Dehydroepiandrosterone
[CAS# 53-43-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Methyl pyrimidine
• Name: Dehydroepiandrosterone
• Synonyms: DHEA; Prasterone; Androstenolone; Dehydroisoandrosterone; trans-Dehydroandrosterone; Hydroxyandrost-5-en-17-one
• Molecular Formula: C₁₉H₂₈O₂
• Molecular Weight: 288.43
• CAS Registry Number: 53-43-0
• EC Number: 200-175-5
• SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)O)C

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 1151 °C
• alpha: 12 ° (c=2, ethanol 96% 25 °C)
• Index of Refraction: 1.560, Calc.^*
• Boiling Point: 426.7±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 182.1±21.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Danger
• Risk Statements: H302-H312-H315-H319-H332-H351-H360-H362-H400-H410
• Safety Statements: P203-P260-P261-P263-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P318-P319-P321-P330-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	1B	H360
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Reproductive toxicity	Lact.	-	H362
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Carcinogenicity	Carc.	2	H351
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

Dehydroepiandrosterone, commonly known as DHEA, is a naturally occurring steroid hormone synthesized primarily in the adrenal glands. Its chemical formula is C19H28O2, and it serves as a precursor to both androgens and estrogens. DHEA was first isolated and identified in the 1930s, with significant advancements in its understanding occurring over the subsequent decades. Researchers recognized its role in steroidogenesis, the process by which steroids are produced from cholesterol, establishing DHEA as a crucial player in human hormonal balance.

The discovery of DHEA is attributed to the work of several scientists in the early 20th century, who were investigating the chemistry of adrenal hormones. The compound was first isolated in 1934 by the biochemist Adolf Butenandt, who identified it as a significant component of human and animal adrenal extracts. The term "dehydroepiandrosterone" reflects its chemical structure, indicating that it is derived from pregnenolone and is an androgenic hormone. Throughout the mid-20th century, further research confirmed its various biological roles, particularly in the regulation of metabolism, immune function, and sexual health.

DHEA serves multiple functions in the human body, primarily acting as a precursor to other hormones. It is converted into testosterone and estrogen in peripheral tissues, thus playing a vital role in the development of secondary sexual characteristics, reproductive health, and overall hormonal balance. DHEA levels peak in early adulthood and gradually decline with age, leading to interest in its supplementation as a means to counteract age-related hormonal decline.

One of the primary applications of DHEA is in the field of hormone replacement therapy. Supplementation with DHEA has been proposed as a method to restore hormonal levels in aging individuals, particularly those experiencing symptoms associated with low levels of androgens and estrogens, such as fatigue, depression, and decreased libido. Clinical studies have suggested that DHEA supplementation may improve mood, enhance cognitive function, and promote overall well-being in some populations, although the results remain mixed and more research is needed to establish definitive benefits.

In addition to its role in hormone therapy, DHEA has been investigated for its potential applications in enhancing athletic performance and muscle strength. Some athletes and bodybuilders use DHEA as a performance-enhancing supplement, as it may aid in increasing muscle mass and improving physical endurance. However, its use in sports is controversial, and regulatory bodies such as the World Anti-Doping Agency (WADA) have banned DHEA in competitive sports due to concerns about its performance-enhancing effects and potential side effects.

DHEA has also been studied for its potential role in various health conditions, including osteoporosis, cardiovascular disease, and metabolic disorders. Some research indicates that DHEA supplementation may enhance bone density and improve insulin sensitivity, although results vary among individuals. Furthermore, DHEA is being explored for its potential neuroprotective effects, with preliminary studies suggesting it may have a role in preventing cognitive decline associated with aging and neurodegenerative diseases.

Despite the interest in DHEA supplementation, safety and efficacy remain subjects of ongoing research. Side effects associated with DHEA use can include hormonal imbalances, acne, hair loss, and changes in mood. As a result, individuals considering DHEA supplementation should consult healthcare professionals to assess their specific needs and potential risks.

In summary, dehydroepiandrosterone is a significant steroid hormone with a complex history and diverse applications in health and wellness. Its discovery has contributed to our understanding of hormonal balance and the role of androgens and estrogens in human physiology. Ongoing research continues to explore its potential benefits and applications, underscoring its importance in the fields of endocrinology and age-related health.

References

1990. Dehydroepiandrosterone and a beta-agonist, energy transducers, alter antioxidant enzyme systems: influence of chronic training and acute exercise in rats. Archives of Biochemistry and Biophysics.
DOI: 10.1016/0003-9861(90)90674-n

1994. Specific binding of dehydroepiandrosterone sulfate to rat liver cytosol: A possible association with peroxisomal enzyme induction. Biochimica et Biophysica Acta (BBA) - Molecular Cell Research.
DOI: 10.1016/0167-4889(94)90121-x

1998. Oxygen free radical scavenger properties of dehydroepiandrosterone. Cell Biochemistry and Function.
DOI: 10.1002/(sici)1099-0844(199803)16:1<57::aid-cbf771>3.0.co;2-s