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Hydrocarbons

Hydrocarbons derivatives

Hydrocarbons

 Organic Acids (_______)

high frequency on living organisms;

participate in essential metabolism;

function in association with

coenzymes;

accumulate as simple salts, ester, and

amides.

C 1 -C 6 Monocarboxylic acid

Fatty acids

Aromatic acids

C 1 to C 6 moncarboxylic acid

 Formic acid : Formica rufa (red ant) , Stinging nettle ( Urtica dioica ), combined in the gitaloxigenin (cardioactive glycosides) and N-formyl-L-methionine

 Acetic acid : a __ metabolite in the form of ___. Common in esterified form.

 Propionic acid: produced in the fatty acid oxidative cycle when an acyl-CoA with an odd number of carbon atoms is involved.  Iso-butyric acid : Ceratonia siliqua (Carob beans), croton oil (ethyl ester); Resin component of Convolvulaceae and minor tropane alkaloids.  Valeric (not common) and iso – valeric acid : combine/free on Valeriana spp., combine (valeroidine) tropane alkaloids, pyranocoumarin, dihyrosamidin.

C 1 to C 6 moncarboxylic acid

 Angelic acid: present in the rhizome of Angelica, schizanthine, chamomile oil. component of cevadine and Symphytum alkaloids.  n-Butyric acid and Caproic acid: occurs in traces in many fats.  Senecioic acid: present in Senecio, alkaloids of Dioscorea and Schizanthus. Present in samidin (pyranocoumarin).

C 1 to C 6 moncarboxylic acid

Fatty Acids

 important components of plant oils, resins, and waxes; aliphatic monocarboxylic acid.  obtained from hydrolysis of fats  usually contains an even number of carbon atoms (C 10 to C 20 )  Occur mainly as esters of natural fats and oils but do occur in the unesterified form as free fatty acids  Saturated – no double bonds (stearic, palmitic acid)  Unsaturated – containing one or more double bonds

 Nomenclature

 – anoic: saturated acid ends (e.g.,octanoic acid)  – enoic: unsaturated acids with double bonds (e.g., octadecenoic acid)  C atoms are numbered from the carboxyl C as C-  Adjacent to carboxyl C as 2, 3 and 4 are also known as , , and  carbons  Terminal methyl C is known as  or n-carbon   indicate the number and position of the double bond, eg., 9, double bond between C-9 and C-

Fatty Acids

 Straight-chain saturated acids (Figure 19.2)

Common name IUPAC name Formula

Caprylic acid n -Octanoic acid CH 3 (CH 2 ) 6 COOH Capric acid n -Decanoic acid CH 3 (CH 2 ) 8 COOH Lauric acid n -Dodecanoic acid CH 3 (CH 2 ) 10 COOH Myristic acid n -Tetradecanoic acid CH 3 (CH 2 ) 12 COOH Palmitic n -Hexadecanoic acid CH 3 (CH 2 ) 14 COOH Stearic acid n -Octadecanoic acid CH 3 (CH 2 ) 16 COOH Arachidic acid n -Eicosanoic acid CH 3 (CH 2 ) 18 COOH

Biosynthesis of saturated f.a (Figure 18.6)

 Cyclic unsaturated acids (Table 19.4)

 Hydnocarpic acid  Chaulmoogric acid  Gorlic acid  Prostanoic  PGA2 [Soft coral: ( Plexaura homomalla )]  Involved in platelet aggregation and inflammatory process  Promote smooth muscle contraction: act as ___ and ____.

Fatty Acids

Aromatic Acids

 Benzoic acid

 Cinnamic acid : Truxillic acid occurs

in coca leaves (polymer of ___).

 Salicylic acid ( o -hydroxybenzoic

acid)

 Protocatechuic acid (3,4-

dihydroxybenzoic acid)

 Veratric acid (3,4-

dimethoxybenzoic acid)

 Gallic acid (3,4,5-trihyroxybenzoic

acid)

Benzoic acid and its salt

 Constituent of Whitfield's Ointment which is used for the treatment of fungal skin diseases such as tinea , ringworm , and athlete's foot.

 Sodium benzoate, sodium salt of benzoic acid, is used preferably as one of the principal anti- microbial preservatives used in foods and beverages

 Sodium Benzoate is also used in medications, anti-fermentation additives and tableting lubricant for pharmaceuticals.

Salicylic acid

 Uses:

 Keratolytic – treatment of hyperpigmentation and warts  Fungicidal – treatment of fungal skin infections such as tinea  treatment of hyperkeratotic, dandruff, ichthyosis and psoriasis  antiseptic in toothpaste