[pcog lec] module 2 - hydrocarbons and derivatives

capsaicin

the compound responsible for the characteristic spiciness of hot peppers, is the active ingredient in several topical creams for pain relief.

alcohols

Compounds that contain a hydroxyl group

hydrocarbons

compounds that contain only the elements of carbon and hydrogen

Tetrahydrocannabinol (THC)

active ingredient in marijuana

THC is an \____ because it contains an O atom bonded to two carbon atoms. In this case the O atom is also part of a ring.

ether

carbonyl compounds

aldehydes, ketones, carboxylic acids, esters, and amides

Hydrocarbons are important in nature as components of \___________

cuticular waxes

organic acids

possess one or more carboxyl groups

monobasic acid

represented by RCOOH

monobasic acids

found in all living organisms and as derivatives of all the major metabolic groups

C1-C6 Monocarboxylic acids

Fatty acids

Aromatic acids

important monobasic acids

Carboxylic acids

belongs to a family of organic molecules that contain a carbonyl group (C\= O) bonded to an element more electronegative than carbon.

C1-C6 Monocarboxylic acids

these acids together with hydroxy- and keto- derivatives are intermediates in the early stages of the biosynthesis of fats, isoprenoid compounds and various amino acids

formic acid

e derives from its first isolation from the ant, Formica rufa. Ant bite release formic acid causing itchiness

formic acid

A decomposition product of many vegetable materials

acetic acid

essential primary metabolite, particularly as acetyl-CoA

propionic acid

Esterified as a tropane alkaloid

iso-butyric acid

Occurs in traces in many fats; Occurs free in carob beans (Ceratonia siliqua) and as its ethyl ester in croton oil

crotonic acid (transbutenoic acid)

Constituent of croton oil - strong cathartic effect

angelic acid

Occurs in the rhizome of Angelica;

senecioic acid

First isolated from a species of Senecio (Compositae)

fatty acids

Naturally occurring animal fats and vegetable oils

12-20 carbon atoms

Fatty acids are carboxylic acids (RCOOH) with long carbon chains of \_____ carbon atoms

insoble

fatty acids are \____ in water

saturated fatty acids

no double bonds

unsaturated fatty acids

one or more double bonds

stearic

one of the two most common saturated fatty acids

oleic acid, linoleic acid

most common unsaturated acids; cannot be synthesized in the human body and must be obtained in the diet

cis

double bonds in naturally occuring fatty acids

decreases

As the number of double bonds in the fatty acid increases, the melting point \_________

fats

solid at room temperature; few double bonds

oils

liquid at room temperature; large number of double bonds

saturated fats

obtained from animal source

unsaturated oils

obtained from plant/vegetable source

coconut oil

exception from generalization; composed largely of unsaturated fatty acids

hydrolysis

Fatty acids are usually obtained by

\________ of fats or oils

lauric acid

myristic acid

palmitic acid

stearic acid

arachidic acid

most common saturated fatty acids

palmitoleic acid

oleic acid

linoleic acid

linolenic acid

arachidonic acid

unsaturated fatty acids

stearic acid

s used as an emulsion adjunct and a tablet lubricant

Calcium stearate and Magnesium stearate

used as tablet lubricants

Zinc stearate

used in dusting poders

sodium stearate

used as an emulsifying and stiffening agent

aluminum monostereate

used as a suspending agent

prostaglandins

group of physiologically active essential fatty acids found in most body tissues and are involved in the platelet-aggregation and inflammatory processes;

prostaglandins

clinical use as effective abortifacients and for inducing labor

prostanoic acid

All the active natural prostaglandins are derivatives of \________

oleic acid

obtained from edible fats and fixed oils; is often obtained as a by product in the production of stearic acid

oleic acid

practically insoluble in water but is miscible with alcohol

oleic acid

used as an emulsion adjunct

Ethyl oleate

pharmaceutic vehicle; s less viscous and more rapidly absorbed by body tissues

oleyl alcohol

employed as an emollient and emulsifying agent;

soybean oil

f essential unsaturated fatty acids that contains primarily linoleic and linolenic acids can be obtained from \________

Undecylenic acid

10-undecenoic acid; . prepared by pyrolysis of ricinoleic acid, which is obtained from castor oil

Calcium undecylenate

used in powders for diaper rash and similar skin irritations

Undecylenic acid

has antifungal properties; n combined with zinc undecylenate or other agents, in ointments and powders for topical application to treat athlete's foot

Sodium morrhuate

sodium salts of the fatty acids of cod liver oil; used as a sclerosing agent to obliterate varicose veins

iodine value

measure of unsaturatedness where in iodine or its equivalent is taken up at these double bonds found in fatty acids.

benzoic acid & cinnamic acid

truxillic acid

common aromatic acids

quinic acid

mandelic acid

shikimic acid

aromatic acids with alcohol group

benzoic acid and cinnamic acid

widely distributed in nature and often occur free and combined in considerable amounts in drugs such as balsams

truxillic acid

polymer of cinnamic acid, occurs in coca leaves

aromatic

refers to compound that contain a benzene ring

quinic acid

acids having an alcohol group; occurs in cinchona bark

mandelic acid

occurs in combination in cyanogenetic glycosides such as those of bitter almonds and other species of Prunus

shikimic acid

-important intermediate metabolite; tarting material for the semisynthesis of the antiviral drug oseltamivir (Tamiflu®) for use against bird flu infections in humans

source: star-anise fruits

Chlorogenic or caffeotannic acid

condensation product of caffeic acid and quinic acid.

malonic acid

succinic acid

dibasic or dicarboxylic acids

oxalic acid

e basic unit of the FIRST of a series of dicarboxylic acids

frurmaric acid

unsaturated, closely related to malonic acid

malic acid

found in fruits such as apples and tamarinds

tartaric acid

occurs in tamarinds and other fruits

citric acid

isocitric acid

acontic acid

Tribasic acids or tricarboxylic acids

citric acid

abundant in fruit juices; It forms part of the Krebs' cycle and the glyoxalate cycle in microorganisms

acontic acid

occurs in Aconitum spp., is anhydrocitric acid

primary alcohol

has an OH group bonded to one carbon

secondary alcohol

has an OH group on a carbon bonded to two carbons

tertiary alcohol

has an OH group on a carbon bonded to three carbon

alcohols

possess one or more hydroxyl groups and exist naturally in either the free state or combined as esters

monohydric alcohols - one hydroxyl

dihydric - two hydroxyls

trihydric - three hydroxyls