651-48-9

Basic information

• Product Name: 10,13-dimethyl-17-oxo-3-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene
• Synonyms: 10,13-dimethyl-17-oxo-3-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene;Formylisoglutamic acid;Dehydroepiandrosterone Sulfate;DEHYDROEPIANDROSTERONESULPHATE;[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate;sulfuric acid [(3S,8R,9S,10R,13S,14S)-17-keto-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] ester;(3β)-3-(Sulfooxy)androst-5-en-17-one;Prasterone Sulfate Sports Nutrition Supplements Prasterone Sodium Sulfate 651-48-9
• CAS NO: 651-48-9
• Molecular Formula: C₁₉H₂₈O₅S
• Molecular Weight: 368.53
• Mol File: 651-48-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 190-192 °C
• Boiling Point: 468.81°C (rough estimate)
• Appearance: /
• Density: 1.1763 (rough estimate)
• Refractive Index: 1.5300 (estimate)
• PKA: -3.51±0.18(Predicted)
• CAS DataBase Reference: 10,13-dimethyl-17-oxo-3-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene(CAS DataBase Reference)
• NIST Chemistry Reference: 10,13-dimethyl-17-oxo-3-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene(651-48-9)
• EPA Substance Registry System: 10,13-dimethyl-17-oxo-3-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene(651-48-9)

Safety Data

• Hazardous Substances Data: 651-48-9(Hazardous Substances Data)

Usage

Definition

ChEBI: A steroid sulfate that is the 3-sulfooxy derivative of dehydroepiandrosterone.

InChI:InChI=1/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1

Synthetic route

pyridine-SO3 complex (42824-16-8) + dehydroepiandrosterone (53-43-0) → dehydroepiandrosterone sulfate (651-48-9)

Conditions	Yield
With benzene als Pyridinium-Salz;

dehydroepiandrosterone (53-43-0) → dehydroepiandrosterone sulfate (651-48-9)

Conditions	Yield
With [35S]-3′-phosphoadenosine-5′-phosphosulfate; phosphate buffer; male Sprague-Dawley rat gastric mucosa cytosol sulfotransferase; Sucrose Product distribution;
With propylene glycol; human adrenal hydroxysteroid sulfotransferase (EC 2.8.2.2); PAPS for 0.166667h; Kinetics; further enzyme: bovine liver hydroxysteroid sulfotransferase, Km;
With pyridine; aminosulfonic acid

dehydroepiandrosterone sulfate (651-48-9) → dehydroepiandrosterone (53-43-0) + 6β-hydroxy-3α,5-cycloandrostan-17-one (663-39-8, 24357-32-2, 57236-38-1, 118013-84-6)

Conditions	Yield
Ausbeute in gepufferten wss. Loesungen (pH 1.2-6.8);

dehydroepiandrosterone sulfate (651-48-9) → dehydroepiandrosterone (53-43-0)

Conditions	Yield
With potassium acetate; glucuronidase; sulphatase from Patella vulgata at 37℃; for 18h;
With arylsulfatase from Helix pomatia In aq. acetate buffer at 21℃; for 24h; pH=7; Enzymatic reaction;

dehydroepiandrosterone sulfate (651-48-9) → (3S)-3-tert-butyldimethylsilyloxyandrost-5-en-17-one (42151-23-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.5 M KOAc, pH 6.1 / glucuronidase/sulphatase from Patella vulgata / 18 h / 37 °C 2: imidazole / dimethylformamide / Ambient temperature View Scheme

C12H24N4O2 (1281702-63-3) + dehydroepiandrosterone sulfate (651-48-9) → C31H50N4O6S

Conditions	Yield
With acetic acid In ethanol; water at 70℃; for 0.5h;

Upstream product

• 42824-16-8 pyridine-SO₃ complex 
• 53-43-0 dehydroepiandrosterone 

Downstream Products

• 53-43-0 dehydroepiandrosterone 
• 663-39-8 6β-hydroxy-3α,5-cycloandrostan-17-one 
• 42151-23-5 (3S)-3-tert-butyldimethylsilyloxyandrost-5-en-17-one 

Relevant articles and documents

Testosterone sulfotransferase: Evidence in the guinea pig that this reaction is carried out by 3α-hydroxysteroid sulfotransferase

During the course of isolating, characterizing, and cloning estrogen and 3-hydroxysteroid sulfotransferases from the guinea pig adrenal gland, it was noted that cytosolic preparations from this tissue would also sulfonate testosterone. Therefore, we set out to isolate and clone the enzyme that performs this reaction. Testosterone sulfotransferase (TST) was isolated from the guinea pig adrenal by using the standard procedures of ion exchange, affinity, and high-performance liquid chromatography. When purified, TST was examined by liquid-phase nondenaturing isoelectric focusing, it was found that the TST activity profile completely overlapped with the activity profile of the 3α-hydroxysteroid sulfotransferase (3αHST) isoform, but not the 3β-hydroxysteroid sulfotransferase (3βHST) isoform. This finding was further investigated by overexpressing the cDNAs for 3αHST and 3βHST in Escherichia coli and examining the expressed proteins for TST activity. This experiment confirmed that 3αHST does indeed function as a TST. In addition, 3αHST was also found to sulfonate estradiol but not estrone, a finding that further suggested that 3αHST may function as a general 17β-hydroxysteroid sulfotransferase. Copyright (C) 1999.

Atherosclerotic plaque specific antigens, antibodies thereto, and uses thereof

An antigen comprising 5,7 cholestadien-3β-ol (7-dehydrocholesterol) or a compound having a structure similar to 5,7 cholestadien-3β-ol and a quaternary ammonium salt is provided. Also provided is a method of generating an antibody using the aforementioned antigen, as well as antibodies produced thereby and fragments of such antibodies. The invention also provides a rat myeloma cell line Z2D3 73/30 1D10 and a murine-human chimeric monoclonal antibody produced thereby. A CDR-grafted antibody comprising a CDR region amino acid sequence from hybridoma Z2D3 or hybridoma Z2D3/3E5 and framework and constant region amino acid sequences from a human immunoglobulin is further provided. Also provided are methods for imaging atherosclerotic plaque, ablating atherosclerotic plaque, detecting and quantitatively determining in a sample an antigen indicative of the presence of atherosclerotic plaque, reducing the amount of atherosclerotic plaque in a blood vessel, and treating atherosclerosis in a subject. The invention also provides peptides having amino acid sequences which are the same or substantially the same as those of the aforementioned murine-human chimeric monoclonal antibody, as well as isolated nucleic acid sequences encoding therefore.

ENZYMATIC SULFATION OF CHOLESTEROL BY RAT GASTRIC MUCOSA

A sulfotransferase which catalyzes transfer of the sulfate group from 3'-phosphoadenosine-5'phosphosulfate to cholesterol has been demonstrated in the rat gastric mucosa.The product of the reaction was characterized as cholesterol sulfate by two-dimensional thin-layer chromatography behavior, and gas-liquid chromatography of cholesterol after acid solvolysis.The bulk of enzyme activity was found in the cytosol fraction.Sulfation of cholesterol did not require added Mg+2, Mn+2, or Ca+2, and was unaffected by ethylenediaminetetraacetate.Triton X-100 moderatly enhanced the enzyme activity.A broad pH optimum from pH 6.0 - 9.0 was exhibited with a maximum at pH 7.0 - 7.5.The apparent Km for PAPS was 0.8 x 10-6M.The possible function of cholesterol sulfate in gastric mucosa is discussed.