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T8390

Testosterone 3-(O-carboxymethyl)oxime

Synonym(s):

17β-Hydroxy-4-androsten-3-one 3-(O-carboxymethyl)oxime, 4-Androsten-17β-ol-3-one 3-(O-carboxymethyl)oxime

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About This Item

Empirical Formula (Hill Notation):
C21H31NO4
CAS Number:
10190-93-9
Molecular Weight:
361.48
NACRES:
NA.77
PubChem Substance ID:
24900526
UNSPSC Code:
51111800
MDL number:
MFCD00056503
Assay:
≥98.00% (TLC)
Form:
powder
Quality level:
200
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sterility

non-sterile

Quality Level

200

assay

≥98.00% (TLC)

form

powder

drug control

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

solubility

ethanol: soluble 49-51 mg/mL, clear, colorless to faintly yellow

shipped in

ambient

storage temp.

room temp

SMILES string

[H][C@@]12CCC3=CC(\CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@@H](O)CC[C@@]24[H])=N\OCC(O)=O

InChI

1S/C21H31NO4/c1-20-9-7-14(22-26-12-19(24)25)11-13(20)3-4-15-16-5-6-18(23)21(16,2)10-8-17(15)20/h11,15-18,23H,3-10,12H2,1-2H3,(H,24,25)/b22-14+/t15-,16-,17-,18-,20-,21-/m0/s1

InChI key

VDYLVWGBLQNNAW-UVTKPVMCSA-N

Application

Testosterone 3-(O-carboxymethyl)oxime has been used to prepare horseradish peroxidase (HRP)-labeled testosterone to measure plasma testosterone concentration by enzyme immunoassay.
Testosterone 3-(O-carboxymethyl)oxime has been used for the hormonal analysis of sexual dimorphism in the electric fish, Apteronotus. This testosterone derivative has also been used for developing environmental biosensors for the detection of testosterone in water samples.

Biochem/physiol Actions

Androgens direct the development of male reproductive system and secondary sexual characteristics. Testosterone is an androgen that is secreted by the testis. This hormone is converted to dihydrotestosterone (DHT) by 5α reductase in the target tissues. Both DHT and testosterone require androgen receptor, a ligand-dependent nuclear transcription factor to mediate their biological functions.
Androgens direct the development of the male phenotype during embryogenesis and at puberty. Testosterone is an androgen that is secreted by the testis. This hormone is converted to dihydrotestosterone in the target tissues where it may mediate several biological functions.

Preparation Note

Testosterone 3-(O-carboxymethyl)oxime is soluble in ethanol at 49-51 mg/ml and yields a clear, colorless to faint yellow solution.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 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
0000508744
0000508744
0000483765
0000483765
0000458110

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Androgen receptor structure, function and biology: from bench to bedside
Davey RA and Grossmann M
The Clinical Biochemist. Reviews / Australian Association of Clinical Biochemists, 37(1), 3-3 (2016)
Testosterone and financial risk preferences
Apicella CL, et al.
Evolution, 29(6), 384-390 (2008)
SB223412, a neurokinin-3 receptor-selective antagonist, suppresses testosterone secretion in male guinea pigs
Nakamura S, et al.
Theriogenology, 102, 183-189 (2017)
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Global Trade Item Number

SKUGTIN
T8390-100MG04061832856889