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Organic acids & juices

Malic acid: (apple juice) active

ingredient in many
sour/tart foods; salts & esters are malates. first
isolated from apple juice by Carl Wilh. Scheele 1785.
Tartaric acid (grape juice), white cryst org acid occ in
many plants: grapes, banana & tamarinds, main acid
in wine. sour taste, antioxidant. tartrates
Citric acid ( lemon juice): natural preservative, benign
cleaning agent & antioxidant. adds sour taste to foods
(spice) Important intermediate of citric acid cycle that
occurs in almost all life. Lemons, limes have particularly
high concentrations: 8% dry weight (6g per 100g juice)
Benzoic acid (cranberry juice) benzoic acid can be
purified by recrystallization from water because of its
high solubility in hot water and poor solubility in cold
water. Strong preservative & antifungal compound.
Urinary tract disinfections common preservative in
many foods, cons. Safe.

Malic acid
Malic acid causes the sourness of green apples
and grapes conferrring a tart taste to wine. From
malus = apple

1 M kg malic acid produced / year. Food additive E


296 as source of tartness in extreme candy like
Sour Punch.
Malic acid is a natural chelator provided as Mg
malate and will detoxify the gut from heavy
metal deposits.

Sourness
Sourness is due to presence of
free H + ions released by acids.

Acetic acid in vinegar


Oxalic acid in Rhubarb, Rumex
dock & spinach
Phosphoric acid in coke
Citric acid in lemonade
Carbonic acid in sodas
Sour receptor protein has COOH groups
with dissociation being affected by H+ ion
concentration
Sour taste means low pH and little danger of
bacterial contamination as in sour milk, cheese,
beer, wine, silage

Acetic acid & Acetaldehyde


Acetic acid is is a colourless liquid & the main
component of vinegar, it has a distinctive sour taste
and pungent smell. Although it is classified as a weak
acid, acetic acid is highly dangerous to skin.
Vinegar was known early in history as the natural result of
wine being exposed to air & the omnipresent acetobacter. In
the 8th century, Jabir Ibn Hayyan (Geber) was the first to
concentrate acetic acid from vinegar through distillation.
Table vinegar is typically 4 - 8% acetic acid by mass.
Vinegar is used as a condiment, and in the pickling of
vegetables.
Acetaldehyde occurs naturally in coffee, bread,
and ripe fruit, It is also produced by oxidation of
ethanol and is popularly believed to be a cause of
hangovers. The drug disulfiram (Antabuse)
prevents the oxidation of acetaldehyde to acetic
acid, and produces a hangover. & is used as a
deterrent for alcoholics.

Sumac - the vinegar or lemonade tree


The drupes of the genus Rhus are ground into a deep-red powder used as a spice in
Middle Eastern cuisine to add a lemony taste to salads or meat (turkish cuisine) In
North America, the smooth sumac (Rhus glabra), and the staghorn sumac (Rhus
typhina), are sometimes used to make a beverage, termed "sumac-ade" or "Indian
lemonade" or "rhus juice". This drink is made by soaking the drupes in cold water,
rubbing them to extract the essence, straining the liquid through a cotton cloth and
sweetening it. Native Americans also used the leaves and berries of the smooth and
staghorn sumacs combined with tobacco in traditional smoking mixtures.

Constituents of the
vinegar tree: tannins,
anthocyanins,

organic acids:
malic, citric, &
tataric plus smaller
amounts of
succinic, maleic,
fumaric and
ascorbic acid

Rhus typha,
staghorn sumach
The leaves of certain sumacs yield tannin (mostly pyrogallol),
a substance used in vegetable tanning. Leather tanned with
sumac is flexible, light in weight, and light in color, even
bordering on being white. Also many organic acids
Dried sumac wood is fluorescent under long-wave UV light

Benzaldehyde
This colorless liquid has a characteristic pleasant almondlike odor & is the primary component of bitter almond oil.
It is commonly employed to confer almond flavor.

Almonds, apricots, apples and cherry kernels, contain


significant amounts of amygdalin.
This glycoside breaks up under enzyme catalysis into
benzaldehyde, hydrocyanic acid and two molecules of
glucose

Benzyl Acetate the smell of Jasmine


This colorless liquid has a characteristic pleasant
almond-like odor & is the primary component of bitter
almond oil. It is commonly employed to confer
almond flavor.

Benzyl acetate is the ester formed by


condensation of benzyl alcohol and acetic
acid.
Benzyl acetate is found naturally in many
flowers. has pleasant sweet aroma
reminiscent of jasmine.
It is the primary constituent of the essential
oils from the flowers jasmine, ylang-ylang
and tobira. It. Consequently, it is used
widely in perfumery and cosmetics for its
aroma and in flavorings to impart apple
and pear flavors.

Benzoic acid in fruits + foods


Benzoic acid occurs naturally free and bound as
benzoic acid esters in many plant and animal
species. Amounts found in most berries are around
0.05%. Ripe fruits of several Vaccinium species (e.g.,
cranberry, V. vitis idaea; bilberry, V. macrocarpon)
contain as 300-1300 mg free benzoic acid per kg fruit
 0.1 % FW.
Use for benzoic acid as a preservative in food requires
between 0.05 0.1%. Concern has been expressed that
benzoic acid may react with ascorbic acid (vitamin C) in
some soft drinks, forming some carcinogenic benzene.
Benzoic acid can be purified by recrystallization from
water because of its high solubility in hot water and
poor solubility in cold water. The avoidance of organic
solvents makes this experiment especially safe.

Food preservation
1762 Italian priest L. Spallanzani : discovered that meat did not
spoil when heated in sealed flask.
1795 Nicholas Appert started to can foods in glass jars for
Napoleons army
1810 English Peter Durand started tin cans.
1860 Isaac Solomon of Baltimore adding CaCl2 raised boiling
temp & shortened processing time from 6 h to 45 min
 canned foods are full with NaCl & sugar

No preservatives added any chemical that retards


deterirotion unless salt, sugar, spices, wood smoke,
insecticides & herbicides  sorbic acid, benzoic acid,
sulfur dioxide, propionate & nitrites
Poppers are bottles filled with liquid alkyl nitrites like amyl,
butyl &isobutyl nitrite dilate the blood vessels and allow
more blood to get to the heart. They're sniffed straight from
the bottle and deliver a short, sharp high. Poppers are sold in
sex shops, clubs and gay bars. Street names: Ram, Thrust,Kix

Benzoic acid in perfumes


Benzoin resin = styrax resin = benzoin is obtained
from the bark of trees in the genus Styrax. Benzoin
Sumatra is obtained from Styrax benzoin grown on the
island of Sumatra. Both varieties are pathogenic resins,
which are exuded from the tree when it is damaged.
Its principle component is benzoic acid.
In perfumery, benzoin is used as a fixative, slowing the
dispersion of essential oils & other fragrances into the air.
It is also used in medicine. Tincture of benzoin has two
main medical uses: aseptic treatment for blisters damaged
skin, and as an inhalant in case of bronchitis & asthma.

Leukoptape +
TOB treats
blisters on trips

Benzoin resin is important aroma in incenses:


major comp. of incense of Russian Orthodox Christians
also in Japanese incense, Indian incense, Chinese
incense, and Papier d'Armnie. Sambrani is a popular
Indian incense used to scent hair and prevent infections.

Lab exercise: isolation of citrate


citric acid is a natural preservative & is concentrated in lemons &
limes having up to 8% of the dry weight powder crystallizes from
hot water , monohydrate from cold water
Isolation from lemon juice: 1. measure 90 ml of thawed frozen lemon juice

concentrate into a 250 ml beaker and carefully add 10 % NaOH


solution until you have reached a slightly alkaline pH. Thank
Gosh, you do not need a pH indicator since at this point the juice
turns from a clear yellow into a brownish color.
2. Strain solution through sieve to remove larger pulp particles &
. seeds (you keep for better days) & than through filter paper
3. place filtrate into a 200-ml beaker and add 5 ml of CaCl2 solutio
. for each 10 ml filtrate while constantly stirring.
4. Heat to boiling & filter off the copious mount of Ca hydro citrate
5. Resuspend in minimum of cold water, heat to boiling & collect
the insoluble Ca Citrate by filtration. Allow salt to air dry.
6. Dissolve Ca citrate in 10 % sulphuric acid toprecipitate CaSO4

Organic acids stop aging for a while


- Hydroxy acids (AHAs) the first over-the-counter antiaging preparations that work. Act as exfoliants = removing
old skin & encourage new growth, fading discoloration
(liver spots = lentigenes) & wrinkle, minimum concentration
that works is 10 % acid.
Results appear after many months of daily use.- Patience
Lactic acid, is hygroscopic substance & natural
preservative found in sour milk, yogurt, cottage cheese
& wheat beers glycolic acid is isolated form sugar
cane, canteloupe
citric acid is a natural preservative & is concentrated
in lemons & limes having up to 8% of the dry weight
powder crystallizes from hot water ,
Facial peels: Increase acid concentration to 30 to 70 %
(plastic surgeon)  light chemical peel (you are temporily
ugly after that!)
Deeper peels: use higher conc. of phenol or tri-chlore-acetic
acid (TCA)  causes crust-like scabs appear after the
application - takes tow weeks to heal but for beauty ..

Citric
acid

Lactic acid

Natural Cosmetics with everyday products


Plant saps & extracts do have various pH values, due to storage of
different amounts and species of organic acids inside the vacuole. All
plant cells have a pH between 6.8 and 7.3 inside of the cytoplasm.
Lemons have a pH of 2.0, cucumber of pH 7.0. The stems of cucumber
and pumpkins may even show a pH that is clearly alkaline or above 7
(establishProduct
Approximate pH
Abalone
6.1 - 6.5
Aloe Vera
6.1
Apples
3.3 - 3.9
Apricots

pH of several plants & plant products


PLANT

pH

Aloe Vera
Asparagus
Avocados
Beers
Beets
Cabbage
Carrots
Coconut
Celery
Horseradish
Mangos
Olives, black
Peas
Potatoes
Pumpkin
Spinach
Squash
Tea

6.1
6.
6.3 - 6.6
4.0 - 5.0
5.3 - 6.6
5.2 - 5.4
5.9 - 6.3
5.5 - 7.8
5.7 - 6.0
5.4
5.8 - 6.0
6.0 - 7.0
5.8 - 6.4
5.6 - 6.0
4.8 - 5.2
5.5 - 6.8
5.0 - 5.4
7.2

PLANT

pH

Apples
3.3 - 3.9
Bananas
4.5 - 5.2
Grapefruit
4.8 5.3
Apricots
3.3 - 4.8
Blackberries 3.9 - 4.5
Blueberries
3.1 - 3.4
Cherries
3.2 - 4.5
Cranberry juice 2.3 - 2.5
Chili sauce
2.8 - 3.7
Grapes
3.5 - 4.5
Limes
1.8 - 2.0
fermented green Olives
3.6 - 3.6
Plums
2.8 - 3.0
Sauerkraut
3.4 - 3.6
Raspberries
3.2 - 3.6
Rhubarb
3.1 - 3.2
Strawberries 3.0 - 3.9
Tomatoes
4.3 - 4.9

proteinogenic amino acids


Amino acids serve as
the monomers of
proteins.
22 amino acids are
naturally incorporated
into polypeptides and
are called
proteinogenic amino
acids.
8 proteinogenic amino
acids are called
"essential" for
humans because they
cannot be created
from other compounds
by the human body,
and so must be taken
in as food.

Essential amino acids


Nine amino acids are essential for humans: phenylalanine, valine,
threonine, tryptophan, isoleucine, methionine, histidine, leucine, and lysine.
Arginine is required by infants and growing kids, it is an important supplement
in producing nitric oxide.
They are called essential not because
they are more important to life than the
others, but because the body does not
synthesize them, making it essential to
include them in one's diet .
Animal sources such as meat,, eggs, fish,
milk, cheese provide all of the essential
amino acids. Complete proteins are
only found in some plant sources
such as spirulina, quinoa, soy,
buckwheat, hempseed, amaranth..
In addition, the amino acids arginine, cysteine, glycine, glutamine and tyrosine
are considered conditionally essential, meaning they must be supplied
exogenously to specific populations that do not synthesize them

Other essential acids


Essential substances are such that humans & other animals must
ingest because their body requires them for functioning although they
cannot synthesize them on their own.
Nine amino acids are essential for humans: phenylalanine, valine,
threonine, tryptophan, isoleucine, methionine, histidine, leucine, lysine.
Essential fatty acids, or EFAs, are those fatty acids that are required
for biological processes, and not those that only act as fuel. Two EFAs
are known for humans: alpha-linolenic acid (an omega-3 fatty acid)
& linoleic acid (an omega-6 fatty acid. When the two EFAs were first
discovered in 1923, they were designated Vitamin F. In 1930, work
showed that the two EFAs are better classified as fats than vitamins
By convention, the term vitamin does refers essential organic
substances that are needed in small quantity and does not
include other essentials such as minerals, essential fatty acids,
or essential amino acids needed in larger amounts . Thirteen
vitamins are universally recognized at present. Ascorbic acid
(vitamin C) is a vitamin for humans, but not for other animals,

Balanced diet of essentail AAs


The four sacred plants of the American SW were aligned with
the four winds
Semah, or tobacco, is one of the four
sacred plants. It represents the Eastern
Direction and the mind. Sopme use a
form of tobacco known as kinikinik,
The squash is the western direction. It
provides water and vessels.
Corn , is one of the most sacred four
plants. It represents the Northern
Direction and is the staple food crop,
The squash are the souther Direction
and they grow in perfect harmony with
corn winding around the stem
The tree sister method of agriculture provides a balanced diet that corn alone
cannot provide. The image here, is from a Navajo healing sandpainting, and
each plant corresponds here to a compass direction as well.

Non-proteinogenic amino acids


Acetyl-L-Carnitine (ALC or ALCAR) has been found
to stimulate capillary blood flow & so to improve brain
performance & cognitive functions, slows Alzheimer's
disease 500 mg/day ALCAR
Carnitine is produced from the AA lysine or
methionine, natural sources are red meat, cottage
cheese, nuts & seeds: pumpkin, sunflower, sesame,
beans, peas, peanuts. C. is required to process fats f
Theanine: in high conc. in tea leaves & some fungi neuroprotective
Nicotianine : from tobacco leaves & Shiitake mushrooms

Stizolobic acid: occurs in plants & toadstools (toxic


mushrooms) possible ijteraction with excitatory
synaptic AA receptors
Cystathione: many plant species & also human urine

Acetyl L Carnitine

Toxic non-proteinogenic amino acids


Canavalia is a genus of vines endemic to the Hawaiian
Islands & commonly known as jack-beans. The
Common Jack-bean is also known as the plant from
which the lectin concanavalin A, con A is produced.
Canavanine is a non-proteinogenic -amino acid found in
in the seeds of certain leguminous plants like jack bean
and the perennial crop alfalfa or lucerne Medicago
sativa. It is structurally related to the proteinogenic amino acid L-arginine. It serves both as a highly
deleterious defensive compound against herbivores and a
vital storage of nitrogen for the growing embryo. This plant
exhibits autotoxicity, it is difficult for alfalfa seed to grow
in existing stands of alfalfa  fields must be rotated.
The mechanism of canavanine's toxicity is that
organisms that consume it typically mistakenly
incorporate it into their own proteins in place of Larginine, thereby producing structurally aberrant
proteins that may not function properly.

Jack beans

alfalfa

non-proteinogenic amino acids as neurotransmitters


GABA or -Aminobutyric acid is not ever
incorporated into a protein. It is the chief inhibitory
neurotransmitter in the mammalian central
nervous system. It controls neuronal excitability. In
humans, GABA is also directly responsible for the
regulation of muscle tone.
Canavanine is a leguminous plants like jack bean
and the perennial crop alfalfa or lucerne
Medicago sativa. It is structurally related to the
proteinogenic -amino acid L-arginine. It serves
both as a highly GABA gradient from stigma to
ovule helps guiding the pollen tube to fertilization.
GHB or -hydroxybutyric acid is a byproduct of the
GABa catabolism. Illegal since 1991, it induces a trance
that mimics sleep. When mixed into alcohol it is used as
a DRD or date-rape-drug by inducing trance + slowed
heart rate & hypothermia. The three most common DRDs
are alcohol and two sleep aids; gamma-hydroxybutyric
acid, and benzodiazepines: Rohypnol (flunitrazepam,)

non-proteinogenic amino acids as neurotransmitters


L-DOPA (L-3,4-dihydroxyphenylalanine) is an AA
that is made from the amino acid L-tyrosine. L-DOPA
is the precursor to the neurotransmitters dopamine,
norepinephrine (noradrenaline), and epinephrine
(adrenaline)  catecholamines.. L-DOPA crosses
the protective blood-brain barrier, whereas
dopamine itself cannot
L-DOPA is dietary supplement and prescription
levopoda- for Parkinson disease ovule helps
guiding the pollen tube to fertilization.
Vicia faba or fava beans contain non-proteinogenic
AA L-DOPA or levopoda in high amounts
500 mg in one cup of beans  same amount in 2 pills.
Another good source is Mucuna pruriens (Velvet Bean)
Caution: Fava beans also contain Tyramine, which
when taken together with MAO inhibitors increase
blood pressure in so-called cheese response.

L-DOPA
Dopamine is a hormone & neurotransmitter in both
vertebrates & invertebrates producing increased heart rate
and blood pressure. Because dopamine cannot cross
blood-brain barrier L-DOPA - a precursor is given.
L-DOPA (3,4-dihydroxy-L-phenylalanine) is an amino
acid found in plants and made from L-Tyrosine in the
human body. L-DOPA is converted into dopamine in
brain & body; also dietary supplement & a prescription
drug Levodopa (INN) administered in Parkinson's
disease; also used as a component in marine adhesives.
Fava beans Vicia faba contain non-proteinogenic AA levodopa:
250 mg in a half-cup = 1 pill L-DOPA given
to Parkinson patients, who do not produce enough DOPA.
Fava beans also contain Tyramine, large dietary intake of
tyramine (especially when taking MAO inhibitors) causes cheese
response defined as an increase in systolic blood pressure of 30 mm
Hg or more + vasoconstriction, increased heart rate & blood pressure

non-proteinogenic amino acids as itchy aphrodisiacs


Mucuna pruriens is a tropical legume known as
velvet bean or cowitch found in Africa, India and
the Caribbean. The plant is infamous for its extreme
itchiness produced on contact, particularly with the
young foliage and the seed pods. The hairs lining
the seed pods contain 5-hydroxytryptamine
(serotonin) which cause the severe itching.
Traditionally, M. pruriens has been used as an
effective aphrodisiac. It is still used to increase libido
in both men and women due to its dopamine inducing
properties. Dopamine has a profound influence on
sexual function.
The plant and its extracts have been long used in
tribal communities as a toxin antagonist for various
snakebites. M.pruriens seeds have also been found
to have antidepressant properties and formulations
of the seed powder have shown promise in the
management and treatment of Parkinson disease

non-proteinogenic amino acids as neurotoxins


The neurotoxic non-proteinogenic AA ODAP acts as
a non-metabolized structural analogue of the
neurotransmitter glutamate. Ingestion of toxin results
mostly from ignorance and despair of malnutrition
(politically correct expression for hunger).
Lathyrism or Neurolathyrism is a
neurological disease of humans animals,
caused by eating legumes of the genus
Lathyrus. This problem is mainly with Lathyrus
sativus (also known as Grass pea,) and to a
lesser degree with L. cicera, L ochrus and L
clymenum containing the toxin ODAP, also N-oxalyl-amino-L-alanine or BOAA)
The related -methyl-amino-alanine (BMAA) is
found in cycad seeds found in Guam, where the
native Chamorro detoxify the seeds of Cycas
micronesia by washing them for weeks. However,
they eat bats that accumulate large amounts of
the BMAA. Do not eat too many bats!

proteinogenic amino acids as flavors; MSG


Monosodium glutamate, also known as
sodium glutamate and MSG, is a
naturally occurring non-essential amino
acid. It is used as a food additive and is
commonly marketed as a flavour
enhancer. It has the HS code 29224220
and the E number E621
Modern commercial MSG is produced by
fermentation] of starch, sugar beets, sugar
cane or molasses. About 1.5 million tons
were sold in 2001. MSG is used
commercially as a flavor enhancer.
Although once associated with foods in
Chinese restaurants, MSG is now used in
many processed foods.
MSG use is controversial although
considered safe by the FDA

a taste of meat, lecture for herbivores (vegetarians)


The taste of oyster mushrooms is mediated by the amino
acid MSG = monosodium glutamate in its tissue. This in
itself however is only a taste enhancer. Plerotus ostreatus
has a slightly meaty taste which is caused by proteins that
contain a high share of glutamate.
Traditional Asian cuisine had used seaweed, which
contains high concentrations of glutamic acid, it was not
until 1907 that MSG was isolated by Kikunae Ikeda.

MSG is a HUGE player with people suffering


needlessly from multiple sclerosis MG and
other "diseases.
Being an excitotoxin, it destroys the myelin
sheath and kills brain cells. Avoiding MSG
will probably eliminate most, if not all MS
symptoms.

Vegetable Fats and Oils


Vegetable fats and oils are
composed of triglyceridides an ester
made of the alcohol glycerol and fatty
acids. Physically, oils are liquid at
room temperature, and fats are solid.
Waxes are also solid lipids, which
however - lack glycerin.
Unsaturated and hence liquid vegetable fats
and oils can be transformed into a fat
(sandwhich culture) through hydrogenation
involveing "sparging" the oil at high
temperature and pressure with hydrogen in
the presence of a catalyst, like powdered
nickel. The elimination of double bonds by
adding hydrogen atoms is called saturation;
the transformed plant oil is trans-fat.

Stearic acid = a fatty acid

Vegetable Oils & Waxes


Olive oil were used since 5 000 years. One tree still grows in the Sahara.
Highly appreciated in the Mediterreanean.
Vegetable oils derive from seeds (coconut, castor beans,peanuts,
soybens, cotton, flax, walnut) or fruits (avocado, olive, palm fruits).
Vege oils contain omega-3 fatty acids which are essential fatty acids.
Most vege oils are unsaturated; except for palm & coconut oil
Coconut oil is a fat since it is hard at room temps. It
is obtained by pressing the dried meat of the nut.
Hydrogenized it became an important fat for baking and
also for margarine.
How do you hydrogenate a plant oil so that it will turn solid at RT? 1896
French chemists found that unsaturated organic compounds mix with hydrogen
gas in their vapor state in the presence of catalytic Nickel powder. A mixture of
Nickel powder + oil is heated while hydrogen gas bubbles through it. The
hardeend oil settles to the bottom outlet.

Essential Fatty Acids: you need to supplement


Two FAs are essential for humans: alpha-linolenic
acid (an omega-3 fatty acid) and linoleic acid
(an omega-6 fatty acid). When the two EFAs
were first discovered in 1923, they were designated
Vitamin F. Later the two were the two were
classified as fats rather than vitamins.
Some fatty acids that are only "conditionally
essential" include gamma-linolenic acid (an
omega-6 fatty acid), lauric acid (a saturated
fatty acid), and palmitoleic acid (a
monounsaturated fatty acid)
-Linolenic acid is a carboxylic acid with an 18carbon chain and three cis double bonds  it is
given the name 18:3 (n3).
-Linolenic acid is found in many common Seed
oils notably rapeseed (canola), soybeans,
walnuts, flaxseed (linseed oil), perilla, chia, and
hemp.

Alpha
& Gamma
linolenic acids

Essential Fatty Acids: Do you need to supplement?


Plant fats differ from animal fats in that the fatty acids in them have more
double bonds, i.e. they are unsaturated. Humans are unable to generate
double bonds in fatty acids. They need the intake of unsaturated linolenic and
alpha linolenic acid, which they can convert to some degree into
eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), from fish.
Omega-3 fatty acids eicosanoids from -3 FA are antiinflammattory and can be converted into
18:3 linolenic acid ALA: in flax oil
20:5 eicopentaenoic acid (EPA) in fish oil (but made by algae)
22:6 docosahexanenoic acid (DHA) in fish oil

Why Fish oil supplements? It is the best source of two


long-chain essential fatty acids, eicosapentaenoic acid
(EPA) and docosahexaenoic acid (DHA)--the omega-3 fats
we hear so much about. Our body can only synthesize a
limited amount, so we must get supplements.

Some active oils


Olive oil is made from macerated fruits from which bitter phenoles
need to be removed. The pulp of the processed fruit is pressed.
Castor oil is pressed from seeds which contain highly toxic
agglutinating protein ricin and mildly toxic alkaloid ricine
plus dangerous allergen CB-A. Laxative action is caused
by ricinoleic acid. Mostly used for soaps, paints, Turkey
red oil and in hydrogenated form used for rocket and
aircraft engines. When seeds are pressed cold ie at temps
below 50 C which supp. excludes ricin from getting out.
Rapeseed oil is obtained from Brassica napus seeds.
Contain erucic acid ( a good lubricating oil) & withstands
very high temperatures (steel production).
Peanut oil obtained from Arachis hypogaea contains
arachidonic acid which support inflammatory responses .
Refers a pleasant taste to fried food and does not smoke
during high temperatures.

Some active oils


Rapeseed oil is obtained from Brassica napus seeds.
Contain erucic acid ( a good lubricating oil) & withstands
very high temperatures (steel production).
Natural rapeseed oil contains 50% erucic acid. Wild
type seeds also contain high levels of glucosinolates
(mustard oil glucosindes), chemical compounds that were
once considered to be toxins.
Erucic acid is a omega-9 fatty acid prevalent in rape and
mustard seed, making up 40-50% of their oils. This was
once considered to be highly toxic to humans, based on rat
experiments Rats have different fat metabolism.
Canola, from the abbreviation "Can.O., L-A." (Canadian
Oilseed, Low-Acid) that was used by the Manitoba
government to label the seed during its experimental
stages, is now a tradename for "double low" (low erucic
acid and low glucosinolate) rapeseed.

Plants that produce oils


The list of plants producing fatty oils or essential oils is indeed a long one. Here we give
some examples for the oil yields of 100 pounds of ...

Castor bean 20-50 lbs


Cloves
15-20 lbs
Nutmeg
10 lbs
Mace
9 lbs
Caraway seed
4 lbs
Aniseed
3 lbs
Lavender
2 lbs
Patchouli
1 lbs
Sandalwood
1 lbs

Peppermint
Calamus root
Cedarwood
Majoram
Cassia
Orange peel
Hops
Rose petals
Violet

15 oz
14 oz
13 oz
12 oz = 1 lbs
12 oz
10 oz
1 oz
0.2 oz
0.1 oz

These values give you an idea of whether it is worthwhile to press or


distill the plants for their oil. Note that most lab exercises call for the
distillation of cloves. Why?
Warning: Do not cold-press or distil Castor beans since it contains
deadly blood-agglutinating proteins plus a fatty acid that acts as a potent
laxative!!!!

Ketone bodies from Cocos oil prevent Alzheimer


First, the brain makes its own insulin. When your brain's production of insulin
decreases, it begins to starve, as it's deprived of the glucose-converted energy
it needs to function normally. This is what happens to Alzheimer's patients -portions of their brain start to atrophy, or starve, leading eventual loss of
memory, speech, movement and personality.

primary source of ketone bodies are the medium chain triglycerides


(MCT) as found in coconut oil  66 % MCTs. This may even restore
and renew neuron and nerve function after damage has set in. MCTs
go directly to your liver, which naturally converts the oil into ketones,
bypassing the bile (routing of long chain triglycerides (LCTs). Your liver
then immediately releases the ketones into the bloodstream  go to
the brain to be used as alternative fuel.

Acrolein the smell of barbecued ( burnt meat)


Acrolein: is an colorless, volatile aldehyde that is
formed from heated fats as a derivative of glycerol.
It has a piercing, disagreeable, acrid smell similar to
that of burning fat. It contributes to the smell of
barbecue and the taste of caramelized sugar. It
combines with wood smoke = formaldehyde, which
attacks the eyes to tears at campfires.
It is a severe pulmonary irritant & lachrymatory agent.
Skin exposure to acrolein causes serious damage.
Studies on rats showed an increase in cancerous tumors
from ingestion, but not from inhalation.
Acrolein test is a test for the presence of glycerin or fats. When a fat is heated
in the presence of a dehydrating agent such as KHSO4, the glycerol portion
of the molecule is dehydrated to form the unsaturated aldehyde, acrolein
(CH2=CH-CHO), which smells like burnt grease. Alternatively, sample is
heated with potassium bisulfate, and acrolein is released if the test is positive
When glycerol is heated to 280 C, it decomposes into acrolein.

Does fat loss leave a bitter taste?


Naringin (Grape juice) major flavonoid glycoside that gives
grapefruit its bitter taste & increases sensitivity of taste
buds. Naringenin & hesperetin (aglycones) occur in citrus
fruits acting as antioxidants, blood lipid-lowering,
cholesterol-reducing, anticarcinogenic substances
Useful ingredient in fat burners: When "fat burner" is used
on the label of a diet pill, the product is usually a brand name
for ephedra or ephedrine, coffeine, green tea extract &
naringin, sesamin = a lignan from sesame seed that
binds receptor Peroxisome Proliferator-Activator Receptor
Rutin: citrus flavonoid glycoside found in buckwheat
seeds, leaves & petioles of Rheum = rhubarb; glycoside
= flavonol quercetin + rutinose. Comb. with cations to
meditate transport into plant cell Antioxidant in humans
attaches to Fe2+ to prevent binding to hydrogen peroxide &
damag. free-radicals
Rutin strengthens capillaries &
reduce haemophilia& prevents unpleasant-looking venous
edema of the legs,

Natural & Synthetic Waxes


Beeswax was used for candles and polishes. Limited supply.
Carnauba wax is scraped from the leaves of the carnauba
palm (Brazil). Sundreid leaves are beaten with sticks &
boiling over open fire dislodges wax from the cuticles. 
grey natural product One tree gives approx. 170 g /year.
Very hard wax. Upon cooling myricyl alcohol forms
characteristic rings. Used for shoe polishes.

Raffia wax is from Raffia palm the Madagascan sago palm which
holds the record for having the largest leaves of all plants.
Candelilla wax is obtained from the stems of a Mexican
weed in the Euphorbiaceae which is boiled with some
water, brown aromatic wax is skimmed off the surface.
Paraffin waxes are distillation products of natural mineral
oil colourless, & odorless. They are soluble in organic
solvents except ethanol & have unusually high melting point.

Cutin is a wax-like polyester of fatty acids


Cutin is a waxy polymes & the main
components of the plant cuticle, which
covers all aerial surfaces of plants. The
other cuticle polymer is cutan, Cutin
consists of fatty acids, which are
interlinked to form a polyester polymer
of indeterminate size.
Cutan is a non-lipid hydrocarbon
polymer
with a structure that is not yet fully
understood.

Cutin is a wax-like polyester of fatty acids


Suberin is a highly hydrophobic cell
wall encrustation = a waxy material
used to prevent water from
penetrating the cell walls. In roots
suberin is deposited in the cell walls
of the Casparian strip, also in the
cork periderm of oak bark.
Suberin consists of two domains,
(1) a polyphenolic backbone
(monomer = hydroxycinnamic
acid) & a polyaliphatic domain
consisting of
(2) fatty acids attached to the
polyphenol backbone

Lipstick wax application


Lipstick contains waxes, oils, pigments, dissolved synthetic
dyes and emollients that applies color and texture to the lips.
Recently also: vit E, Aloe vera, collagen, sunscreen have been added
The wax (beeswax or carnauba wax, from the stomata of leaves of
Brazilian wax palm tree, candelilla wax obtained from candelilla plant
immersed in boiling sulfuric acid) gives shape & ease of application..
The oils in lipstick are olive, castor (a laxative!! used for its shiny film
when dried), mineral oils + cocoa butter, lanolin & Vaseline.
D&C Reds # 21, 27 are fat-soluble dyes, insoluble dyes
called lakes: D&C Red # 34. Pink: Red mix with TiO2
Cleopatra had her lips made up from crushed carmine beetles
(deep red pigment), and ants for a base. A shimmering effect
was made using a substance found in fish scales: pearlescence.
Abulcasis - the Arab Andalusian cosmetologist Abu al-Qasim
al-Zahrawi invented solid lipsticks as perfumed stocks rolled
and pressed in special molds.

Policosanol (or polycosanol)


Policosanol (or polycosanol) is generic term for an extract of plant
waxes that consists of a mixture of a few fatty alcohols derived from
the waxes of such plants as sugar cane, yams, beeswax. Most prevalent
alcohol in policosanol is octacosanol, followed by triacontanol.
Used as supplement to lower (bad) LDL cholesterol and increase (good)
HDL cholesterol and so to prevent  artherosclerosis, Rayleighs
disease, coronary and stroke.

Policosanol (PPG) is produced, promoted & studied extensively in Cuba,


where pharmaceutical research & sugar cane both exist in abundance.

Detergents and Polishes


Soap is the oldest manufactured detergent. Before it people
used plants with saponins like soap nuts etc to produce lather and also
creams. Nowadays soap is replaced by synthetic detergents .

Romans used a paste made of Fullers earth ( a clay-like


material able to absorb fats), soda (sodium carbonate) &
urine for cleaning cloth & pots (see Pompeii). Pliny
mentions the use of sapo as hair crme made from
Beachwood ashes boiled in sheep tallow. Probably soap
was discovered when animal sacrifices were saponified in
wood ashes. Galen is first to mention washing with soap.
Ancient Egyptians used nitre (sodium carbonate) &
castor oil to wash clothing but seemed to have kept their
secret well as many others: batteries, glass making
Southern Europe (Spain) used barilla (ashes from seaweeds) with
olive oil to make soap. Castile soap made in Venice and Castile.

Soap Manufacturing
Soaps are Na or K salts of fatty acids with 12-18 C atoms. Na soaps
are normally harder than K soaps. Highly saturated fats like tallow give
harder soaps than low molecular weight fats like coconut oil.
Soaps are produced by the saponificastion of fat blends
with an alkaline solution. The fats hydrolyse into
glycerol & fatty acids. Brine or solid salt is then added
to the solution. Since soap but not glycerol is insoluble
in salt solution, soap will float on top. Glycerol will be
in the salt solution & can be recovered from it.
Soap can be purified ( and made less alkaline) by dissolving it in hot
water, boiling it for a short time and then salting it out. Last boiling
is with added water to make the appearance less greasy.

Transparent soap can be produced by dissolving soap


in ethanol or glycerol, evaporating it off before
molding the soap (glycerin soap)

Soap Making
Rendering & Clarifying of Fat: 1. Any oil can be used for making soap, diesel
fuel, glycerin, nitroglycerin , candles, emulsifiers etc. If you use unpurified fat like
kitchen drippings etc you should first render the fat. Rendering is the process of
melting solid fat particles. Cut fat in pieces and let it melt. Remove solid particles =
cracklings by straining. Unclear greasy mixtures can be clarified by placing the fat
, an equal amount of water & 2 tablespoons of NaCl in the pan, and bring to a boil.
When removing from heat cool and add cold water (one quart to 1 gallon of fat).
Mixture will separate into 3 layers: on top purified or clarified fat, on the bottom
water and in the center impurities.

What happens when we add HCl to soap and


heat it up?
Soap is the Na or K salt of fatty acids. The H+ ions
will drive the Na or potassium ions out of their
connection with the fatty acids & hence liberate
fatty acids like oleic acid or stearic acid. Both are
good emulgators and can also be used together with
paraffin to make non-dripping candles.

Soap Making Alternatives


How to make soap without heat:
Henriques R (Z angew Chem 1895, 8, 721; 1896, 9, 221) reported that fats can be
saponified readily at room temperature. The process may be carried out by dissolving
260 g of KOH in 250 ml water. After some minutes, a liter of the oil to be saponified is
added to this solution. Ethanol (10 ml) is then added. This process was applied to fats
containing easily altered fatty acids (i.e. conjugated fatty acids, highly unsaturated).
Separation of unsaponifiable matter
After saponification, approximately half of the alcohol is removed under vacuum, the
residue is diluted with water and the unsaponifiable matter (hydrocarbons, tocopherols,
sterols) extracted by shaking with an organic solvent, diethyl ether or petroleum ether.

Recovery of acids from soaps

Fatty acids are liberated by the addition of mineral acid, usually a 10% excess
of sulfuric acid or HCl. When very short-chain acids are present, the alcohol is
removed prior acidification under vacuum with the addition of sufficient water
to keep soaps in solution. If the amount of acids is important, the long-chain
acids are separated from the aqueous medium by allowing the mixture to stand
in the cold.

Plants that can be used as soap ersatz


Plants that produce foam do not contain Na salts of fatty acids ( the
manmade soap) but saponins - foaming terpenoids
Agave
root, leaves & stem
Jujuba or Zizyphus
fruit
Morning glory Ipomea
plant ashes
Pigweed Chenopodium
root
Pokeweed Phytolacca
fruit
Soapberry Sapindus
berry
Soapwort Saponaria
root
Yucca
root
Wild gourd Cucurbita
fruit
quinoa
seeds
lentil Lens culinaris
seeds
potatoes Solanum tuberosum fruit

Shepherdia soapberry is bitter

Zizyphus jujuba

The role of the foaming quality of saponins in plants is yet to be


established. They are feeding repellents and also play a role to stabilize
plant emulsions like latex etc.

Saponins in fish-poisoning plants


Fish poisons = icthyotoxins or piscicides, occur in several plant species.
Some chemicals like saponins will only stun the fish when it passes
through the gills. The fish then floats to the surface for easy capture.
Saponins normally must enter the bloodstream to be toxic, but fish take in
saponins directly into their bloodstream through their gills. Saponins
cause the breakdown of red blood cells that help the toxin to spread quickly.
Even though the effects of the poison are powerful, they are not usually fatal.
Fish that are washed away into untainted water recover quickly.

The roots twigs and buds of the common


horse chestnut Aesculus h. contains
much saponin and was used to poison fish.

Another source of poisonous saponins


is pokeweed Phytolacca americana.
Indians use the leaves.

Other fish-poisoning plants


Fish poisons = icthyotoxins or piscicides, occur in several
plant species. Some chemicals will actually paralyze the CNS of
fish when taken up through the gills. The fish does not recover.
Not all fish poisons are saponins. A most
frequently used one is an alkaloid called
rotenone. Rotenone is extracted from the
roots, seeds and leaves of tropical
legumes. See 2 examples below. In mice it
produced a model Parkinsons disease.
Acacia
ditricha
seed
pods are
effective
poison

Saponins
Saponins are secondary metabolites found in
particular abundance in various plant species. Most
of them are glycosides that form soap-like foaming
when shaken in aqueous solutions. The aglycone
(glycoside-free portion) of the saponins are termed
sapogenins; it is either a triterpene or steroid.
Most saponins, which readily dissolve in water, are
poisonous to fish. Therefore, in ethnobotany, saponins
are primarily known for their use by indigenous people
in obtaining aquatic food sources

A candle relies upon capillary action to burn.


The wick of a candle is made of many fibers wound closely
together. The capillary spaces between the fibers draw molten wax
upward to the flame.

Stearic acid
comes in
flakes

Candles the path to illumination


Early candles were made from wicks covered with a mixture of
beeswax & tallow. Tallow made candles are smoky & sputter.

1830 Industry provided a mixture of palmitic and stearic acid


called stearine by hydrolysing animal fats. See making stearic
acid: animal fat is hydrolyzed with acid or lime. The fatty acid
mixture is dissolved in 1:9 water:methanol mixture before
chilling and filtering oof the solid stearine, which crystallizes in
the cold. You get two fractions: a solid one = steric acid and a
liquid one = oleine. Stearine candles were very brittle and later
paraffin wax was added. Paraffin is a byproduct of petroleum.
Modern candles. The paraffin contents was gradually increased
until it completely replaced stearine  paraffin candles
A candle relies upon capillary action to burn.
The wick of a candle is made of many fibers wound closely
together. The capillary spaces between the fibers draw molten wax
upward to the flame.

Stearic acid
comes in
flakes

Candle Making
Early candles were made from beeswax. Rind\se the empty
comb and place it in a pan together with 2 parts of water to
prevent the wax from catching fire. Heat until wax is melted &
continue cooking for a while. You can add Paraffin wax of up
to 90 % to make the candles cheaper. In the old days they
added tallow from beef, and a half pound of saltpeter = nitrate.

Bayberry candles. Bayberries grow in the sandy soil of


the New England coastland to welcome the pilgrims.
Gather berries in the fall, then boil them in water for two
hours. Today bayberry bush are protected by law & you
buy the ready wax from a berry farm.
Dipped candles: you need two tall beakers or pots: one
filled with water (RT) & one filled with wax (160 F).
You tie 3 wicks (10 cm longer than candle) to a stick and
weigh their ends with washers. It takes 30-40 alternating
dips in both liquids cooling and wax adding) to make a
candle of 1 inch diameter.