Biomaterial Database

Synthesis of (19E)-3 beta,17-dihydroxy-20-oxopregn-5-en-19-al 19-(O-carboxymethyl)oxime, new steroidal hapten for 17-hydroxypregnenolone. 1994

V Pouzar, and J Fajkos

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague.

A synthesis of (19E)-3 beta,17-dihydroxy-20-oxopregn-5-en-19-al 19-(O-carboxymethyl)oxime (15), is reported. Hydride reduction of ketone 1 gave the (20R)-hydroxy derivative 2 as the main product. Formylation of 2 followed by cleavage of the epoxide ring and mild Jones oxidation afforded aldehyde 6. Oximation with (O-carboxymethyl)hydroxylamine and subsequent methylation yielded methyl ester 8 which was selectively hydrolyzed to alcohol 9 and oxidized to ketone 10. Enolacetylation, epoxidation, and hydrolysis led to the desired 19-(O-carboxymethyl)oxime derivative of 17-hydroxypregnenolone 15.

UI	MeSH Term	Description	Entries
D011283	Pregnenes	Unsaturated derivatives of PREGNANES.
D006241	Haptens	Small antigenic determinants capable of eliciting an immune response only when coupled to a carrier. Haptens bind to antibodies but by themselves cannot elicit an antibody response.	Hapten,Contact-Sensitizing Agents,Agents, Contact-Sensitizing,Contact Sensitizing Agents
D006907	17-alpha-Hydroxypregnenolone	A 21-carbon steroid that is converted from PREGNENOLONE by STEROID 17-ALPHA-HYDROXYLASE. It is an intermediate in the delta-5 pathway of biosynthesis of GONADAL STEROID HORMONES and the adrenal CORTICOSTEROIDS.	17 alpha-Hydroxypregnenolone,17-Hydroxypregnenolone,17-Hydroxypregnenolone, (3alpha)-Isomer,17-Hydroxypregnenolone, (3beta,13alpha)-Isomer,17-Hydroxypregnenolone, (3beta,13alpha,17alpha)-Isomer,17-Hydroxypregnenolone, (3beta,17alpha)-Isomer,17alpha-Hydroxypregnenolone,Hydroxypregnenolone,17 Hydroxypregnenolone,17 alpha Hydroxypregnenolone,17alpha Hydroxypregnenolone
D015415	Biomarkers	Measurable and quantifiable biological parameters (e.g., specific enzyme concentration, specific hormone concentration, specific gene phenotype distribution in a population, presence of biological substances) which serve as indices for health- and physiology-related assessments, such as disease risk, psychiatric disorders, ENVIRONMENTAL EXPOSURE and its effects, disease diagnosis; METABOLIC PROCESSES; SUBSTANCE ABUSE; PREGNANCY; cell line development; EPIDEMIOLOGIC STUDIES; etc.	Biochemical Markers,Biological Markers,Biomarker,Clinical Markers,Immunologic Markers,Laboratory Markers,Markers, Biochemical,Markers, Biological,Markers, Clinical,Markers, Immunologic,Markers, Laboratory,Markers, Serum,Markers, Surrogate,Markers, Viral,Serum Markers,Surrogate Markers,Viral Markers,Biochemical Marker,Biologic Marker,Biologic Markers,Clinical Marker,Immune Marker,Immune Markers,Immunologic Marker,Laboratory Marker,Marker, Biochemical,Marker, Biological,Marker, Clinical,Marker, Immunologic,Marker, Laboratory,Marker, Serum,Marker, Surrogate,Serum Marker,Surrogate End Point,Surrogate End Points,Surrogate Endpoint,Surrogate Endpoints,Surrogate Marker,Viral Marker,Biological Marker,End Point, Surrogate,End Points, Surrogate,Endpoint, Surrogate,Endpoints, Surrogate,Marker, Biologic,Marker, Immune,Marker, Viral,Markers, Biologic,Markers, Immune