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
• Empirical Formula (Hill Notation): C₂₁H₃₁NO₄
• CAS Number: 10190-93-9
• Molecular Weight: 361.48
• MDL number: MFCD00056503
• UNSPSC Code: 51111800
• PubChem Substance ID: 24900526
• NACRES: NA.77

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Warning
• Hazard Statements: H302 + H312 + H332,H351
• Precautionary Statements: P202 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves