Dehydroepiandrosterone acetate
[CAS# 853-23-6]

Identification

• Classification: Analytical chemistry >> Standard >> Analytical standard
• Name: Dehydroepiandrosterone acetate
• Synonyms: Prasterone acetate; Dehydroepiandrosterone 3-acetate; Dehydroisoandrosterone acetate; 3b-Hydroxy-5-androstene-17-one acetate
• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.47
• CAS Registry Number: 853-23-6
• EC Number: 212-714-1
• SMILES: CC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC=C2C1)CCC4=O)C)C

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 168-170 °C (Expl.)
• Index of Refraction: 1.541, Calc.^*
• Boiling Point: 434.8±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 188.1±28.8 °C, Calc.^*

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H302-H312-H332-H351-H360-H361
• Safety Statements: P203-P261-P264-P270-P271-P280-P301+P317-P302+P352-P304+P340-P317-P318-P321-P330-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	2	H361
Carcinogenicity	Carc.	2	H351
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Reproductive toxicity	Repr.	1B	H360
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Dehydroepiandrosterone acetate (DHEA acetate) is a synthetic derivative of dehydroepiandrosterone (DHEA), a naturally occurring steroid hormone produced by the adrenal glands. With the molecular formula C24H34O4, DHEA acetate is an ester of DHEA and acetic acid, making it more stable and easier to handle in various applications. DHEA itself is a precursor to both estrogen and testosterone and plays a key role in the production of these sex hormones.

The discovery of DHEA acetate follows closely with the identification of DHEA itself in the 1930s, when researchers first isolated the compound from human adrenal glands. However, DHEA acetate was developed later, in the 1950s, as a synthetic variant for use in medical treatments. The primary advantage of DHEA acetate over its parent compound is its improved bioavailability and longer-lasting effects, as the ester bond must be broken down by the body to release DHEA.

One of the primary applications of DHEA acetate is in hormone replacement therapy (HRT). This therapy is often used to treat conditions related to age-related decline in hormone levels, including osteoporosis, cognitive decline, and reduced sexual function. Because DHEA acetate can be converted into both estrogen and testosterone, it has been studied for its potential benefits in men and women experiencing symptoms related to aging or hormonal imbalances. In particular, DHEA acetate has been explored as a treatment for women going through menopause, as it is thought to alleviate symptoms like hot flashes, mood swings, and reduced libido.

Furthermore, DHEA acetate has been studied for its possible effects on physical performance. Some research has suggested that the use of DHEA acetate could enhance muscle strength, improve athletic performance, and assist with weight loss, though results are inconclusive. Despite these potential benefits, the use of DHEA acetate for performance enhancement remains controversial and is banned by many sports organizations.

In addition to its use in hormone therapy, DHEA acetate has found applications in skincare products. As an ingredient in creams, lotions, and other topical formulations, it is believed to help reduce the appearance of wrinkles, promote skin rejuvenation, and increase skin elasticity. Some studies have also investigated the role of DHEA acetate in combating skin aging, with some positive outcomes suggesting that it may improve skin thickness and hydration.

While DHEA acetate is available as a prescription medication in some countries, its use in over-the-counter supplements has led to concerns regarding its safety and efficacy. Long-term use of DHEA acetate can lead to side effects such as acne, hair loss, and changes in mood, as well as potential risks related to hormone-sensitive cancers, such as breast and prostate cancer. For these reasons, it is crucial that individuals use DHEA acetate under the supervision of a healthcare professional.

In conclusion, dehydroepiandrosterone acetate is a steroid compound with a broad range of medical and cosmetic applications. Originally synthesized to enhance the effects of the naturally occurring hormone DHEA, it has since found use in hormone replacement therapies, skin care products, and even as a potential performance-enhancing agent. While it offers several benefits, the compound's use requires careful consideration due to potential side effects and the need for medical supervision.

References

2016. A search for microscopic fungi with directed hydroxylase activity for the synthesis of steroid drugs. Applied Biochemistry and Microbiology, 52(3).
DOI: 10.1134/s000368381603008x

2009. Studies of synthesis routes for biologically active 14α-hydroxylated steroids. Pharmaceutical Chemistry Journal, 43(1).
DOI: 10.1007/s11094-009-0229-8

2007. Transformation of steroids by actinobacteria: A review. Applied Biochemistry and Microbiology, 43(1).
DOI: 10.1134/s0003683807010012