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Margaric acid is a long-chain saturated fatty acid with the molecular formula C17H34O2.
Margaric acid is used in research as a biomarker for certain dietary studies, particularly in assessing the intake of dairy fat.
Margaric acid plays a significant role in dietary studies as a biomarker for dairy fat consumption because of its unique presence in ruminant-derived products.
CAS Number: 506-12-7
EC Number: 208-022-0
Chemical Formula: C17H34O2
Molecular Weight: 270.45 g/mol
Synonyms: Heptadecylic acid, n-Heptadecanoic acid, Margarinic acid, HEPTADECANOIC ACID, n-Heptadecylic acid, n-Heptadecoic acid, Fatty acids, C14-22, Daturinic acid, Heptadecanoate, Heptadecanoic acid, Heptadecoate, Heptadecoic acid, heptadecanoic acid, Margarate, Margaric acid, Margarinate, Margarinic acid, margaroate, margaroic acid, n-Heptadecanoate, n-Heptadecanoic acid, n-Heptadecoate, n-Heptadecoic acid, n-Heptadecylate, n-Heptadecylic acid, Normal-heptadecanoate, Normal-heptadecanoic acid, Heptadecanoate, Heptadecoic acid, Heptadecylic acid, Margaric acid, Margarinic acid, Margarinsaeure, N-Heptadecanoic acid, N-Heptadecoic acid, N-Heptadecylic acid, Heptadecoate, Heptadecylate, Margarate, Margarinate, N-Heptadecanoate, N-Heptadecoate, N-Heptadecylate, Margaroate, Margaroic acid, Normal-heptadecanoate, Normal-heptadecanoic acid, Margaric acid, 1-(11)C-labeled, Margaric acid, nickel (2+) salt, Omega I-123 heptadecanoic acid, Margaric acid, potassium salt, Margaric acid, sodium salt, FA(17:0), Heptadecanoic acid, 3-Hydroxyheptadecane, 7,8-Dihydroxyheptadecane, 7-Ethylheptadecanoic acid, 11-Hydroxyheptadecanoic acid, 2,3-Dihydroxyheptadecane, Heptadecyl ester, 1-Heptadecene-3-carboxylic acid, Heptadecan-1-oic acid, Heptadecane-oic acid, Decane-1-carboxylic acid, Methyl heptadecanoate, 17-Octadecenoic acid, 1,2-Heptadecanediol, Heptadecanoic acid (short chain derivative), Heptadecanol, 15-Methylheptadecane, 7-Carboxyheptadecane, 1,5-Hexadecane carboxylic acid, 2-Heptadecanone, 1-Heptadecyl-2-carboxylic acid, Hydroxyheptadecanoate, Heptadecanoic acid ethyl ester, 17-Undecanoic acid, 9-Hydroxyheptadecane, 11-Ethylheptadecane
Margaric acid is a saturated fatty acid with the chemical formula C17H34O2.
Margaric acid is composed of a 17-carbon alkyl chain with a carboxylic acid group (-COOH) at one end.
Margaric acid is less common compared to other saturated fatty acids like palmitic and stearic acids but is found naturally in trace amounts in animal fats, dairy products, and some plants.
Margaric acid is used in research as a biomarker for certain dietary studies, particularly in assessing the intake of dairy fat.
Margaric acid also plays a role in lipid metabolism research and industrial applications, including lubricants, cosmetics, and chemical synthesis.
Margaric acid's physical properties include being a white, crystalline solid with a melting point of approximately 59–61°C.
Though not essential in human nutrition, Margaric acid provides valuable insights into fatty acid distribution in biological systems.
Margaric acid is a long-chain saturated fatty acid with the molecular formula C17H34O2.
Structurally, Margaric acid consists of a straight 17-carbon alkyl chain terminated with a carboxylic acid functional group (-COOH), making it part of the saturated fatty acid family.
Margaric acid is relatively uncommon compared to other fatty acids like palmitic acid (C16) or stearic acid (C18).
However, Margaric acid is naturally present in small quantities in various sources, including animal fats, dairy products such as milk and cheese, and certain plants.
Margaric acid plays a significant role in dietary studies as a biomarker for dairy fat consumption because of its unique presence in ruminant-derived products.
Researchers often use Margaric acid to assess the intake of dairy and its association with health outcomes, including cardiovascular disease and metabolic syndrome.
In addition to its biological significance, Margaric acid has several industrial and scientific applications.
Margaric acid is employed in lipid metabolism research to understand the distribution and behavior of fatty acids in biological systems.
Margaric acid's chemical properties make it suitable for use in the synthesis of esters, which are widely utilized in the production of lubricants, surfactants, and cosmetic formulations.
Furthermore, this fatty acid can serve as an intermediate in the preparation of specialty chemicals and materials.
Physically, Margaric acid is a white, waxy, or crystalline solid at room temperature, with a melting point in the range of 59–61°C and a boiling point above 300°C.
Margaric acid is insoluble in water but soluble in organic solvents like ethanol, ether, and chloroform.
Margaric acid's relatively high melting and boiling points are due to the strong intermolecular interactions typical of saturated fatty acids.
While not essential in human nutrition, Margaric acid's trace presence in the diet has intrigued scientists for its potential benefits in certain contexts, such as its hypothesized role in supporting lipid profiles and cardiovascular health.
Overall, Margaric acid serves as a valuable compound in both scientific research and industrial applications, offering insights into the roles of saturated fatty acids in biological and chemical systems.
Margaric acid is a fatty acid of exogenous (primarily ruminant) origin.
Many "odd" length long chain amino acids are derived from the consumption of dairy fats (milk and meat).
Margaric acid constitutes 0.61% of milk fat and 0.83% of ruminant meat fat.
The content of Margaric acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products.
Margaric acid is a crystalline saturated fatty acid.
Margaric acid's molecular formula is CH3(CH2)15CO2H.
Classified as an odd-chain fatty acid,Margaric acid occurs as a trace component of the fat and milkfat of ruminants, but Margaric acid does not occur in any natural animal or vegetable fat at high concentrations.
For example, Margaric acid comprises only 2.2% of the fats from the fruit of the durian species Durio graveolens.
Margaric acid's name is derived from the Ancient Greek μάργαρος (márgar(on)), meaning "pearl(y)", due to its appearance.
Margaric acid is a C17 saturated fatty acid and trace component of fats in ruminants.
Margaric acid has a role as a mammalian metabolite, a Daphnia magna metabolite and an algal metabolite.
Margaric acid is a long-chain fatty acid and a straight-chain saturated fatty acid.
Margaric acid is a conjugate acid of a margarate.
Margaric acid is a saturated long-chain fatty acid with a 17-carbon backbone.
Margaric acid is found naturally as a minor component of the fat and milk fat of ruminants.
Margaric acid is a natural product found in Agelas conifera, Myrmekioderma rea, and other organisms with data available.
Margaric acid, belongs to the class of organic compounds known as long-chain fatty acids.
These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
Margaric acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Margaric acid is a constituent of Erythrina crista-galli trunkwood and bark.
Margaric acid is a fatty acid of exogenous (primarily ruminant) origin.
Many "odd" lengths long chain amino acids are derived from the consumption of dairy fats (milk and meat).
Margaric acid is usually found in trace amounts and constitutes 0.61% of milk fat and 0.83% of ruminant meat fat.
The content of Margaric acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products.
Margaric acid is a common constituent of lipids, such as those present in Physalia physalis (Portuguese-man-of-war).
Margaric acid has pheromonic and allomonic properties for insects and reptiles.
The subcaudal gland secretions of the European badger (Meles meles) and the occipital gland secretions of male bactrian camels (Camelus bactrianus) contain many pheromonic chemicals, including Margaric acid, that aid in finding and selection of mates.
Margaric acid is an attractant of the khapra beetle (Trogoderma granarium) and the yellow fever mosquito (Aedes aegypti) but as a repellent of the common house mosquito.
Margaric acid is also found in the precloacal gland secretions of many reptiles belonging to the order squamata, including the common leopard gecko and the European viper (Vipera berus), where Margaric acid is used for the identification of sexual partners.
Belongs to the class of organic compounds known as long-chain fatty acids.
These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
Margaric acid, also known as 17:0 or heptadecoate, belongs to the class of organic compounds known as long-chain fatty acids.
Margaric acid is a crystalline saturated fatty acid.
Margaric acid's molecular formula is CH₃(CH₂)₁₅CO₂H.
Classified as an odd-chain fatty acid, Margaric acid occurs as a trace component of the fat and milkfat of ruminants, but Margaric acid does not occur in any natural animal or vegetable fat at high concentrations.
For example, Margaric acid comprises only 2.2% of the fats from the fruit of the durian species Durio graveolens.
However, in the 19th and early 20th centuries, there were numerous reports of the acid being found in natural fats in significant amounts.
Most likely, these were cases of misidentifying a eutectic mixture of palmitic and stearic acids.
Salts and esters of Margaric acid are called heptadecanoates.
Margaric acid's name is derived from the Ancient Greek μάργαρος, meaning "pearl", due to its appearance.
Margaric acid methyl ester is an esterified form of Margaric acid.
Margaric acid has been found in biodiesel produced by C.
Sorokiniana microalgae as well as in several types of animal fat biodiesel.
Margaric acid methyl ester has been used as an internal standard for the quantification of fatty acid methyl esters in human plasma.
Margaric acid is an odd-chain saturated fatty acid that contains seventeen carbons and has been found in milk fat.
Margaric acid has been used as an internal standard for the quantification of fatty acids in human plasma by LC- and GC-MS and as a biomarker for dairy fat intake.
Margaric acid is a saturated fatty acid.
Margaric acid's molecular formula is CH3(CH2)15COOH.
Margaric acid occurs as a trace component of the fat and milkfat of ruminants, but Margaric acid does not occur in any natural animal or vegetable fat at concentrations over half a percent.
Uses of Margaric acid:
Margaric acid is used as a reference during the analysis of medium-chain fatty acids from biomaterials such as seed oils and plant and animal oils.
Margaric acid is intended for Food & beverage applications.
Margaric acid is a versatile compound with applications across dietary research, industry, and scientific studies.
Margaric acid is widely used as a biomarker for dairy fat intake in nutritional studies, helping researchers assess the relationship between dairy consumption and health outcomes such as cardiovascular health and metabolic syndrome.
In the industrial sector, Margaric acid finds use in the production of cosmetics, biodegradable lubricants, and surfactants, owing to its chemical stability and functional properties.
Additionally, Margaric acid serves as an intermediate in the synthesis of specialty chemicals and esters for various applications.
In scientific research, Margaric acid plays a crucial role in lipid metabolism studies, helping to understand fatty acid distribution and behavior in biological systems.
Margaric acid is also used as a standard in analytical methods like gas chromatography.
These diverse applications highlight Margaric acid's importance in advancing knowledge in health sciences, chemistry, and food technology.
Applications of Margaric acid:
Margaric acid has several important uses across various fields, including dietary research, industrial applications, and scientific studies.
Below are Margaric acid's primary applications:
Dietary and Nutritional Research:
Biomarker for Dairy Fat Intake:
Margaric acid is used as a reliable biomarker in studies assessing the consumption of dairy fat, as it is uniquely present in ruminant-derived foods like milk, cheese, and butter.
Health Studies:
Margaric acid's role in improving cardiovascular health, lipid metabolism, and reducing risks of metabolic syndrome is being explored, particularly as part of studies on saturated fatty acids in the diet.
Industrial Applications:
Cosmetics:
Margaric acid and its derivatives, such as esters, are used in the formulation of creams, lotions, and other skincare products for their emollient properties.
Lubricants:
Margaric acid serves as a component in the production of biodegradable and specialty lubricants due to its chemical stability and smooth consistency.
Surfactants and Emulsifiers:
Margaric acid is utilized in creating surfactants for cleaning products and as emulsifiers in various formulations.
Chemical Synthesis:
As an intermediate, Margaric acid is used in producing specialty chemicals and esters for industrial applications.
Scientific Research:
Lipid Metabolism Studies:
Margaric acid is used to investigate how saturated fatty acids are metabolized and distributed within the human body.
Analytical Standards:
Margaric acid serves as a reference compound in gas chromatography and mass spectrometry for identifying and quantifying fatty acids in biological samples.
Food Science:
Flavor Enhancement:
In some applications, Margaric acid's derivatives are used in food formulations to enhance texture or flavor.
Quality Control:
Margaric acid is monitored in food products to assess the presence and quality of dairy fat content.
Pharmaceutical Applications (Exploratory):
Potential Therapeutic Role:
Studies are exploring Margaric acid's anti-inflammatory properties and effects on cardiovascular health, though this is still in the research phase.
Semiochemistry of Margaric acid:
For many species, Margaric acid plays a role as a semiochemical - specifically it possesses pheromonic and allomonic properties.
Margaric acid has been identified in the subcaudal gland secretions of the European badger (Meles meles) and in the occipital gland secretions of male Bactrian camels (Camelus bactrianus) where it is one of the many pheromonic chemicals responsible for aiding in the finding and selection of mates.
Margaric acid is an attractant of the khapra beetle (Trogoderma granarium) and the yellow fever mosquito (Aedes aegypti) but is a repellent of the common house mosquito (Culex pipiens).
Margaric acidthe common leopard gecko (Eublepharis macularius) and the European viper (Vipera berus), where Margaric acid is used for the identification of sexual partners.
Unsaturated Forms of Margaric acid:
Unsaturated derivatives of it are found in nature, although rare.
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.
C17:1 cis-9 (ω-8) is found at trace amounts in ruminant fats and some varieties of olive oils.
Minor amounts (< 1%) of C17:1 cis-10 and C17:2 cis-8,11 were detected in seed oil of Portia tree (Thespesia populnea).
Alternative Parents of Margaric acid:
Straight chain fatty acids
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
Substituents of Margaric acid:
Long-chain fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound
Production of Margaric acid:
The production of Margaric acid can occur naturally or through synthetic processes.
Below are the primary methods of production:
Natural Sources:
Animal Fats and Dairy Products:
Margaric acid is naturally found in trace amounts in ruminant-derived fats, such as those in milk, butter, and cheese.
Margaric acid is produced in the digestive systems of ruminants during the fermentation of dietary fiber by gut microbes and incorporated into their fat stores.
Marine Sources:
Small amounts can also be found in certain fish oils and marine organisms.
Chemical Synthesis:
Saponification of Fats:
Margaric acid can be produced through the saponification of triglycerides containing heptadecanoate esters.
This process involves hydrolyzing fats or oils in the presence of a strong base, followed by acidification to yield the free fatty acid.
Oxidation of Hydrocarbons:
Margaric acid can be synthesized by oxidizing long-chain hydrocarbons or alcohols with the appropriate carbon chain length.
Kolbe Electrolysis:
This method involves the electrochemical decarboxylation of sodium salts of hexadecanoic acid (palmitic acid) to form Margaric acid as one of the products.
Biosynthesis in Laboratory Settings:
Microbial Fermentation:
Certain microbes, such as genetically engineered strains, can produce Margaric acid under controlled fermentation conditions.
This method is being explored as a sustainable alternative to chemical synthesis.
Plant Metabolic Engineering:
Research is ongoing to modify the fatty acid biosynthesis pathways in plants to produce odd-chain fatty acids like Margaric acid.
Industrial Processing:
Fractional Distillation:
Natural fats and oils can be processed to isolate specific fatty acids, including Margaric acid, through fractional distillation or advanced separation techniques like urea fractionation and chromatography.
Manufacturing of Margaric acid:
Margaric acid can be manufactured through both natural extraction and synthetic processes.
Naturally, Margaric acid is isolated from animal fats and dairy products, where it occurs in trace amounts, using processes such as saponification followed by acidification or advanced separation techniques like fractional distillation and chromatography.
Chemically, Margaric acid can be synthesized by oxidizing long-chain hydrocarbons or through the saponification of triglycerides containing heptadecanoate esters.
Innovative methods such as microbial fermentation and plant metabolic engineering are also being explored to produce Margaric acid sustainably.
These techniques utilize engineered microbes or modified plants to biosynthesize odd-chain fatty acids under controlled conditions.
Industrially, Margaric acid's production often involves refining raw materials from animal or plant sources to isolate this fatty acid for use in research, food, and industrial applications.
Handling and Storage of Margaric acid:
Handling:
Handle Margaric acid with care to avoid skin and eye contact.
Wear appropriate personal protective equipment (PPE) such as gloves, safety goggles, and lab coats.
Avoid inhaling dust or vapors.
Ensure adequate ventilation in work areas.
Storage:
Store in a cool, dry, well-ventilated area, away from incompatible materials such as strong oxidizers or acids.
Keep containers tightly sealed.
Store at room temperature to prevent degradation.
Do not store near open flames or heat sources.
Stability and Reactivity of Margaric acid:
Stability:
Margaric acid is stable under normal handling and storage conditions.
Margaric acid is a relatively stable organic acid with a long shelf life when kept in dry, sealed containers.
Reactivity:
Margaric acid is not reactive under normal conditions but may react with strong oxidizing agents, strong acids, or bases.
Conditions to Avoid:
Avoid high temperatures and direct sunlight.
Keep away from strong oxidizers and acids, as they may cause unwanted reactions.
Hazardous Decomposition Products:
When heated to decomposition, Margaric acid may produce carbon monoxide, carbon dioxide, and other toxic gases.
First Aid Measures of Margaric acid:
Inhalation:
Move the person to fresh air immediately.
If breathing is difficult, administer oxygen.
Seek medical attention if symptoms persist.
Skin Contact:
Wash the affected area thoroughly with soap and water.
If irritation occurs, seek medical advice.
Eye Contact:
Rinse eyes with plenty of water for at least 15 minutes, lifting eyelids occasionally.
Seek medical attention if irritation persists.
Ingestion:
Rinse the mouth with water and drink one or two glasses of water.
Do not induce vomiting unless instructed by a healthcare professional.
Seek immediate medical attention.
Firefighting Measures of Margaric acid:
Suitable Extinguishing Media:
Use water spray, foam, dry chemical, or carbon dioxide (CO2) to extinguish fires involving Margaric acid.
Special Hazards:
Combustion may produce toxic fumes, including carbon monoxide and carbon dioxide.
Containers may explode when heated.
Protective Equipment:
Firefighters should wear self-contained breathing apparatus (SCBA) and full protective gear when fighting fires involving Margaric acid.
Accidental Release Measures of Margaric acid:
Personal Precautions:
Evacuate the area if necessary.
Avoid direct contact with the spill.
Wear appropriate PPE, including gloves, safety goggles, and respiratory protection if needed.
Environmental Precautions:
Prevent the material from entering drains, sewers, or water sources.
Prevent further contamination of the surrounding area.
Spill Cleanup:
Absorb small spills with an inert material like sand or vermiculite.
For large spills, contain the spill and transfer to an appropriate waste container.
Dispose of the material in accordance with local environmental regulations.
Exposure Controls / Personal Protective Measures of Margaric acid:
Exposure Limits:
Margaric acid does not have established occupational exposure limits, but workers should avoid prolonged or repeated skin contact and inhalation of vapors or dust.
Engineering Controls:
Ensure good ventilation in work areas.
Use fume hoods, especially when handling large quantities of the substance.
Personal Protective Equipment (PPE):
Respiratory Protection:
Use a dust mask or respirator if necessary, especially in poorly ventilated areas.
Gloves:
Wear chemical-resistant gloves such as nitrile or neoprene gloves to prevent skin contact.
Eye Protection:
Wear safety goggles or face shield to prevent eye contact.
Skin Protection:
Wear appropriate clothing to minimize skin exposure, such as a lab coat or apron.
Identifiers of Margaric acid:
IUPAC Name: Margaric acid
Chemical Formula: C₁₇H₃₄O₂
Molecular Weight: 270.45 g/mol
CAS Number: 506-12-7
EC Number: 208-022-0
PubChem CID: 10465
Structural Identifiers
SMILES: CCCCCCCCCCCCCCCC(=O)O
InChI: InChI=1S/C17H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19)
InChI Key: QIQXTHQIDYTFRH-UHFFFAOYSA-N
CAS Number: 506-12-7
EC Number: 208-027-1
MDL number: MFCD00002751
Linear Formula: CH3(CH2)15COOH or C17H34O2
Beilstein Reference: 1720575
EINECS Number: 208-022-0
UNII (FDA): 9H26L3TK79
Synonyms: Margaric acid, C17:0 fatty acid, n-Margaric acid
Abbreviation: C17:0 (denoting its 17-carbon saturated structure)
ChEBI ID: 30831
CHEMSPIDER ID: 10038
KEGG Compound ID: C06410
ZINC Database ID: ZINC01515521
Molecular Formula: C17H34O2
Exact Mass: 270.2559 Da
Monoisotopic Mass: 270.2559 g/mol
Properties of Margaric acid:
Molecular Weight: 270.45 g/mol
Appearance Form: solid
Odour: No data available
Odour Threshold: No data available
pH: No data available
Melting point/freezing point:
Melting point/range: 59 - 61 °C - lit.
Initial boiling point and boiling range: 227 °C at 133 hPa - lit.
Melting point:59-61 °C(lit.)
Boiling point: 227 °C100 mm Hg(lit.)
Density: 0,853 g/cm3
Refractive index: 1.4348 (589.3 nm 40℃)
Flash point: 227°C/100mm
Storage temp.: room temp
Form: Shiny Flakes or Crystalline Powder
pKa: 4.78±0.10(Predicted)
Color: White to off-white
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 61.00 to 62.00 °C. @ 760.00 mm Hg
Boiling Point: 363.00 to 364.00 °C. @ 760.00 mm Hg
Boiling Point: 298.00 to 299.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.000300 mmHg @ 25.00 °C. (est)
Flash Point: 317.00 °F. TCC ( 158.40 °C. ) (est)
logP (o/w): 7.320 (est)
Soluble in: alcohol; water, 4.2 mg/L @ 25 °C (exp)
Insoluble in: water
Names of Margaric acid:
Common Names:
Heptadecanoic acid
Margaric acid
C17:0 fatty acid
n-Heptadecanoic acid
Chemical Names:
Heptadecanoic acid
Hexadecylacetic acid
