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Structure and Nomenclature

Carbon chains can bite their own tails, giving rise to an unlimited variety of cyclic structures.

(-)-Menthol
(m.p. 44ºC)
S-(-)-limonene
(b.p. 176ºC)
R-(+)-limonene
(b.p. 176ºC)
Camphor
(m.p. 180ºC)
Grandisol
(m.p. <25ºC)
Structure of menthol

Menthol has slightly anaesthetic or, rather, refreshing properties. It is used as an antipruritic in dermatology and as a very mild anaesthetic in otorhinolaryngology to treat pharyngitis. It also displays antiseptic properties.

Structure of (S)-limonene

Limonene can be dextrorotatory, levorotatory or racemic. Levorotatory limonene (-) is extracted from orange peel and is responsible for its smell.

Structure of (R)-limonene

Dextrorotatory limonene (+) is very abundant in Nature. It is an oily liquid easily extracted from lemon peel and responsible for its smell.

Structure of camphor

Camphor is a solid, crystalline and volatile substance with a burning taste and characteristic smell, found in the camphor tree and other plants of the laurel family. It is a mild topical anaesthetic (camphorated spirits).

Structure of grandisol

Grandisol is a sex-attractant pheromone secreted by the male of an insect that is a pest of cotton plants.

Cholesterol
(m.p. 149ºC)
Cholic acid
Cortisone
Testosterone
Estradiol
Progesterone
Structure of cholesterol

Cholesterol was isolated from bile in 1769 but its structure was not established until 1932. Woodward performed its total synthesis in 1951. It is found in all animal fats. Cholesterol intercalates among the phospholipids forming the cell membranes in animals. It makes the membranes more rigid and less permeable. Without cholesterol, the animal cells would need a wall like that of bacteria.

Structure of cholic acid

The structural elucidation of cholic acid by Wieland was one of the most important achievements in classic organic chemistry. It is formed in the liver from cholesterol degradation and acts as an emulsifier in bile.

Structure of cortisone

Cortisone is an adrenocortical hormone with a notable anti-inflammatory activity.

Structure of testosterone

Testosterone is the main androgenic hormone, secreted by the interstitial tissue of the testicles. It controls sperm formation, the development of genitals and the secondary sexual characteristics.

Structure of estradiol

Estradiol is a hormone that accounts for almost all the estrogen secreted by women during their reproductive years. A synthetic analogue is used in contraceptive pills.

Structure of progesterone

Progesterone is a hormone secreted by the corpus luteum of the ovary. It prepares the uterine lining for the implantation, maintenance and development of the fertilized egg. It was isolated in 1934 and its structure was established in 1935.

The empirical formula of a cycloalkane with only one ring is CnH2n. Each ring in a compound removes two hydrogen atoms from the formula of the corresponding acyclic alkane.

Cyclopropane
Cyclobutane
Cyclopentane
Cyclohexane
Cyclopropane: expanded, skeletal and perspective formulas
Cyclopropane
Cyclobutane: expanded, skeletal and perspective formulas
Cyclobutane
Cyclopentane: expanded, skeletal and perspective formulas
Cyclopentane
Cyclohexane: expanded, skeletal and perspective formulas
Cyclohexane

Examples of nomenclature:

Examples of nomenclature of substituted cycloalkanes

Cycloalkanes with two or more substituents may display geometrical isomerism:

cis-1,2-dimethylcyclopropane
trans-1,2-dimethylcyclopropane
cis-1,2-Dimethylcyclopropane
cis-1,2-dimethylcyclopropane
trans-1,2-Dimethylcyclopropane
trans-1,2-dimethylcyclopropane