IngredientsMargaroleic acid is the common name for (9Z)-heptadecenoic acid, a 17-carbon monounsaturated fatty acid (MUFA) belonging to the odd-chain fatty acid (OCFA) family. It is a monounsaturated fatty acid, also designated C17:1(9Z), FA 17:1, and Margaroleic Acid. Its chemical formula is C₁₇H₃₂O₂ and it has a molecular mass of 268.24 daltons, with PubChem CID 5282748 and the isomeric SMILES notation CCCCCCC/C=C\CCCCCCCC(=O)O, reflecting its single cis double bond.
(9Z)-heptadecenoic acid is a heptadecenoic acid in which the double bond is located at the 9–10 position and has Z (cis) configuration. It is therefore an omega-8 fatty acid, as the double bond falls at the 8th carbon counting from the methyl end. The CAS registry number is 1981-50-6.
Margaroleic acid is the principal unsaturated derivative of its saturated parent compound, margaric acid (heptadecanoic acid, C17:0). Unsaturated derivatives of margaric acid are found in nature, although rarely; unsaturation occurs at position 9 or both at 9 and 12 positions of the fatty chain, giving heptadecenoic (C17:1) and heptadecadienoic (C17:2) acids, respectively.
Margaroleic acid has a molecular weight of 268.4 Da, XLogP3 of 6.9, hydrogen bond donor count of 1, hydrogen bond acceptor count of 2, rotatable bond count of 14, exact mass of 268.240230259, topological polar surface area of 37.3, and heavy atom count of 19. Its high lipophilicity (LogP ~6.9) makes it substantially water-insoluble and membrane-permeable, consistent with the behavior of other long-chain fatty acids.
It has a role as a fungal metabolite and an antifungal agent, and is classified as a heptadecenoic acid and a straight-chain fatty acid.
cis-9-Heptadecenoic acid is a monounsaturated fatty acid that is a major constituent of ruminant fat and milk. Among the isomers of heptadecenoic acid found in animal fats, the cis-9 form (margaroleic acid) strongly predominates. Heptadecenoic acid (17:1) is a minor constituent of ruminant fats and its isomeric definition remains undefined in most reports on ruminant milk and intramuscular fat. However, research using gas chromatography and chemical ionization tandem mass spectrometry has since resolved the isomeric composition definitively: the isomer 17:1 cis-9 is the overwhelming heptadecenoic isomer in ruminant milk and intramuscular fat; 17:1 cis-10 is virtually absent.
Margaroleic acid has been detected in the milk of bovine, ovine (sheep), and caprine (goat) species, as well as in the intramuscular fat of ruminant animals. Samples of milk and intramuscular fat of bovine, ovine, and caprine origin were analyzed by gas chromatography using multiple capillary columns; additionally, cis isomers of ovine milk fat samples were isolated as methyl esters by preparative thin-layer chromatography, and the structural analysis of 17:1 present in samples was achieved by chemical ionization tandem mass spectrometry techniques.
C17:1 cis-9 (ω-8) is found at trace amounts in ruminant fats and some varieties of olive oils. As with margaric acid (C17:0), margaroleic acid is present in trace to minor quantities; it does not constitute a major proportion of total lipids in any commonly consumed food source. The concentrations in milk are subject to variation based on the animal's diet, particularly lipid content. cis-9-Heptadecenoic acid is a monounsaturated fatty acid that is a major constituent of ruminant fat and milk, and the levels of cis-9-heptadecenoic acid in milk are negatively correlated with methane production in cows fed a high-lipid diet.
Margaroleic acid has extremely limited occurrence in plant lipids. Minor amounts (<1%) of C17:1 cis-10 and C17:2 cis-8,11 were detected in seed oil of portia tree (Thespesia populnea). It is worth noting that the isomer found in Thespesia populnea is the cis-10 form, which is chemically distinct from margaroleic acid (cis-9). In vegetable oils derived from common crops, margaric acid (and by extension its monounsaturated derivatives) levels are minimal, often below detectable limits or less than 0.05%; for instance, levels are under 0.05% in soybean and corn oils.
Beyond dietary animal fats, margaroleic acid is also a known secondary metabolite of certain fungi. cis-9-Heptadecenoic acid (CHDA) is an antifungal fatty acid produced by the biocontrol agent Pseudozyma flocculosa. This yeast-like basidiomycete naturally secretes CHDA as part of its ecological strategy on leaf surfaces, where it helps suppress competing fungal pathogens such as powdery mildew fungi.
In mammals, margaroleic acid (C17:1) is primarily derived through the enzymatic desaturation of margaric acid (C17:0). Unsaturated forms of margaric acid are produced through enzymatic desaturation processes that introduce one or more double bonds into the saturated hydrocarbon chain, primarily via delta-9 desaturase activity, which enhances membrane fluidity compared to the parent saturated compound. The monounsaturated derivative, heptadecenoic acid (C17:1), predominantly exists as the cis-Δ9 isomer, with the structural formula CH₃(CH₂)₆CH=CH(CH₂)₇COOH. This isomer is biosynthesized by the action of stearoyl-CoA desaturase (delta-9 desaturase, SCD1) on margaric acid, inserting a cis double bond between carbons 9 and 10.
The precursor substrate, margaric acid (C17:0), itself reaches humans primarily through two pathways: direct dietary intake from dairy and ruminant meat, and endogenous synthesis via propionate. OCSFAs mainly originate from dairy fat since microbiome fermentation in ruminant animals is a primary source of production; the human body can also synthesize them by elongating propionic acid, a short-chain fatty acid formed in the microbiome. New research is also showing they may be formed by shortening very-long-chain fatty acids by removing carbon molecules using α-oxidation.
Margaroleic acid has no independent history of traditional use as a distinct herbal or dietary supplement preparation. Its identity as a specific chemical entity was only established through modern analytical chemistry (gas chromatography, mass spectrometry). Nevertheless, its saturated parent compound, margaric acid, has a notable place in the history of fat chemistry.
The modern age of lipid chemistry started with the discovery of glycerol by Scheele in 1783; the chemical nature of fats, as esters of glycerol, was recognized by Chevreul in the first part of the 19th century. Chevreul obtained margaric acid through the saponification process, in which he treated animal fats with alkali to break them down into glycerol and fatty acid salts, isolating the acid from the resulting mixture. Chevreul named the compound "margaric acid" (from the Greek margaritēs, meaning "pearl") due to the iridescent, pearly appearance of its lead salt, which distinguished it visually from other fatty acids like stearic and oleic acids.
During the 19th and early 20th centuries, margaric acid was frequently misidentified in analyses of natural fats and soaps as a major component, but these observations were likely due to a eutectic mixture of palmitic acid (C16:0) and stearic acid (C18:0), which exhibited similar melting behaviors to the purported pure compound. The specific unsaturated variant, margaroleic acid (C17:1), was not isolated and rigorously characterized as an individual molecular entity until modern chromatographic techniques became available. Early 1960s animal incorporation studies using radiolabeled cis-9-heptadecenoic acid in rats are among the earliest formal experimental examinations of the compound.
Humans have consumed margaroleic acid as an intrinsic trace component of dairy products and ruminant animal fats throughout history, wherever these foods formed part of traditional diets. Cultures reliant on dairy products — including pastoral and nomadic communities across Eurasia, sub-Saharan Africa, and South Asia — would have received dietary exposure to this fatty acid through butter, ghee, milk, cheese, and meat fat, without any awareness of its existence as a discrete chemical entity. No traditional herbal, Ayurvedic, Traditional Chinese Medicine, or other ethnopharmacological preparation identifies margaroleic acid specifically.
Margaroleic acid belongs to the broader class of odd-chain fatty acids (OCFAs), which are distinguished from the far more abundant even-chain fatty acids by having an odd number of carbon atoms. Most research in fatty acid metabolism has focused on even-chain fatty acids since they represent more than 99% of total human lipid concentration; for years, it had been concluded that odd-chain saturated fatty acids were of little significance and used only as internal standards in laboratory methodology. However, there is now a realization that they are, in fact, relevant and important physiologically.
Margaroleic acid, like other odd-chain fatty acids, undergoes β-oxidation, but with a distinctive terminal step. Metabolism of OCFAs is a bit different than even-numbered chained fatty acids. Both odd and even chain fatty acids undergo oxidation, though OCFAs produce a molecule of propionyl-CoA and a molecule of acetyl-CoA instead of two acetyl-CoAs. Propionyl-CoA requires a vitamin B12-dependent enzyme to be converted into succinyl-CoA and used in the citric acid cycle. This means that normal metabolism of margaroleic acid requires adequate vitamin B12 status; deficiency of this vitamin could theoretically impair the complete oxidation of odd-chain fatty acids, though this is not specifically documented for margaroleic acid in the clinical literature.
As a monounsaturated fatty acid, margaroleic acid contributes to membrane fluidity when incorporated into phospholipids. The cis double bond at carbon-9 introduces a kink in the acyl chain, preventing tight packing. Odd-chain fatty acids increase membrane fluidity more than PUFAs, and they are being studied as a form of treatment for Alzheimer's disease. These membrane effects, while studied for the OCFA class broadly, have not been specifically characterized for margaroleic acid at the cellular level in rigorous published human experiments.
In its role as a microbially produced antifungal agent, the mechanism of margaroleic acid has been more closely investigated. Inhibition of fungal growth and/or germination varied considerably and revealed CHDA sensitivity groups within tested fungi. Analysis of lipid composition demonstrated that sensitivity was related primarily to a low intrinsic sterol content, and that a high level of unsaturation of phospholipid fatty acids was not as involved as hypothesized previously. CHDA does not act directly with membrane sterols, nor is it utilized or otherwise modified in fungi. The probable mechanism involves partitioning of CHDA into fungal membranes and causing structural disruption proportional to the fungi's baseline lipid composition.
Note: The great majority of research concerning C17:1 margaroleic acid is either in vitro, animal-based, or consists of indirect epidemiological evidence linking odd-chain fatty acids as a class (C15:0, C17:0) to health outcomes — rather than margaroleic acid (C17:1) specifically. Where the evidence is for the OCFA class broadly, or for C17:0 (the saturated parent compound), this is clearly stated. Direct human clinical evidence specifically targeting margaroleic acid as an intervention is absent from the published literature at present.
The strongest epidemiological evidence in this space involves odd-chain fatty acids in general — predominantly the saturated forms pentadecanoic acid (C15:0) and heptadecanoic acid (C17:0) — as biomarkers of dairy fat consumption and their associations with cardiometabolic outcomes. Margaroleic acid (C17:1), as the monounsaturated analog of heptadecanoic acid, is detected alongside these markers in plasma fatty acid profiles and shares their dietary source in ruminant milk fat, though it has received comparatively less individual attention in epidemiological literature.
The risk of type 2 diabetes is inversely correlated with plasma concentrations of odd-chain fatty acids (OCFAs; pentadecanoic acid (15:0) and heptadecanoic acid (17:0)), which are considered as biomarkers for dairy fat intake in humans. A major pooled analysis assembled to investigate these associations systematically found: sixteen prospective cohorts from 12 countries performed new harmonised individual-level analyses; in total, 63,682 participants with a broad range of baseline ages and BMIs and 15,180 incident cases of type 2 diabetes over an average of 9 years of follow-up were evaluated; study-specific results were pooled using inverse-variance-weighted meta-analysis.
Circulating and adipose proportions of pentadecanoic acid (15:0), heptadecanoic acid (17:0), and trans-palmitoleic acid (t16:1n7) have been used as biomarkers correlated with dairy fat consumption. Levels of these biomarkers correlate with self-reported consumption of total dairy, high-fat dairy, and dairy fat (r = 0.4 to 0.7) based on 24-hour recalls or 7-day food records.
An important refinement to the interpretation of these associations came from research demonstrating that OCFAs are not exclusively derived from dairy. Gut-derived propionate is used for the hepatic synthesis of OCFAs in humans. The association of OCFAs with a decreased risk of type 2 diabetes may therefore also relate to dietary fiber intake and not only dairy fat. This complicates the use of plasma OCFAs as specific dairy biomarkers, and also suggests that any inverse association with diabetes risk could partly reflect high dietary fiber intake rather than dairy fat per se.
Evidence strength: The epidemiological association between plasma odd-chain fatty acids (C15:0 and C17:0) and lower type 2 diabetes incidence is supported by large multi-cohort prospective data. However, this evidence is observational and pertains primarily to the saturated odd-chain forms (C15:0, C17:0), not specifically to margaroleic acid (C17:1). Causality has not been established, and a 2023 mechanistic mouse study found that neither long-term milk fat intake nor C17:0 supplementation improved diet-induced hepatic lipid accumulation and insulin resistance in mice. Treatment of primary hepatocytes with C15:0 and C17:0 suppressed JAK2/STAT3 signaling, but only C15:0 enhanced insulin-stimulated phosphorylation of AKT; overall, the data indicate that the intake of milk fat and C17:0 do not mediate health benefits, whereas C15:0 might be promising in further studies. No comparable interventional data exist for margaroleic acid (C17:1) specifically.
Odd-chain fatty acids have been examined in relation to cardiovascular outcomes, primarily via their use as biomarkers for dairy fat. Several epidemiological studies show a positive association between OCSFAs and reduced risk for inflammation, cardiometabolic disease, multiple sclerosis, and nonalcoholic steatohepatitis. These associations are class-level observations applying broadly to OCFAs and have not been specifically attributed to margaroleic acid (C17:1) in cardiovascular clinical research.
A clinical study involving 111 participants with type 2 diabetes examined dairy-specific fatty acid biomarkers and their associations with glycemic control and cardiovascular risk markers. Pentadecanoic acid, heptadecanoic acid, and trans-palmitoleic acid are fatty acids not synthesized endogenously but obtained from the diet, particularly dairy, making them reasonable biomarkers of dairy consumption. The researchers investigated the association of dairy fatty acid biomarkers with glycated hemoglobin (HbA1c) and cardiovascular risk factors in type 2 diabetes; in a clinical trial, 111 participants with T2D were randomized into three groups — a control group, a low-fat dairy group, and a high-fat dairy group — and fatty acid composition was compared between the three groups at 24 weeks. Margaroleic acid as an isolated intervention was not tested.
Evidence strength: Indirect and observational. No randomized controlled trials specifically using margaroleic acid as an intervention for cardiovascular outcomes have been published. The available evidence for cardiovascular benefit relates to odd-chain fatty acids as a class, and confounding by overall dairy diet quality is a significant limitation.
Margaroleic acid has the most directly studied specific biological activity in the domain of antifungal research. cis-9-Heptadecenoic acid (CHDA), an antifungal fatty acid produced by the biocontrol agent Pseudozyma flocculosa, was studied for its effects on growth and/or spore germination in fungi. Inhibition of growth and/or germination varied considerably and revealed CHDA sensitivity groups within tested fungi. Analysis of lipid composition in these fungi demonstrated that sensitivity was related primarily to a low intrinsic sterol content and that a high level of unsaturation of phospholipid fatty acids was not as involved as hypothesized previously. The data indicate that CHDA does not act directly with membrane sterols, nor is it utilized or otherwise modified in fungi.
The probable molecular events implicated in the sensitivity of fungi to CHDA include partitioning of CHDA into fungal membranes; this work gives greater insight into the means by which P. flocculosa protects its habitat on the leaf surface and thus how it is able to exert its biocontrol activity against powdery mildew fungi such as S. fuliginea, with which it shares its ecological niche.
The synthesis of (Z)-9-heptadecenoic acid was developed by researchers to enable reproducible bioassay studies. Difficulties in isolating and purifying antibiotic fatty acids from culture filtrates of Pseudozyma flocculosa had been limiting factors in studying their properties; researchers reported a new protocol for synthesizing (Z)-9-heptadecenoic acid, allowing reproducible and quantifiable means of assaying biological activity; both margaroleic acid and the related 6-methyl-9-heptadecenoic acid exhibited antifungal activity corresponding to their expected potency in bioassays.
By applying a direct bioassay approach with the fungus Cladosporium cucumerinum, researchers were able to characterize two antifungal fatty acids produced by P. flocculosa: 9-heptadecenoic acid and 6-methyl-9-heptadecenoic acid. These findings indicate antifungal specificity and represent a concrete, replicated biological activity of margaroleic acid — though entirely in microbiological and plant-pathology contexts, with no clinical applications to human antifungal therapy established or proposed.
Evidence strength: Moderate, but limited in scope to in vitro microbiological and plant-pathology research. There are no human clinical data on the antifungal effects of margaroleic acid.
Research-grade reagent suppliers reference studies suggesting that cis-9-heptadecenoic acid may influence metabolic pathways. cis-9-Heptadecenoic acid is investigated for its involvement in cellular signaling and metabolism; studies suggest it may influence insulin sensitivity, as well as glucose and lipid metabolism; its potential impact on cell growth is also a subject of research, with a focus on understanding its interaction with various bodily pathways such as insulin signaling, the PPAR-alpha pathway — which is linked to fatty acid oxidation and insulin response — and the mTOR pathway, associated with protein synthesis and cellular development. However, these assertions come from a reagent-supplier product page and are not directly accompanied by primary citation to human clinical data. No specific human interventional trials have been identified for margaroleic acid and insulin sensitivity.
Evidence strength: Preclinical and speculative at this time. The pathways mentioned (PPARα, mTOR) are biologically plausible based on what is known about MUFAs and odd-chain fatty acids as a class, but direct human evidence for margaroleic acid specifically is absent.
Odd-chain fatty acids are also being studied as adjuvant therapies in cancer due to their cell signaling properties which induce targeted apoptosis. The cis-10 isomer of heptadecenoic acid (not margaroleic acid, which is cis-9) has been described as having possible antitumor activity. This property has not been specifically demonstrated for the cis-9 form (margaroleic acid) in peer-reviewed published cancer research, and the characterization of anti-tumor activity remains preliminary and is based solely on preclinical observations at this stage.
Evidence strength: Very preliminary; in vitro or class-level observations only. No clinical oncology evidence exists for margaroleic acid specifically.
Emerging research in model organisms has pointed to a role for heptadecenoic acid in gut homeostasis. Research has explored how C. elegans fatty acid two-hydroxylase regulates intestinal homeostasis by affecting heptadecenoic acid production. This line of research remains entirely at the model organism (Caenorhabditis elegans) level and has not been translated into mammalian or human studies for margaroleic acid specifically.
Odd-chain fatty acids (OCFAs) are inversely associated with type 2 diabetes in epidemiological studies; they are considered as a biomarker for dairy intake because fermentation in ruminants yields high amounts of propionate, which is used as the primer for lipogenesis. Endogenous OCFA synthesis from propionate in humans and mice has been demonstrated, but how this is affected by microbial colonization remains unexplored.
Evidence strength: Very preliminary; model organism and mechanistic research only. No human clinical evidence exists specifically for margaroleic acid in gut health.
Margaroleic acid is not commercially available as a standalone dietary supplement for human consumption. Exposure in healthy populations occurs through the diet, primarily via consumption of full-fat dairy products (milk, butter, cheese, yogurt) and ruminant meat fat. Concentrations in foods are trace-level; no specific dietary intake reference values for margaroleic acid have been established by regulatory or scientific bodies.
Margaroleic acid is commercially available in research-grade form (purity ≥98%) for in vitro and preclinical research use. cis-9-Heptadecenoic acid with CAS Number 1981-50-6, synonyms C17:1(9Z), FA 17:1, Margaroleic Acid, is available at purity ≥98%. These preparations are not formulated for human consumption and are designated for research use only.
In the antifungal biocontrol research, CHDA (margaroleic acid) was studied using concentrations determined by bioassay of culture filtrates of P. flocculosa; the synthesis protocol established by Avis and Bélanger allowed "reproducible and quantifiable means of assaying biological activity" (Avis & Bélanger, 2001, Applied and Environmental Microbiology 67:956–960), though specific minimal inhibitory concentrations for fungal species are not available in the publicly accessible abstracts reviewed.
Early rat incorporation studies from 1965 (Grimmer et al., Arzneimittelforschung 15:184–8) examined the incorporation of cis-9-heptadecenoic acid into rat lymph and blood lipids, but detailed dose parameters from those studies are not available in the reviewed sources.
No clinical dosage ranges in human supplementation trials for margaroleic acid have been established or published.
Margaroleic acid has been consumed as a trace constituent of traditional whole-food diets (dairy, ruminant meat) throughout human history without any documented population-level adverse effects attributable to this specific fatty acid. No formal toxicology studies, adverse event reports, or regulatory safety assessments specific to margaroleic acid as an isolated supplement have been identified in the peer-reviewed literature or from regulatory bodies (NIH, EFSA, WHO, or EMA).
A physiologically relevant consideration for any odd-chain fatty acid, including margaroleic acid, relates to its metabolic dependence on vitamin B12. Both odd and even chain fatty acids undergo oxidation, though OCFAs produce a molecule of propionyl-CoA and a molecule of acetyl-CoA instead of two acetyl-CoAs; propionyl-CoA requires a vitamin B12-dependent enzyme to be converted into succinyl-CoA and used in the citric acid cycle. In individuals with vitamin B12 deficiency, propionyl-CoA accumulation and impaired metabolism of odd-chain fatty acids is theoretically possible, though this has not been specifically documented for dietary margaroleic acid at physiological intake levels.
Because no human supplementation trials with isolated margaroleic acid have been published, there are no safety data from controlled human intervention studies — no documented tolerable upper intake levels, dose–response toxicology, or drug–nutrient interaction data. The majority of research only focuses on the role of OCFAs as biomarkers for dietary food intake assessment. The absence of safety concerns in the literature should therefore be interpreted as absence of data rather than as confirmed safety at supplemental doses.
All commercial sources of isolated margaroleic acid are labeled explicitly for research use only and are not sold for human ingestion. The compound does not currently hold status as a regulated dietary supplement ingredient in major jurisdictions (United States, European Union).
Margaroleic acid (cis-9-heptadecenoic acid, C17:1) is a minor but naturally occurring monounsaturated odd-chain fatty acid found principally in ruminant milk fat and meat, produced endogenously via desaturation of margaric acid by stearoyl-CoA desaturase (SCD1), and also secreted as an antifungal metabolite by the yeast-like fungus Pseudozyma flocculosa.
Its most rigorously studied biological role is as an antifungal compound in microbiological and plant-pathology research, where its mechanism of action — membrane intercalation in sterol-poor fungi — has been characterized in vitro. It is increasingly recognized as a trace component of the dairy fat lipid signature, co-occurring with the better-studied C15:0 and C17:0 odd-chain fatty acids that have been associated epidemiologically with lower risks of type 2 diabetes and cardiometabolic disease. However, margaroleic acid itself has received far less direct investigation than these saturated analogs.
Human clinical evidence specifically targeting margaroleic acid as a dietary supplement or therapeutic agent does not exist. Existing epidemiological associations are class-level (OCFAs broadly) and observational, and mechanistic animal studies have challenged the assumption that C17:0 specifically mediates the metabolic benefits attributed to dairy fat. The research status of margaroleic acid as a bioactive compound of pharmacological or nutraceutical interest is therefore best characterized as early-stage and exploratory.
Health conditions that Margaroleic acid may help support.
Body systems that Margaroleic acid may help support.
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