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Record W2041574859 · doi:10.1002/ejlt.200390004

Directed sequential synthesis of conjugated linoleic acid isomers from Δ<sup>7, 9</sup> to Δ<sup>12, 14</sup>

2003· article· en· W2041574859 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueEuropean Journal of Lipid Science and Technology · 2003
Typearticle
Languageen
FieldNursing
TopicFatty Acid Research and Health
Canadian institutionsUniversité Laval
Fundersnot available
KeywordsIsomerizationConjugated linoleic acidPericyclic reactionDouble bondCis–trans isomerismChemistryConjugated systemStereochemistryLinoleic acidFatty acidOrganic chemistryCatalysisPolymer

Abstract

fetched live from OpenAlex

Abstract Position and configuration isomers of conjugated linoleic acid (CLA), from 7, 9‐ through 12, 14‐C18:2, were synthesized by directed sequential isomerizations of a mixture of rumenic ( cis ‐9, trans ‐11 C18:2) and trans ‐10, cis ‐12 C18:2 acids. Indeed, the synthesized conjugated fatty acids cover the range of unsaturated systems as found in milk fat CLA. The two‐step sequence consisted in initial sigmatropic rearrangement of cis/trans CLA isomers at 200 °C for 13 h under inert atmosphere (Helium, He), followed by selenium‐catalyzed geometrical isomerization of double bonds at 120 °C for 20 h under He. Product analysis was achieved by gas‐liquid chromatography using a 120 m polar capillary column coated with 70% cyanoalkylpolysiloxane equivalent polymer. Migration of conjugated systems was geometrically controlled as follows: the cis ‐C n , trans ‐C n+2 double bond system was rearranged through a pericyclic [1, 5] sigmatropic mechanism into a trans ‐C n‐1 , cis ‐C n+1 unsaturated system, while the trans ‐C n , cis ‐C n+2 double bond system was rearranged through a similar pericyclic mechanism into a cis ‐C n+1 , trans ‐C n+3 unsaturated system. Selenium‐catalyzed geometrical isomerization under mild conditions then allowed cis/trans double bond configuration transitions, resulting in the formation of all cis , all trans , cis‐trans and trans‐cis isomers. A sequential combination of the two reactions resulted in a facile controlled synthesis of CLA isomers, useful for the chromatographic identification of milk fat CLA, as well as for the preparation of CLA standard mixture.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.003
metaresearch head score (Gemma)0.005
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.099
Threshold uncertainty score0.826

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0030.005
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0020.002
Science and technology studies0.0000.002
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.022
GPT teacher head0.272
Teacher spread0.251 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it