PRODUCTS

DOCOSAPENTAENOIC ACID

CAS NUMBER: 24880-45-3

UNII NUMBER: NS3OZT14QT

MOLECULAR FORMULA: C22H34O2

MOLECULAR WEIGHT: 330.5

IUPAC NAME: (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid

Docosapentaenoic Acid (DPA) designates any straight chain 22:5 fatty acid, that is a straight chain open chain type of polyunsaturated fatty acid (PUFA) which contains 22 carbons and 5 double bonds.
Docosapentaenoic Acid is primarily used to designate two isomers, all-cis-4,7,10,13,16-docosapentaenoic acid (i.e. 4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid) and all-cis-7,10,13,16,19-docosapentaenoic acid (i.e. 7Z,10Z,13Z,16Z,19Z-docosapentaenoic acid).

They are also commonly termed n-6 Docosapentaenoic Acid and n-3 DPA, respectively; these designations describes the position of the double bond being 6 or 3 carbons closest to the (omega) carbon at the methyl end of the molecule and is based on the biologically important difference that n-6 and n-3 PUFA are separate PUFA classes, i.e. the omega-6 fatty acids and omega-3 fatty acids, respectively. Mammals, including humans, can not interconvert these two classes and therefore must obtain dietary essential PUFA fatty acids from both classes in order to maintain normal health (see essential fatty acids).
Docosapentaenoic Acid (DPA) is an n-3 fatty acid that is structurally similar to eicosapentaenoic acid (EPA) with the same number of double bonds, but two more carbon chain units.

Dietary Sources:
These are the top five sources for Docosapentaenoic Acid according to the USDA Agricultural Research Service:

-Fish oil, menhaden 0.668g in 1 tbsp. (13.6g)

-Fish oil, salmon 0.407g in 1 tbsp. (13.6g)

-Salmon, red (sockeye), filets with skin, smoked (Alaska Native) 0.335g in 1 filet (108g)

-Fish, salmon, Atlantic, farmed, raw 0.334g in 3 oz (85g)

-Beef, variety meats and by-products, brain, cooked, simmered 0.326g in 3oz (85g)

Seal meat and human breast milk are rich in Docosapentaenoic Acid.
Docosapentaenoic Acid, an omega-3 fatty acid, along with its metabolite DHA and other long chain omega-3 fatty acids, is under study to determine properties of omega-3 fats in humans, such as in inflammation mechanisms.

Docosapentaenoic Acid is the all-cis-isomer of a C22 polyunsaturated fatty acid having five double bonds in the 7-, 10-, 13-, 16- and 19-positions. It has a role as a human metabolite and an algal metabolite.
Docosapentaenoic Acid is a docosapentaenoic acid and an omega-3 fatty acid.
Docosapentaenoic Acid is a conjugate acid of a (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate.

Docosapentaenoic Acid is a polyunsaturated very long-chain fatty acid with a 22-carbon backbone and 5 double bonds, originating from the 3rd, 6th, 9th, 12th and 15th positions from the methyl end, with all double bonds in the cis- configuration.
Docosapentaenoic Acid is a natural product found in Homo sapiens with data available.

Docosapentaenoic Acid is an omega-3 polyunsaturated fatty acid corresponding to all- cis -Δ 7,10,13,16,19 - docosapentaenoic acid (22:5) .
Docosapentaenoic Acid takes its name from Clupanodon thrissa 2 , a fish of the family Clupeidae — which also includes herrings and sardines .

Alternative Classes:
-Unsaturated fatty acids

-Straight chain fatty acids

-Monocarboxylic acids and derivatives

-Carboxylic acids

-Organic oxides

-Hydrocarbon derivatives

-Carbonyl compounds

Docosapentaenoic Acid is an intermediate metabolite in the conversion of eicosapentaenoic acid (EPA) to docosahexaenoic acid (DHA).
Docosapentaenoic Acid is present in abundance in the blubber of pinnipeds — seals , walruses , and sea lions .

Docosapentaenoic Acid (DPA) is an omega-3 fatty acid that is known chemically as all-cis-4,7,10,13,16-docosapentaenoic acid.
Docosapentaenoic Acid also has an omega-6 isomer, although this form is rare in mammals except for the testes.
The structure of Docosapentaenoic Acid is similar to that of eicosapentaenoic acid (EPA), except that DPA has two more carbon units in its chain.

The most abundant dietary source of Docosapentaenoic Acid is oil from the bearded seal, which contains 5.6 grams of DPA per 100-gram serving, and some researchers feel that it may be a contributing factor to the overall good cardiovascular health of the Greenland Intuits.
Fatty fish such as menhaden and salmon also have high levels of Docosapentaenoic Acid.

Raw salmon oil contains 393 milligrams of Docosapentaenoic Acid per 100-gram serving.
Atlantic mackerel and Florida pompano (which contains even more Docosapentaenoic Acid than EPA) deliver over 200 mg of DPA per 100 gram portion.
Small-fin tuna is also another good source of Docosapentaenoic Acid.

Substituents:
-Very long-chain fatty acid

-Unsaturated 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

Laboratory studies show that Docosapentaenoic Acid and EPA are readily converted into each other in the liver, so DPA serves as a precursor for EPA.
However, neither of these fatty acids appears to be metabolized into docosahexaenoic acid (DHA), which is another nutritionally important omega-3 fatty acid.

Docosapentaenoic Acid is also present in many other tissues, especially the heart, kidneys and skeletal muscle.
Docosapentaenoic Acid serves many functions in the human body that primarily deal with blood health and cell proliferation.

Uses of Docosapentaenoic Acid:
The support of healthy clotting is one of the most common reasons for taking Docosapentaenoic Acid.
Docosapentaenoic Acid is also commonly used to support healthy inflammation management and blood vessel function.

Docosapentaenoic Acid is used in preparation method of rape bee pollen long-chain Fatty Acid and its derivatives.
Docosapentaenoic Acid, also known as DPA, is a fatty acid derived from fish oils that potently inhibits platelet aggregation.
Docosapentaenoic Acid has been reported to block the cyclooxygenase pathway and stimulate the lipoxygenase pathway, which results in effective platelet aggregation inhibition.

PHYSICAL PROPERTIES:

-Molecular Weight: 330.5

-XLogP3-AA: 6.7

-Exact Mass: 330.255880323

-Monoisotopic Mass: 330.255880323

-Topological Polar Surface Area: 37.3 Å²

-Physical Description: Solid

-Density: 0.9±0.1 g/cm3

-Boiling Point: 465.1±24.0 °C at 760 mmHg

-Vapour Pressure: 0.0±2.5 mmHg at 25°C

-Enthalpy of Vaporization: 79.6±6.0 kJ/mol

-Flash Point: 361.7±18.0 °C

-Index of Refraction: 1.509

-Molar Refractivity: 105.8±0.3 cm3

-Polarizability: 42.0±0.5 10-24cm3

-Surface Tension: 35.5±3.0 dyne/cm

-Molar Volume: 354.4±3.0 cm3

Docosapentaenoic Acid (DPA) is ideal as a standard and for biological systems.
Very long-chain polyunsaturated omega- 3 fatty acids such as Docosapentaenoic Acid are thought to influence memory and cognition, protect neurons, and reduce inflammation.

Docosapentaenoic Acid is an intermediate in the invivo synthesis of docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA), polyunsaturated fatty acids that have been demonstrated as critical for many biological functions.
Docosapentaenoic Acid in humans is converted to EPA much more readily than to DHA. In animals and humans DPA is usually found acylated to phospholipids.

Omega-3 fatty acids such as Docosapentaenoic Acid and DHA have been shown to reduce the risk of acute coronary events in humans.
Seal oil has been suggested as more efficient than fish oil at promoting healthy plasma lipid profiles and lowering thrombotic risk, possibly due to its high DPA and EPA content.

Docosapentaenoic Acid is more effective in inhibition of aggregation in platelets obtained from rabbit blood than EPA and DHA
Docosapentaenoic Acid possesses greater endothelial cell migration ability than EPA, which is important in wound-healing processes.
Recently Docosapentaenoic Acid has been found to down-regulates the expression of genes involved in fat synthesis in liver cells.

CHEMICAL PROPERTIES:

-Hydrogen Bond Donor Count: 1

-Hydrogen Bond Acceptor Count: 2

-Rotatable Bond Count: 15

-Heavy Atom Count: 24

-Formal Charge: 0

-Complexity: 425

-Isotope Atom Count: 0

-Defined Atom Stereocenter Count: 0

-Undefined Atom Stereocenter Count: 0

-Defined Bond Stereocenter Count: 5

-Undefined Bond Stereocenter Count: 0

-Covalently-Bonded Unit Count: 1

-Compound Is Canonicalized: Yes

Docosapentaenoic Acid is an unsaturated fatty acid found in fish oils.
Docosapentaenoic Acid is a minor constituent of the total serum unsaturated fatty acids in humans.

Docosapentaenoic Acid (22n-6) is practically insoluble (in water)
Docosapentaenoic Acid is a weakly acidic compound (based on its pKa).
Docosapentaenoic Acid (22n-6) can be found in blood and urine, as well as in human adipose tissue, fibroblasts, and platelet tissues.

Within the cell, Docosapentaenoic Acid (22n-6) is primarily located in the membrane (predicted from logP).
Docosapentaenoic Acid can also be found in the extracellular space.

In humans, Docosapentaenoic Acid (22n-6) is involved in alpha-linolenic acid and linoleic acid metabolism.
Docosapentaenoic Acid is also commonly used to support healthy inflammation management and blood vessel function.

Docosapentaenoic Acid (DPA) is a minor omega-3 fatty acid (FA) which has been frequently overlooked in lipid research.
Docosapentaenoic Acid is a highly unsaturated acid C21H33COOH obtained as a light yellow oil from fish or fish liver oils and blubber oil
Docosapentaenoic Acid is more effective in inhibition of aggregation in platelets obtained from rabbit blood than EPA and DHA

Docosapentaenoic Acid possesses greater endothelial cell migration ability than EPA, which is important in wound-healing processes.
Recently Docosapentaenoic Acid has been found to down-regulates the expression of genes involved in fat synthesis in liver cells.

Docosapentaenoic Acid is used in preparation method of rape bee pollen long-chain Fatty Acid and its derivatives.
Docosapentaenoic Acid (DPA) is ideal as a standard and for biological systems.
Very long-chain polyunsaturated omega- 3 fatty acids such as Docosapentaenoic Acid are thought to influence memory and cognition, protect neurons, and reduce inflammation.

SYNONYMS:

Clupanodonic acid
docosapentaenoic acid
(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoic acid
cis-7,10,13,16,19-Docosapentaenoic acid
7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid
all-cis-7,10,13,16,19-Docosapentaenoic acid
(all Z)-7,10,13,16,19-Docosapentaenoic acid
Docosapentaenoic acid (22n-3)
Docosapentaenoic acid 22n-3
(7Z,10Z,13Z,16Z,19Z)-Docosapentaenoic acid
7,10,13,16,19-docosapentaenoic acid, (7Z,10Z,13Z,16Z,19Z)-
(all-cis)-7,10,13,16,19-Docosapentaenoic Acid
C22:5n-3,6,9,12,15
Clupanodonate
Osbond's acid
7,10,13,16,19-Docasapentaenoic acid, (all-Z)-
7,10,13,16,19-Docosapentaenoic acid, (all Z)-
7,10,13,16,19-docosapentaenoate
Docosapentaenoic acid (22:5(n-3))
HY-113159
CS-0062313
Docosa-7c,10c,13c,16c,19c-pentaensaeure
Delta7,10,13,16,19-Docosapentaenoic acid
docosa-7Z,10Z,13Z,16Z,19Z-pentaenoic acid
(all-Z)-7,10,13,16,19-Docosapentaenoic acid
SR-01000946652
cis-7,10,13,16,19-DOCOSA-PENTAENOIC ACID
J-015716
Q3278345
SR-01000946652-1
7,10,13,16,19-Docosapentaenoic acid, (all-Z)- (8CI)
(7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoate
(7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoic acid
7,10,13,16,19-Docosapentaenoicacid,(7Z,10Z,13Z,16Z,19Z)-
all-cis-7,10,13,16,19-Docosapentaenoic acid, synthetic, >=97%
7,10,13,16,19-Docosapentaenoic acid, (7Z,10Z,13Z,16Z,19Z)- (9CI)
Docosapentaenoic acid (cis-7,10,13,16,19)