Waxes Definition: esters resulting from the condensation of high MW, straight chain FAs and high MW, primary, straight chain alcohols.

Contd…. Waxes are defined as mixtures of different MW acids and alcohols Waxes may also contain paraffins In plants- outer cell walls of epidermal tissue particularly in fruits and leaves Function- Protection against the penetration or loss of water Carnauba wax and Bayberry wax-vegetable wax Lac Wax and Bees Wax –Animal/Insect Wax

Uses: In Pharmaceuticals…..to harden ointments and cosmetic creams In preparation of cerates In industry and the arts….. Protective coating

Synthetic Spermaceti Spermaceti, a waxy substance obtained from the head of the Sperm Whale (Physeter macrocephalus Fam. Physeteridae) Quality emollient In cold creams and cosmetics Spermaceti is no longer available-synthetic spermaceti or jojoba oil

Consists of Mixture hexadecyl esters of FA -hexadecyl dodecanoate (cetyl laurate) -hexadecyl tetradecanoate (cetyl myristate) -hexadecyl hexadecanoate (cetyl pailmitate) -hexadecyl octadecanoate (cetyl stearate) WAXES Wax Alcohol Fatty Acid Carnuba CH 3 (CH 2 ) 28 CH 2 -OHCH 3 (CH 2 ) 24 COOH Beeswax CH 3 (CH 2 ) 28 CH 2 -OH CH 3 (CH 2 ) 14 COOH Spermacetic CH 3 (CH 2 ) 14 CH 2 -OHCH 3 (CH 2 ) 14 COOH

Contd…. Synthetic spermaceti or cetyl esters wax is a mixture consisting primarily of esters of saturated fatty alcohol (C14 to C18) and saturated FA (C14 to C18). Cetyl alcohol-mixture of solid alcohol consist not less than 90% of cetyl alcohol or 1-hexadecanol. Emulsifying aid Stiffening agent Stearyl alcohol-mixture of solid alcohol consist not less than 90% of stearyl alcohol or 1-octadecanol Alternative to cetyl alcohol Cetostearyl alcohol-40% stearyl alcohol and 90% cetyl and stearyl alcohol.

Jojoba oil Liquid wax expressed from seeds of Simmondsia chinensis (Fam. Buxaceae) Bushy shrub Native to northern Mexico and to the south western US Seeds-45 to 50% of an ester mixture (not triglycerides) Liquid at ambient temperature

On Hydrolysis… 35% eicosenoic acid (a C-20 unsaturated acid) 22% eicosenol (a C-20 unsaturated alcohol) 21% docosenol (a C-22 unsaturated alcohol)  Hydrogenation –crystalline wax that has appearance and properties of spermaceti  emollients

Beeswax Yellow wax or beeswax is purified wax from honeycomb of the bee, Apis mellifera (fam. Apidae) Abdomen of worker bee Honeycomb-after separation from honey, is melted in water- cooled- re-melted- strained- allowed to harden in molds

Characteristics Solid Yellow to grayish brown Agreeable, honey like odor Faint, characteristic taste Cold – brittle, non crystalline structure

Contains…. Alkyl esters of fatty and wax acids (about 72%) chiefly myricyl palmitate Free wax acids (14%) Cerotic acid and homologs HCs (12%) Minor- moisture - Pollen - Propolis (bee glue) Pollen and Propolis are responsible for most of the color of the wax

Uses: Stiffening agent Ingredient in yellow ointment Base for cerates and plasters In polishes

White wax Bleached, purified from honeycomb Also referred to as bleached wax Uses:  In ointments  Cold creams  Plasters

Prostaglandins: A prostaglandin is any member of a group of lipid compounds that are derived enzymatically from fatty acids and have important functions in the animal body. Every prostaglandin contains 20 carbon atoms, including a 5-carbon ring. lipidfatty acids C-20 lipid metabolite From essential, unsaturated FA Occur nearly all mammalian tissue (But in low conc.) 4 main classes-A, B, E, F PGs have cyclopentane ring with 2 aliphatic side chain Subscript indicate the number of double bond in the side chain & seriochemistry

Contd…. Act in cellular level may modulate the transmission of hormonal / extra cellular stimuli into cyclic AMP for internal regulation of cellular function Actions- Contraction; relaxation of smooth muscles female reproductive system, of cardiovascular system, of the intestinal tract, of the bronchi. Influence gastric secretion renal function

Contd…  They are mediators and have a variety of strong physiological effects, such as regulating the contraction and relaxation of smooth muscle tissue. Prostaglandins are not endocrine hormones, but autocrine or paracrine, which are locally acting messenger molecules. They differ from hormones in that they are not produced at a discrete site but in many places throughout the human body. Also, their target cells are present in the immediate vicinity of the site of their secretion. physiologicalhormonesautocrineparacrinesecretion  The prostaglandins, together with the thromboxanes and prostacyclins, form the prostanoid class of fatty acid derivatives, a subclass of eicosanoids.thromboxanes prostacyclinsprostanoideicosanoids

Prostaglandins prostaglandine E 1 (PGE 1 ) PGI 2 - Prostacyclin

Biosynthesis of eicosanoids

Biosynthesis Prostaglandins are found in most tissues and organs. They are produced by almost all nucleated cells. They are autocrine and paracrine lipid mediators that act upon platelets, endothelium, uterine and mast cells. They are synthesized in the cell from the essential fatty acids (EFAs).autocrine paracrineplatelets endotheliumuterinemast cellsessential fatty acids

Contd……. An intermediate arachidonic acid is created from diacylglycerol via phospholipase-A 2, then brought to either the cyclooxygenase pathway or the lipoxygenase pathway to form either prostaglandin and thromboxane or leukotriene respectively. The cyclooxygenase pathway produces thromboxane, prostacyclin and prostaglandin D, E and F. Alternatively, the lipoxygenase enzyme pathway is active in leukocytes and in macrophages and synthesizes leukotrienes.arachidonic acid diacylglycerolphospholipase-A 2cyclooxygenase pathwaylipoxygenase pathway leukotrienethromboxaneprostacyclinleukocytesmacrophages

Functions of Prostaglandins: There are a variety of physiological effects including: 1. Activation of the inflammatory response, production of pain, and fever. When tissues are damaged, white blood cells flood to the site to try to minimize tissue destruction. Prostaglandins are produced as a result. 2. Blood clots form when a blood vessel is damaged. A type of prostaglandin called thromboxane stimulates constriction and clotting of platelets. Conversely, PGI2, is produced to have the opposite effect on the walls of blood vessels where clots should not be forming.

Contd… 3. Certain prostaglandins are involved with the induction of labor and other reproductive processes. PGE2 causes uterine contractions and has been used to induce labor. 4. Prostaglandins are involved in several other organs such as the gastrointestinal tract (inhibit acid synthesis and increase secretion of protective mucus), increase blood flow in kidneys, and leukotriens promote constriction of bronchi associated with asthma.