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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.
CAS Number: 506-12-7
EC Number: 208-027-1
IUPAC Name: heptadecanoic acid
Chemical Formula: C17H34O2
Other names: 506-12-7, Margaric acid, n-Heptadecanoic acid, Margarinic acid, n-Heptadecylic acid, n-Heptadecoic acid, Heptadecylic acid, C17:0, V987Y9OZ8L, DTXSID5021596, NSC-3743, CHEBI:32365, fatty acid 17:0, RefChem:922841, DTXCID201596, 208-027-1, MFCD00002751, Normal-heptadecanoic acid, FA 17:0, 63399-94-0, NSC 3743, EINECS 208-027-1, BRN 1781004, UNII-V987Y9OZ8L, Margarinsaeure, margaroic acid, heptadecoic acid, AI3-36481, eptadecanoic acid, Heptadecanoic acic, N-Heptadecylicacid, X90, Normal-heptadecanoate, heptadecansäure, Lead(2+) heptadecanoate, Heptadecanoic acid, 98%, DSSTox_CID_1596, MARGARIC ACID [MI], SCHEMBL5941, DSSTox_RID_78651, DSSTox_GSID_28306, Heptadecanoic acid, >=98%, 4-02-00-01193 (Beilstein Handbook Reference), WLN: QV16, SCHEMBL250323, SCHEMBL450491, orb1221468, orb1302463, orb3025480, SCHEMBL1276040, SCHEMBL9615666, CH3-[CH2]15-COOH, CHEMBL1172910, FA 17:0a, SCHEMBL10610041, SCHEMBL28742630, SCHEMBL28742632, SCHEMBL28742732, SCHEMBL28742833, SCHEMBL28824176, MSK1715, NSC3743, EINECS 264-123-3, Tox21_202550, BBL013181, EBC-04214, LMFA01010017, s3336, SBB060275, STL163960, AKOS005716689, CS-W004284, FH63213, HY-W004284, NSC 122836, NCGC00260099-01, AS-57021, BP-27918, BP-30092, SY010570, CAS-67701-03-5, H0019, NS00019727, ST51046494, T4903, EN300-19173, H10748, F240381, Q902204, 8EBAABCC-09B2-43FB-945D-A70E5905BFBE, Z104473032
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
