35048-47-6

Basic information

• Product Name: 1,3,5[10]-ESTRATRIENE-3,17-DIOL-6-ONE 6-[O-CARBOXYMETHYL]OXIME
• Synonyms: estradiol-6-(o-carboxymethyl)oxime;BETA-ESTRADIOL-6-ONE 6-(O-CARBOXYMETHYLOXIME);6-KETOESTRADIOL 6-(O-CARBOXYMETHYL)OXIME;17BETA-ESTRADIOL-6-[O-CARBOXYMETHYL]OXIME;1,3,5[10]-ESTRATRIENE-3,17-DIOL-6-ONE 6-[O-CARBOXYMETHYL]OXIME;1,3,5-ESTRATRIENE-3,17BETA-DIOL-6-ONE6-(O-CARBOXYMETHYLOXIME);3,17BETA-DIHYDROXY-1,3,5[10]-ESTRATRIENE 6-[O-CARBOXY-METHYL]OXIME;oestradiol-6-one 6-(O-carboxymethyloxime)
• CAS NO: 35048-47-6
• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.42
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 35048-47-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 195-197 °C (decomp)
• Boiling Point: 572.6°Cat760mmHg
• Flash Point: 300.1°C
• Appearance: /
• Density: 1.46g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.68
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• PKA: 3.10±0.10(Predicted)
• BRN: 2484202
• CAS DataBase Reference: 1,3,5[10]-ESTRATRIENE-3,17-DIOL-6-ONE 6-[O-CARBOXYMETHYL]OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5[10]-ESTRATRIENE-3,17-DIOL-6-ONE 6-[O-CARBOXYMETHYL]OXIME(35048-47-6)
• EPA Substance Registry System: 1,3,5[10]-ESTRATRIENE-3,17-DIOL-6-ONE 6-[O-CARBOXYMETHYL]OXIME(35048-47-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 35048-47-6(Hazardous Substances Data)

Usage

Uses

β-Estradiol-6-one 6-(O-carboxymethyloxime) was shown to exhibit regulatory activities towards the expression of leptin, a protein hormone that coordinate appetite/hunger and metabolism.β-Estradiol-6-one 6-(O-carboxymethyloxime) was shown to control the secretion of leptin via membrane associated estrogen receptor alpha in human placental cells.

Definition

ChEBI: A derivative of 17beta-estradiol having an O-(carboxymethyl)oxime group at the 6-position.

General Description

β-Estradiol-6-one 6-(O-carboxymethyloxime) is a derivative of 17β-estradiol.

InChI:InChI=1/C20H25NO5/c1-20-7-6-13-12-3-2-11(22)8-15(12)17(21-26-10-19(24)25)9-14(13)16(20)4-5-18(20)23/h2-3,8,13-14,16,18,22-23H,4-7,9-10H2,1H3,(H,24,25)/b21-17+/t13?,14?,16?,18-,20-/m0/s1

Upstream product

• 571-92-6 6-ketoestradiol 
• 2921-14-4 (aminooxy)acetic acid hemihydrochloride 
• 3434-45-5 6-oxo-3,17β-estradiol diacetate 
• 1474-52-8 estradiol-3,17-diacetate 
• 645-88-5 aminooxyacetic acid 
• 65132-67-4 Benzoic acid (8R,9S,13S,14S,17S)-6-[(E)-carboxymethoxyimino]-17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl ester 
• 20295-82-3 O-carboxymethylhydroxylamine hydrochloride 

Relevant articles and documents

Facile synthesis of CIDs: Biotinylated estrone oximes efficiently heterodimerize estrogen receptor and streptavidin proteins in yeast three hybrid systems

We synthesized estrone oximes as chemical inducers of protein heterodimerization (CIDs). Estrone-17-(O-carboxymethyl)oxime coupled to biotinamidocaproic acid via N,N′-dimethylhexane-1,6-diamine efficiently heterodimerizes estrogen receptors (ERs) and stre

Specificity of antibodies to ovarian hormones in relation to the site of attachment of the steroid hapten to the peptide carrier

Estradiol-17β, estriol and progesterone were rendered antigenic by covalent attachment to bovine serum albumin through ring B or C of the steroid molecule. Coupling to lysine residues of the protein was effected via the 6-(O-carboxymethyl)-oximes of the estrogens and via the 6-(carboxymethylene) thioether or the 11α-hemisuccinate of progesterone, by use of the carbodiimide reagent. Antisera to the estradiol 6-conjugate raised in rabbits or goats distinguished estradiol-17β more efficiently from estrone, estradiol-17α and estriol than did antisera to estradiol-17β-hemisuccinate-BSA; neither serum reacted with non-phenolic steroids or non-steroidal estrogens. Antisera to estriol 6-conjugates showed minimal cross-reaction with estradiol-17β and estrone. Rabbit antisera against the progesterone 6-conjugate did not react with phenolic or C19-steroids, cr with corticosterone, and only feebly with 11-deoxycorticosterone and 20α-or 20β-dihydroprogesterone; significant crossreaction occurred with 17β-hydroxyprogesterone and 3β,17α-dihydroxypregn-5-en-20-one (3-4%), Δ5-pregnenolone (8-14%) and with 5β- and 5β-dihydro-progesterone (100%). Sera against the 11-conjugate were better able to recognize changes about the A-ring and failed to cross-react with 5α-dihydroprogesterone ( 3%). Both sera showed greater specificity than reported for antibodies to 20-conjugates of progesterone towards the D-ring and 17-sidechain and were similar in this respect to antibodies elicited by 3-conjugates described in the literature. It is concluded that the site of attachment of steroid haptens to the peptide carrier importantly affects the specificity of the antibodies produced.