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T8390

Sigma-Aldrich

Testosterone 3-(O-carboxymethyl)oxime

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Synonym(s):
17β-Hydroxy-4-androsten-3-one 3-(O-carboxymethyl)oxime, 4-Androsten-17β-ol-3-one 3-(O-carboxymethyl)oxime
Empirical Formula (Hill Notation):
C21H31NO4
CAS Number:
Molecular Weight:
361.48
MDL number:
PubChem Substance ID:
NACRES:
NA.77

sterility

non-sterile

Quality Level

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

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This Item
T1500K8250H2898
vibrant-m

T1500

Testosterone

vibrant-m

K8250

11-Ketotestosterone

vibrant-m

H2898

6β-Hydroxytestosterone

drug control

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

drug control

-

drug control

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

drug control

-

form

powder

form

powder

form

powder

form

powder

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

solubility

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

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble 18.2 mg/ml, absolute ethanol: soluble 0.5 mg/ml, chloroform: soluble 100 mg/mL, clear, colorless to very faintly yellow, H2O: insoluble, dioxane: soluble, methanol: soluble, methyl oleate: slightly soluble, vegetable oils: soluble

solubility

ethanol: 9.80-10.20 mg/mL, clear, colorless to faintly yellow

solubility

methanol: 50 mg/mL, clear, colorless

shipped in

ambient

shipped in

ambient

shipped in

ambient

shipped in

ambient

Application

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.
Testosterone 3-(O-carboxymethyl)oxime has been used to prepare horseradish peroxidase (HRP)-labeled testosterone to measure plasma testosterone concentration by enzyme immunoassay.

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

Exclamation markHealth hazard

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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


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Testosterone and financial risk preferences
Apicella CL, et al.
Evolution, 29(6), 384-390 (2008)
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)
SB223412, a neurokinin-3 receptor-selective antagonist, suppresses testosterone secretion in male guinea pigs
Nakamura S, et al.
Theriogenology, 102, 183-189 (2017)
K D Dunlap et al.
Journal of comparative physiology. A, Sensory, neural, and behavioral physiology, 183(1), 77-86 (1998-08-06)
Gymnotiform electric fish emit an electric organ discharge that, in several species, is sexually dimorphic and functions in gender recognition. In addition, some species produce frequency modulations of the electric organ discharge, known as chirps, that are displayed during aggression
Jens Tschmelak et al.
Talanta, 69(2), 343-350 (2008-10-31)
Nowadays, little technology exists that can monitor various water sources quickly and at a reasonable cost. The ultra-sensitive, fully automated and robust biosensor River Analyser (RIANA) is capable of detecting multiple organic targets rapidly and simultaneously at a heterogeneous assay

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