantity of it to a bottle of Jicky (1889) perfume, creating the main accord for the perfume house's flagship fragrance, Shalimar (perfume) (1925). This is one of the earliest uses of synthetic molecules that freed scent artists from the limits of natural materials. [2]

Related Research Articles

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<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology.

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<span class="mw-page-title-main">Vanillin</span> Chemical compound

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Cinnamaldehyde is an organic compound with the formula or C6H5CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90% cinnamaldehyde. Cinnamaldehyde decomposes to styrene because of oxidation as a result of bad storage or transport conditions. Styrene especially forms in high humidity and high temperatures. This is the reason why cinnamon contains small amounts of styrene.

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Catechol, also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula C6H4(OH)2. It is the ortho isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances.

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Balsam of Peru or Peru balsam, also known and marketed by many other names, is a balsam derived from a tree known as Myroxylon balsamum var. pereirae; it is found in El Salvador, where it is an endemic species.

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Benzylideneacetone is the organic compound described by the formula C6H5CH=CHC(O)CH3. Although both cis- and trans-isomers are possible for the α,β-unsaturated ketone, only the trans isomer is observed. Its original preparation demonstrated the scope of condensation reactions to construct new, complex organic compounds. Benzylideneacetone is used as a flavouring ingredient in food and perfumes.

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Notes in perfumery are descriptors of scents that can be sensed upon the application of a perfume. Notes are separated into three classes: top/head notes, middle/heart notes, and base/soul notes; which denote groups of scents which can be sensed with respect to the time after the application of a perfume. These notes are created with knowledge of the evaporation process and intended use of the perfume. The presence of one note may alter the perception of another—for instance, the presence of certain base or heart notes will alter the scent perceived when the top notes are strongest, and likewise the scent of base notes in the dry-down will often be altered depending on the smells of the heart notes.

<span class="mw-page-title-main">Benzyl salicylate</span> Chemical compound

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2-Methylundecanal is an organic compound that is found naturally in kumquat peel oil. This compound smells herbaceous, orange, and ambergris-like. At high dilution it has a flavor similar to honey and nuts. It is a colorless or pale yellow liquid that is soluble in organic solvents such as ether and ethanol. It is used as a fragrance component in soaps, detergents, and perfumes.

<span class="mw-page-title-main">Tetramethyl acetyloctahydronaphthalenes</span> Chemical compound

Tetramethyl acetyloctahydronaphthalenes is a synthetic ketone fragrance also known as OTNE and by other commercial trade names such as: Iso E Super, Iso Gamma Super, Anthamber, Amber Fleur, Boisvelone, Iso Ambois, Amberlan, Iso Velvetone, Orbitone, Amberonne. It is a synthetic woody odorant and is used as a fragrance ingredient in perfumes, laundry products and cosmetics.

Mathilde Laurent is a French perfumer. After studying perfumery at ISIPCA in Versailles, Laurent began her career as an apprentice to Jean-Paul Guerlain. She went on to work at Guerlain for 11 years. Since 2006, she has been the in-house perfumer for Cartier, creating perfumes like Baiser Volé.

α-Isomethyl ionone Chemical compound

α-Isomethyl ionone, also known as α-cetone, is a synthetically made and naturally occurring organic compound found in Brewer's yeasts or the species known as Saccharomyces cerevisiae. The compound is an isomer of methyl ionone. Alpha-isomethyl ionone can be colorless or pale-straw coloured liquid. Its primary scent is flowery and secondary scent is violet. It may also have a woody or orris-like scent. and is often used in flavouring and cosmetic industries for example, aftershave lotions, bath products, hair care products, moisturizers, perfumes, shampoos and skin care products. It is also an ingredient used in Chanel No. 5, and other branded products such as Fidji by Guy Laroche. Perfume fragrances that α-isomethyl ionone is used in are for example, amber, chypre, violet, mimosa, reseda, iris, orris, cyclamen, chypre, berries, woody notes, ylang-ylang, leather, orange, nut, pistachio, muscatel, and tobacco.

References

  1. 1 2 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.