Carboxylic Acids

Carboxylic AcidsElino, M.M.H. Biochemistry

2010 22A Bio II

Carboxylic Acids

-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.

Carboxylic Acids

Structure

Carboxylic Acids

Types 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

Monocarboxylic Acids ( Fatty Acids)

Carbon-Chain Common Name

IUPAC name Molecular formula

Structural formula

C-12 LAURIC ACID dodecanoic acid C12H24O2

C-14 MYRISTIC ACID Tetradecanoic acid

C14H28O2

C-16 PALMITIC ACID Hexadecanoic acid

C16H32O2

C-18 STEARIC ACID Octadecanoic acid

C18H36O2

C-18(unsaturated)

OLEIC ACID cis-9-Octadecenoic

acid

C18H32O2

C-18(polyunsaturat

ed)

LINOLEIC ACID cis, cis-9,12-octadecadienoi

c acid

C18H34O2

Monocarboxylic Acids

-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.

Lauric Acid ( C12H24O2 )


Lauric Acid



Lauric AcidImportance/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.



Lauric AcidHarmful 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.



-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

Myristic Acid ( C14H28O2 )


Myristic AcidMyristic Acid ( C14H28O2 )


Myristic Acid-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.



Myristic AcidHarmful 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



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.

Palmitic Acid ( C16H32O2 )


Palmitic AcidPalmitic Acid ( C16H32O2 )


Palmitic AcidImportance/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



Palmitic AcidHarmful 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



-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

Stearic Acid ( C18H36O2 )


Stearic AcidStearic Acid ( C18H36O2 )


Stearic AcidImportance/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.



Stearic AcidImportance/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.



Stearic AcidHarmful 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



-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

Oleic Acid ( C18H32O2 )


Oleic AcidOleic Acid ( C18H32O2 )


Oleic AcidHarmful 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.

Oleic Acid ( C18H32O2 )


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.

Linoleic Acid ( C18H34O2 )


Linoleic AcidLinoleic Acid ( C18H34O2 )


Linoleic AcidImportance/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



Linoleic AcidHarmful 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.


Dicarboxylic Acids

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

http://en.wikipedia.org/wiki/File:Oxalic_acid.png

http://en.wikipedia.org/wiki/File:Malonic_acid_structure.png

http://en.wikipedia.org/wiki/File:Succinic_acid.png

http://en.wikipedia.org/wiki/File:Glutaric_acid.png

http://en.wikipedia.org/wiki/File:Adipic_acid_structure.png

http://en.wikipedia.org/wiki/File:Pimelic_acid.png

Dicarboxylic Acids

- 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(C2O4

2-), 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.

Oxalic Acid (HOOC-COOH )

Dicarboxylic Acids

Oxalic AcidOxalic Acid (HOOC-COOH )

Dicarboxylic Acids

Oxalic AcidImportance/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.


Dicarboxylic Acids

Oxalic AcidImportance/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.


Dicarboxylic Acids

Oxalic AcidHarmful 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.


Dicarboxylic Acids

Oxalic AcidHarmful 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.


Dicarboxylic Acids

Malonic Acid-(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'.

Malonic Acid (HOOC-(CH2)-COOH )

Dicarboxylic Acids

Malonic AcidMalonic Acid (HOOC-(CH2)-COOH )

Dicarboxylic Acids

Malonic AcidImportance/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.


Dicarboxylic Acids

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.


Dicarboxylic Acids

Succinic Acid(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.

Succinic Acid (HOOC-(CH2) 2-COOH )

Dicarboxylic Acids

Succinic AcidSuccinic Acid (HOOC-(CH2) 2-COOH )

Dicarboxylic Acids

Succinic AcidImportance/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.


Dicarboxylic Acids


-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.


Dicarboxylic Acids


-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.


Dicarboxylic Acids

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.


Dicarboxylic Acids

Glutaric Acid-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%.

Glutaric Acid (HOOC-(CH2) 3-COOH )

Dicarboxylic Acids

Glutaric AcidGlutaric Acid (HOOC-(CH2) 3-COOH )

Dicarboxylic Acids

Glutaric AcidImportance/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).


Dicarboxylic Acids

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.


Dicarboxylic Acids

-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.

Adipic Acid (HOOC-(CH2) 4-COOH)

Dicarboxylic Acids


Dicarboxylic Acids


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.

Dicarboxylic Acids

Adipic AcidImportance/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.


Dicarboxylic Acids

Adipic AcidImportance/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.


Dicarboxylic Acids

Adipic AcidHarmful 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.


Dicarboxylic Acids

Pimelic Acid-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.

Pimelic Acid (HOOC-(CH2) 5-COOH )

Dicarboxylic Acids

Pimelic AcidPimelic Acid (HOOC-(CH2) 5-COOH )

Dicarboxylic Acids

Harmful Effects -high-toxicity to humans, including carcinogenicity, reproductive and developmental toxicity, neurotoxicity, and acute toxicity

- teratogenic in animals or humans

Pimelic Acid (HOOC-(CH2) 5-COOH )

Carboxylic Acids

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