1099-87-2

Basic information

• Product Name: Sodium prasterone sulfate
• Synonyms: Androst-5-en-17-one, 3-(sulfooxy)-, sodium salt, (3.beta.)-;Androst-5-en-17-one, 3.beta.-hydroxy-, hydrogen sulfate, sodium salt;Dehydroepiandrosterone-3-sulfate Sodium Salt Sodium Dehydroisoandrosterone-3-sulfate;DHEA sulfate,sodiuM salt;Dehydroepiandrosterone 3-sulfate (DHEAS) sodium salt solution;dha-s;mylis;sodiumandrost-5-en-17-one-3-beta-ylsulfate
• CAS NO: 1099-87-2
• Molecular Formula: C₁₉H₂₇O₅S*Na
• Molecular Weight: 390.47
• EINECS: 214-152-2
• Product Categories: Steroids.;Intermediates & Fine Chemicals;Pharmaceuticals;17-Ketosteroids;Biochemistry;Steroids;pharmaceutical intermediate and chemical research
• Mol File: 1099-87-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 148-149 °C (dec.)(lit.)
• Flash Point: 9℃
• Appearance: white to off-white/powder
• Refractive Index: 10 ° (C=4, MeOH)
• Storage Temp.: ?20°C
• Solubility: methanol: clear to hazy
• Merck: 14,2871
• CAS DataBase Reference: Sodium prasterone sulfate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium prasterone sulfate(1099-87-2)
• EPA Substance Registry System: Sodium prasterone sulfate(1099-87-2)

Safety Data

• Hazard Codes: F,C,T
• Statements: 11-34-39/23/24/25-23/24/25
• Safety Statements: 16-26-36/37/39-45-36/37-7
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 3
• RTECS: BV8397400
• Hazardous Substances Data: 1099-87-2(Hazardous Substances Data)

Usage

Description

Dehydroepiandrosterone sulfate (DHEAS) is a metabolite of dehydroepiandrosterone that is the major secretory product of adrenal glands and is the predominant circulating precursor for active steroid hormones in humans. For example, in the fetoplacental-maternal unit, DHEAS acts as the primary precursor for placental estrogen biosynthesis. A normal circulating concentration of DHEAS is ~10 μM in young adults and is dramatically increased in some adrenocortical disorders.

Chemical Properties

White to Off-White Solid

Uses

An active agent in the preparation of a pharmaceutical for the treatment of asthma or other respiratory diseases.

Definition

ChEBI: An organic sodium salt that is the monosodium salt of dehydroepiandrosterone sulfate.

InChI:InChI=1/C19H28O5S.Na/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;/h11,13-16H,3-10H2,1-2H3,(H,21,22,23);/q;+1/p-1/rC19H27NaO5S/c1-18-9-7-13(24-26(22,23)25-20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,13-16H,3-10H2,1-2H3

Synthetic route

pyridinium salt of 3β-sulfooxy-androsten-(5)-one-(17) → Sodium prasterone sulfate (1099-87-2)

Conditions	Yield
With water; sodium chloride

dehydroepiandrosterone (53-43-0) → Sodium prasterone sulfate (1099-87-2)

Conditions	Yield
With pyridine; chlorosulfonic acid at 22℃; for 2h;

hydrogenchloride (7647-01-0) + Sodium prasterone sulfate (1099-87-2) → dehydroepiandrosterone (53-43-0)

Conditions	Yield
at 25℃;

Sodium prasterone sulfate (1099-87-2) + aqueous BaCl2 → dehydroepiandrosterone (53-43-0)

Conditions	Yield
at 100℃;

Upstream product

• 53-43-0 dehydroepiandrosterone 

Downstream Products

• 53-43-0 dehydroepiandrosterone 

Relevant articles and documents

5α-Androst-16-en-3α-ol β-D-glucuronide, precursor of 5α-androst-16-en-3α-ol in human sweat

5α-Androst-16-en-3α-ol (α-androstenol) is an important contributor to human axilla sweat odor. It is assumed that α-andostenol is excreted from the apocrine glands via a H2O-soluble conjugate, and this precursor was formally characterized in this study for the first time in human sweat. The possible H2O-soluble precursors, sulfate and glucuronide derivatives, were synthesized as analytical standards, i.e., α-androstenol, β-androstenol sulfates, 5α-androsta-5,16-dien- 3β-ol (β-androstadienol) sulfate, α-androstenol β-glucuronide, α-androstenol α-glucuronide, β-androstadienol β-glucuronide, and α-androstenol β-glucuronide furanose. The occurrence of α-androstenol β-glucuronide was established by ultra performance liquid chromatography (UPLC)/MS (heated electrospray ionization (HESI)) in negative-ion mode in pooled human sweat, containing eccrine and apocrine secretions and collected from 25 female and 24 male underarms. Its concentration was of 79 ng/ml in female secretions and 241 ng/ml in male secretions. The release of α-androstenol was observed after incubation of the sterile human sweat or α-androstenol β-glucuronide with a commercial glucuronidase enzyme, the urine-isolated bacteria Streptococcus agalactiae, and the skin bacteria Staphylococcus warneri DSM 20316, Staphylococcus haemolyticus DSM 20263, and Propionibacterium acnes ATCC 6919, reported to have β-glucuronidase activities. We demonstrated that if α- and β-androstenols and androstadienol sulfates were present in human sweat, their concentrations would be too low to be considered as potential precursors of malodors; therefore, the H2O-soluble precursor of α-androstenol in apocrine secretion should be a β-glucuronide. Copyright