All about Carboxylic Acids

2. -are organic acids characterized by the presence of at least
one carboxyl group
-the general formula of a carboxylic acid is R-COOH, where
R is some monovalent functional group
-A carboxyl group is a functional group consisting of
a carbonyl and a hydroxyl, which has the formula -
C(=O)OH, usually written as
-COOH or -CO2H.

4. Monocarboxylic Acids – are the organic acids that contain
one carboxyl group ( one –COOH )
ex: Formic Acid, Acetic Acid, Propionic Acid, Butyric Acid,
Fatty Acids: Palmitic Acid, Myristic Acid, Linolic Acid, Stearic Acid
Dicarboxylic Acids - are the organic acids that contain two
carboxyl group ( two –COOH )
ex: Oxalic Acid, Malonic Acid, Succinic Acid, Glutaric Acid, Adipic Acid,
Pimelic Acid
Tricarboxylic Acids - are the organic acids that contain two
carboxyl group ( three –COOH )
ex: Citric Acid, Isocitric acid, Aconitic Acid, Carballylic acid,
Trimetic Acid

5. Carbon-Chain Common Name IUPAC name Molecular formula Structural formula
C-12 LAURIC ACID dodecanoic acid C12H24O2
C-14 MYRISTIC ACID Tetradecanoic C14H28O2
acid
C-16 PALMITIC ACID Hexadecanoic C16H32O2
acid
C-18 STEARIC ACID Octadecanoic C18H36O2
acid
C-18 OLEIC ACID cis-9- C18H32O2
(unsaturated) Octadecenoic
acid
C-18 LINOLEIC ACID cis, cis-9,12- C18H34O2
(polyunsaturated) octadecadienoic
acid

6. C12H24O2
-also called as dodecanoic acid, a saturated fatty acid, is
a white, powdery solid with a faint odor of bay oil or soap.
-Lauric acid is a medium chain fatty acid which is
abundant in coconut oil and is considered responsible for
many of its health benefits. Coconut oil is about 50
percent lauric acid. The only other abundant source
found in nature is in human breast milk.

7. C12H24O2

8. C12H24O2
Importance/Uses
-Lauric acid is inexpensive, has a long shelf-life, and is non-
toxic and safe to handle. Thus, it is often used in laboratory
investigations offreezing-point depression. Lauric acid is a
solid at room temperature but melts easily in boiling water,
so liquid lauric acid can be treated with various solutes and
used to determine their molecular masses.
- a useful component in a treatment for acne and skin
disorders.
-Used mainly in nutritional supplements
- slightly increases cholesterol but it decreases triglyceride
levels and it contains anti-viral, anti-bacterial and anti-
protozoal properties.

9. C12H24O2
Harmful Effects
-even though it only slightly increases the cholesterol in the
blood and good for the heart, high-intake of lauric acid will
cause blurred vision, painful migraine, chapped lips and liver
damage.

10. C14H28O2
-also called tetradecanoic acid
- is a common saturated fatty acid with the molecular
formula CH3(CH2)12COOH. Amyristate is a salt or ester of
myristic acid.
Myristic acid is named after the nutmeg Myristica fragrans.
Nutmeg butter is 75% trimyristin, the triglyceride of myristic
acid. Besides nutmeg, myristic acid is also found in palm
kernel oil, coconut oil, butter fat and is a minor component of
many other animal fats

11. C14H28O2

12. C14H28O2
-Myristic acid is also commonly added co-translationally to
the penultimate, nitrogen-terminus, glycine in receptor-
associated kinases to confer the membrane localisation of
the enzyme.
-The myristic acid has a sufficiently high hydrophobicity to
become incorporated into the fatty acyl core of
the phospholipid bilayer of the plasma membrane of
the eukaryotic cell. In this way, myristic acid acts as a lipid
anchor in biomembranes.

13. C14H28O2
Harmful Effects
-Food that contains myristic acid increases the amount-level
of bad cholesterol in the body and so increases risk of
coronary heart and cerebrovascular disease
-too much intake may cause obesity

14. C16H32O2
CH3(CH2)14COOH or hexadecanoic acid in IUPAC
nomenclature, is one of the most common saturated fatty
acids found in animals and plants.
-As its name indicates, it is a major component of the oil
from palm trees (palm oil, palm kernel oil and coconut oil).
The word palmitic is from the French "palmitique", the pith of
the palm tree. Palmitic acid was discovered by Edmond
Frémy in 1840, in saponified palm
oil.Butter, cheese, milk and meat also contain this fatty acid.

15. C16H32O2

16. C16H32O2
Importance/uses
-Derivatives of palmitic acid were used in combination
with naphtha during World War II to
produce napalm (aluminumnaphthenate and
aluminum palmitate
-is an essential ingredient in soap making
-Palmitic acid derivatives are used in different anti-psychotic
medicines, especially in the treatment of schizophrenia

17. C16H32O2
Harmful Effects
-palmitic acid has been found to cause obesity and insulin
resistance
-In contrast, too content of palmitic acid in the body,
impairs hypothalamic insulin and leptin signaling. Leptin is
an adipocyte synthesized hormone that influences appetite
control and signaling. Regardless of obesity, excess
dietary palmitic acid impairs leptin and insulin's ability to
regulate food intake and body weight.
-dietary intake of palmitic acid increases risk of developing
cardiovascular diseases

18. C18H36O2
-is a saturated fatty acid with the formal IUPAC
name octadecanoic acid. It is a waxy solid, and its chemical
formula is C18H36O2, or CH3(CH2)16COOH. Its name comes
from the Greek word stéar (genitive:stéatos), which
means tallow. The salts and esters of stearic acid are
called stearates
-It occurs in many animal and vegetable fats and oils, but it
is more common in animal fat than vegetable fat. The
important exceptions are cocoa butter and shea
butter whose fatty acids consist of 28–45% stearic acid

19. C18H36O2

20. C18H36O2
Importance/Uses
-is useful as an ingredient in
making candles, plastics, dietary supplements, oil
pastels and cosmetics, and for softeningrubber.
-It is used to harden soaps, particularly those made with
vegetable oil. Stearic acid is used in aerosol shaving
cream products.
-is also used as a parting compound when making plaster
castings from a plaster piece mold or waste mold and when
making the mold from a shellacked clay original
-used to produce a pearly effect in shampoos, soaps, and
other cosmetic products.

21. C18H36O2
Importance/Uses
-In fireworks, stearic acid is often used to coat metal powders
such as aluminium and iron. This prevents oxidation, allowing
compositions to be stored for a longer period of time.
-It is used along with simple sugar or corn syrup as a hardener
in candies.
-It is used with zinc as zinc stearate as fanning powder for
cards to deliver smooth fanning motion.
-Stearic acid is one of most commonly used lubricants
during injection molding and pressing of ceramic powders.
-Stearic acid serves as an epilame (or barrier film) treatment,
applied to precision mechanical components to modify
the surface properties to reduce the spreading (or creep) of
subsequently-applied lubricant films.

22. C18H36O2
Harmful Effects
-like the other saturated fats, a high-diet in stearic acid
increases LDL in the blood (hypercholesterolemia) that
leads to coronary heart disease and cerebrovascular
diseases
-it also leads to obesity

23. C18H32O2
-is a mono-unsaturated omega-9 fatty acid found in various
animal and vegetable sources. It has the formula
CH3(CH2)7CH=CH(CH2)7COOH. The trans-isomer of oleic
acid is called elaidic acid.
The term Oleic means related to, or derived from, oil or olive
Importance/Uses
-As an excipient in pharmaceuticals, oleic acid is used as an
emulsifying or solubilizing agent in aerosol products.
-may hinder the progression of ALD, or
adrenoleukodystrophy, a fatal disease that affects the brain
and adrenal glands
-may help boost memory

24. C18H32O2

25. C18H32O2
Harmful Effects
-Oleic and monounsaturated fatty acid levels in the
membranes of red blood cells have been associated with
increased risk of breast cancer.
-too much body content of Oleic acid may be responsible for
the hypotension ( lower blood pressure) effects of olive oil.

26. C18H34O2
Linoleic acid (LA) is an unsaturated omega-6 fatty acid. It is
a colorless liquid at room temperature. In physiological
literature, it is called 18:2(n-6). Chemically, linoleic acid is
a carboxylic acid with an 18-carbon chain and two cis double
bonds; the first double bond is located at the sixth carbon
from the omega end.

27. C18H34O2

28. C18H34O2
Importance/Uses
- polyunsaturated fatty acid used in the biosynthesis
of arachidonic acid (AA) and thus some prostaglandins. It is
found in the lipids of cell membranes. It is abundant in
many vegetable oils, comprising over half (by weight)
of poppy seed, safflower, sunflower, and corn oils.
-use for treatment of cancer, Cystic fibrosis, Dermatitis,
Diabetes
-use for the treatment of hypothyroidism

29. C18H34O2
Harmful Effects
-high-diet in linoleic acid cause suppresses the normal of
tissue sensitivity to thyroid hormones; greatly
suppresses the liver's response to thyroxine and
triiodothyronine, it causes excessive adipose [fat] tissue
development.

30. Common name IUPAC name Chemical formula Structural formula
OXALIC ACID Ethanedioic acid HOOC-COOH
MALONIC ACID Propanedioic acid HOOC-(CH2)-COOH
SUCCINIC ACID Butanedioic acid HOOC-(CH2) 2-COOH
GLUTARIC ACID Pentanedioic acid HOOC-(CH2) 3-COOH
ADIPIC ACID Hexanedioic acid HOOC-(CH2) 4-COOH
PIMELIC ACID Heptanedioic acid HOOC-(CH2) 5-COOH

31. HOOC-COOH
- is the chemical compound with the IUPAC name,
ethanedioic acid.
-This colourless solid is a dicarboxylic acid.
-In terms of acid strength, it is about 3,000 times stronger
than acetic acid. Its conjugate base, known as
oxalate(C2O42-), is a reducing agent as well as a chelating
agent for metal cations. Typically oxalic acid occurs as the
dihydrate with the formula C2O4H2·2H2O.

32. HOOC-COOH

33. HOOC-COOH
Importance/Uses
-Oxalic acid's main applications include cleaning or
bleaching, especially for the removal of rust
-About 25% of produced oxalic acid is used as a mordant in
dyeing processes.
-It is used in bleaches, especially for pulpwood
-an important reagent in lanthanide chemistry.

34. HOOC-COOH
Importance/Uses
-Oxalic acid is used in the restoration of old wood. Its
reducing properties are utilized in platinotype, the early
photographic platinum/palladium printing process.
-Vaporized oxalic acid, or a 6% solution of oxalic acid in
sugar syrup, is used by some bee keepers as
a miticide against the parasitic Varroa mite.

35. HOOC-COOH
Harmful Effects
-Those with kidney disorders, gout, rheumatoid arthritis, or
certain forms of chronic vulvar pain (vulvodynia) are typically
advised to avoid foods high in oxalic acid.
- The calcium oxalate crystals or precipitate (better known
as kidney stones) can obstruct the kidney tubules. An
estimated 80% of kidney stones are formed from calcium
oxalate.

36. HOOC-COOH
Harmful Effects
- Oxalic acid is corrosive to body tissue. When ingested,
oxalic acid removes calcium from the blood. Kidney damage
can be expected as the calcium is removed from the blood
in the form of calcium oxalate. The calcium oxalate then
obstructs the kidney tubules.

37. HOOC-(CH2)-COOH
-(IUPAC systematic name: propanedioic acid) is
a dicarboxylic acid..
- is a white crystalline C-3 dicarboxylic acid; melting at 135 -
136 C; readily soluble in water, alcohol and ether; solution in
water is medium-strong acidic. It can be derived by oxidizing
malic acid or by the hydrolysis of cyanacetic acid. Malonic
acid itself is rather unstable and has few applications. It's
diethyl ester (diethyl malonate) is more important
commercially.Malonic acid and its esters contain active
methylene groups which have relatively acidic alpha-protons
due to H atoms adjacent to two carbonyl groups.The name
originates from the Greek word μᾶλον (malon) meaning
'apple'.

38. HOOC-(CH2)-COOH

39. HOOC-(CH2)-COOH
Importance/Uses
-It decomposes above its melting point to ethanoic acid.
Propanedioic acid is used in the synthesis of other
dicarboxylic acids.
-they are important intermediates in syntheses of vitamins
B1 and B6, barbiturates, non-steroidal anti-inflammatory
agents, other numerous pharmaceuticals, agrochemicals
and flavors & fragrances compounds.

40. HOOC-(CH2)-COOH
Harmful Effects
-When inhaled causes Cough. Sore throat. Skin and Eyes:
Redness and PainIngestion: Abdominal pain. Diarrhoea.
Nausea. Vomiting.
- Chronic administration of malonic acid produces selective
neural degeneration and transient changes in calbindin
immunoreactivity in humans.

41. HOOC-(CH2) 2-COOH
(IUPAC systematic name: butanedioic acid; historically
known as spirit of amber), a dicarboxylic acid. The name
derives from Latin succinum, meaning amber, from which
the acid may be obtained.
-Succinic Acid (Butanedioic Acid) is a dicarboxylic acid of
four carbon atoms. It occurs naturally in plant and animal
tissues.
-Succinic acid is a colourless crystalline solid with a melting
point of 185 -187 C; soluble in water; slightly dissolved in
ethanol, ether, acetone and glycerine; not dissolved in
benzene, carbon sulfide, carbon tetrachloride and oil ether.
The common method of synthesis of succinic acid is the
catalytic hydrogenation of maleic acid or its anhydride.

42. HOOC-(CH2) 2-COOH

43. HOOC-(CH2) 2-COOH
Importance/Uses
-plays a significant role in intermediary metabolism (Krebs
cycle) in the body. Krebs cycle (also called citric acid cycle;
tricarboxylic acid cycle) is a sequence process of enzymatic
reaction which a two-carbon acetyl unit is oxidized to carbon
dioxide and water to provide energy in the form of high-
energy phosphate bonds
-helpful in normalizing red blood cell glutathione levels in
children with autism.

44. HOOC-(CH2) 2-COOH
Importance/Uses
-Flavoring agent for food and beverages;
-Intermediate for dyes, perfumes, lacquers, photographic
chemicals, alkyd resins, plasticizer, Metal treatment
chemical, vehicle water cooling systems and coatings.
-Medicines of sedative, antispasmer, antiplegm,
antiphogistic, anrhoter, contraception and cancer-curing.

45. HOOC-(CH2) 2-COOH
Importance/Uses
-Succinate helps reduce the effects of alcohol toxicity
including hangover by activating the second half-cycle of
tricarboxylic acids to help accelerate the decomposition of
acetaldehyde and the energization of the oxidation
processes in the mitochondria into CO2 and H2O through
aerobic metabolism.

46. HOOC-(CH2) 2-COOH
Harmful Effects
-the lack production of succinic acid by the GABA in the
brain may cause Succinic semialdehyde dehydrogenase
deficiency (SSADHD), also known as 4-hydroxybutyric
aciduria or gamma-hydroxybutyric aciduria.
- Over-production of succinic acid by the GABA in the brain
may inhibits metabolic and neuronal disorders and abnormal
function of the body systems. It may cause such disorder
like epilepsy.

47. HOOC-(CH2) 3-COOH
-is the organic compound with the IUPAC name
Pentanedioic acid. Although the related "linear" dicarboxylic
acids adipic and succinic acids are water-soluble only to a
few percent at room temperature, the water-solubility of
glutaric acid is over 50%.

48. HOOC-(CH2) 3-COOH

49. HOOC-(CH2) 3-COOH
Importance/Uses
-is a dicarboxylic acid with five carbon atoms, occurring in
plant and animal tissues. Glutaric acid is found in the blood
and urine. Alpha-ketoglutaric acid, a derivative of glutaric
acid which has a ketone group on the carbon atom next to
the acid group, is produced from glutamate in amino group
and found as an intermediate in the Krebs cycle in the body.
-In industrial field, ketoglutaric acid exhibits typical carboxyl
group chemistry useful in a variety of industrial applications.
It is a white crystalline solid having has the lowest melting
point among dicarboxylic acids (98 C).

50. HOOC-(CH2) 3-COOH
Harmful Effects
-excessive breakdown of Glutaric acid in the body may
cause Glutaric acidemia/glutaric aciduria, it can accumulate
and cause damage to the brain (and also other organs), but
particularly the basal ganglia, which are regions that help
regulate movement. GAtype1 causes secondary carnitine
deficiency, as glutaric acid, like other organic acids, is
detoxified by carnitine. Mental retardation may also occur.

51. HOOC-(CH2) 4-COOH
-is the organic compound with is the organic compound with
the IUPAC name, hexanedioic acid. From the industrial
perspective, it is the most important dicarboxylic acid: About
2.5 billion kilograms of this white crystalline powder are
produced annually, mainly as a precursor for the production
of nylon. Adipic acid otherwise rarely occurs in nature.

52. HOOC-(CH2) 4-COOH

53. HOOC-(CH2) 4-COOH
Importance/Uses
-adipic acid produced annually is used as monomer for the
production of nylon by a polycondensation reaction with
hexamethylene diamine forming 6,6-nylon. Other major
applications also involve polymers: it is a monomer for
production of Polyurethane and its esters are plasticizers,
especially in PVC.

54. HOOC-(CH2) 4-COOH
Importance/Uses
-In medicine, adipic acid has been incorporated into
controlled-release formulation matrix tablets to obtain pH-
independent release for both weakly basic and weakly acidic
drugs. It has also been incorporated into the polymeric
coating of hydrophilic monolithic systems to modulate the
intragel pH, resulting in zero-order release of a hydrophilic
drug.

55. HOOC-(CH2) 4-COOH
Importance/Uses
In foods, small but significant amounts of adipic acid are
used as a food ingredient as a flavorant and gelling aid. It is
used in some calcium carbonate antacids to make them tart.

56. HOOC-(CH2) 4-COOH
Harmful Effects
-The large amount of adipic acid production per year, due to
the common product that it produces, has led to an
enormous amount of this greenhouse gas to be emitted.
There are several specific facts about why N2O is so bad for
the environment. First, N2O is a radioactively and chemically
active trace gas believed to contribute to the recent increase
in the Earth's surface temperature. N2O absorbs reflected
infrared radiation. Also, estimated atmospheric lifetime of
N2O is 150 years. Last, the estimated impact of anthrogenic
N2O is a 6% increase in ozone depletion rate. N2O from the
production of adipic acid is harmful to the environment
because of its heat absorbing and ozone depleting qualities.

57. HOOC-(CH2) 5-COOH
-is the organic compound with -is the organic
compoundwith the IUPAC name, heptanedioic acid,
heptanedioic acid . Derivatives of pimelic acid are involved
in the biosynthesis of the amino acid called lysine. Pimelic
acid is one methylene longer than a related dicarboxylic
acid, adipic acid, a precursor to many polyesters and
polyamides. It is the final member of the mnemonic used to
aid recollection of the order of the first six dicarboxylic acids
using their common (not IUPAC) nomenclature.
-Pimelic acid has been synthesized from cyclohexanone and
from salicylic acid. In the former route, the additional carbon
is suppled by dimethyl oxalate, which reacts with the
enolate.

58. HOOC-(CH2) 5-COOH

59. HOOC-(CH2) 5-COOH
Harmful Effects
-high-toxicity to humans, including carcinogenicity,
reproductive and developmental toxicity, neurotoxicity, and
acute toxicity
- teratogenic in animals or humans