Androsterone
Encyclopedia
Androsterone is a steroid hormone
with weak androgenic activity. It is made in the liver
from the metabolism
of testosterone
. Its beta-isomer is Epiandrosterone
.
.
pollen
and is well known in many animal
species
.
Celery
is claimed to contain androsterone; however, this is inaccurate. Celery actually contains androstenone
, which has a different structure to androsterone and is otherwise unrelated.
.
, epiandrosterone, are naturally produced by an enzyme 5α-reductase from the adrenal hormone dehydroepiandrosterone
(DHEA). Androsterone can also be converted from the natural steroids 5α-androstanediol via 17β-hydroxysteroid dehydrogenase or from 5α-androstanedione via 3α-hydroxysteroid dehydrogenase.
Steroid hormone
A steroid hormone is a steroid that acts as a hormone. Steroid hormones can be grouped into five groups by the receptors to which they bind: glucocorticoids, mineralocorticoids, androgens, estrogens, and progestogens...
with weak androgenic activity. It is made in the liver
Liver
The liver is a vital organ present in vertebrates and some other animals. It has a wide range of functions, including detoxification, protein synthesis, and production of biochemicals necessary for digestion...
from the metabolism
Metabolism
Metabolism is the set of chemical reactions that happen in the cells of living organisms to sustain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments. Metabolism is usually divided into two categories...
of testosterone
Testosterone
Testosterone is a steroid hormone from the androgen group and is found in mammals, reptiles, birds, and other vertebrates. In mammals, testosterone is primarily secreted in the testes of males and the ovaries of females, although small amounts are also secreted by the adrenal glands...
. Its beta-isomer is Epiandrosterone
Epiandrosterone
Epiandrosterone is a steroid hormone with weak androgenic activity. It is a natural metabolite of dehydroepiandrosterone via the 5-alpha reductase enzyme. It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning...
.
History
It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17000 litres of male urine, from which they got 50 milligrams of crystalline androsterone, which was sufficient to find that the chemical formula was very similar to estroneEstrone
Estrone is an estrogenic hormone secreted by the ovary as well as adipose tissue.Estrone is one of several natural estrogens, which also include estriol and estradiol...
.
Sources
Androsterone has been shown to naturally occur in pinePine
Pines are trees in the genus Pinus ,in the family Pinaceae. They make up the monotypic subfamily Pinoideae. There are about 115 species of pine, although different authorities accept between 105 and 125 species.-Etymology:...
pollen
Pollen
Pollen is a fine to coarse powder containing the microgametophytes of seed plants, which produce the male gametes . Pollen grains have a hard coat that protects the sperm cells during the process of their movement from the stamens to the pistil of flowering plants or from the male cone to the...
and is well known in many animal
Animal
Animals are a major group of multicellular, eukaryotic organisms of the kingdom Animalia or Metazoa. Their body plan eventually becomes fixed as they develop, although some undergo a process of metamorphosis later on in their life. Most animals are motile, meaning they can move spontaneously and...
species
Species
In biology, a species is one of the basic units of biological classification and a taxonomic rank. A species is often defined as a group of organisms capable of interbreeding and producing fertile offspring. While in many cases this definition is adequate, more precise or differing measures are...
.
Celery
Celery
Apium graveolens is a plant species in the family Apiaceae commonly known as celery or celeriac , depending on whether the petioles or roots are eaten: celery refers to the former and celeriac to the latter. Apium graveolens grows to 1 m tall...
is claimed to contain androsterone; however, this is inaccurate. Celery actually contains androstenone
Androstenone
Androstenone is a steroid found in both male and female sweat and urine. It is also found in boar's saliva, and in celery cytoplasm. Androstenone was the first mammalian pheromone to be identified. It is found in high concentrations in the saliva of male pigs, and, when sniffed by a female pig...
, which has a different structure to androsterone and is otherwise unrelated.
Effects
Androsterone is often advertised as influencing human behavior, but there is little data to substantiate its use as a pheromonePheromone
A pheromone is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting outside the body of the secreting individual to impact the behavior of the receiving individual...
.
Synthesis
Androsterone and its 3β isomerIsomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
, epiandrosterone, are naturally produced by an enzyme 5α-reductase from the adrenal hormone dehydroepiandrosterone
Dehydroepiandrosterone
5-Dehydroepiandrosterone is a 19-carbon endogenous steroid hormone. It is the major secretory steroidal product of the adrenal glands and is also produced by the gonads and the brain. DHEA is the most abundant circulating steroid in humans....
(DHEA). Androsterone can also be converted from the natural steroids 5α-androstanediol via 17β-hydroxysteroid dehydrogenase or from 5α-androstanedione via 3α-hydroxysteroid dehydrogenase.
Synonyms
Synonyms include 3α-hydroxy-17-androstanone; 3α-Hydroxy-5-α-androstan-17-one; 3α-hydroxyetioallocholan-17-one; 3α-hydroxy-17-androstanone; 3α-hydroxyetioallocholan-17-one; 3α-hydroxy-17-androstanone; 3α-hydroxy-5α-androstan-17-one; 3α-hydroxyetioallocholan-17-oneSee also
- AndrostadienoneAndrostadienoneAndrostadienone, also known as androsta-4,16,-dien-3-one, is a chemical compound that has been described as having strong pheromone-like activities in humans. It is a metabolite of the sex hormone testosterone: however, androstadienone does not exhibit any known androgenic or anabolic effects...
- Androstatrione
- AndrostenolAndrostenolAndrostenol is a sex pheromone in pigs, possessing a musk-like odor.It is found in large quantities in boar saliva, but also in smaller quantities in human sweat glands. It is analogous to sex hormones yet has minimal or no androgenic activity...
- AndrostenoneAndrostenoneAndrostenone is a steroid found in both male and female sweat and urine. It is also found in boar's saliva, and in celery cytoplasm. Androstenone was the first mammalian pheromone to be identified. It is found in high concentrations in the saliva of male pigs, and, when sniffed by a female pig...
- AdrenosteroneAdrenosteroneAdrenosterone is a steroid hormone with weak androgenic effect. It was first isolated in 1936 from the adrenal cortex by Tadeus Reichstein at the Pharmaceutical Institute in the University of Basel. Originally, adrenosterone was called Reichstein's substance G...
- DehydroepiandrosteroneDehydroepiandrosterone5-Dehydroepiandrosterone is a 19-carbon endogenous steroid hormone. It is the major secretory steroidal product of the adrenal glands and is also produced by the gonads and the brain. DHEA is the most abundant circulating steroid in humans....
- EstratetraenolEstratetraenolEstratetraenol, also known as estra-1,3,5,16-tetraen-3-ol, is a chemical compound produced by women that has been described as having pheromone-like activities in primates, including humans...