7-Keto-dehydroepiandrosterone Chemical Properties

Melting point:

245-248 °C

Boiling point:

477.1±45.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

solubility 

DMF: 25 mg/ml; DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml; DMSO: 15 mg/ml; Ethanol: 10 mg/ml

form 

A crystalline solid

pka

14.67±0.60(Predicted)

InChI

InChI=1/C19H26O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-14,17,20H,3-9H2,1-2H3/t12-,13-,14-,17-,18-,19-/s3

InChIKey

KPRGOTLNGIBVFL-YQJRJXGQNA-N

SMILES

C[C@]12CC[C@H](O)CC1=CC(=O)[C@@]1([H])[C@]3([H])CCC(=O)[C@@]3(C)CC[C@]21[H] |&1:1,4,11,13,19,23,r|

CAS DataBase Reference

566-19-8(CAS DataBase Reference)

7-Keto-dehydroepiandrosterone Usage And Synthesis

Regulation

The FDA has proposed that 7-Keto-DHEA be included among substances banned from use in compounded drugs.

Description

7-Ketodehydroepiandrosterone (7-Keto-dehydroepiandrosterone; 7-keto-DHEA), chemically known under 3-acetyl-7-oxo-dehydroepiandrosterone, is a naturally occurring metabolite of the steroid hormone dehydroepiandrosterone (DHEA) and is marketed as such an anti-obesity dietary supplement. The synthesis of 7-keto-DHEA begins with an irreversible hydroxylation of DHEA in the position C7 by cytochrome P450 7B1 (CYP7B1) under the formation of 7 α-hydroxy-dehydroepiandrosterone (7 α-OH-DHEA). β-hydroxysteroid dehydrogenase type 1 (11 β-HSD 1) then catalyzes the interconversion of 7 α-OH-DHEA and 7 β-hydroxy-dehydroepiandrosterone (7 β-OH-DHEA) through a 7-keto-DHEA intermediary. DHEA is a "parent hormone" produced by glands near the kidneys. However, unlike DHEA, 7-keto-DHEA is not converted to steroid hormones such as androgen and estrogen. Taking 7-keto-DHEA by mouth or applying it to the skin does not increase the level of steroid hormones in the blood. People take 7-keto-DHEA for obesity, muscle strength, anxiety, depression, and other conditions. However, there is no good scientific evidence to support these uses[1].

Uses

7-Keto Dehydro Epiandrosterone-d6 is the isotope labelled analog of 7-Keto Dehydro Epiandrosterone (K187700); a metabolite of Dehydroepiandrosterone (DHEA) (D229585) which is the major secretory steroidal product of the adrenal gland.

Definition

ChEBI: 7-ketodehydroepiandrosterone is a 3beta-hydroxy-Delta(5)-steroid that is dehydroepiandrosterone carrying an additional oxo group at position 7. It has a role as a human blood serum metabolite, a nutraceutical and a prohormone. It is a 17-oxo steroid, a 3beta-hydroxy-Delta(5)-steroid, an androstanoid and a 7-oxo steroid. It is functionally related to a dehydroepiandrosterone.

Side effects

7-Keto-dehydroepiandrosterone might cause mild side effects such as nausea, dizziness, or low blood pressure in some people. 

Physiological effects

In the past ten years, a large number of studies have shown that 7-keto dehydroepiandrosterone has stronger physiological activity than DHEA, especially in anti-aging, enhancing immunity, improving memory, enhancing brain function, preventing Alzheimer’s and diabetes , It has a strong effect on reducing the risk of heart disease, losing weight, increasing bone density and muscle vitality.

References

[1] Nishanthini Jeyaprakash. “A systematic review of the impact of 7-keto-DHEA on body weight.” Archives of Gynecology and Obstetrics 308 3 (2022): 777–785.

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