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Merck
CN

UC288

16α-Hydroxytestosterone

Synonym(s):

16α, 17β-Dihydroxyandrost-4-en-3-one, 4-Androstene-16α,17β-diol-3-one

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About This Item

Empirical Formula (Hill Notation):
C19H28O3
CAS Number:
63-01-4
Molecular Weight:
304.42
UNSPSC Code:
12161501

Key Documents

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InChI key

YMCWOAZGWMZGQT-FPNLOETNSA-N

InChI

1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h9,13-17,21-22H,3-8,10H2,1-2H3/t13-,14+,15+,16-,17+,18+,19+/m1/s1

form

powder

drug control

USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada

color

white

mp

192-194 °C

storage temp.

2-8°C

Application

16αHydroxytestosterone has been used as a reference standard for the evaluation of testosterone metabolites using ultra-performance liquid chromatography/tandem mass spectrometric (UPLC/MS/MS) techniques. This product has also been used to analyze the developmental profiles of testosterone hydroxylases in chickens.

Biochem/physiol Actions

CYP2C11 (rat) metabolite; androgenic

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
129K3350
107K3260
117K3251
066K3253

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M Paolini et al.
British journal of pharmacology, 122(2), 344-350 (1997-10-06)
1. The sensitivity of the developing embryo to xenobiotics is highly dependent on the expression of metabolizing enzymes including cytochromes P450 (CYP). In the present study, therefore, the ontogeny of the CYP-dependent system in the chick was investigated with testosterone
M Numazawa et al.
Analytical biochemistry, 146(1), 75-81 (1985-04-01)
A sensitive nonradiometric assay of aromatization of 16 alpha-hydroxylated androgens, 16 alpha-hydroxy-4-androstene-3,17-dione (16 alpha-OHA), and 16 alpha-hydroxytestosterone (16 alpha-OHT), has been developed using reverse-phase high-performance liquid chromatography with voltametric detector. The estrogens produced by human placental microsomes, estriol (E3) and
H B Lim et al.
Biochemistry international, 28(3), 543-550 (1992-11-01)
The metabolism of 16 alpha-hydroxytestosterone by cytochrome P-450 system was studied with two different inductions. At least 5 different metabolites with higher polarity were produced from 16 alpha-hydroxytestosterone. MT-B, one of their products, appeared to be specifically increased by 3-methylcholanthrene-
Ganfeng Wang et al.
Rapid communications in mass spectrometry : RCM, 20(14), 2215-2221 (2006-06-23)
This paper describes the development and partial validation of a fast, sensitive and specific ultra-performance liquid chromatography/tandem mass spectrometric (UPLC/MS/MS) method for the determination of testosterone (T) and its four metabolites, 6beta-OH-T, 16alpha-OH-T, 16beta-OH-T and 2alpha-OH-T, in in vitro samples.
K Sugiyama et al.
Drug metabolism and disposition: the biological fate of chemicals, 22(4), 584-591 (1994-07-01)
P450 2C11 from rat liver is known to metabolize testosterone to 2 alpha-, 16 alpha-, and 6 beta-hydroxytestosterone, and to androstenedione and 16 alpha-hydroxyandrostenedione. Because Waxman (J. Biol. Chem. 259, 15481-15490) has reported that the enzyme converts androstenedione to 16
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