Synthesis of Deuterium‐Labeled Perfume Ingredients as Internal Standards for Their GC/MS Quantification

Chapuis, Christian; Cantatore, Carole; Fankhauser, Péter; Challand, René; Riedhauser, Jean-Jacques

doi:10.1002/hlca.200900076

Cited by 8 publications

(6 citation statements)

References 48 publications

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“…13 C NMR (75 MHz, CDCl 3 ): δ 221.4 (CO, s), 55.0 (s), 53.6 (d), 50.4 (t), 45.2 (s), 34.2 (t), 29.3 (t), 19.7 (q), 14.3 (q), 8.8 (q) ppm. EI-MS (m/z, relative intensity): 152 (M + , 20), 137 (3), 109 (13), 95 (100), 81 (16), 69 (14), 55 (5), 41 (14). IR (neat, ν/cm −1 ): 2957, 2870, 1745, 1455, 1378, 1322, 1182, 1029, 955, 526, 493.…”

mentioning

confidence: 99%

Sequential Diels–Alder Reaction/Rearrangement Sequence: Synthesis of Functionalized Bicyclo[2.2.1]heptane Derivatives and Revision of Their Relative Configuration

et al. 2014

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A sequential Diels-Alder reaction/rearrangement sequence was developed for the synthesis of diverse functionalized bicyclo[2.2.1]heptanes as novel floral and woody odorants. The outcome of the rearrangement depended on the substitution pattern of the dienes. 2D NMR analysis has established the correct relative configuration of the bicyclo[2.2.1]heptanone, which was originally misassigned. Furthermore, when the initiating DA reaction was catalyzed by a chiral Lewis acid, the bicyclo[2.2.1]heptane derivatives including (+)-herbanone can be obtained in an enantiomeric ratio (er) up to 96.5:3.5.

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mentioning

confidence: 99%

Sequential Diels–Alder Reaction/Rearrangement Sequence: Synthesis of Functionalized Bicyclo[2.2.1]heptane Derivatives and Revision of Their Relative Configuration

et al. 2014

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“…Polysantol ® ((–)‐(1′ R , E )‐3,3‐dimethyl‐5‐(2′,2′,3′‐trimethyl‐3′‐cyclopenten‐1′‐yl)‐4‐penten‐2‐ol), Myrrhone ® ((+–)‐( E )‐4‐(2,2,c‐3, t ‐6‐tetramethyl‐r‐1‐cyclohexyl)‐3‐buten‐2‐one), Helvetolide ® ((+)‐(1 S ,1′ R )‐2‐[1‐(3′,3′‐dimethyl‐1′‐cyclohexyl)ethoxy]‐2‐methylpropyl propanoate), Muscenone™ (3‐methyl‐4‐cyclopentadecen‐1‐one), Dartanol ((–)‐(2 E )‐2‐ethyl‐4‐[(1 R )‐2,2,3‐trimethyl‐3‐cyclopenten‐1‐yl]‐2‐buten‐1‐ol), and Cetalox ® ((+–)‐8,12‐epoxy‐13,14,15,16‐tetranorlabdane) are from Firmenich SA (Geneva, Switzerland). Corresponding deuterated compounds Polysantol ® D3 ((–)‐(4 E )‐3‐methyl‐3‐(trideuteriomethyl)‐5‐[(1 R )‐2,2,3‐trimethyl‐3‐cyclopenten‐1‐yl]‐4‐penten‐2‐ol), Myrrhone ® D5 ((+–)‐( E )‐1,1,1,3‐tetradeuterio‐4‐(1‐deuterio‐2,2,c‐3, t ‐6‐tetramethyl‐r‐1‐cyclohexyl)‐3‐buten‐2‐one), Helvetolide ® D3 ((+)‐2‐(1 S )‐1‐[(1 R )‐3,3‐dimethylcyclohexyl]ethoxy‐2‐methylpropyl 3,3,3‐trideuteriopropionate), Muscenone™ D3 ((+–)‐(5 Z )‐3,3,3‐trideuteriomethylcyclopentadec‐5‐enone), Dartanol D3 ((–)‐(2 E )‐2‐ethyl‐4‐[(1r)‐2,2,3‐trimethyl‐3‐cyclopenten‐1‐yl]‐1,4,4‐trideuterio‐2‐buten‐1‐ol), and Cetalox ® D4 ((3AR,5AS,9AS,9BR)‐1,1,2,2‐tetradeuterio‐3A,6,6,9A‐tetramethyldodecahydronaphtho[2,1‐b]furan) were synthesized internally according to a protocol developed by Chapuis et al 14. Deionized water (resistivity=17 MΩ) was produced by a Synergy 185 UV Ultrapure Water System (Millipore, Billerica, MA, USA).…”

Section: Methodsmentioning

confidence: 99%

Extraction, thermal cleanup, and GC/MS quantification with disposable solid extractants: Application to hydrophobic analytes in aqueous surfactant solutions

Begnaud

Debonneville

Chaintreau

2011

J of Separation Science

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Fragranced consumer products are generally formulated together with surfactants. In application, these products are often highly diluted with water. Analyzing trace amounts of fragrance ingredients in such mixtures is challenging and usually requires either time-consuming sample cleanup or extensive cleaning of the trapping device to avoid memory effect and cross-contamination between samples. To overcome these limitations, a new disposable extraction device has been developed to be used in combination with a thermodesorption-GC-MS unit. Made of PDMS foam cylinders, it efficiently extracts trace amounts of hydrophobic compounds from complex aqueous solutions and provides an online sample cleanup, thanks to the controlled desorption temperature, which allows retaining the low volatile constituents of the matrix within the absorptive foam. Combined with a stable isotope dilution assay, accurate quantifications of Cetalox(®), Muscenone™, Helvetolide(®), Polysantol(®), Dartanol, and Myrrhone(®) from aqueous solution containing surfactant and from water from the aeration tank of a sewage plant were successfully conducted. LOQ varied between 1 and 25 ppb (20% confidence interval, α = 0.1).

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“…Triton X100 was supplied by AppliChem (Darmstadt, Germany). The deuterated isomers of Cetalox® and Polysantol® were internally synthesized according to Chapuis et al [5] The polydimethylsiloxane (PDMS) cylinders (5 mm diameter × 5 mm height) were prepared from PDMS foam sheets (Extra Soft Cellular Silicone, Rogers Corporation, Ghent, Belgium).…”

Section: Experimental Materialsmentioning

confidence: 99%

REACH‐driven developments in analysis and physicochemistry

Chaintreau

Begnaud

Debonneville

et al. 2009

Flavour & Fragrance J

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The enforcement of the REACH regulation in the fragrance domain has created new challenges for the analytical and physical chemist. Many chemicals used as perfumery ingredients are hydrophobic, because low-polar compounds exhibit a higher substantivity (i.e. persistence after application) than do polar compounds. As a result, the usual protocols are often unsuitable and new methods must be developed. Biodegradation studies sometimes call for the quantifi cation of traces of such hydrophobic analytes in complex media (e.g. waste water, aqueous surfactant solutions). Existing sample preparation techniques are either ineffi cient or time consuming. A new approach is proposed, based on single-use absorbants, which allows accurate quantifi cation down to the 100 ppb range. This extremely simple technique allows good throughput analyses. Determining the environmental profi le of a compound requires the determination of some physical constants. Among these, solubility in water can be obtained from theoretical models or experimentally, but the resulting values may greatly diff er as a function of the model or the protocol. Several experimental approaches are critically discussed and compared with a reference technique. The air-to-water partition coeffi cients are determined by using an improved version of the previously developed static-and-trapped headspace technique.

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Synthesis of Deuterium‐Labeled Perfume Ingredients as Internal Standards for Their GC/MS Quantification

Cited by 8 publications

References 48 publications

Sequential Diels–Alder Reaction/Rearrangement Sequence: Synthesis of Functionalized Bicyclo[2.2.1]heptane Derivatives and Revision of Their Relative Configuration

Sequential Diels–Alder Reaction/Rearrangement Sequence: Synthesis of Functionalized Bicyclo[2.2.1]heptane Derivatives and Revision of Their Relative Configuration

Extraction, thermal cleanup, and GC/MS quantification with disposable solid extractants: Application to hydrophobic analytes in aqueous surfactant solutions

REACH‐driven developments in analysis and physicochemistry

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