Ueber die Veilchenketone und die in Beziehung dazu stehenden Verbindungen der Citral‐(Geranial‐)reihe

Tiemann, Fred.

doi:10.1002/cber.189803101165

Cited by 33 publications

(4 citation statements)

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“…To our best knowledge, however, this route to 1 has not been commercialized. Regardless, the laborious techniques of asymmetric synthesis of ionones (11) are out of the focus of this paper, but the traditional Tiemann route (8,9) allows easy production of 1 and 2 from synthetic and/or natural educts. As racemic 1 declared to be natural is on the flavor market, the application of this route has to be considered.…”

Section: Introductionmentioning

confidence: 99%

“…Despite the already existing fundamental information about the isotope ratios of 1 and 2 , in particular, regarding those from raspberry fruit, isotope data are still lacking concerning various synthetic ways to produce these ketones. The initial synthetic route to ionones is based on the condensation of citral and acetone with subsequent cyclization of the resulting isomeric pseudoionones ( , ) ( Figure ). Later, the selective preparation of ionones was investigated, with growing interest over the past decade ().…”

Section: Introductionmentioning

confidence: 99%

“…In the following, the term natural is used for EU-conforming educts and products, whereas the quoted (‘natural') characterizes U.S.- but not EU-conforming materials.

1 Production of ionones by condensation of citral and acetone with subsequent acid-catalyzed cyclization of intermediary regioisomeric pseudoionones ( , ); stereochemical control by the catalyst, for example, predominance of α- ( 1 ), β- ( 2 ), and γ-ionone using phosphoric acid, sulfuric acid, and a Lewis acid such as BF 3 /DMF, respectively (). …”

Section: Introductionmentioning

confidence: 99%

“…Production of ionones by condensation of citral and acetone with subsequent acid-catalyzed cyclization of intermediary regioisomeric pseudoionones ( , ); stereochemical control by the catalyst, for example, predominance of α- ( 1 ), β- ( 2 ), and γ-ionone using phosphoric acid, sulfuric acid, and a Lewis acid such as BF 3 /DMF, respectively ().…”

Section: Introductionmentioning

confidence: 99%

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Flavor Authentication Studies of α-Ionone, β-Ionone, and α-Ionol from Various Sources

Caja

Preston

Kempf

et al. 2007

J. Agric. Food Chem.

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In addition to the already available information on the authenticity of alpha- (1) and beta-ionone (2) from plant tissues, there is an interest in the stable isotope data of 1 and 2 available by synthesis from citral and acetone, as European Union regulations, in contrast to the United States and other countries, do not allow a product to be declared as 'natural' that has been chemically synthesized (e.g., by using a natural catalyst) from natural educts. Analyses performed by on-line capillary gas chromatography-isotope ratio mass spectrometry in the combustion and pyrolysis modes (HRGC-C/P-IRMS) as well as by elemental analyzers (EA-C/P-IRMS) measuring delta(13)C(V)-PDB and delta(2)H(V)-SMOW values provide for the first time isotope data of such 'natural' 1 and 2 as well as of synthetic and 'ex plant' alpha-ionol (3). The isotope data recorded for synthesized 1 and 2 reflected the influence of the origin of the used citral, whereas that of acetone was less remarkable. For instance, 'natural' 1 ex citral from lemongrass showed, as expected for a C4 plant, an enriched delta(13)C(V)-PDB value of -18.5 per thousand. In addition, the use of synthetic citral resulted in an enriched delta(2)H(V)-SMOW value of -43 per thousand, whereas with citral ex Litsea cubeba and ex lemongrass values of -242 and -232 per thousand, respectively, were recorded. IRMS analyses of 'natural' 2 revealed delta(13)C(V)-PDB and delta(2)H(V)-SMOW values that were nearly identical to that recorded for 'natural' 1. As to both 1 and 2, variations of synthesis conditions led to distinct changes in the delta(13)C(V)-PDB but not the delta(2)H(V)-SMOW values. Synthetic 3 showed delta(13)C(V)-PDB and delta(2)H(V)-SMOW values of -24.5 and -184 per thousand, respectively. These data differed from those found in raspberry fruit under study (n = 8), that is, ranging from -33.6 to -36.6 per thousand for delta(13)C(V)-PDB and from -200 to -225 per thousand for delta(2)H(V)-SMOW. The values determined additionally for 1 and 2 in raspberry fruit samples ranged from -30.3 to -35.1 per thousand and from -176 to -221 per thousand for delta(13)C(V)-PDB and delta(2)H(V)-SMOW, respectively, and thus corresponded to the already known literature information.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…In the following, the term natural is used for EU-conforming educts and products, whereas the quoted (‘natural') characterizes U.S.- but not EU-conforming materials.

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Flavor Authentication Studies of α-Ionone, β-Ionone, and α-Ionol from Various Sources

Caja

Preston

Kempf

et al. 2007

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Optically Active Ionones and Derivatives: Preparation and Olfactory Properties

Brenna¹,

Fuganti²,

Serra³

et al. 2002

Eur. J. Org. Chem.

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The isomeric ionones 1−3 are of both academic and commercial interest. Since their first preparation at the end of the 19th century they have been widely used as fragrances and as starting materials or building blocks in the synthesis of many relevant products. The regioselective and/or enantioselective preparation of ionones has therefore been investigated with growing interest over the last decades. In this Microreview, we summarize the syntheses of optically active α‐ and γ‐ionones (1, 3) and the epoxy and dihydro ionones 4−7. In addition, the olfactory properties of most of them are reported comprehensively.

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Total Synthesis of Sequiterpenes

Heathcock

1973

Total Synthesis of Natural Products

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Ueber die Veilchenketone und die in Beziehung dazu stehenden Verbindungen der Citral‐(Geranial‐)reihe

Abstract: S a k o w n i n , Dr. N i c o l a u s , Bolchowskaja Poststation, Gouvernement Sirnbirsk (Russland) (durch N. hI * n s chl;,tk i u und A. W o l k o f f) ; S c h n l l. Max, cand. chem., Landsbergerstr. 36, Berlin NO.

Cited by 33 publications

References 18 publications

Flavor Authentication Studies of α-Ionone, β-Ionone, and α-Ionol from Various Sources

Flavor Authentication Studies of α-Ionone, β-Ionone, and α-Ionol from Various Sources

Optically Active Ionones and Derivatives: Preparation and Olfactory Properties

Total Synthesis of Sequiterpenes

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