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">Lipid</span> Substance of biological origin that is soluble in nonpolar solvents

Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins, monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing energy, signaling, and acting as structural components of cell membranes. Lipids have applications in the cosmetic and food industries, and in nanotechnology.

<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 humans and other animals must ingest because the body requires them for good health, but cannot synthesize them.

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">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 is 16:0. It is a major component of the oil from the fruit of oil palms, 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. Palmitates are the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4). Major sources of C16:0 are palm oil, palm kernel oil, coconut oil, and milk fat.

<span class="mw-page-title-main">Oleic acid</span> Monounsaturated omega-9 fatty acid

Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9, and a main product of Δ9-desaturase. It has the formula CH3−(CH2)7−CH=CH−(CH2)7−COOH. The name derives from the Latin word oleum, which means oil. It is the most common fatty acid in nature. The salts and esters of oleic acid are called oleates. It is a common component of oils, and thus occurs in many types of food, as well as in soap.

Linoleic acid (LA) is an organic compound with the formula HOOC(CH
2)
7CH=CHCH
2CH=CH(CH
2)
4CH
3. 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>

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.

Dihomo-γ-linolenic acid (DGLA) is a 20-carbon ω−6 fatty acid. In physiological literature, it is given the name 20:3 (ω−6). DGLA is a carboxylic acid with a 20-carbon chain and three cis double bonds; the first double bond is located at the sixth carbon from the omega end. DGLA is the elongation product of γ-linolenic acid. GLA, in turn, is a desaturation product of linoleic acid. DGLA is made in the body by the elongation of GLA, by an efficient enzyme which does not appear to suffer any form of (dietary) inhibition. DGLA is an extremely uncommon fatty acid, found only in trace amounts in animal products.

Elaidic acid is a chemical compound with the formula C
18H
34O
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">Medium-chain triglyceride</span> Medium-chain fatty acids

Medium-chain triglycerides (MCTs) are triglycerides with two or three fatty acids having an aliphatic tail of 6–12 carbon atoms, i.e. medium-chain fatty acids (MCFAs). Rich food sources for commercial extraction of MCTs include palm kernel oil and coconut oil.

<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.

<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) has set a goal to make the world free from industrially produced trans fat by the end of 2023.

References

  1. ↑ Bowerman, Susan (May 19, 2008). "Now there are good trans fats?". Los Angeles Times.
  2. ↑ Precht D, Molkentin J (August 1999). "C18:1, C18:2 and C18:3 trans and cis fatty acid isomers including conjugated cis delta 9, trans delta 11 linoleic acid (CLA) as well as total fat composition of German human milk lipids". Nahrung. 43 (4): 233–44. doi:10.1002/(SICI)1521-3803(19990801)43:4<233::AID-FOOD233>3.0.CO;2-B. PMID   10481820.
  3. ↑ Friesen R, Innis SM (October 2006). "Trans fatty acids in human milk in Canada declined with the introduction of trans fat food labeling". J. Nutr. 136 (10): 2558–61. doi: 10.1093/jn/136.10.2558 . PMID   16988126.
  4. 1 2 Destaillats F, Buyukpamukcu E, Golay PA, Dionisi F, Giuffrida F (2005). "Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats". Journal of Dairy Science . 88 (449): 449. doi: 10.3168/jds.S0022-0302(05)72705-3 . PMID   15653508.
  5. ↑ Bauman, Dale. "cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat". Archived from the original on 2006-09-07. Retrieved 2007-01-15.
  6. ↑ Banni S, Angioni E, Murru E, Carta G, Melis M, Bauman D, Dong Y, Ip C (2001). "Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland". Nutr Cancer. 41 (1–2): 91–7. doi:10.1080/01635581.2001.9680617. PMID   12094634. S2CID   2920114.
  7. ↑ Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C (October 1, 2004). "The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats". J Nutr. 134 (10): 2698–704. doi: 10.1093/jn/134.10.2698 . PMID   15465769 . Retrieved 2007-01-15.
  8. ↑ Federal Research Centre for Nutrition and Food - Institute for Lipid Research. "Seed Oil Fatty Acids Database".
  9. ↑ Bainbridge, Melissa L.; Cersosimo, Laura M.; Wright, André-Denis G.; Kraft, Jana (2016-03-01). Brockmann, Gudrun A. (ed.). "Content and Composition of Branched-Chain Fatty Acids in Bovine Milk Are Affected by Lactation Stage and Breed of Dairy Cow". PLOS ONE. 11 (3): e0150386. Bibcode:2016PLoSO..1150386B. doi: 10.1371/journal.pone.0150386 . ISSN   1932-6203. PMC   4773160 . PMID   26930646.
  10. ↑ Trans Fats From Ruminant Animals May Be Beneficial – Health News. redOrbit (8 September 2011). Retrieved 22 January 2013.
  11. ↑ Bassett, C. M. C.; Edel, A. L.; Patenaude, A. F.; McCullough, R. S.; Blackwood, D. P.; Chouinard, P. Y.; Paquin, P.; Lamarche, B.; Pierce, G. N. (Jan 2010). "Dietary Vaccenic Acid Has Antiatherogenic Effects in LDLr-/- Mice". The Journal of Nutrition. 140 (1): 18–24. doi: 10.3945/jn.109.105163 . PMID   19923390.
  12. ↑ Wang, Flora & Proctor, Spencer (2 April 2008). "Natural trans fats have health benefits, University of Alberta study shows" (Press release). University of Alberta.
  13. ↑ Wang Y, Jacome-Sosa MM, Vine DF, Proctor SD (20 May 2010). "Beneficial effects of vaccenic acid on postprandial lipid metabolism and dyslipidemia: Impact of natural trans-fats to improve CVD risk". Lipid Technology. 22 (5): 103–106. doi:10.1002/lite.201000016.
  14. ↑ Bassett C, Edel AL, Patenaude AF, McCullough RS, Blackwood DP, Chouinard PY, Paquin P, Lamarche B, Pierce GN (2010). "Dietary Vaccenic Acid Has Antiatherogenic Effects in LDLr−/− Mice". The Journal of Nutrition. 140 (1): 18–24. doi: 10.3945/jn.109.105163 . PMID   19923390.
  15. ↑ David J. Baer, PhD. US Department of Agriculture, Agricultural Research Service, Beltsville Human Nutrition Research Laboratory. New Findings on Dairy Trans Fat and Heart Disease Risk, IDF World Dairy Summit 2010, 8–11 November 2010. Auckland, New Zealand
  16. ↑ AFNS. Alberta natural trans fat research earns global recognition Archived 2008-06-15 at the Wayback Machine . April 2, 2008.
  17. ↑ Wang, Ye; Jacome-Sosa, M. Miriam; Vine, Donna F.; Proctor, Spencer D. (May 2010). "Beneficial effects of vaccenic acid on postprandial lipid metabolism and dyslipidemia: Impact of natural trans -fats to improve CVD risk". Lipid Technology. 22 (5): 103–106. doi:10.1002/lite.201000016. ISSN   0956-666X.
  18. ↑ McNamara, RK; Jandacek, R; Rider, T; Tso, P; Hahn, CG; Richtand, NM; Stanford, KE (2007). "Abnormalities in the fatty acid composition of the postmortem orbitofrontal cortex of schizophrenic patients: gender differences and partial normalization with antipsychotic medications". Schizophr Res. 91 (1–3): 37–50. doi:10.1016/j.schres.2006.11.027. PMC   1853256 . PMID   17236749.
  19. ↑ McNamara, RK; Jandacek, R; Rider, T; Tso, P; Stanford, KE; Hahn, CG; Richtand, NM (2008). "Deficits in docosahexaenoic acid and associated elevations in the metabolism of arachidonic acid and saturated fatty acids in the postmortem orbitofrontal cortex of patients with bipolar disorder". Psychiatry Research. 160 (3): 285–299. doi:10.1016/j.psychres.2007.08.021. PMC   2620106 . PMID   18715653.
  20. ↑ Haze S, Gozu Y, Nakamura S, Kohno Y, Sawano K, Ohta H, Yamazaki K (April 2001). "2-Nonenal newly found in human body odor tends to increase with aging". J. Invest. Dermatol. 116 (4): 520–4. doi: 10.1046/j.0022-202x.2001.01287.x . PMID   11286617.
  21. ↑ Hamazaki K, Suzuki N, Kitamura K, Hattori A, Nagasawa T, Itomura M, Hamazaki T (June 2016). "Is vaccenic acid (18:1t n-7) associated with an increased incidence of hip fracture? An explanation for the calcium paradox". Prostaglandins Leukot. Essent. Fatty Acids. 109: 8–12. doi:10.1016/j.plefa.2016.04.001. PMID   27269708.
  22. ↑ Fan H, Xia S, Xiang J, et al. (22 November 2023). "Trans-vaccenic acid reprograms CD8+ T cells and anti-tumour immunity". Nature. 623 (7989): 1034–1043. doi: 10.1038/s41586-023-06749-3 . PMC   10686835 . PMID   37993715.
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