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Alkenones are unique lipids produced by certain species of microalgae, well-known for use in paleoclimatology, and more recently pursued to advance sustainability across multiple industries. Beginning in 2018, the biosynthesis of alkenones by commercially grown Tisochrysis lutea ( T - Iso ) microalgae from one of the world's most established producers, Necton S.A., changed dramatically from structures containing 37 and 38 carbons, to unusual shorter-chain C35 and C36 diunsaturated alkenones (C35:2 and C36:2 alkenones). While the exact reasons for this change remain unknown, analysis of alkenones isolated from T-Iso grown in 2021 and 2023 revealed that this change has persisted. The structure of these rare shorter-chain alkenones, including double bond position, produced by Necton T-Iso remained the same over the last five years, which was determined using a new and optimized cross-metathesis derivatization approach with analysis by comprehensive two-dimensional gas chromatography and NMR. However, noticeable differences in the alkenone profiles among the different batches were observed. Combined with fatty acid compositional analysis, the data suggest a connection between these lipid classes ( e.g. , increased DHA corresponds to lower amounts of shorter-chain alkenones) and the ability to manipulate their biosynthesis in T-Iso with changes to cultivation conditions., Competing Interests: The authors declare no competing financial interest., (© 2024 The Authors. Published by American Chemical Society.)