Vaccenic acid is a naturally occurring
trans fatty acid
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.
The term often refers specifically to triglycerides (triple e ...
. It is the predominant kind of trans-fatty acid found in
human milk
Breast milk (sometimes spelled as breastmilk) or mother's milk is milk produced by mammary glands located in the breast of a human female. Breast milk is the primary source of nutrition for newborns, containing fat, protein, carbohydrates (lacto ...
, in the fat of
ruminant
Ruminants (suborder Ruminantia) are hoofed herbivorous grazing or browsing mammals that are able to acquire nutrients from plant-based food by fermenting it in a specialized stomach prior to digestion, principally through microbial actions. The ...
s, and in
dairy products such as
milk
Milk is a white liquid food produced by the mammary glands of mammals. It is the primary source of nutrition for young mammals (including breastfed human infants) before they are able to digest solid food. Immune factors and immune-modula ...
,
butter
Butter is a dairy product made from the fat and protein components of churned cream. It is a semi-solid emulsion at room temperature, consisting of approximately 80% butterfat. It is used at room temperature as a spread, melted as a condimen ...
, and
yogurt
Yogurt (; , from tr, yoğurt, also spelled yoghurt, yogourt or yoghourt) is a food produced by bacterial fermentation of milk. The bacteria used to make yogurt are known as ''yogurt cultures''. Fermentation of sugars in the milk by these bac ...
.
Trans fat in human milk may depend on trans fat content in food.
[
Its ]IUPAC
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
name is (11''E'')-11-octadecenoic acid, and its lipid shorthand name is 18:1 ''trans''-11. The name was derived from the Latin
Latin (, or , ) is a classical language belonging to the Italic branch of the Indo-European languages. Latin was originally a dialect spoken in the lower Tiber area (then known as Latium) around present-day Rome, but through the power of the ...
''vacca'' (cow
Cattle (''Bos taurus'') are large, domesticated, cloven-hooved, herbivores. They are a prominent modern member of the subfamily Bovinae and the most widespread species of the genus ''Bos''. Adult females are referred to as cows and adult ma ...
).
Vaccenic acid was discovered in 1928 in animal fats and butter
Butter is a dairy product made from the fat and protein components of churned cream. It is a semi-solid emulsion at room temperature, consisting of approximately 80% butterfat. It is used at room temperature as a spread, melted as a condimen ...
.
Mammals convert it into rumenic acid
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 b ...
, a conjugated linoleic acid
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 (i.e., separated ...
,
where it shows anticarcinogenic properties.
Its stereoisomer, ''cis''-vaccenic acid, is an omega-7 fatty acid, is found in Sea Buckthorn
''Hippophae'' is the genus of sea buckthorns, deciduous shrubs in the family Elaeagnaceae. The name sea buckthorn may be hyphenated to avoid confusion with the unrelated true buckthorns (''Rhamnus'', family Rhamnaceae). It is also referred to as ...
(''Hippophae rhamnoides'') oil. Its IUPAC
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
name is (11''Z'')-11-octadecenoic acid, and its lipid shorthand name is 18:1 ''cis''-11.
Health
Vaccenic acid is also found in human orbitofrontal cortex
The orbitofrontal cortex (OFC) is a prefrontal cortex region in the frontal lobes of the brain which is involved in the cognitive process of decision-making. In non-human primates it consists of the association cortex areas Brodmann area 11, 1 ...
of patients with bipolar disorder
Bipolar disorder, previously known as manic depression, is a mental disorder characterized by periods of depression and periods of abnormally elevated mood that last from days to weeks each. If the elevated mood is severe or associated with ...
and schizophrenia
Schizophrenia is a mental disorder characterized by continuous or relapsing episodes of psychosis. Major symptoms include hallucinations (typically hearing voices), delusions, and disorganized thinking. Other symptoms include social wit ...
.
Alkaline phosphatase inhibited 25% by vaccenic acid in osteoblasts.
Oxidation of omega-7 unsaturated fatty acids on the skin surface, such as palmitoleic acid
Palmitoleic acid, or (9''Z'')-hexadec-9-enoic acid, is an omega-7 monounsaturated fatty acid (16:1n-7) with the formula CH3(CH2)5CH=CH(CH2)7COOH that is a common constituent of the glycerides of human adipose tissue. It is present in all tissues ...
and vaccenic acid, may be the cause of the phenomenon commonly known as old person smell
Old person smell is the characteristic odor of elderly humans. Much like many animal species, human odor undergoes distinct stages based on chemical changes initiated through the aging process. Research suggests that this enables humans to determi ...
.
When fed vaccenic acid over 16 weeks, rats exhibited in lowered total cholesterol
Cholesterol is any of a class of certain organic molecules called lipids. It is a sterol (or modified steroid), a type of lipid. Cholesterol is biosynthesized by all animal cells and is an essential structural component of animal cell mem ...
, lowered LDL
Low-density lipoprotein (LDL) is one of the five major groups of lipoprotein that transport all fat molecules around the body in extracellular water. These groups, from least dense to most dense, are chylomicrons (aka ULDL by the overall densit ...
cholesterol and lower triglyceride
A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids (from ''wikt:tri-#Prefix, tri-'' and ''glyceride'').
Triglycerides are the main constituents of body fat in humans and other ...
levels.
Two Canadian studies have shown that vaccenic acid could be beneficial compared to vegetable shortening
Shortening is any fat that is a solid at room temperature and used to make crumbly pastry and other food products. Although butter is solid at room temperature and is frequently used in making pastry, the term ''shortening'' seldom refers to b ...
s containing trans fats, or a mixture of pork lard and soy fat, by lowering total LDL
Low-density lipoprotein (LDL) is one of the five major groups of lipoprotein that transport all fat molecules around the body in extracellular water. These groups, from least dense to most dense, are chylomicrons (aka ULDL by the overall densit ...
and triglyceride levels. 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.[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
References
{{Fatty acids
Fatty acids
Animal fats
Dairy products
Alkenoic acids