7-Keto-dehydroepiandrosterone

HCID 193313

Basic information

CAS
566-19-8
Standard SMILES
C[C@]12CC[C@H](O)CC1=CC(=O)[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
InChIKey
KPRGOTLNGIBVFL-GINZOMEDSA-N
Molecular formula
C19H26O3
Average molar mass
302.4 g/mol
Monoisotopic mass
302.18819469

Overview

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

Names & identifiers

Preferred name
7-Keto-dehydroepiandrosterone
IUPAC
(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-7,17-dione
English name
7-Keto-dehydroepiandrosterone
Molecular formula
C19H26O3
Molecular weight
302.41

Names & synonyms

7-Keto-dehydroepiandrosterone7-Keto-DHEA7-Oxodehydroepiandrosterone7-oxo-dehydroepiandrosterone2334LJD2E9RefChem:1065273 beta-hydroxyandrost-5-ene-7,17-dione566-19-87-Ketodehydroepiandrosterone7-Oxo-DHEA7-Keto Dehydro Epiandrosterone3beta-Hydroxyandrost-5-ene-7,17-dione
Show more names
7-Ketoprasterone7-KETO DHEA, HPLC 98%ABiraterone Impurity I7-Keto DHEA (Standard)7-keto DHEA(7-Oxo DHEA)7-Keto-dehydroepiandrosteKetodehydroepiandrosterone7-keto DHEA Acetate Powder
MFCD00198500(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-7,17-dioneAndrost-5-ene-7,17-dione, 3-hydroxy-, (3b)-7-keto DHEA7-KetoDHEA, 7-keto-3-Hydroxy-10,13-dimethyl-3,4,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-7,17(2H,8H)-dione7-Keto Dehydro Epiandrosterone (1.0mg/ml in Methanol)

Database identifiers

CAS
566-19-8
PubChem CID
193313
DTXSID
DTXSID801024029
ChEMBL
CHEMBL1875999
ChEBI
CHEBI:183808
UNII
2334LJD2E9
EC Number
111-754-6
Nikkaji
J672.472H

Properties

Computed structural properties

XLogP
2
Topological polar surface area
54.4 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
22

Physicochemical properties

Melting point
245 · 245-248 °C
Boiling point
477.1 · 477.1±45.0 °C(Predicted)
Density
1.19 · 1.19±0.1 g/cm3(Predicted)
solubility
25 mg/ml; · 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 · 14.67±0.60(Predicted)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesCarc. 2 (100%)

Chemistry & industry

Applications · 2 items

Description7-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].

Uses7-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.

Suppliers100 total

Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

4 records

Compound notes

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