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HEPTADECANOIC ACID

HEPTADECANOIC ACID = MARGARIC ACID = DATURIC ACID   


CAS Number: 506-12-7
EC Number: 208-027-1
MDL number: MFCD00002751
Linear Formula: CH3(CH2)15COOH or C17H34O2

Heptadecanoic 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). 
Heptadecanoic acid constitutes 0.61% of milk fat and 0.83% of ruminant meat fat. 
The content of heptadecanoic 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, or heptadecanoic acid, is a crystalline saturated fatty acid. 
Heptadecanoic acid's molecular formula is CH3(CH2)15CO2H. 
Classified as an odd-chain fatty acid,Heptadecanoic acid occurs as a trace component of the fat and milkfat of ruminants, but Heptadecanoic acid does not occur in any natural animal or vegetable fat at high concentrations. 
For example, Heptadecanoic acid comprises only 2.2% of the fats from the fruit of the durian species Durio graveolens. 


Salts and esters of margaric acid are called heptadecanoates. 
Heptadecanoic acid's name is derived from the Ancient Greek μάργαρος (márgar(on)), meaning "pearl(y)", due to its appearance.
Heptadecanoic acid is a C17 saturated fatty acid and trace component of fats in ruminants. 
Heptadecanoic acid has a role as a mammalian metabolite, a Daphnia magna metabolite and an algal metabolite. 
Heptadecanoic acid is a long-chain fatty acid and a straight-chain saturated fatty acid. 


Heptadecanoic acid is a conjugate acid of a margarate.
Heptadecanoic acid is a saturated long-chain fatty acid with a 17-carbon backbone. 
Heptadecanoic acid is found naturally as a minor component of the fat and milk fat of ruminants.
Heptadecanoic acid is a natural product found in Agelas conifera, Myrmekioderma rea, and other organisms with data available.


Heptadecanoic acid, also known as 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. 
Heptadecanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 
Heptadecanoic acid is a constituent of Erythrina crista-galli trunkwood and bark. 
Heptadecanoic 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). 
Heptadecanoic acid is usually found in trace amounts and constitutes 0.61% of milk fat and 0.83% of ruminant meat fat. 
The content of heptadecanoic 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.


Heptadecanoic acid is a common constituent of lipids, such as those present in Physalia physalis (Portuguese-man-of-war). 
Heptadecanoic 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 heptadecanoic acid, that aid in finding and selection of mates.


Heptadecanoic 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. 
Heptadecanoic 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 Heptadecanoic 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.
Heptadecanoic acid, also known as 17:0 or heptadecoate, belongs to the class of organic compounds known as long-chain fatty acids. 
Margaric acid, or heptadecanoic acid, is a crystalline saturated fatty acid. 


Heptadecanoic acid's molecular formula is CH₃(CH₂)₁₅CO₂H. 
Classified as an odd-chain fatty acid, Heptadecanoic acid occurs as a trace component of the fat and milkfat of ruminants, but Heptadecanoic acid does not occur in any natural animal or vegetable fat at high concentrations. 
For example, Heptadecanoic 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.
Heptadecanoic acid's name is derived from the Ancient Greek μάργαρος, meaning "pearl", due to its appearance.
Heptadecanoic acid methyl ester is an esterified form of heptadecanoic acid. 
Heptadecanoic acid has been found in biodiesel produced by C. 
Sorokiniana microalgae as well as in several types of animal fat biodiesel. 


Heptadecanoic acid methyl ester has been used as an internal standard for the quantification of fatty acid methyl esters in human plasma.
Heptadecanoic acid is an odd-chain saturated fatty acid that contains seventeen carbons and has been found in milk fat. Heptadecanoic 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.


Long chain saturated fatty acid. 
Metabolite in glutamate and lipid metabolism in vivo. 
Blood-brain barrier permeable. 
Orally active.
Margaric acid or Heptadecanoic Acid is an odd chain fatty acid.


Fatty acids with odd numbers of carbon atoms are produced primarily by initiating the synthetic series with the three carbon compound, propionic acid.
Vitamin B12 is required for the conversion of propionate into succinate for oxidation in the central energy pathways.
Deficiency of vitamin B12 results in accumulation of propionate and subsequent buildup of the odd numbered fatty acids, pentadecanoic, heptadecanoic, nonadecanoic, heneicosanoic, and tricosanoic acids.


The bacteria in the gut of ruminants (grazing animals like cows and sheep) produce large amounts of propionate, which is absorbed and enters the metabolism of the animal. 
High intake of animal and dairy products favor high levels of these fatty acids.
Alternatively, Heptadecanoic Acid is possible that the bacteria in the human gut could produce sufficient amounts of propionate to lead to elevation in the odd-carbon fatty acids. 
This would only occur under conditions of significant gut dysbiosis.


Carnitine is required for fatty acid oxidation. 
In carnitine insufficiency, fatty acids are oxidized via an omega oxidation pathway that creates odd chain units. 
Therefore, odd chain fatty acid accumulation may indicate carnitine deficiency and the need for carnitine supplementation.
The odd numbered fatty acids containing 15, 17, 19, or 21 carbon atoms (heptadecanoic acid, nonadecanoic acid, tricosanoic acid, pentadecanoic acid) accumulate in vitamin B12 deficiency.


Heptadecanoic acid, or margaric acid, is a saturated fatty acid. 
Heptadecanoic acid's molecular formula is CH3(CH2)15COOH. 
Heptadecanoic acid occurs as a trace component of the fat and milkfat of ruminants, but Heptadecanoic acid does not occur in any natural animal or vegetable fat at concentrations over half a percent.


USES and APPLICATIONS of HEPTADECANOIC ACID:
-Heptadecanoic 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.
-Heptadecanoic acid is intended for Food & beverage applications. 


SEMIOCHEMISTRY of HEPTADECANOIC ACID:
For many species, Heptadecanoic acid plays a role as a semiochemical - specifically it possesses pheromonic and allomonic properties. 
Heptadecanoic 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.

Heptadecanoic 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).
Heptadecanoic acidthe common leopard gecko (Eublepharis macularius) and the European viper (Vipera berus), where Heptadecanoic acid is used for the identification of sexual partners.


UNSATURATED FORMS of HEPTADECANOIC ACID:
Unsaturated derivatives of margaric acid 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 HEPTADECANOIC ACID:    
-Straight chain fatty acids 
-Monocarboxylic acids and derivatives 
-Carboxylic acids 
-Organic oxides 
-Hydrocarbon derivatives 
-Carbonyl compounds 


SUBSTITUENTS of HEPTADECANOIC 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


PHYSICAL and CHEMICAL PROPERTIES of HEPTADECANOIC 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.
Flash point: No data available
Evaporation rate: No data available
Flammability (solid, gas): No data available
Upper/lower flammability or explosive limits: No data available
Vapour pressure: No data available
Vapour density: No data available


Relative density: No data available
Water solubility: No data available
Partition coefficient: n-octanol/water: No data available
Auto-ignition temperature: No data available
Decomposition temperature: No data available
Viscosity: No data available
Explosive properties: No data available
Oxidizing properties: No data available


Other safety information: No data available
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
Water Solubility: 
Soluble in ether. 
Slightly soluble in alcohol. 
Insoluble in water.
Stability:
Stable. 
Incompatible with bases, oxidizing agents, reducing agents.


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


FIRST AID MEASURES of HEPTADECANOIC ACID:
-Description of first aid measures:
*If inhaled:
If breathed in, move person into fresh air. 
If not breathing, give artificial respiration.

*In case of skin contact:
Wash off with soap and plenty of water.

*In case of eye contact:
Flush eyes with water as a precaution.

*If swallowed:
Never give anything by mouth to an unconscious person. 
Rinse mouth with water.

-Indication of any immediate medical attention and special treatment needed:
No data available

ACCIDENTAL RELEASE MEASURES of HEPTADECANOIC ACID:
-Environmental precautions:
No special environmental precautions required.
-Methods and materials for containment and cleaning up:
Sweep up and shovel. 
Keep in suitable, closed containers for disposal.

FIRE FIGHTING MEASURES of HEPTADECANOIC ACID:
-Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
-Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
-Further information: No data available

EXPOSURE CONTROLS/PERSONAL PROTECTION of HEPTADECANOIC ACID:
-Control parameters:
Components with workplace control parameters:
-Exposure controls:
*Appropriate engineering controls:
General industrial hygiene practice.

Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

*Skin protection:
Handle with gloves. 
Gloves must be inspected prior to use. 
Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. 
Wash and dry hands.

Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Splash contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min

*Respiratory protection:
Respiratory protection is not required. 
Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. 
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
*Control of environmental exposure:
No special environmental precautions required.


HANDLING AND STORAGE of HEPTADECANOIC ACID:
-Conditions for safe storage, including any incompatibilities:
Store in cool place. 
Keep container tightly closed in a dry and well-ventilated place.

STABILITY and REACTIVITY of HEPTADECANOIC ACID:
-Reactivity: No data available
-Chemical stability: Stable under recommended storage conditions.
-Possibility of hazardous reactions: No data available
Other decomposition products - No data available

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

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