Olive Oil Flavor Research Articles

Evaluation of the Shelf Life of Myristica-fragrans Powder-Flavored Oils Obtained through the Application of Two Processes: Infusion and Co-Pressing Technology.

This work aimed to evaluate the impact of enrichment processing on the quality parameters, bioactivity and sensorial aspects of Myristica fragrans (mace)-flavored olive oil storage for one year. The mace powder was added to extra virgin olive oil through two different processes: immediately after crushing the olives by mixing mace (1% weight/weight (w/w)) with the olive paste (MAVOO-M) and by adding mace to extra virgin olive oil (C) (2% w/w) (MAVOO-I). A multi-analytical approach was applied to measure the main qualitative indexes, such as the free acidity, peroxide value and ultraviolet parameters. The total phenolic and carotenoid contents (TPC and TCC, respectively) and α-tocopherol were also evaluated, as well as the sensory attributes. The radical scavenging potential was estimated by using two different in vitro tests, namely, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH). A significant increase in the free acidity parameter was found in all the flavored oils, and particularly in the MAVOO-M (1.27% oleic acid); at the same time, this oil was the sample with the lowest peroxide value (i.e., 9.68 meqO2/kg) after 360 days of storage. At the end of the storage, an increase in L* values was found in both the MAVOO-M and -I vs. the C (43.88 and 43.02, respectively, vs. 42.62). The TCC was strongly influenced by the addition of mace, especially when the infusion process was used. In fact, after one year of storage, the TCC in the MAVOO-I resulted in ~34.7% more than the MAVOO-M. A promising DPPH radical scavenging activity was observed independently by the applied aromatization process, with IC50 values of 19.77 and 17.80 μg/mL for the MAVOO-M and MAVOO-I, respectively. However, this activity decreased during storage, and a similar trend was observed using the ABTS test. In conclusion the infusion as enrichment methodology led to more promising results in terms of functionality compared with the co-mixing one.

Exploring the Connection between the Occurrence and Intensity of "Grubby" Defect and Volatile Composition of Olive Oil.

In order to investigate the relationship between the occurrence of the "grubby" sensory defect caused by olive fruit fly (Bactrocera oleae (Rossi)) infestation and the resulting volatile composition, virgin olive oils were extracted from olives of the Leccino cultivar with 0%, 50%, and 100% olive fly infestations and subjected to analysis of the basic chemical quality parameters, fatty acids and volatiles, and sensory analysis by the Panel test. A 100% olive fly infestation reduced the basic chemical quality of the oil, while the fatty acid composition was not affected in any case. The overall sensory quality score and intensity of the positive sensory attributes decreased, while the intensity of the "grubby" defect increased proportionally to the degree of infestation. The occurrence and intensity of this defect were clearly causally related to the concentrations of 3-methylbutanal, 2-methylbutanal, β-ocimene, ethyl 2-methylbutyrate, dimethyl sulfoxide, 4-methyl-5H-furan-2-one, α-farnesene, 6-methyl-5-hepten-2-one, 1-octanol, E-2-nonen-1-ol, benzeneacetaldehyde, heptanal, and octanal, implying that the perception of "grubby" comes from their joint contribution to the overall olive oil flavour. In addition to contributing to the understanding of the chemical origin of "grubby", the results obtained could potentially be used to develop strategies to support sensory analysis in the classification of olive oil quality and the confirmation of the presence of this sensory defect in oil samples.

Evaluation of Quality Parameters and Functional Activity of Ottobratica Extra Virgin Olive Oil Enriched with Zingiber officinale (Ginger) by Two Different Enrichment Processes during One-Year Storage.

The aim of this work was to evaluate the impact of two enrichment processes on the quality parameters and bioactivity of Ottobratica extra virgin olive oil (EVOO) with ginger during storage. The first procedure was conducted by including ginger powder with olive fruits in the malaxer, and the second by infusion into the EVOO. The obtained oils were stored at room temperature for one year in the dark and periodically analysed. To evaluate the effect on the shelf-life of flavoured olive oils (FVOOs), physical, chemical and sensory parameters were evaluated. The FVOOs were investigated for antioxidant activity through a multi-target approach. The inhibition of lipase and carbohydrate hydrolysing enzymes was analysed. The addition of ginger in the malaxer generated a product that preserved the lowest values of peroxide after storage (10.57 mEq O2 kg-1) and maintained the highest α-tocopherol level (101.16 mg kg-1). The FVOOs, regardless of the enrichment technique used, showed a higher antioxidant activity than EVOO. Generally, a reduction in the inhibitory activity of the carbohydrate inhibitory enzymes was observed, especially after 60 days of storage. The addition of ginger improved the lipase inhibitory effect, especially if added during malaxation, and helped the FVOOs maintain this activity during storage.

Ultrasound Assisted Coextraction of Cornicabra Olives and Thyme to Obtain Flavored Olive Oils.

Flavoring olive oils is a new trend in consumer preferences, and different enrichment techniques can be used. Coextraction of olives with a flavoring agent is an option for obtaining a flavored product without the need for further operations. Moreover, ultrasound (US) assisted extraction is an emergent technology able to increase extractability. Combining US and coextraction, it is possible to obtain new products using different types of olives (e.g., cultivar and ripening stage), ingredient(s) with the greatest flavoring and/or bioactive potential, as well as extraction conditions. In the present study, mastic thyme (Thymus mastichina L.) (TM) and lemon thyme (Thymus x citriodorus) (TC) were used for flavoring Cornicabra oils by coextraction. The coextraction trials were performed by (i) thyme addition to the olives during crushing or malaxation and (ii) US application before malaxation. Several parameters were evaluated in the oil: quality criteria parameters, total phenols, fatty acid composition, chlorophyll pigments, phenolic profile and oxidative stability. US application did not change the phenolic profile of Cornicabra olive oils, while the enrichment of olive oils with phenolic compounds or pigments by coextraction was very dependent on the thyme used. TM enrichment showed an improvement of several new phenolic compounds in the oils, while with TC, fewer new phenols were observed. In turn, in the trials with TC, the extraction of chlorophyll pigments was higher, particularly in crushing coprocessing. Moreover, the oils obtained with US and TM added in the mill or in the malaxator showed lower phenol decrease (59%) than oils flavored with TC (76% decrease) or Cornicabra virgin olive oil (80% decrease) over an 8-month storage period. Multivariate data analysis, considering quality parameters, pigments and phenolic contents, showed that flavored oils were mainly grouped by age.

The effect of form and method of flavoring on microbiota of olive oil.

Flavoring olive oil is an increasing trend in olive oil processing. Growing consumer interest in flavored olive oils by natural material brings the need to evaluate the key limiting factors which is its microbiological stability. The present research compares the microbiological quality of olive oil flavored by 3 flavors (rosemary, garlic, and lemon), prepared by 3 methods to determine changes during storage. The comprehensive microbiological analyses (total number of microorganisms [TCM], anaerobic sporulates, yeasts, molds, bacteria of the family Enterobacteriaceae, bacteria of the genus Salmonella spp., Clostridium botulinum, and lactic acid bacteria) were conducted during 12 months of storage. The best results in TCM were observed in the oil flavored by fresh garlic (0.24 log CFU/mL). The highest counts of anaerobic sporulates were detected in the dried rosemary olive oil (1.10 log CFU/mL). The flavoring materials have significantly higher counts of microorganism than flavored oils (p < .05). The obtained results demonstrated that microorganisms are capable to survive in flavored olive oil and the method of flavoring can affect their growth in a selective way according to the chemical characteristics.

How storage time affects sensory, chemical, and physical characteristics of flavored olive oil.

The objectives of this study were to evaluate sensory, chemical, and physical characteristics of olive oil prepared by three flavoring methods and analyze changes during storage (0, 3, and 6 months). Favored olive oil was prepared by three flavoring methods (fresh, dried, and essential oil). Selected sensory, chemical, and color parameters were monitored based on international standards. The color was determined by spectrophotometer. The results confirmed that storage time and flavoring method affect sensory characteristics of the oil. Fresh garlic oil had significantly lower (p < .05) fruity smell. The level of pungent taste significantly increased (p < .05) in the dried rosemary oil, rosemary essential oil, and fresh and dried garlic flavored oils. The intensity of rosemary smell in the sample flavored with essential oil significantly decreased (p < .05) during storage. Opposite effect was observed in the sample flavored with dried rosemary, where the smell significantly increased (p < .05) during storage. The intensity of taste significantly increased (p < .05) in samples flavored by dried rosemary during storage. The peroxide value of all flavored oils samples increased (p < .05) during storage compared to unflavored oil where peroxide value did not change. Color indicators L*, a*, and b* show that addition of fresh rosemary causes the greatest change in olive oil color. The color change, especially the turbidity, was not perceived positive by tasters.

A survey of phthalates in flavored olive oils from Turkey

Phthalates are organic contaminants that are used as plasticizers in many plastic food packaging materials. Because of their lipophilic character, oils are the primary source of human exposure to phthalates. In this study, the presence of five phthalate esters; diethylhexyl phthalate (DEHP), dibutyl phthalate (DBP), butyl benzyl phthalate (BBP), diisononyl phthalate (DINP) and diisodecyl phthalate (DIDP) in olive oils flavored with different materials and marketed in Turkey in 2020 was determined. The samples included BBP, DINP, DIDP at lower concentrations than their LOQ. DEHP was the most abundant phthalate in all samples at varying concentrations between &lt; LOQ to 1.81 mg/kg. The highest amount of DEHP was found in the oil sample flavored with bergamot (1.81 mg/kg). DBP was detected in 9 of the 25 samples at concentrations from 0.11 to 0.27 mg/kg.

Effect of Flavoring with Rosemary, Lemon and Orange on the Quality, Composition and Biological Properties of Olive Oil: Comparative Study of Extraction Processes

The goal of this work was to investigate the impact of the flavoring of some aromatic plants/spices, including rosemary (R), lemon (L) and orange (O) at the concentration of 5% and 35% (w/w) added by 2 methods (conventional maceration and direct flavoring), on quality attributes, chemical changes and oxidative stability of extra virgin olive oil (EVOO). Six flavored oils were obtained (EVOO + O, O + O, EVOO + R, O + R, EVOO + L and O + L). The physicochemical parameters (water content, refractive index, acidity and peroxide value, extinction coefficient, fatty acids, volatile aroma profiles, Rancimat test, phenols and pigments composition) of the flavored oils were investigated. Based on the results obtained, it was observed that flavoring with a conventional process provided increased oxidative stability to the flavored oils, especially with rosemary (19.38 ± 0.26 h), compared to that of unflavored oil. The volatile profiles of the different flavored oils revealed the presence of 34 compounds with the dominance of Limonene. The fatty acid composition showed an abundance of mono-unsaturated fatty acids followed by poly-unsaturated ones. Moreover, a high antioxidant activity, a significant peripheral analgesic effect (77.7% of writhing inhibition) and an interesting gastroprotective action (96.59% of ulcer inhibition) have been observed for the rosemary-flavored oil. Indeed, the flavored olive oils of this study could be used as new functional foods, leading to new customers and further markets.

Characterization of Flavoured Olive Oils of ‘Madural’ Variety

Flavoured oils arouse great interest among consumers in many countries due to their variety of flavours and versatility, especially in the culinary field. The aromatization of oils seeks to improve their sensory and nutritional properties, and extend their useful life due to the added substances can be beneficial as antioxidant and antimicrobial agent. In this research, olive oils of the ‘Madural’ variety from Trasos Montes region of Portugal have been obtained and flavoured with different aromatics herbs and condiments (flower of salt and bay leaf, garlic, rosemary and dehydrated lemon peel). The objective is to study the influence of the aromatic herbs and condiments on the physicochemical parameters of the oils: quality, purity, oxidative stability and microbiological analysis. It can be noted that the flavourings do not significantly alter the quality of the monovarietal oil, although, for some parameters, the excessive contact times can affect the category of the oil. On the other hand, the high content of antioxidants provided by flavouring agents can favour its stability and prolong its expiration. In this sense, the flavouring agent that contributes to stop the oxidation of the oil over time is salt + bay leaves, as higher oxidative stability values were detected than those obtained in monovarietal oil. However, oils flavoured with rosemary or lemon show a decrease over time for this parameter, which could indicate that this flavouring accelerates oxidation. In the case of oxidative stability referred to those flavoured with garlic, they present similar values to the monovarietal. The effect exerted by flavourings on the different parameters of the oils is complex, since it is influenced by the method followed and the operating variables established for flavouring.

Quality Indices, Phenolic Compounds and Sensory Evaluation of Flavored Olive Oil.

In this study, the effect of adding some aromatic plants (garlic, rosemary, thyme, and hot-red pepper) on the quality and organoleptic properties of flavored olive oil extracted from the olive fruits Maraqi variety are studied after adding aromatic plants at a concentration of 2%. Acidity, peroxide value, K232, K270, sensorial attributes, oxidative stability, and phenolic contents had been monitored. Also, phenolic compounds are identified in the flavored and unflavored olive oil samples. These results demonstrated that the aromatic plant had enhanced the flavored olive oil stability; the levels of addition of aromatic plants could be distinguished by the taster's sensory attributes of flavored olive oil. As the plan of the experiment includes process preparation and consumer preference, it is possible to apply the obtained results to the production of flavored olive oil. The producers will gain a new product with more added values due to the nutritional and antioxidant strength of the aromatic plants.

Co-milling of sound olives with fresh chili peppers improves the volatile compound, capsaicinoid and sensory profiles of flavoured olive oil with respect to the typical infusion

In the context of the olive oil flavoured with chili peppers, the aim of this study was to compare co-milling of sound olives and fresh chili peppers at mill scale to infusion of dried chili peppers in oil, using the same batch of olives for all oils. Capsaicinoids by HPLC-DAD, volatile profile by HS-SPME-GC-MS and HS-GC-IMS and sensory profile were characterized. Capsaicinoids were statistically higher in oils prepared with green (52.0–68.0 mg/kg) than red (48.0–60.2 mg/kg) chili peppers. Oils flavoured by infusion showed higher contents of volatile compounds linked to defects such as acetic acid, with winey/vinegary sensory defect (median, 1.72–2.02) and no fresh pepper flavour. Oils prepared by co-milling resulted rich in the typical esters of chili pepper (6.175 and 4.156 mg/kg with green and red chili peppers, respectively), with pleasant hotness sensation and fresh pepper flavour. Overall, the co-milling approach allowed obtaining flavoured samples with improved sensory quality.

Bay Laurel (Laurus nobilis L.) Essential Oil as a Food Preservative Source: Chemistry, Quality Control, Activity Assessment, and Applications to Olive Industry Products.

Essential oils (EOs) find application as flavoring agents in the food industry and are also desirable ingredients as they possess preservative properties. The Mediterranean diet involves the use of a lot of herbs and spices and their products (infusions, EOs) as condiments and for the preservation of foods. Application of EOs has the advantage of homogeneous dispersion in comparison with dry leaf use in small pieces or powder. Among them, Laurus nobilis (bay laurel) L. EO is an interesting source of volatiles, such as 1,8-cineole and eugenol, which are known for their preservative properties. Its flavor suits cooked red meat, poultry, and fish, as well as vegetarian dishes, according to Mediterranean recipes. The review is focused on its chemistry, quality control aspects, and recent trends in methods of analysis and activity assessment with a focus on potential antioxidant activity and applications to olive industry products. Findings indicate that this EO is not extensively studied in comparison with those from other Mediterranean plants, such as oregano EO. More work is needed to establish authenticity and activity methods, whereas the interest for using it for the preparation of flavored olive oil or for the aromatization and preservation of table oils must be further encouraged.

Quality of frozen stored flavoured olive oils

The purpose of the current research was to study the effects of 6-month frozen storage on the quality parameters and the phenolic profiles of flavoured olive oils (FOO) produced by co-malaxation or infusion using basil, chilli, or chilli–garlic as flavouring ingredients. The results demonstrated that during frozen storage, FOOs underwent degradative processes that caused a progressive depletion of phenolic compounds and the rising of oxidative and hydrolytic markers. A clear interaction appeared between storage time, flavouring ingredient and flavouring technique. Infusion caused a greater quality loss than co-malaxation, and in basil flavoured oils the drawbacks of infusion were greater than in other flavoured oils. The impact of flavouring method on the phenolic profiles of oil became more evident at the end of the storage period. It was confirmed that oleocanthal is less affected by storage in freezing conditions than other secoiridoids.

Market Segmentation Using Intrinsic Product Attributes: Evidence From the Tunisian Olive Oil Market

Market segmentation using consumer preferences is important for the marketing strategy. For staple foods, like olive oil in the Mediterranean region, intrinsic attributes of the product lead these preferences and should prevail in determining consumer groups. In this paper, we apply conjoint analysis and clustering methods to identify olive oil consumer segments in the Tunisian market. A survey was carried out among 274 consumers who were required to blind taste of samples and give scores for 12 different samples of Tunisian Extra Virgin Olive Oil (EVOO). Results revealed three differentiated segments of consumers; 43.8% of consumers prefer strongly flavored olive oil with deep green color while 38.9% support light yellow olive oil with lower flavor. These preferences are described by age, income category, and consumption frequency. Our results indicate that in countries where olive oil is a traditional food ingredient, the marketing strategy must focus on the product’s intrinsic attributes to better target customers.

Carolea olive oil enriched with an infusion of Capsicuum annuum and C. chinense dried pepper powders to produce an added value flavoured olive oils

This work aimed to evaluate the impact on quality parameters and of flavored virgin olive oils (FVOOs) obtained by the infusion of Capsicuum annuum and Capsicuum chinense fine dry powder to Carolea extra virgin olive oil (EVOO). The total phenol, flavonoid, and carotenoid content were monitored in EVOO, and FVOOs phenolic fractions. The Rancimat method was applied to compare EVOO and FVOOs oxidative stability. The EVOO and FVOOs antioxidant activity was investigated by ABTS and DPPH radical scavenging assays. FVOO formulated with Aji limo resulted the most active as radical scavenger with IC50 value of 18.8 and 27.6 μg/ml in DPPH and ABTS test, respectively. All the FVOOs obtained a positive judgment from the judges although FVOO obtained by the enrichment of Aji limo and Red Mushroom were the strongest both for the olfactory hint of chilli and for the gustatory hint of spiciness. Novelty impact statment Recently, the European Food Safety Authority established that Extra virgin olive oil (EVOO) due the content in bioactive compounds should be considered a functional food. The enrichment of EVOO with herbs and spice lead to flavored olive oil (FVOO) or “gourmet oils” that are particularly appreciated by consumers due their ability to enhance aroma and taste of food. This research should propose the formulation of new FVOOs by using Carolea EVOO as starting oil and different Capsicuum species to generate products with enriched sensory characteristics and a greater added value.

Kinetic study of the microwave‐induced thermal degradation of cv. Arbequina olive oils flavored with lemon verbena essential oil

AbstractThe effect of typical domestic microwave heating (0–15 min, at 800 W) on the thermal degradation of unflavored and flavored olive oils' minor bioactive compounds and related antioxidant activity was studied. Olive oils from cv. Arbequina were flavored with lemon verbena essential oil (0%, 0.2% and 0.4%, w/w) leading to a linear increase of total phenols (112–160 mg gallic acid kg−1 oil, R‐Pearson = +0.9870), total carotenoids (2.19–2.56 mg lutein kg−1 oil, R‐Pearson = +0.9611), and, to a less extent, of chlorophyll (2.32–3.19 mg pheophytin kg−1 oil, R‐Pearson = +0.8238). However, no such linear trend was observed for the oxidative stability (6.5–7.8 h) or the radical scavenging activity (inhibition rates: 40%–43%). The contents of total phenols, total carotenoids, and chlorophyll decreased with the rise of the microwave heating time, following their thermal degradation, a second‐order kinetic model (0.8784 ≤ R‐Pearson ≤ 0.9926). The essential oil addition did not influence the estimated second‐order rate reaction constants of total phenols (0.00070–0.00072 kg oil min−1 mg−1 gallic acid)and total carotenoids (0.14–0.17 kg oil min−1 mg−1 lutein), with a broader variation observed for chlorophyll (0.014–0.022 kg oil min−1 mg−1 pheophytin). Globally, total carotenoids degraded faster than total phenols and chlorophyll (half‐life of 2.3–3.4, 8.8–12.8, and 14.5–30.8 min, respectively). Moreover, except for chlorophyll, the half‐life of total phenols and carotenoids linearly decreased with the essential oil addition (R‐Pearson: −0.9999 and −0.9421, respectively), showing that flavoring did not have a protective effect against degradation when subjected to a microwave heating.

Marinated Anchovies (Engraulis encrasicolus) Prepared with Flavored Olive Oils (Chétoui cv.): Anisakicidal Effect, Microbiological, and Sensory Evaluation

To meet the food demand of future generations, more sustainable food production is needed. Flavored olive oils (FOOs) have been proposed as natural additives to ensure food safety and quality through a more sustainable approach. The chemical composition and antioxidant potential of two different olive oils flavored, respectively, with cumin (Cm) and with a mixture of parsley, garlic, and lemon (Mix) were investigated. Cm-FOO and Mix-FOO were tested against Anisakis both in vitro and ex vivo through an exposure test of anchovy fillets experimentally parasitized with Anisakis larvae. Microbiological and sensory analysis were carried out on marinated anchovy fillets exposed to both FOOs to evaluate their effects on the shelf life and their sensory influence. The addition of herbs and spices did not affect the chemical composition of the olive oil (free acidity, UV absorbance, and fatty acid composition). Only Mix showed antioxidant activity, while Cm had no effect in this regard. Cm-FOO and Mix-FOO devitalized the Anisakis larvae both in vitro within 24 h and ex vivo after 8 and 10 days of exposure, respectively. The results of microbiological analyses showed that FOOs inhibited the growth of typical spoilage flora in the marinated anchovies without negatively affecting their sensory characteristics, as observed from the sensory analysis.

Flavored Olive Oil as a Preservation Means of Reduced Salt Spanish Style Green Table Olives (cv. Chalkidiki).

Reformulation of products fermented in brine is a challenging area of research. Continuing the efforts toward the establishment of table olives as a healthy food for all population groups, this study aimed at examining whether olive oil flavored with essential oils can be used as a preservation means for reduced salt Spanish style green table olives (cv. Chalkidiki). Response surface methodology was applied to organize experimentation and assess data. As independent factors, concentrations of the essential oils used (oregano, lemon balm and bay laurel) and time of storage under vacuum were set. Microbiological parameters (pathogens and fermentation-related microbes), color and firmness attributes were used as responses. Models indicated that each essential oil exerted a preservative role to maintain microbiological quality of reduced salt table olives. Concurrently, appearance attributes of the latter were retained at desirable values. Oregano essential oil had a profound role against pathogens. Lemon balm and bay laurel essential oils were found to be important for yeast population control. The results are promising toward the use of flavored olive oil as a preservation means for tailor-made reduced salt table olives, a practice that may enhance local industry innovative activity in a practical and effective way.

The addition of Capsicum baccatum to Calabrian monovarietal extra virgin olive oils leads to flavoured olive oils with enhanced oxidative stability

This study aimed to evaluate the influence of Capsicum baccatum L. Aji Angelo and Bishop crown cultivars to the quality parameters of flavoured olive oils (FOOs) obtained by the addition of both fresh and dried pepper powders (1%) to Dolce di Rossano and Roggianella monovarietal extra virgin olive oils (EVOOs). First, pepper extracts were investigated for their total phenolic, flavonoid, carotenoid content as well as phenolic acids, fatty acid profile, and vitamin C and E content. In order to evaluate the impact of both fresh and dried peppers on the oxidative stability of FOOs, the Rancimat test was applied. 2,2-Azinobis(3-ethylbenzothiazoline-6-sulfonic) acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), ?-carotene bleaching (B-CB) and ferric reducing antioxidant power (FRAP) assays were used to investigate the antioxidant potential. Bishop crown dried extracts showed the highest phenolic, carotenoid and vitamin content, whereas Aji Angelo had the highest amount of capsaicinoids. Among EVOOs, Roggianella EVOO showed the highest antioxidant activity as well as the highest induction time (39.6 h). Remarkably, FOO obtained by the addition of Bishop crown dried pepper extract to Roggianella EVOO showed a higher induction time (44.9 h) with respect to the corresponding EVOO.

Two bi-functional cytochrome P450 CYP72 enzymes from olive (Olea europaea) catalyze the oxidative C-C bond cleavage in the biosynthesis of secoxy-iridoids - flavor and quality determinants in olive oil.

Olive (Olea europaea) is an important crop in Europe, with high cultural, economic and nutritional significance. Olive oil flavor and quality depend on phenolic secoiridoids, but the biosynthetic pathway of these iridoids remains largely uncharacterized. We discovered two bifunctional cytochrome P450 enzymes, catalyzing the rare oxidative C-C bond cleavage of 7-epi-loganin to produce oleoside methyl ester (OeOMES) and secoxyloganin (OeSXS), both through a ketologanin intermediary. Although these enzymes are homologous to the previously reported Catharanthus roseus secologanin synthase (CrSLS), the substrate and product profiles differ. Biochemical assays provided mechanistic insights into the two-step OeOMES and CrSLS reactions. Model-guided mutations of OeOMES changed the product profile in a predictable manner, revealing insights into the molecular basis for this change in product specificity. Our results suggest that, in contrast to published hypotheses, in planta production of secoxy-iridoids is secologanin-independent. Notably, sequence data of cultivated and wild olives point to a relation between domestication and OeOMES expression. Thus, the discovery of this key biosynthetic gene suggests a link between domestication and secondary metabolism, and could potentially be used as a genetic marker to guide next-generation breeding programs.