FOOD CHEMISTRY

Pandez, Cir Bryant J.

BS Chemistry 4 - 1
 LIPIDS

Myristic Acid

Palmitoleic Acid

Linoleic Acid
 Myristic Acid
Myristic acid (14 carbon
atoms) was discovered by
Playfair L. in 1841 in the
nutmeg that is the seed of the
tropical tree Myristica
fragrans, from which its
name.

It is a saturated fatty acid (no

Molecular weight: 228.37092 g/mol
Molecular formula: C14H28O2
IUPAC name: Tetradecanoic Acid
double bond so in shorthand
14:0) member of the sub-
group called long chain fatty
acids (LCFA), from 14 to 18
carbon atoms.
Other names of myristic acid

n-tetradecanoic acid
crodacid
n-tetradecoic acid
n-tetradecan-1-oic acid
1-tridecanecarboxylic acid
14:0
 Food sources of myristic acid
Myristic acid occurs, as glycerol ester, in most animal
and vegetable fats and oils.
In animal fats, such as meat, eggs, milk, fish, shellfish,
and crustacean fats, it is present in small quantities, <1.5
g/100 g of edible portion (maximum content: 1.4 g/100 g of
edible portion in eel, and 1 g in herring).

The exception is represented by the fat in dairy

products, such as:
cheeses, especially the seasoned types (a good source is
Parmigiano, with 3.4 g/100 g of edible portion);
butter, the richest source, 8.3 g/100 g of edible portion.
 Among vegetable fats and oils, a particularly rich source
is coconut oil, with about 17 g/100 g of edible portion.
In the other vegetable oils, only palm oil has
concentrations that reach 1 g/100 g of edible portion,
whereas it does not exceed 0.86 g/100 g of edible portion
in margarine (it is absent in peanut butter).
It should be noted that nutmeg butter is 75%
trimyristin, the triglyceride of myristic acid (myristic acid
predominates in the fats of the Myristicaceae).
In fruit, it is present in high amounts only in dried and
fresh coconut (like lauric acid), 9.5 g and 5.4 g/100 g of
edible portion, respectively.
It is present in small quantities in a few cereals (corn,
with a 0.28 g/100 g of edible portion, is the richest
source).
Its not present in legumes.
 Uses of myristic acid in cosmesis and
personal-care products

It is used as ingredient in soaps, cosmetic and shaving

creams, often in the form of the ester isopropyl myristate.
 Palmitoleic Acid
Palmitoleic acid (16 carbon atoms) was
noticed first in 1854 by Hofstdter P.G. in
sperm whale oil and named physetoleic
acid.

In 1906 Bull H. discovered its molecular

composition, at the time when
Lewkowitsch gave the present name.
The structure was established in 1925 by
Armstrong E.F. et al.

It is a monounsaturated fatty acid (one cis

double bond, from the methyl end is in
Molecular weight: 254.4082 g/mol omega-7 (-7) or n-7, so in shorthand
Molecular formula: C16H30O2 16:1n-7) member of the sub-group called
IUPAC name: (Z)-hexadec-9-enoic long chain fatty acids (LCFA) (from 14 to
acid 18 carbon atoms).
Both in plants and animals it is produced
de novo by the 9 desaturation of palmitic
acid.
Other names of palmitoleic acid

zoomaric acid
cis-9-hexadecenoic acid
palmitolinoleic acid
(9Z)-hexadecenoic acid
(Z)-hexadec-9-enoic acid
(9Z)-hexadec-9-enoic acid
cis-delta(9)-hexadecenoic acid
16:1n-7
Sources of palmitoleic acid
It occurs as glycerol ester mainly in animal fats,
particularly in fish and marine mammals, but also in
vegetable oils; in the latter sources it is abundant in
Roureopsis obliquifoliata, Macadamia ternifolia,
Hippophae rhamnoides (featured image), Asclepis
syriaca seed oils, respectively 32, 20, 16-22, 10 % of
the total fatty acids.

In humans is a common component of triglycerides in

adipose tissues and is present in higher
concentrations in the liver.
 Palmitoleic acid: a new lipokine

A work of Cao H. et al. (2008) pointed out that

adipose tissue communicates with other organs
also by palmitoleic acid (so it is a lipokine); in
particular researchers demonstrated that this
fatty acid strongly stimulates muscle and liver
insulin action. This further underscore the
highly interconnection between fat metabolism
and glucose homeostasis.
 Linoleic Acid
Molecular weight: 280.44548 [g/mol]
Molecular formula: C18H32O2
IUPAC name: (9Z,12Z)-octadeca-9,12-
dienoic acid
Linoleic acid (18 carbon atoms), from
the Latin linon, meaning flax, plus
oleic, meaning oil or olive oil, was
isolated by Sacc F. in 1844 from
linseed oil.
The exact structure was clarified by
Hilditch T.P. et al. in 1939, and was
synthesized by Raphael R.A. and
Sondheimer F. in 1950.
It is a polyunsaturated fatty acid
(PUFA) with two cis double bounds
(the first one from the methyl end is in
omega-6 (-6) or n-6, so in shorthand
18:2n-6) member of the sub-group
called long chain fatty acids (LCFA),
from 14 to 18 carbon atoms.
Other names of linoleic acid

LA
(Z,Z)-9,12-octadecadienoic acid
a-linoleic acid
linolic acid
9-cis,12-cis-linoleic acid
9Z,12Z-linoleic acid
cis-delta9,12-octadecadienoic acid
9,12-linoleic acid
18:2n-6
Metabolism of linoleic acid
It is produced de novo, from oleic
acid, only by plant.

It is a primary product of plant

polyunsaturated fatty acid synthesis,
and the commonest one in plants and
animal tissue.

Animals cant synthesize it because

they lack of 12-desaturase, the
enzyme that catalyzes its synthesis,
and are obliged to obtain it from
plant foodstuff: so it is an essential
fatty acid (EFA).
Linoleic acid, omega-6, and
arachidonic acid

It is the precursor of all the omega-6

fatty acids.

It is converted in gamma-linolenic
acid in the reaction catalyzed by 6-
desaturase; then it is elongated to
form dihomo-gamma-linolenic acid,
which in turn is desaturated in the
reaction catalyzed by 5-desaturase
to form arachidonic acid which is
elongated to form adrenic acid (so far
all omega-6).
 Linoleic Acid is important in that it is required
for the synthesis ofarachidonic acid, the
precursor for all eicosanoids:
prostaglandins;
thromboxanes;
leukotrienes.

For this role in eicosanoids synthesis, its

deficiency causes growth retardation, wound healing
retardation and dermatitis, reproductive failure,
fatty liver and polydipsia.
 Sources of linoleic acid

Although nature produces LA at concentrations fairly equitable with

those of alpha-linolenic acid, modern agriculture has greatly
enriched its plant content and consequently some plant foodstuff and,
in minor extent, livestock fed diets particularly rich in this fatty acid,
can be good source for humans.

It occurs in large amount as glycerol ester in fats of walnut, peanut,

seeds of cotton, poppy, sunflower, grape, corn, sesame and soy and in
ther oils.

With oleic and palmitic acids, it is one of the three most abundant
fatty acids in triacylglycerols of adipose tissue and plasma
lipoproteins.).
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