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H2898

Sigma-Aldrich

6β-Hydroxytestosterone

≥97% (HPLC)

Synonym(s):

4-Androstene-6β,17β-diol-3-one, 6β, 17β,-Dihydroxyandrost-4-en-3-one

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About This Item

Empirical Formula (Hill Notation):
C19H28O3
CAS Number:
62-99-7
Molecular Weight:
304.42
MDL number:
MFCD00171612
UNSPSC Code:
12352200
PubChem Substance ID:
24895541
NACRES:
NA.77

sterility

non-sterile

Quality Level

200

Assay

≥97% (HPLC)

form

powder

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

solubility

methanol: 50 mg/mL, clear, colorless

shipped in

ambient

storage temp.

room temp

SMILES string

C[C@]12CC[C@H]3[C@@H](C[C@@H](O)C4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@H]2O

InChI

1S/C19H28O3/c1-18-7-5-11(20)9-15(18)16(21)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h9,12-14,16-17,21-22H,3-8,10H2,1-2H3/t12-,13-,14-,16+,17-,18+,19-/m0/s1

InChI key

XSEGWEUVSZRCBC-ZVBLRVHNSA-N

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Application

6β-Hydroxytestosterone has been used as a standard in high-performance liquid chromatography (HPLC) analysis to measure testosterone 6 β -hydroxylase activity in rat liver microsomes, and measure cytochrome P450 3A (CYP3A) activity in the intestinal spheroid model.

Biochem/physiol Actions

6β-Hydroxytestosterone is a metabolite generated by brain testosterone cytochrome P450 1B1 (CYP1B1). It may elicit angiotensin II-induced neurogenic hypertension and inflammation in male mice.
6β-Hydroxytestosterone is a CYP3A4 metabolite; androgenic.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H351,H360

Hazard Classifications

Carc. 2 - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Purnima Singh et al.
Hypertension (Dallas, Tex. : 1979), 76(3), 1006-1018 (2020-08-07)
Previously, we showed that peripheral administration of 6β-hydroxytestosterone, a CYP1B1 (cytochrome P450 1B1)-generated metabolite of testosterone, promotes angiotensin II-induced hypertension in male mice. However, the site of action and the underlying mechanism by which 6β-hydroxytestosterone contributes to angiotensin II-induced hypertension
Laura M Langan et al.
Frontiers in pharmacology, 9, 947-947 (2018-09-07)
Compared to two-dimensional (2D) cell culture, cellular aggregates or spheroids (3D) offer a more appropriate alternative in vitro system where individual cell-cell communication and micro-environment more closely represent the in vivo organ; yet we understand little of the physiological conditions
Yong Liu et al.
Biological & pharmaceutical bulletin, 27(10), 1555-1560 (2004-10-07)
The intestinal bacterial metabolites of ginsenosides are responsible for the main pharmacological activities of ginseng. The purpose of this study was to find whether these metabolites influence hepatic metabolic enzymes and to predict the potential for ginseng-prescription drug interactions. Utilizing
Annalise Di Marco et al.
Drug metabolism and disposition: the biological fate of chemicals, 33(3), 349-358 (2004-12-21)
A rapid and sensitive radiometric assay for assessing the potential of drugs to inhibit cytochrome P450 (P450) 3A4/5 in human liver microsomes is described. In contrast to the conventional testosterone 6beta-hydroxylation assay, the new method does not require high-performance liquid
Zhen Lou et al.
The Journal of steroid biochemistry and molecular biology, 82(4-5), 413-424 (2003-02-19)
Intestinal or hepatic microsomes from channel catfish converted [4-14C]-testosterone to three major metabolites: 6 beta-hydroxytestosterone, androstenedione and a third metabolite. Formation of the unknown metabolite required NADPH as cofactor. When incubated with 200 microM testosterone, the rate of formation of
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