Androsta-4,6-diene-3,17-dione

Base Information

• Chemical Name: Androsta-4,6-diene-3,17-dione
• CAS No.: 633-34-1
• Molecular Formula: C19H24O2
• Molecular Weight: 284.398
• UNII: 7RS0NIL39S
• DSSTox Substance ID: DTXSID20979385
• Nikkaji Number: J58.212C
• Wikidata: Q27268767
• Pharos Ligand ID: FS6QTSTMXW52
• ChEMBL ID: CHEMBL3754473
• Mol file: 633-34-1.mol

Synonyms:4,6-androstadiene-3,17-dione;4,6-androstadiene-3,17-dione, (9beta,10alpha)-isomer;6-dehydroandrostene-3,17-dione;androsta-4,6-diene-3,17-dione

Chemical Property of Androsta-4,6-diene-3,17-dione

Chemical Property:

• Vapor Pressure: 2.88E-08mmHg at 25°C
• Refractive Index: 1.568
• Boiling Point: 449.3 °C at 760 mmHg
• Flash Point: 167.5 °C
• PSA: 34.14000
• Density: 1.14 g/cm³
• LogP: 3.86340
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 284.177630004
• Heavy Atom Count: 21
• Complexity: 584

Purity/Quality:

99%, ^*data from raw suppliers

4,6-ANDROSTADIEN-3,17-DIONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)C=CC4=CC(=O)CCC34C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)C=CC4=CC(=O)CC[C@]34C
• Use Description: 4,6-Androstadien-3,17-dione, often referred to as androstadienone, is a chemical compound with various applications across different fields. In the field of perfumery and fragrance industry, it is used as a fragrance compound, sometimes described as having a musky or pheromone-like odor. Its role in perfumery is to enhance and modify the scent profiles of various perfumes and fragrances. In addition to perfumery, androstadienone has also been studied in the field of psychology and neuroscience for its potential role in human behavior, particularly in relation to social and sexual interactions. Some studies have suggested that androstadienone may have subtle effects on mood and attraction. However, it's important to note that the role of androstadienone in human behavior is still an area of ongoing research, and its effects may be complex and context-dependent. Its multifaceted roles as a fragrance compound and a subject of scientific investigation underscore its significance in perfumery and psychology in various fields.

Technology Process of Androsta-4,6-diene-3,17-dione

There total 13 articles about Androsta-4,6-diene-3,17-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 40.0%

dehydroepiandrosterone (53-43-0) → androst-4,6-diene-3,17-dione (633-34-1) + 5-androstenedione (571-36-8) + Androsta-1,4-diene-3,17-dione (897-06-3)

Guidance literature:

With 2,2'-bipyridylchromium peroxide; In benzene; for 3h; Product distribution; Heating; effect of various chromium(VI) based oxidants;

DOI:10.1016/S0040-4020(01)87476-7

Reference yield: 33.0%

methanol (67-56-1) + Androstenedione (63-05-8) → androst-4,6-diene-3,17-dione (633-34-1) + 4-methoxyandrost-4-ene-3,17-dione (20986-46-3) + (6R,8R,9S,10R,13S,14S)-6-methoxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[α]phenanthrene-3,17(2H,6H)-dione (13163-89-8,111266-35-4,13163-86-5)

Guidance literature:

With potassium hydroxide; o-iodosobenzoic acid; at 70 ℃; for 1h;

DOI:10.1039/c39860001092

Reference yield: 32.0%

C19H26O2 → (8R,9S,10R,13S)-10,13-dimethyl-9,10,11,12,13,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,8H)-dione (633-34-1,3963-45-9,4080-56-2,4105-45-7,61217-25-2)

Guidance literature:

With C₁₂H₁₂F₆O₄Pt; chlorobenzene; p-benzoquinone; barium(II) oxide; at 80 ℃; for 12h; Inert atmosphere; Glovebox;

DOI:10.1002/anie.202013628

upstream raw materials:

methanol

Androstenedione

dehydroepiandrosterone

6β-bromoandrost-4-ene-3,17-dione

Downstream raw materials:

(7R,8R,9S,10R,13S,14S)-7-(4-Bromo-phenylsulfanyl)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione

(7R,8R,9S,10R,13S,14S)-7-Benzylsulfanyl-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione

7α-<(4-aminophenyl)thio>androst-4-ene-3,17-dione

cholic acid

Refernces

• 1、 Chen, Kaixiong,Liu, Chang,Deng, Le,Xu, Guangyu. "A practical Δ1-dehydrogenation of Δ4-3-keto-steroids with DDQ in the presence of TBDMSCl at room temperature". experimental part. p. 513 - 516. Retrieved 2010/06/21.
• 2、 Numazawa, Mitsuteru,Ogata, Mieko. "Methoxylation of Enolizable Steroidal 4-Ene-3-ones using Hypervalent Iodine". . p. 1092 - 1093. Retrieved 2007/10/02.