Vaccenic acid

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Vaccenic acid
Trans-vaccenic acid.svg
Vaccenic-acid-3D-balls.png
Names
Preferred IUPAC name
(11E)-Octadec-11-enoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.691 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+ Yes check.svgY
    Key: UWHZIFQPPBDJPM-BQYQJAHWSA-N Yes check.svgY
  • InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+
    Key: UWHZIFQPPBDJPM-BQYQJAHWBK
  • CCCCCC/C=C/CCCCCCCCCC(O)=O
Properties
C18H34O2
Molar mass 282.461 g/mol
Melting point 44 °C (111 °F)
Boiling point 172 °C (342 °F)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Vaccenic acid is a naturally occurring trans fatty acid and an omega-7 fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. [1] [2] Trans fat in human milk may depend on trans fat content in food. [3] [4]

Its IUPAC name is (11E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow). [4]

Vaccenic acid was discovered in 1928 in animal fats and butter. Mammals convert it into rumenic acid, a conjugated linoleic acid, [5] [6] where it shows anticarcinogenic properties. [7]

Its stereoisomer, cis-vaccenic acid, is found in Sea Buckthorn (Hippophae rhamnoides) oil. [8] Its IUPAC name is (11Z)-11-octadecenoic acid, and its lipid shorthand name is 18:1 cis-11.

Cows milk had highest trans-vaccenic acid content in the first few days of the cows being milked, [9] indicating that it is stockpiled similarly to omega-3 fatty acids.

Health

Two Canadian studies have shown that vaccenic acid could hold benefits over trans fats derived from vegetable shortenings, or a mixture of pork lard and soy fat, by lowering total LDL and triglyceride levels. [10] [11] [12] [13] [14] A study by the US Department of Agriculture showed that vaccenic acid raises both HDL and LDL cholesterol, whereas industrial trans fats only raise LDL with no beneficial effect on HDL. [15]

Obese rats fed a diet enriched with vaccenic acid for 16 weeks had a reduction in total cholesterol, LDL cholesterol and lower triglyceride levels, [16] with an effect comparable to CLA. This effect was not seen in lean rats. [17]

Vaccenic acid accumulates in the orbitofrontal cortex to a higher extent in patients with bipolar disorder and schizophrenia. [18] [19]

Oxidation of omega-7 unsaturated fatty acids on the skin surface, such as palmitoleic acid and vaccenic acid, may be the cause of the phenomenon commonly known as old person smell. [20]

Alkaline phosphatase was inhibited 25% by vaccenic acid in osteoblasts. [21]

A 2023 University of Chicago study found that trans-vaccenic acid enhances anti-tumor immunity by activating CD8+ T cells. This effect is accomplished by deactivating a GPR43 receptor, which activates the CREB pathway instead. The effect was produced with a diet containing 1% w/w TVA. [22]


Related Research Articles

<span class="mw-page-title-main">Fatty acid</span> Carboxylic acid

In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, from 4 to 28. Fatty acids are a major component of the lipids in some species such as microalgae but in some other organisms are not found in their standalone form, but instead exist as three main classes of esters: triglycerides, phospholipids, and cholesteryl esters. In any of these forms, fatty acids are both important dietary sources of fuel for animals and important structural components for cells.

<span class="mw-page-title-main">Fat</span> Esters of fatty acid or triglycerides

In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food.

<span class="mw-page-title-main">Triglyceride</span> Any ester of glycerol having all three hydroxyl groups esterified with fatty acids

A triglyceride is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils.

Essential fatty acids, or EFAs, are fatty acids that are required by humans and other animals for normal physiological function that cannot be synthesized in the body.⁠ As they are not synthesized in the body, the essential fatty acids – alpha-linolenic acid (ALA) and linoleic acid – must be obtained from food or from a dietary supplement. Essential fatty acids are needed for various cellular metabolic processes and for the maintenance and function of tissues and organs. These fatty acids also are precursors to vitamins, cofactors, and derivatives, including prostaglandins, leukotrienes, thromboxanes, lipoxins, and others.

α-Linolenic acid Chemical compound

α-Linolenic acid, also known as alpha-linolenic acid (ALA), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils.

<span class="mw-page-title-main">Margarine</span> Semi-solid oily spread often used as a butter substitute

Margarine is a spread used for flavoring, baking, and cooking. It is most often used as a substitute for butter. Although originally made from animal fats, most margarine consumed today is made from vegetable oil. The spread was originally named oleomargarine from Latin for oleum and Greek margarite. The name was later shortened to margarine.

<span class="mw-page-title-main">Palmitic acid</span> Chemical compound

Palmitic acid is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D ratio is 16:0. It is a major component of palm oil from the fruit of Elaeis guineensis, making up to 44% of total fats. Meats, cheeses, butter, and other dairy products also contain palmitic acid, amounting to 50–60% of total fats.

Linoleic acid (LA) is an organic compound with the formula HOOC(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups are cis. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.

<span class="mw-page-title-main">Conjugated linoleic acid</span> Group of compounds found in meat and dairy from ruminants

Conjugated linoleic acids (CLA) are a family of isomers of linoleic acid. In principle, 28 isomers are possible. CLA is found mostly in the meat and dairy products derived from ruminants. The two C=C double bonds are conjugated. CLAs can be either cis-fats or trans-fats.

Butterfat or milkfat is the fatty portion of milk. Milk and cream are often sold according to the amount of butterfat they contain.

<span class="mw-page-title-main">Caprylic acid</span> Fatty acid (CH3−(CH2)6−COOH)

Caprylic acid, also known under the systematic name octanoic acid or C8 Acid, is a saturated fatty acid, medium-chain fatty acid (MCFA). It has the structural formula H3C−(CH2)6−COOH, and is a colorless oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell and taste. Salts and esters of octanoic acid are known as octanoates or caprylates. The name of the related acyl group is octanoyl, capryloyl, or caprylyl. It is a common industrial chemical, which is produced by oxidation of the C8 aldehyde. Its compounds are found naturally in the milk of various mammals and as a minor constituent of coconut oil and palm kernel oil.

Elaidic acid is a chemical compound with the formula C
18
H
34
O
2
, specifically the fatty acid with structural formula HOOC−(CH2)7−CH=CH−(CH2)7−CH3, with the double bond in trans configuration. It is a colorless oily solid. Its salts and esters are called elaidates.

<span class="mw-page-title-main">Rumenic acid</span> Chemical compound

Rumenic acid, also known as bovinic acid, is a conjugated linoleic acid (CLA) found in the fat of ruminants and in dairy products. It is an omega-7 trans fatty acid. Its lipid shorthand name is cis-9, trans-11 18:2 acid. The name was proposed by Kramer et al. in 1998. It can be considered as the principal dietary form, accounting for as much as 85-90% of the total CLA content in dairy products.

<span class="mw-page-title-main">Conjugated fatty acid</span>

Conjugated fatty acids is jargon for polyunsaturated fatty acids containing at least one pair of conjugated double bonds. An example of a conjugated fatty acid is the rumenic acid, found in the meat and milk of ruminants. Most unsaturated fatty acids that are doubly unsaturated do not feature conjugation, e.g., linoleic acid and linoelaidic acid.

<span class="mw-page-title-main">Punicic acid</span> Chemical compound

Punicic acid is a polyunsaturated fatty acid, 18:3 cis-9, trans-11, cis-13. It is named for the pomegranate,, and is obtained from pomegranate seed oil. It has also been found in the seed oils of snake gourd.

Linolelaidic acid is an omega-6 trans fatty acid (TFA) and is a cis–trans isomer of linoleic acid. It is found in partially hydrogenated vegetable oils. It is a white viscous liquid.

<span class="mw-page-title-main">Organic milk</span>

Organic milk refers to a number of milk products from livestock raised according to organic farming methods. In most jurisdictions, use of the term "organic" or equivalents like "bio" or "eco", on any product is regulated by food authorities. In general these regulations stipulate that livestock must be: allowed to graze, be fed an organically certified fodder or compound feed, not be treated with most drugs, and in general must be treated humanely.

Omega-7 fatty acids are a class of unsaturated fatty acids in which the site of unsaturation is seven carbon atoms from the end of the carbon chain. The two most common omega-7 fatty acids in nature are palmitoleic acid and vaccenic acid. They are widely used in cosmetics due to their moisturizing properties. Omega-7 fats are not essential fatty acids in humans as they can be made endogenously. Diets rich in omega-7 fatty acids have been shown to have beneficial health effects, such as increasing levels of HDL cholesterol and lowering levels of LDL cholesterol.

<span class="mw-page-title-main">Trans fat</span> Type of unsaturated fat

Trans fat, also called trans-unsaturated fatty acids, or trans fatty acids, is a type of unsaturated fat that occurs in foods. Trace concentrations of trans fats occur naturally, but large amounts are found in some processed foods. Since consumption of trans fats is unhealthy, artificial trans fats are highly regulated or banned in many nations. However, they are still widely consumed in developing nations, resulting in hundreds of thousands of deaths each year. The World Health Organization (WHO) had set a goal to make the world free from industrially produced trans fat by the end of 2023. The goal was not met, and the WHO announced another goal "for accelerated action till 2025 to complete this effort" along with associated support on 1 February 2024.

Lactobacillic acid, scientifically 10-(2-hexylcyclopropyl)­ decanoic acid, is a naturally occurring chemical compound from the group of fatty acids. Its salts are called lactobacillates. A special feature is the cyclopropane ring in the carbon chain. Lactobacillic acid, with 19 carbon atoms, is a fatty acid with an odd number of carbon atoms.

References

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